1. Dear Drugs-Forum readers: We are a small non-profit that runs one of the most read drug information & addiction help websites in the world. We serve over 4 million readers per month, and have costs like all popular websites: servers, hosting, licenses and software. To protect our independence we do not run ads. We take no government funds. We run on donations which average $25. If everyone reading this would donate $5 then this fund raiser would be done in an hour. If Drugs-Forum is useful to you, take one minute to keep it online another year by donating whatever you can today. Donations are currently not sufficient to pay our bills and keep the site up. Your help is most welcome. Thank you.
    PLEASE HELP
    Dismiss Notice

Drug info - Cannabinoid CB1/CB2 Binding Affinity Chart - BETA

Discussion in 'Cannabinoids' started by msimm, Feb 10, 2010.

  1. msimm

    msimm Newbie

    Reputation Points:
    703
    Joined:
    Dec 5, 2004
    Messages:
    360
    45 y/o Male from U.S.A.
    Column 1 Column 2 Column 3 Column 4 Column 5 Column 6 Column 7 Column 8
    0 CB1 CB2 CB1 Ki CB2 Ki Notes Source CAS
    1 JWH-015 28x 383nM 13.8nM Selective CB2 agonist (Ki values are 13.8 and 383 nM as measured at human cloned CB2 and CB1 receptors expressed in CHO cells). Griffin et al (1999) Evidence for the presence of CB2-like receptor on peripheral nerve terminals. Eur.J.Pharmacol. 339 53. Pertwee et al (1999) Pharmacology of cannabinoid receptor ligands. Curr.Med.Chem. 6 635. Chin et al (1999) The third transmembrane helix of the cannabinoid receptor plays a role in the selectivity of aminoalkylindoles for CB2, peripheral cannabinoid receptor. J.Pharmacol.Exp.Ther. 291 837. - via tocris.com 155471-08-2
    2 JWH-018 3x 9.0nM 2.94nM Potent cannabinoid receptor agonist with mild selectivity for CB2 (Ki values are 2.94 and 9.0 nM for CB2 and CB1 receptors respectively). Chin et al (1999) The third transmembrane helix of the cannabinoid receptor plays a role in the selectivity of aminoalkylindoles for CB2, peripheral cannabinoid receptor. J.Pharmacol.Exp.Ther. 291 837. Aung et al (2000) Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug Alcohol Depend. 60 133. Huffman et al (2003) 3-Indolyl-1-naphthylmethanes: New cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB1 cannabinoid receptor. Bioorg.Med.Chem. 11 539. - via tocris.com 209414-07-3
    3 JWH-073 4x 8.9nM 38nM JWH 073 is a mildly selective agonist of the central cannabinoid (CB1) receptor derived from the aminoalkylindole WIN 55,212-2. The Ki values for binding CB1 and the peripheral cannabinoid (CB2) receptor are 8.9 and 38 nM, respectively for a CB1:CB2 ratio of 0.23.1 Its effects on suppression of spontaneous activity, maximum possible antinociceptive effect in the tail-flick assay, and rectal temperature are comparable to those of WIN 55,212-2 when tested in rats.2 1 Aung, M.M., Griffin, G., Huffman, J.W., et al. Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence 60 133-140 (2000). 2 Wiley, J.L., Compton, D.R., Dai, D., et al. Structure-activity relationships of indole- and pyrrole-derived cannabinoids. J Pharmacol Exp Ther 285(3) 995-1004 (1998). - via caymanchem.com 208987-48-8
    4 JWH-081 10x 1.2nM 12.4nM JWH-081, the N-pentyl analog of 28, R=C5H11, has very high affinty for the CB1 receptor with Ki=1.2+/-0.1 nM and is very potent in vivo. Huffman et al (2009) Cannabimimetic Indoles, Pyrroles, and Indenes: Structure–Activity Relationships and Receptor Interactions Huffman et al (2005) Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists. 210179-46-7
    5 JWH-133 200x 3.4nM Potent CB2 selective agonist (Ki = 3.4 nM). Approx. 200-fold selective over CB1 receptors. Active in vivo, reducing spasticity in a murine model of multiple sclerosis. Huffman et al (1999) 3-(1'-Dimethylbutyl)-1-deoxy-D8-THC and related compounds: synthesis of selective ligands for the CB2 receptor. Bioorg.Med.Chem. 7 2905. Pertwee (1999) Pharmacology of cannabinoid receptor ligands. Curr.Med.Chem. 6 635. Baker et al (2000) Cannabinoids control spasticity and tremor in a multiple sclerosis model. Nature 404 84. - via tocris.com 259869-55-1
    6 JWH-200 42nM acts as a cannabinoid receptor agonist. Its binding affinity at the CB1 receptor is 42nM, around the same as that of THC, but interestingly, its analgesic potency in vivo was higher than that of other analogues with stronger CB1 binding affinity in vitro, around 3 times that of THC but with less sedative effect, most likely reflecting favourable pharmacokinetic characteristics. Huffman, J. W.; Padgett, L. W. (2005) Recent Developments in the Medicinal Chemistry of Cannabimimetic Indoles, Pyrroles and Indenes, Current Medicinal Chemistry, Volume 12, Number 12, June 2005 , pp. 1395-1411 103610-04-4
    7 JWH-250 3x 11nM 33nM JWH 250 is a cannabimimetic indole that shows a high-affinity for both the central cannabinoid (CB1) and the peripheral cannabinoid (CB2) receptors. The affinities of JWH 250 for both CB1 (Ki = 11 nM) and CB2 (Ki = 33 nM) are comparable to those of the traditional cannabinoid, Δ9-tetrahydrocannabinol (Δ9-THC; Ki = 40.7 and 36.4 nM, respectively). Huffman, J.W., Szklennik, P.V., Almond, A., et al. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg Medicinal Chem Letters 15, 4110-4113 (2005). - via caymanchem.com 864445-43-2
    8 CP 47,497 2.2nM Potent CB1 receptor agonist (Ki = 2.2 nM). Display 3-28-fold > potency than Δ9-THC. Exhibits analgesic, motor depressant, anticonvulsant and hypothermic effects in vivo. Weissman et al (1982) Cannabimimetic activity from CP-47,497, a derivative of 3-phenylcyclohexanol. J.Pharmacol.Exp.Ther. 223 516. Melvin et al (1993) Structure-activity relationships for cannabinoid receptor-binding and analgesic activity: studies of bicyclic cannabinoid analogs. Mol.Pharmacol. 44 1008. Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322. - via tocris.com 70434-82-1
    9 CP 55,244 0.11nMr ND CP 55,244 was the most potent of the compounds, and also produced the highest percentage stimulation of binding, with EC50 and Emax values of 0.47 (0.22–0.96) nM and 165% (148 –183%), respectively. Griffin et al. (1998) Evaluation of cannabinoid receptor agonists and antagonists using the guanosine-5'-O-(3-[35S]thio)-triphosphate binding assay in rat cerebellar membranes.; Melvin LS, Milne GM, Wilken GH and Howlett AC (1995) Structure-activity relationships defining the ACD-tricyclic cannabinoids: cannabinoid receptor binding and analgesic activity. Drug Des Discov 13(2):155–166. 79678-32-3
    10 CP 55,940 0.6nM 0.7nM Cannabinoid agonist which is considerably more potent than Δ9-THC in both behavioral tests and receptor binding assays. Displays high and roughly equal affinity for both central and peripheral cannabinoid receptors (Ki = 0.6-5.0 and 0.7-2.6 nM at CB1 and CB2 respectively; EC50 values are 0.2, 0.3 and 5 nM at CB1, CB2 and GRP55 respectively). Wiley et al (1995) Discriminative stimulus effects of CP 55,940 and structurally dissimilar cannabinoids in rats. Neuropharmacology 34 669. Gatley et al (1997) Binding of the non-classical cannabinoid CP 55,940, and the diarylpyrazole AM251 to rodent brain cannabinoid receptors. Life Sci. 61 191. Griffin et al (1998) Evaluation of cannabinoid receptor agonists and antagonists using the guanosine-5¢-O-(3-[35S]thio)-triphosphate binding assay in rat cerebellar membranes. J.Pharmacol.Exp.Ther. 285 553. Thomas et al (1998) Comparative receptor binding analyses of cannabinoid agonists and antagonists. J.Pharmacol.Exp.Ther. 285 285. Ryberg et al (2007) The orphan receptor GPR55 is a novel cannabinoid receptor. Br.J.Pharmacol. 152 1092. - via tocris.com 83003-12-7
    11 HU-210 8x 0.061nM 0.52nM A highly potent cannabinoid receptor agonist (Ki values are 0.061 and 0.52 nM at cloned human CB1 and CB2 receptors respectively). Induces spatial memory deficits and suppresses hippocampal firing rates in rats. Also displays agonist activity at GPR55 (EC50 = 26 nM). Mechoulam et al (1988) Enantiomeric cannabinoids: stereospecificity of psychotropic activity. Experientia 44 762. Howlett et al (1990) Stereochemical effects of 11-OH-D8-tetrahydrocannabinol-dimethylheptyl to inhibit adenylate cyclase and bind to the cannabinoid receptor. Neuropharmacology 29 161. Robinson et al (2007) The synthetic cannabinoid HU210 reduces spatial memory deficits and suppresses hippocampal firing rates in rats. Br.J.Pharmacol. 151 688. Ryberg et al (2007) The orphan receptor GPR55 is a novel cannabinoid receptor. Br.J.Pharmacol. 152 1092. - via tocris.com 112830-95-2
    12 WIN 55212-2 19x 3.3nM 62.3nM WIN 55212-2 (mesylate) is a potent aminoalkylindole cannabinoid (CB) receptor agonist with a Ki of 3.3 and 62.3 nM for human recombinant CB1 and CB2 receptors, respectively.1 In primary cultures of rat cerebral cortex neurons, WIN 55212-2 (mesylate) (0.01-100 nM) increases extracellular glutamate levels, displaying a bell-shaped concentration-response curve.2 This effect at a concentration of 1 nM was fully counteracted by SR141716A (10 nM), by decreasing Ca2+ concentrations below 0.2 mM, and by the IP3 receptor antagonist xestospongin C at 1 µM. WIN 55212-2 (mesylate) induces release of the proinflammatory neuropeptide CGRP from trigeminal ganglion (TG) neurons in a calcium-dependent manner with an EC50 of 26 µM.3 In addition, WIN 55212-2 (mesylate)-evoked CGRP release is not stereospecific, as the CB receptor-inactive enantiomer WIN 55212-3 also stimulates CGRP exocytosis. 1 Felder, C.C., Joyce, K.E., Briley, E.M., et al. Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors. Mol Pharmacol 48 443-450 (1995). 2 Ferraro, L., Tomasini, C., Gessa, G.L., et al. The cannabinoid receptor agonist WIN 55,212-2 regulates glutamate transmission in rat cerebral cortex: An in vivo and in vitro study. Cerebral Cortex 11 728-733 (2001). 3 Price, T.J., Patwardhan, A., Akopian, A.N., et al. Cannabinoid receptor-independent actions of the aminoalkylindole WIN 55,212-2 on trigeminal sensory neurons. Br J Pharmacol 142 257-266 (2004). - via caymanchem.com 131543-23-2

    ND = No Data
    NR = Need Reference

    Additional experimental/research cannabinoid agonists
    Column 1 Column 2 Column 3 Column 4 Column 5 Column 6 Column 7 Column 8
    0 CB1 CB2 CB1 Ki CB2 Ki Notes Source CAS
    1 ACEA >2000x 1.4nM >2000nM ACEA is a analog of N-arachi-donylethanolamine (AEA) that binds to the CB1 receptor with very high affinity (KI value of 1.4 +/- 0.3 nM) and to the CB2 receptor with low affinity (KI values of 3.1 +/- 1.0 µM) showing a greater than 2000-fold selectivity for CB1. Hillard et al. (1999) Synthesis and Characterization of Potent and Selective Agonists of the Neuronal Cannabinoid Receptor (CB1) 220556-69-4
    2 ACPA 325x 2.2nM 715nM ACPA is a analog of N-arachi-donylethanolamine (AEA) that binds to the CB1 receptor with very high affinity (KI value of 2.2 +/- 0.4 nM) and to the CB2 receptor with low affinity (KI values of 0.7 +/- 0.01 µM) showing a greater than 300-fold selectivity for CB1. Hillard et al. (1999) Synthesis and Characterization of Potent and Selective Agonists of the Neuronal Cannabinoid Receptor (CB1) 229021-64-1
    3 AM630 165x 5152nM 31.2nM PENDING Ross et al (1999) Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656 and AM630. Br.J.Pharmacol. 126 665. 164178-33-0
    4 AM6527 95x 4.88nM 463nM AM6527, a pyrazole-3-carboxamide analog of AM251, was assessed for its affinity for CB1 and CB2 receptors using membrane preparations from rat brain or HEK293 cells expressing hCB2, respectively. AM6527 showed a relatively high affinity for CB1 receptors (4.88 nM), but a much lower affinity for CB2 receptors (463.0 nM). These results indicate that AM6527 shows approximately 100-fold selectivity for CB1 receptors relative to CB2 receptors. Sink et al. (2009) Oral bioavailability of the novel cannabinoid CB1 antagonist AM6527: effects on food-reinforced behavior and comparisons with AM4113. Pharmacol Biochem Behav. 2009 January
    5 BAY 38-7271 3x 1.85nM 5.96nM (-)-(R)-3-(2-Hydroxymethylindanyl-4-oxy)phenyl-4,4,4-tri-fluoro-1-sulfonate (BAY 38-7271) is a new high-affinity cannabinoid receptor subtype 1 (CB1 receptor) ligand (Ki ϭ 0.46 – 1.85 nM; rat brain, human cortex, or recombinant human CB1 receptor), structurally unrelated to any cannabinoid receptor ligand known so far. [1] BAY 38-7271 shows pronounced neuroprotective properties that do not result from drug-induced hypothermia and that occur in a dose range devoid of typical cannabinoid-like side effects. [2] Mauler et al. (2002) Characterization of the Diarylether Sulfonylester (-)-(R)-3-(2-Hydroxymethylindanyl-4-oxy)phenyl-4,4,4-trifluoro-1-sulfonate (BAY 38-7271) as a Potent Cannabinoid Receptor Agonist with Neuroprotective Properties [1] [2] p. 359 212188-60-8
    6 L759633 414x 4888nM 11.8nM L759633 has been shown to be a highly efficiant CB2 agonist [1] (Ki = 1043 +/- 296 and Ki = 6.4 +/- 2.2 nM at CB1 and CB2 respectively). [2] The CB2/CB1 affinity ratios of L759633 and L759656 were both higher in the previous investigation (793 and >1000 respectively) and reported here (163 and 414 respectively). [3] Ross et al (1999) Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656 and AM630. Br.J.Pharmacol. 126 665. [1] p. 671 [2] p. 668, Table 1 [3] p. 669 174627-50-0
    7 L759656 163x 1043nM 6.40nM L759656 has been shown to be a highly efficiant CB2 agonist [1] (Ki = 4888 +/- 950 and Ki = 11.8 +/- 2.5 nM at CB1 and CB2 respectively). [2] The CB2/CB1 affinity ratios of L759633 and L759656 were both higher in the previous investigation (793 and >1000 respectively) and reported here (163 and 414 respectively). [3] Ross et al (1999) Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656 and AM630. Br.J.Pharmacol. 126 665. [1] p. 671 [2] p. 668, Table 1 [3] p. 669 174627-56-6
    8 O-585 38x 8.60nM 324nM PENDING *Showalter, V.M. et al. (1996) Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): Identification of cannabinoid receptor subtype selective ligands. J. Pharmacol. Exp. Ther. 278, 989-999
    9 O-1812 1138x 3.40nM 3870nM PENDING *Di Marzo, V. et al. (2001) Highly selective CB1 cannabinoid receptor ligands and novel CB1/VR1 vanilloid receptor "hybrid" ligands. Biochem. Biophys. Res. Comm. 281, 444-451.
    10 SR144528 >1786x >10000nM 5.60nM SR144528 is a highly selective inverse agonist [1] that binds to the CB2 receptor with very high affinity (KI value of 5.6 +/- 1.1 nM). [2] Ross et al (1999) Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656 and AM630. Br.J.Pharmacol. 126 665. [1] p. 665 [2] p. 668 Table 1 192703-06-3

    *Taken from: Bela Szabo (2008) Pharmacology of Cannabinoid Receptors, BIOTREND Reviews No. 02, February 2008

    And all of the data I'd collected (originally in this thread). May contain some duplication, this is a rather large spread-sheet parsed by a small/simple app I'd written to simplify dumping/formatting the data and posting it:
    Column 1 Column 2 Column 3 Column 4 Column 5 Column 6
    0 CB1 Ki (nM) CB2 Ki (nM) CB1 A CB2 A Source
    1
    2 JWH-004 48 4.02 11.94 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    3
    4 JWH-007 9.5 2.94 3.23 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    5
    6 JWH-009 311 141 2.21 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    7
    8 JWH-009 10000 141 70.92 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    9
    10 JWH-015 336 13.8 24.35 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    11
    12 JWH-015 164 13.8 11.88 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    13
    14 JWH-016 22 4.29 5.13 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    15
    16 JWH-018 9.00 2.94 3.06 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    17
    18 JWH-019 9.80 5.55 1.77 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    19
    20 JWH-020 128.00 205.00 1.60 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    21
    22 JWH-042 10000 5050 1.98 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    23
    24 JWH-043 1180 964 1.22 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    25
    26 JWH-046 343 16.3 21.04 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    27
    28 JWH-047 58.7 3.47 16.92 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    29
    30 JWH-047 59 0.9 65.56 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    31
    32 JWH-048 10.70 0.49 21.84 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    33
    34 JWH-049 55.10 32.30 1.71 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    35
    36 JWH-049 55.00 6.00 9.17 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    37
    38 JWH-050 342.00 526.00 1.54 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    39
    40 JWH-050 342.00 424.00 1.24 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    41
    42 JWH-070 10000.00 10000.00 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    43
    44 JWH-071 1340.00 2940.00 2.19 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    45
    46 JWH-072 1050.00 170.00 6.18 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    47
    48 JWH-073 8.90 38.00 4.27 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    49
    50 JWH-073 8.90 27.00 3.03 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    51
    52 JWH-076 214.00 106.00 2.02 Huffman, J. W., Zengin, G., Wu, M., Lu, J., Hynd, G., Bushell, K., et al. (2005). Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists. Bioorganic & medicinal chemistry, 13(1), 89-112. doi: 10.1016/j.bmc.2004.09.050.
    53
    54 JWH-077 10000.00 10000.00 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    55
    56 JWH-078 817.00 633.00 1.29 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    57
    58 JWH-079 63.00 32.00 1.97 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    59
    60 JWH-080 5.60 2.21 2.53 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    61
    62 JWH-080 7.60 ND Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    63
    64 JWH-081 1.20 12.40 10.33 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    65
    66 JWH-082 5.30 6.40 1.21 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    67
    68 JWH-083 106.00 102.00 1.04 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    69
    70 JWH-093 40.70 59.10 1.45 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    71
    72 JWH-094 476.00 97.30 4.89 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    73
    74 JWH-095 140.00 312.00 2.23 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    75
    76 JWH-096 33.70 13.30 2.53 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    77
    78 JWH-097 455.00 121.00 3.76 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    79
    80 JWH-098 4.50 ND Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    81
    82 JWH-099 35.30 17.80 1.98 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    83
    84 JWH-100 381.00 155.00 2.46 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.
    85
    86 JWH-120 1054.00 6.10 172.79 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    87
    88 JWH-122 0.69 1.20 1.74 Huffman, J. W., Zengin, G., Wu, M., Lu, J., Hynd, G., Bushell, K., et al. (2005). Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists. Bioorganic & medicinal chemistry, 13(1), 89-112. doi: 10.1016/j.bmc.2004.09.050.
    89
    90 JWH-133 677.00 3.00 225.67 Bela Szabo (2008) Pharmacology of Cannabinoid Receptors, BIOTREND Reviews No. 02, February 2008
    91
    92 JWH-139 2290.00 14.00 163.57 Bela Szabo (2008) Pharmacology of Cannabinoid Receptors, BIOTREND Reviews No. 02, February 2008
    93
    94 JWH-145 14.00 6.40 2.19 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    95
    96 JWH-146 21.00 62.00 2.95 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    97
    98 JWH-147 11.00 7.10 1.55 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    99
    100 JWH-148 123.00 14.00 8.79 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    101
    102 JWH-149 5.00 0.73 6.85 Huffman, J. W., Zengin, G., Wu, M., Lu, J., Hynd, G., Bushell, K., et al. (2005). Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists. Bioorganic & medicinal chemistry, 13(1), 89-112. doi: 10.1016/j.bmc.2004.09.050.
    103
    104 JWH-150 60.00 15.00 4.00 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    105
    106 JWH-151 10000.00 30.00 333.33 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    107
    108 JWH-153 250.00 11.00 22.73 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    109
    110 JWH-156 404.00 104.00 3.88 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    111
    112 JWH-159 45.00 10.40 4.33 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    113
    114 JWH-160 1568.00 441.00 3.56 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    115
    116 JWH-163 2358.00 138.00 17.09 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    117
    118 JWH-164 6.60 6.90 1.05 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    119
    120 JWH-165 204.00 71.00 2.87 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    121
    122 JWH-166 44.00 1.90 23.16 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    123
    124 JWH-167 90.00 159.00 1.77 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    125
    126 JWH-167 64.00 190.00 2.97 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    127
    128 JWH-180 26.00 9.60 2.71 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    129
    130 JWH-181 1.30 0.62 2.10 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    131
    132 JWH-182 0.65 1.10 1.69 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    133
    134 JWH-189 52.00 12.00 4.33 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    135
    136 JWH-201 1064.00 444.00 2.40 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    137
    138 JWH-202 1678.00 645.00 2.60 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    139
    140 JWH-203 8.00 7.00 1.14 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    141
    142 JWH-204 13.00 25.00 1.92 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    143
    144 JWH-205 124.00 180.00 1.45 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    145
    146 JWH-206 389.00 498.00 1.28 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    147
    148 JWH-207 1598.00 3723.00 2.33 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    149
    150 JWH-208 179.00 570.00 3.18 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    151
    152 JWH-209 746.00 1353.00 1.81 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    153
    154 JWH-210 0.46 0.69 1.50 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    155
    156 JWH-211 70.00 12.00 5.83 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    157
    158 JWH-212 33.00 10.00 3.30 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    159
    160 JWH-213 1.50 0.42 3.57 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    161
    162 JWH-231 10000.00 10000.00 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    163
    164 JWH-232 10000.00 10000.00 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    165
    166 JWH-234 8.40 3.80 2.21 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    167
    168 JWH-235 338.00 123.00 2.75 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    169
    170 JWH-236 1351.00 240.00 5.63 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    171
    172 JWH-237 38.00 106.00 2.79 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    173
    174 JWH-239 342.00 52.00 6.58 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    175
    176 JWH-240 14.00 7.20 1.94 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    177
    178 JWH-241 147.00 49.00 3.00 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    179
    180 JWH-242 42.00 6.50 6.46 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    181
    182 JWH-243 285.00 104.00 2.74 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    183
    184 JWH-244 130.00 15.00 8.67 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    185
    186 JWH-245 276.00 6.40 43.13 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    187
    188 JWH-246 70.00 18.00 3.89 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    189
    190 JWH-248 1028.00 657.00 1.56 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    191
    192 JWH-249 8.40 20.00 2.38 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    193
    194 JWH-250 11.00 33.00 3.00 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    195
    196 JWH-251 29.00 146.00 5.03 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    197
    198 JWH-252 23.00 19.00 1.21 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    199
    200 JWH-253 62.00 84.00 1.35 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    201
    202 JWH-258 4.60 10.50 2.28 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    203
    204 JWH-259 220.00 74.00 2.97 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    205
    206 JWH-260 29.00 25.00 1.16 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    207
    208 JWH-261 767.00 221.00 3.47 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    209
    210 JWH-262 28.00 5.60 5.00 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    211
    212 JWH-265 3788.00 80.00 47.35 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    213
    214 JWH-266 10000.00 455.00 21.98 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    215
    216 JWH-267 381.00 7.20 52.92 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    217
    218 JWH-268 1379.00 40.00 34.48 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    219
    220 JWH-292 29.00 3.30 8.79 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    221
    222 JWH-293 100.00 25.00 4.00 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    223
    224 JWH-294 10000.00 3972.00 2.52 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    225
    226 JWH-295 10000.00 3759.00 2.66 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    227
    228 JWH-296 10000.00 2060.00 4.85 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    229
    230 JWH-297 8626.00 1506.00 5.73 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    231
    232 JWH-302 17.00 89.00 5.24 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    233
    234 JWH-303 117.00 138.00 1.18 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    235
    236 JWH-304 3363.00 2679.00 1.26 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    237
    238 JWH-305 15.00 29.00 1.93 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    239
    240 JWH-306 25.00 82.00 3.28 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    241
    242 JWH-307 7.70 7.10 1.08 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    243
    244 JWH-308 41.00 62.00 1.51 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    245
    246 JWH-311 23.00 39.00 1.70 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    247
    248 JWH-312 72.00 91.00 1.26 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    249
    250 JWH-313 422.00 365.00 1.16 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    251
    252 JWH-314 39.00 76.00 1.95 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    253
    254 JWH-315 430.00 182.00 2.36 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    255
    256 JWH-316 2862.00 781.00 3.66 Huffman, J. W.; Szklennik, P. V.; Almond, A.; Bushell, K.; Selley, D. E.; He, H.; Cassidy, M. P.; Wiley, J. L.; Martin, B. R. 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg. Med. Chem. Lett. 2005, 15, 4110-4113.
    257
    258 JWH-323 10000.00 639.00 15.65 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    259
    260 JWH-324 2954.00 231.00 12.79 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    261
    262 JWH-325 579.00 700.00 1.21 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    263
    264 JWH-337 547.00 238.00 2.30 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    265
    266 JWH-337 203.00 118.00 1.72 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    267
    268 JWH-342 645.00 178.00 3.62 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    269
    270 JWH-343 10000.00 1362.00 7.34 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    271
    272 JWH-344 308.00 221.00 1.39 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    273
    274 JWH-345 266.00 173.00 1.54 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    275
    276 JWH-346 67.00 49.00 1.37 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    277
    278 JWH-348 218.00 41.00 5.32 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    279
    280 JWH-363 245.00 20.00 12.25 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    281
    282 JWH-364 34.00 23.00 1.48 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    283
    284 JWH-365 17.00 39.00 2.29 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    285
    286 JWH-367 53.00 33.00 1.61 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    287
    288 JWH-368 16.00 71.00 4.44 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    289
    290 JWH-369 7.90 29.00 3.67 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    291
    292 JWH-370 5.60 3.40 1.65 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    293
    294 JWH-371 42.00 24.00 1.75 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    295
    296 JWH-373 60.00 9.10 6.59 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    297
    298 JWH-384 10000.00 10000.00 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    299
    300 JWH-385 566.00 421.00 1.34 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    301
    302 JWH-386 161.00 27.00 5.96 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    303
    304 JWH-387 1.20 1.10 1.09 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    305
    306 JWH-392 77.00 24.00 3.21 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    307
    308 JWH-392 3795.00 1782.00 2.13 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    309
    310 JWH-394 2.80 14.00 5.00 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    311
    312 JWH-395 372.00 30.00 12.40 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    313
    314 JWH-397 8.90 2.30 3.87 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    315
    316 JWH-398 2.30 2.80 1.22 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    317
    318 JWH-399 187.00 22.00 8.50 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    319
    320 JWH-400 93.00 44.00 2.11 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    321
    322 JWH-401 1707.00 1120.00 1.52 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    323
    324 JWH-402 749.00 1077.00 1.44 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    325
    326 JWH-403 2113.00 460.00 4.59 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    327
    328 JWH-404 786.00 672.00 1.17 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    329
    330 JWH-405 193.00 154.00 1.25 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    331
    332 JWH-406 1028.00 215.00 4.78 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    333
    334 JWH-407 1731.00 546.00 3.17 Huffman et al (2008) Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940. Bioorg.Med.Chem. 16 322.
    335
    336 JWH-412 7.20 3.20 2.25 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    337
    338 JWH-413 14.00 2.20 6.36 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    339
    340 JWH-414 240.00 33.00 7.27 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    341
    342 JWH-415 530.00 38.00 13.95 Huffman, J. W. (2009), ‘Cannabimimetic indoles, pyrroles, and indenes: structure–activity relationships and receptor interactions’, in Reggio, P. H. (ed.), The cannabinoid receptors, Humana Press, Totowa, NJ.
    343
    344 BAY 38-7271 1.85 5.96 3.22 Mauler et al. (2002) Characterization of the Diarylether Sulfonylester (-)-(R)-3-(2-Hydroxymethylindanyl-4-oxy)phenyl-4,4,4-trifluoro-1-sulfonate (BAY 38-7271) as a Potent Cannabinoid Receptor Agonist with Neuroprotective Properties
    345
    346 CP 55,940 1.10 0.52 2.12 Mauler et al. (2002) Characterization of the Diarylether Sulfonylester (-)-(R)-3-(2-Hydroxymethylindanyl-4-oxy)phenyl-4,4,4-trifluoro-1-sulfonate (BAY 38-7271) as a Potent Cannabinoid Receptor Agonist with Neuroprotective Properties
    347
    348 HU-210 0.41 0.14 2.93 Mauler et al. (2002) Characterization of the Diarylether Sulfonylester (-)-(R)-3-(2-Hydroxymethylindanyl-4-oxy)phenyl-4,4,4-trifluoro-1-sulfonate (BAY 38-7271) as a Potent Cannabinoid Receptor Agonist with Neuroprotective Properties
    349
    350 WIN 55.212-2 11.70 0.41 28.54 Mauler et al. (2002) Characterization of the Diarylether Sulfonylester (-)-(R)-3-(2-Hydroxymethylindanyl-4-oxy)phenyl-4,4,4-trifluoro-1-sulfonate (BAY 38-7271) as a Potent Cannabinoid Receptor Agonist with Neuroprotective Properties
    351
    352 Delta9-THC 15.30 25.06 1.64 Mauler et al. (2002) Characterization of the Diarylether Sulfonylester (-)-(R)-3-(2-Hydroxymethylindanyl-4-oxy)phenyl-4,4,4-trifluoro-1-sulfonate (BAY 38-7271) as a Potent Cannabinoid Receptor Agonist with Neuroprotective Properties
    353
    354 AM6527 4.88 463.00 94.88 Sink et al. (2009) Oral bioavailability of the novel cannabinoid CB1 antagonist AM6527: effects on food-reinforced behavior and comparisons with AM4113. Pharmacol Biochem Behav. 2009 January
    355
    356 ACPA 2.20 715.00 325.00 Hillard et al. (1999) Synthesis and Characterization of Potent and Selective Agonists of the Neuronal Cannabinoid Receptor (CB1)
    357
    358 ACEA 1.40 2000.00 1428.57 Hillard et al. (1999) Synthesis and Characterization of Potent and Selective Agonists of the Neuronal Cannabinoid Receptor (CB1)
    359
    360 O-585 8.60 324.00 37.67 Bela Szabo (2008) Pharmacology of Cannabinoid Receptors, BIOTREND Reviews No. 02, February 2008
    361
    362 O-1812 3.40 3870.00 1138.24 Bela Szabo (2008) Pharmacology of Cannabinoid Receptors, BIOTREND Reviews No. 02, February 2008
    363
    364 L759656 4888.00 11.80 414.24 R.A Ross et al. (1999) Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656 and AM630
    365
    366 L759633 1043.00 6.40 162.97 R.A Ross et al. (1999) Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656 and AM630
    367
    368 AM630 5152.00 31.20 165.13 R.A Ross et al. (1999) Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656 and AM630
    369
    370 SR144528 10000.00 5.60 1785.71 R.A Ross et al. (1999) Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656 and AM630
    371
    372 HU-308 10000.00 23.00 434.78 Bela Szabo (2008) Pharmacology of Cannabinoid Receptors, BIOTREND Reviews No. 02, February 2008
    373
    374 WIN 55.212-2 1.89 0.28 6.75 Aung, M.M., G. Griffin, J.W. Huffman, M.J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin, Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence, 2000. 60(2): p. 133-140.


    Having thrown this together in the Which cannabinoids produce the most physical stone? thread I thought maybe we could break this out and create a proper thread about CB1/CB2 binding affinity.

    Obviously there's some data missing and if anyone could find/point out where I might find additional (or corrected!) ki values I think this could become a fairly interesting thread...

    Looking over the chart SWIM thinks he might have a preference for cannabinoids that are more selective CB1 agonists and would like to hear more (and find more affinity data) from other swimmers out there!

    Naturally, let me know if you catch any errors or can provide any corrections or additional information!

    Change Log:
    20100524 2:30 AM
    *Added/merged 188 more entries I'd collected and put into the this thread.
    20100225 9:50 AM
    *Passing co-ownership of post to moderator Shampoo, who's very helpful/knowledgeable on the subject and can edit or whatever. Thanks for your help!
    20100214 4:15 PM
    *Updated SR144528 Notes/Description
    20100214 3:50 PM
    *Updated L759633 Notes/Description
    *Updated L759656 Notes/Description
    20100214 2:50 PM
    *Updated BAY 38-7271 Notes/Description
    20100214 2:20 PM
    *Added additional table with data on several experimental CB1/2 agonists: ACEA, ACPA, AM630, AM6527, BAY 38-7271, L759633, L759656, O-585, O-1812 and SR144528
    20100212 7:37 PM
    *Updated CP 55,244 data and sources
    20100212 10:50 AM
    *Updated JWH-200 Source
    20100212 1:30 AM
    *Updated JWH-081 CB2 data
    2010/02/10 23:00 PM
    *Updated JWH-081 Notes/Source
    *Added small key at bottom of table explaining NR and ND entries
    2010/02/10 13:30 PM
    *Updated JWH-073,250 Notes/Source
    *Added entry for WIN 55212-2
    *Added column for CAS
    *Corrected JWH-250 binding affinty (was in CB2 column, should be CB1)
     
    Last edited: May 26, 2010
  2. Shampoo

    Shampoo entity of sorts Staff Member

    Reputation Points:
    7,531
    Joined:
    Nov 10, 2007
    Messages:
    2,977
    Male from france
    Binding affinity

    Ki = EC50/(1+[L/Kd])

    Ki: Binding affinity/Equilibrium dissociation constant
    EC50: Concentration of an agonist at which the effect of the agonist is exactly halfway between baseline and the maximal effect
    L: Ligand concentration
    Kd: Dissociation constant

    The number which you see as the final figure (i.e. the reported Ki) is in M (molar) (usually nM-- nanomolar), which specifies a concentration.

    If the affinity is high, the EC50 will be low.

    In simple terms, a lower Ki == a greater affinity. Molecules with higher affinities for target proteins usually require lower doses(/concentrations).


    For reference...

    Dissociation constant

    Kd = [P][L]/[C]

    [P]: Protein concentration
    [L]: Ligand concentration
    [C]: Complex concentration

    The protein in this case is the CB1r or CB2r, the ligand is the Cannabinoid, and the complex is the Cannabinoid bound to a CBr.

    --------------------------------------------------------------------------------------

    CB1

    -- Primarily expressed in the central nervous system

    * Most widely expressed GPCR in the brain

    * Found in cortical regions (pyriform cortex, neocortex, amygdala, hippocampus, cerebellar cortex), as well as sensory (olfactory bulb, occipital lobe), and other important regions of the brain (thalamus/hypothalamus, basal ganglia, PAG).

    -- Primarily involved in DSI (Depolarization-Induced Suppression of Inhibition), a GABA-mediating form of short-term neuroplasticity

    -- Peripheral effects on blood-vessel inervation and oxygenated blood-distribution

    -- Expressed on sensory neurons involved in late-pain transmission, likely playing a role in endogenous regulation of systemic pain

    -- The CB1r may also be modulated allosterically, thus allowing for greater overall variability of ligand control

    In simple terms, the CB1r is the Cannabinoid receptor which is more widely expressed in the central nervous system (e.g. brain). Its modulation likely accounts for the psychoactive effects of Cannabinoids (altered time perception, anxiety/anxiolysis, depersonalization, heightened creativity, enhanced well-being, visual/auditory distortions/hallucinations...etc.). It may also play a role in some of the analgesic properties of Cannabinoids. In general, compounds with higher CB1/2 ratios are more prone (as compared to a compound with a higher CB2/1 ratio) to anxiety/panic-attacks, hallucinations, and other psychoactive extremes.


    CB2

    -- Primarily expressed in the peripheral nervous system

    -- Expression in the brain is limited to microglia

    * The role of CB1r on microglia is largely unknown

    -- Primarily involved in the mediation of pain-transduction

    -- Very low behavioral profile

    -- May act to prevent or slow the development of certain forms of neurodegeneration

    -- Recent evidence suggests the expression of the CB2r in dendritic processes and glial cells, in both cortical regions and the hippocampus, where it is postulated to play a role in mood and behavioral regulation (possibly in addictive/appetitive behaviors)
     
    Last edited: Feb 11, 2010
  3. msimm

    msimm Newbie

    Reputation Points:
    703
    Joined:
    Dec 5, 2004
    Messages:
    360
    45 y/o Male from U.S.A.
    The simple explanation is in there too:

    "In simple terms, a lower Ki == a greater affinity."

    The greater the affinity the more potent the chemical (kind of):

    "Molecules with higher affinities for target proteins usually require lower doses(/concentrations)."

    So the lower the Ki value generally means a smaller dose will be required. It doesn't translate 100% because there's a lot more involved then just the receptor and the chemical but it's still a useful indicator.

    The affinity ratio is just a way to show how a chemical might be more active at one receptor/protein sub-type then the other. Of course it's also more complicated then that, but it's a rough indicator.
     
    Last edited: Feb 10, 2010
  4. msimm

    msimm Newbie

    Reputation Points:
    703
    Joined:
    Dec 5, 2004
    Messages:
    360
    45 y/o Male from U.S.A.
    Just added a second table "Additional experimental cannabinoid agonists" to original post with several interesting, mainly highly selective experimental CB1/2 agonists.

    Unlike the cannabinoids in the first table these appear to be strictly used for research purposes.

    msimm added 339 Minutes and 22 Seconds later...

    As an aside, here's an interesting tidbit from Alkylamides from Echinacea, a New Class of Cannabinomimetics: Cannabinoid Type 2 Receptor-Dependent and -Independant Immunomodulatory Effects (S. Raduner et al. 2006):

    "...alkylamides dodeca-2E,4E,8Z,10Z-tetraenoic acid isobutylamide (A1) and dodeca-2E,4E-dienoic acid isobutylamide (A2) bind to the CB2 receptor more strongly than the endogenous cannabinoids. The Ki values of A1 (CB2 ~57 nM; CB1 >6000 nM) and A2 (CB2 ~60 nM; CB1 >1500 nM) were determined by displacement of the synthetic high affinity cannabinoid ligand [3H]CP-55,940. Molecular modeling suggests that alkylamides bind in the solvent-accessible cavity in CB2, directed by H-bonding and π-π interactions. In a screen with 49 other pharmacologically relevant receptors, it could be shown that A1 and A2 specifically bind to CB2 and CB1."

    Column 1 Column 2 Column 3 Column 4 Column 5 Column 6 Column 7 Column 8
    0 CB1 CB2 CB1 Ki CB2 Ki Notes Source CAS
    1 A1 109x 6210+/-800 57+/-14nM S. Raduner et al. (2006) Alkylamides from Echinacea Are a New Class of Cannabinomimetics: Cannabinoid Type 2 Receptor-Dependent and -Independant Immunomodulatory Effects. J. Biol. Chem., May 19, 2006; 281(20): 14192 - 14206.
    2 A2 32x 1940+/-370nM 60+/-13nM S. Raduner et al. (2006) Alkylamides from Echinacea Are a New Class of Cannabinomimetics: Cannabinoid Type 2 Receptor-Dependent and -Independant Immunomodulatory Effects. J. Biol. Chem., May 19, 2006; 281(20): 14192 - 14206.
     
    Last edited: Feb 16, 2010
  5. methylenedioxy

    methylenedioxy Newbie

    Reputation Points:
    1
    Joined:
    Mar 14, 2010
    Messages:
    7
    24 y/o Male
    On those chemicals that lack a number for one receptor or the other (JWH-133, -200, CP 47,497, etc.) can it be safely assumed that the missing number is too large to matter, or is it possible that they do have a fair affinity, but there's just no reliable sources for the chart?
     
  6. msimm

    msimm Newbie

    Reputation Points:
    703
    Joined:
    Dec 5, 2004
    Messages:
    360
    45 y/o Male from U.S.A.
    Sorry, I missed this post. If a chemical is missing binding data it means I couldn't find it or... I made a mistake.

    Some research papers aren't easily obtainable (the original CP data produced by Pfizer example) and some research specifically focuses on a single binding site.
     
  7. bufalantan

    bufalantan Newbie

    Reputation Points:
    22
    Joined:
    May 12, 2010
    Messages:
    94
    Male from isle_of_man
    From the chart observation, the CB1:CB2 ratio of Ki value for binding, represented in the x on the charts column under CB1/CB2 (multiple of Ki value in one receptor compared to the other) and from observation of reported experiences (in the JWH series at least), those with x in the CB1 column are the sedating type (stony) and those with x in the CB2 are the psychedelic type (tripy).

    But again it is all relevant to the potency of the compound, for example JWH 018 has almost the same Ki value as JWH 073 for the CB1 receptor, but the psychedelic effects are very different, I would presume it has nothing to do with the ratio to CB2, but the actual potency of the compound.


    Am i correct in my observation?

    Have to crack the duration effect from the chart now.
     
  8. Shampoo

    Shampoo entity of sorts Staff Member

    Reputation Points:
    7,531
    Joined:
    Nov 10, 2007
    Messages:
    2,977
    Male from france
    In general, CB2 agonists have a more peripheral (body-oriented) effect while CB1 agonists have a more central (mental) effect as a result of differential receptor expression, though so many other factors are at play here (e.g. lipophilicity/solubility gradients).
    Keep in mind that CB receptors are not autonomous lone-proteins, but rather part of an intricate system (the endocannabinoid system) which has effects on (and is effected by) such neurotransmitter systems as GABA, GLU, DA, 5-HT, and NE-- CB receptors may also regulate eachother's activity.

    Thus, the ratio is more than just: x effect at CB1 and y effect at CB2, therefore * affinity for CB1 + ** affinity for CB2 == *x+**Y. Rather, it is a much more interdependent system effect.

    It should be noted that many factors aside from the kinetic midpoint of a molecule/protein interaction play a significant role in a given compound's activity. In other words, to look for correlations such as duration with Ki may be to commit a type I error (drawing a conclusion where there is none). Duration has much more to do with half-life, metabolic routes and adipose tissue & albumin binding.
     
  9. bufalantan

    bufalantan Newbie

    Reputation Points:
    22
    Joined:
    May 12, 2010
    Messages:
    94
    Male from isle_of_man
    O-2545
    Ki values of 1.5nM at CB1 and 0.32nM at CB2
    water soluble!!!

    Need your thoughts on this, specially Shampoo, msimm, Gradient and mean ALFA.
     
  10. msimm

    msimm Newbie

    Reputation Points:
    703
    Joined:
    Dec 5, 2004
    Messages:
    360
    45 y/o Male from U.S.A.
    Citation needed (so I can get a hold of the paper).
     
  11. Shampoo

    Shampoo entity of sorts Staff Member

    Reputation Points:
    7,531
    Joined:
    Nov 10, 2007
    Messages:
    2,977
    Male from france
    re: O-2545
    Martin et al., 2006 -- PMID: 16757541

    As with some of the other dibenzopyrans from this research facility (the O in O-2545 and many other O-XXX/XXXX compounds is a trademark of a specific chemical research firm, a la JWH), it may have limited efficacy (if it is active at all) when administered orally or via pyrolysis/vaporization.

    It's water solubility allows for intranasal administration (insufflation), though it's Ki suggests that it will be highly active at low, low quantities so insufflation may be active in the ng (yes, nanogram) or low µg range.

    Based on its enzymatic affinity and solubility, it will likely be metabolized and excreted rapidly and due to the lack of albumin affinity, some subjective 'crash' may be elicited following acute administration.

    A water-soluble CB with a Ki in this range should be approached with caution.
     
  12. bufalantan

    bufalantan Newbie

    Reputation Points:
    22
    Joined:
    May 12, 2010
    Messages:
    94
    Male from isle_of_man
    How would you explain the minimal or lack of psychedelic effects for JWH 081, 200 and 250 while they are exclusive or have 10 x more affinity to CB1.

    On the other hand, 018 has 3 x the affinity to CB2 and yet is described as more trippy?



    My guess GPR55, a GPCR and 5-HT (specially 1A) are more at play, efficacy is an issue at CB1/2, but the reports of high heart rates might discounts 5-HT1A theory. Am sure in the future, some research will "flip" on some described agonists to antagonists.
     
    Last edited: Aug 22, 2010
  13. fatal

    fatal Newbie

    Reputation Points:
    400
    Joined:
    Feb 19, 2006
    Messages:
    1,029
    Male from U.S.A.
    If you think JWH250 is not psychedelic the JWH250 you are talking about sucks big time or the subject is not smoking enough. It gives fabulous tracers etc. I hear... I also hear JWH200 can be trippy but you have to really smoke alot of it before getting very high at all.


    It would be really cool if this list had chemical names so you could get an idea of what compound it is actually talking about. Otherwise it's all kind of arbitrary numbers. This thread does rock though. Just saying...


    :joint:
     
  14. Shampoo

    Shampoo entity of sorts Staff Member

    Reputation Points:
    7,531
    Joined:
    Nov 10, 2007
    Messages:
    2,977
    Male from france
    GPR55 is only a putative eCBr, there is a great deal of evidence to suggest that it's atypical CB response is the result of it not actually falling under the eCB heading, and that CBs act as allosteric ligands. Many CBs have been shown to have no effect at the receptor, or to exert inverse effect profiles as they do at CB1/2.

    Note that even if these compounds do act as GPR55 ligands, this orphan receptor appears to be primarily expressed outside of the CNS (though to be fair, the vast majority of the work on GPR55 is in silico), so its effects likely do not contribute to any psychedelia.

    Furthermore, a recent study actually investigated JWH-015 at GPR55 and found no affinity.


    As for a 5-HT1A Ki, this is highly doubtful-- the AA-sequence of the binding region should not interact with these napthoylindoles. What inspired that postulation? Is there some evidence to suggest 5-HT1A activation?
     
    Last edited: Nov 22, 2010
  15. fatal

    fatal Newbie

    Reputation Points:
    400
    Joined:
    Feb 19, 2006
    Messages:
    1,029
    Male from U.S.A.
    In fairness to the idea at first glance they do look like some kind of weird DMT analogue. I had wondered about this also. It seems kind of unlikely but the structures are very similar. It would be interesting to see if these compounds had any binding affinity at 5HTXX receptor sites. It would go a long way towards explaining why people trip out on these chemicals. Either way it would make for interesting research eh?


    :joint:
     
  16. fatal

    fatal Newbie

    Reputation Points:
    400
    Joined:
    Feb 19, 2006
    Messages:
    1,029
    Male from U.S.A.
    Column 1 Column 2 Column 3 Column 4 Column 5
    0 Compound CB1 Ki(nm) CB2 Ki(nm)
    1 AM664* 40 80.0
    2 AM665* 206 20.3
    3 AM669 47.2 38.6
    4 AM671* 155 59.1
    5 AM672 1603 1511
    6 AM679 13.5 49.5
    7 AM682 332 693
    8 AM683 272 281
    9 AM684* 181 44.8
    10 AM689 2279 1019
    11 AM690 4850 1972
    12 AM692 2656 1519
    13 AM693 835 526
    14 AM694 0.08 1.44
    15 AM697 1306 1116
    16 AM698 135.8 314.7
    17 AM1201 106 110
    18 AM1202 98.9 22.9
    19 AM1203 63.6 88.9
    20 AM1204 5659 3353
    21 AM1205 116.9 195.7
    22 AM1206 105.1 150.5
    23 AM1215* 40.7 21.9
    24 AM1216* 210 25.2
    25 AM1217* 255 81.5
    26 AM1218* 11.2 3.98
    27 AM1219* 96.6 31.3
    28 AM1220* 3.88 73.4
    29 AM1221* 52.3 0.28
    30 AM1224* 20.2 0.73
    31 AM1225* 439.6 38.5
    32 Am1230 1.1 2.4
    33 AM1231* 31.2 34.2
    34 AM1233 141.7 153.9
    35 AM1234 77.6 196.8
    36 AM1235 1.5 20.4
    37 AM1236 1127 558.8
    38 AM1237 836.8 244.4
    39 AM1238 3.1 17.3
    40 AM1248* 100 332
    41 AM1253* 60.3 126
    42 AM1256 4.74 18.6
    43 AM1282 133.4 100.8
    44 AM1283 117.2 196.5
    45 AM1284 126.8 102.8
    46 AM1286 1509 1289
    47 AM1288 1.3 10.5
    48 AM1289 359.6 78.64
    49 AM1291 2958 1804
    50 AM1292 3.1 18.1
    51 AM1294 283.3 237.3
    52 AM1295 2.5 30.7
    53 AM1296* 7.57 3.88
    54 AM1299* 12.4 13.5
    55 AM2201 1.0 2.6
    56 AM2202 33.1 110.6
    57 AM2203 7.8 45.8
    58 AM2204 7.5 24.4
    59 AM2209* 48.8 41.8
    60 AM2210 1.8 11.3
    61 AM2212* 31.0 2.90
    62 AM2213 3.0 30
    63 AM2215* 235 99.6
    64 AM2216 42.4 213
    65 AM2223* 64.8 29.9
    66 AM2225 5.97 3.8
    67 AM2227 1024 2968
    68 AM2229 116.5 46.2
    69 AM2230 195 29.5
    70 AM2231 4.90 23.9
    71 AM2232 0.28 1.48



    Source: patent filed by Alexandros Makriyannis and Hongfeng Deng
    Cannabimimetic Indole Derivatives (2008)

    here

    *-Racemic
     
    Last edited: Aug 12, 2011
  17. Phenoxide

    Phenoxide Super Moderator Staff Member

    Reputation Points:
    8,533
    Joined:
    Oct 11, 2009
    Messages:
    5,738
    Male from United States
    Are these computational or experimental values?
     
  18. fatal

    fatal Newbie

    Reputation Points:
    400
    Joined:
    Feb 19, 2006
    Messages:
    1,029
    Male from U.S.A.
    This is why I provided the link. Here you go


    :joint:
     
  19. machineelf368

    machineelf368 Silver Member

    Reputation Points:
    10
    Joined:
    Feb 14, 2012
    Messages:
    23
    37 y/o Male from U.S.A.
    Thanks for all the hard work putting this stuff together! Much appreciated!
     
  20. liamfairley

    liamfairley Newbie

    Reputation Points:
    -5
    Joined:
    Apr 20, 2012
    Messages:
    20
    26 y/o Male from U.K.
    So could someone please put this into terms that i can understand. Does binding mean it has changed my CB1 receptors forever because ever since I smoked a blend called 'doob' I have been havin anxiety and very very bad panic attacks. I am now on diazepam to stop them. Will i ever get better?