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Drug info - AM-2201 (1-(5-fluoropentyl)-3-(1-naphthoyl)indole) Drug Info

Discussion in 'Cannabinoids' started by Phenoxide, Oct 5, 2010.

  1. Phenoxide

    Phenoxide Super Moderator Staff Member

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    Please note: This thread is for discussion of the pure compound only. Discussion of blend products that are reported or speculated to contain this compound belongs in separate dedicated thread(s)

    Please post info about AM-2201 here.



    Can anyone add information about:
    • names / synonyms
    • molecule
    • dose
    • duration
    • side effects
    • have there been any reported incidents with this compound?
    • since when has this research chemical been available?
    • legal status
    • stability of the molecule / compound
    A thread for experiences with AM-2201 will be created when necessary.

    _____________________________________

    Short Name: AM-2201
    Full Chemical Name: 1-(5-fluoropentyl)-3-(1-naphthoyl)indole
    Molecular Mass: 359.44 g/mol

    [​IMG]

    This compound is one of a number of novel putative cannabinoids covered in a US patent application filed by Alexandros Makriyannis (hence the AM- prefix) in 2004, and approved in 2007. Structurally it bears a close resemblence to the more frequently reported cannabinoid JWH-018. The only difference is that the pentyl chain emerging from the tertiary amine in JWH-018 is substituted with a fluoropentyl chain in AM-2201. The 1-(5-fluoropentyl)indole moiety is one characteristic feature of the AM-x series of compounds and is also present in the the first AM-x compound to be reported as commercially available, AM-694.

    Distribution of this compound and others in the AM-x series may be of questionable legality under patent law depending on location.
     
    Last edited: Oct 5, 2010
  2. freebird218

    freebird218

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    Me Panda got 'is hands on a Half G of this today. Not a very happy fellow, since he only recently had to quit vaporizing pure jwh-018 because of legal status in his area, and he was hoping AM-2201 would be his salvation. Unfortunately, it will not be, at least as a smoked, pure RC. Initial reaction was horror, as his throat constricted similar to military CS gas. Taste was very reminiscent of the wind blowing back some RAID wasp and hornet killer into his mouth, and he immediately retched. Burning sensation lasted about 5 minutes, drinking water or 7up did nothing to make it go away. Substance turned from white powder into yellowish puddle, then swiftly to an orange glow like a Popsicle or a BIC lighter. Didn't even finish what he'd laid out, it was so bad, he said. Mild buzz, definitely cannabinoid-ish, but subtly different that the -018. :thumbsdown:
     
  3. reformer

    reformer Newbie

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    Oh No... sounds horrible. Thanks so much for the information. Do you ever use DMSO/transdermal application? I just wonder what the effects would be like if you were actually able to get a good dose inside ya?
     
  4. Recklesslg

    Recklesslg Newbie

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    My friend had good experiences with this cannabanoid.. He mixed a gram with 2 oz of damiana, and is good after two or three tokes.. :thumbsup:
     
  5. divinemomentsoftruth

    divinemomentsoftruth Silver Member

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    Recklesslg, mind elaborating on what the experience was like? Like duration, side effects or similarity to JWH-018/others and marijuana. Also possibly explaining the method used to put the AM-2201 on Damiana? Dimitri finds the info in swiys post shocking after the utterly negative response given by swifreebird218.
     
    Last edited: Oct 6, 2010
  6. StonySmurf90

    StonySmurf90 Newbie

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    A. Are you sure this was PURE AM-2201?
    B. Have you tried smoking it in a blend?
    C. How effective is it in comparison to JWH-018?

    SWIM's cat, Artemis, is getting 4 grams of the pure substance in the mail and will be blending it with 8 grams of JWH-250 and distributing over 300 grams of herbal. Will update you with Artemis's opinion.
     
  7. ronpintx

    ronpintx Newbie

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    Given the striking geometric similarity between AM-2201 and JWH-018 -- could the two be confused in a urine test for JWH-018?

    Sure the molecular weight is different - but are false positives more likely in a case like this?

    Maybe someone with a chemistry background could help?
     
  8. 5-MeO-NAZ

    5-MeO-NAZ Silver Member

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    so an associate of mine has been quite intrested in sampling a few of these new AM series rcs. He contracted a reliable distributor and a week later he had 1g samples of am694, am1221, and jwh122. A very accurate sample of am1221(yellow chrystaline powder)was weighted (5mg) and placed in a colored glass 1 hitter on top of damiana and was very slowly vaporized in 2-3 inhalations. What followed was described as horrifying. Upon the 2nd exhalation the subject became aware that this rc is certainly active. As more time passed he explained that it was incredibly potent and was escalating to one of the most potent experiences of his whole life. The subject compared this dosage to a 20 mg hit of 5meodmt. In less than 2 minutes after ingestion the subject described a very very intense stoning far beyond that of any prior od experienced with mass amounts of jwh18 or any other synthetic cannabinoid for that matter. The whole experience lasted the duration of consciousness until he fell asleep about 4 hours later. So in reflection the subject described am1221 as a incredibly potent cannibanoid with a very new and different reaction compared to jwh. This new chem should be handled with extreme care and has the ability to propel a researcher to a whole new level of rc cannibaniod experiences. The only drawback is that the dosage curve is very very sensitive. He has since mixed a blend of am1221 and damania using the acetone evaporation method for even distribution and has found that 5 mg per gram of damiana is more than enough for a one and done experience. Please remember that this chem is incredibly potent and just 3 mg almost instantainioulsy caused oev and cev halucinations and extreme anxiety and paranoia. I will report back as he experiment with am 694, jwh122, am2201, jwh210 and jwh19 in the following weeks
     
  9. Shampoo

    Shampoo entity of sorts Staff Member

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    As far as I can tell, the metabolism of this would likely mirror JWH-018, ending with a nearly identical metabolite.

    First, the biggest difference between these two molecules is the existence of the fluoropentyl indole side-chain (in AM-2201, which is absent in JWH-018). This is the first site of cleavage in napthoylindole metabolism, at least it seems to be the major trend in human metabolism. The molecular weight difference between these two molecules is entirely the result of the flourine atom, which will be removed with the rest of the pentyl side-chain (this, of course, is the site of debate for potential fluorotoxicity of fluoropentyl-indoles).

    After this, the metabolic route continues to attack the indole ring, resulting in the detectable (via GC/MS or LC/MS-MS) indole-n-dealkyl metabolite, which as far as I can tell should look basically identical in either of the aforementioned methods.

    Metabolic hydroxylation also occurs, but the metabolites of this route seem less extensive and are almost entirely conjugated with glucuronide.

    READ: JWH-018 and AM-2201 will likely appear identical on basic laboratory drug-testing.

    Two caveats--
    - This is entirely speculation, the fluoropentyl side-chain could alter metabolism in an unforeseen manner (unlikely, but worth a caveat).
    - This is based on oral consumption and degradation via first-pass metabolism. Pyrolytic byproducts may differ in their structure and retain activity, in theory. These products may not be metabolized via this mechanism. However, JWH-018 or AM-2201 which is systemically circulated will almost certainly follow the above scheme.
     
    Last edited: Nov 17, 2010
  10. Phenoxide

    Phenoxide Super Moderator Staff Member

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    Redwood Toxicology's test for JWH-018 and JWH-073 seems to be based around detecting metabolites rather than the parent drug. According to their promotional materials the major metabolites of JWH-018 and JWH-073 in human urine are hydroxylated and carboxylated derivatives, in addition to glucuronide conjugates. Surprisingly they make no mention of N-dealkylation. I would've expected this to be at least a minor metabolic route but perhaps that's not the case. If so then there is also a chance that the N-haloalkyl of AM-2201 is stable and that therefore no common metabolites with JWH-018.

    I will make further enquiries into exactly how their test is designed, but as Shampoo says there certainly is a reasonable possibility that there are metabolites common to JWH-018 and AM-2201. This all hinges on whether dehalogenation of AM-2201 into JWH-018 occurs at appreciable levels, and that is something for which there is simply no publicly available data at this time. It also will be highly dependent on the specific details of the testing procedure.
     
    Last edited: Nov 16, 2010
  11. Shampoo

    Shampoo entity of sorts Staff Member

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    Yes, this seems to be, at least in part, a product of the fact that the parent compounds cannot be detected in urine due to extensive metabolism.
    This seems to be supported. Sobolevsky, Prasolov & Rodchenkov, 2010, report that hydroxylation of the indole ring and n-alkyl chain present the most common and detectable metabolites.
    Kraemer et al. suggested N-dealkylation as the primary metabolic route in JWH-018, and this (the route, not the fact that it is the most common route) was supported by Wintermeyer et al., 2010 (though they also found a number of other metabolites via mono-di and trihydroxylation).
     
  12. Phenoxide

    Phenoxide Super Moderator Staff Member

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    It's worth noting that the experiments Kraemer reported on were conducted in rats so there may be metabolic differences. In their hands the parent drug for JWH-018 apparently was detectable in urine. There's certainly some inconsistencies between what they observed and how Redwood have designed their screen, but it's difficult to say whether there is a species-specific difference, whether the rat study doses were abnormal or whether this is an issue of methodology.

    I would say that it's highly unusual even for a heavily metabolized drug for the parent compound to be totally undetectable by MS these days. For that reason alone I'm inclined to believe there is something to Kraemer's findings and that N-dealkylation of JWH-018 may also occur in humans. Perhaps Redwood have picked the "best" metabolites in terms of reliable identification and have only reported those?
     
  13. Jasim

    Jasim Gold Member

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    Typically samples are hydrolyzed to remove metabolic conjugate groups, leaving the free metabolite to be detected. So any conjugation shouldn't affect the detection of the drug.

    Given the extreme similarity between JWH-018 and AM-2201, How likely is it that common MS fragments would be formed during the testing procedure? This may be another point of consideration.

    Regardless this is all speculation. I would really like to see some empirical data on the metabolism of these compounds.
     
  14. ronpintx

    ronpintx Newbie

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    Yes, that paper closed with a clear statement that the "parent compound" should also be detected.

    That makes sense if the associated metabolites are not unique enough to definitively declare a positive hit (i.e. fail a drug test). The "72 hour test window" required seems to allow for detection of a parent compound yes?

    So, if Redwood thinks they can declare positive hits for JWH-018 usage - without any detectable "parent compound" - they're in for some lawsuits right? False positives are clearly possible without that constraint.

    So, requiring a detectable level of the parent compound being tested for should prevent false positives right?
     
  15. Phenoxide

    Phenoxide Super Moderator Staff Member

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    This is where there seems to be some ambiguity. Some of Redwood's documentation refers to the parent drug, but elsewhere in their promotional materials they make the bold statement that the parent drug of JWH-018 cannot be detected in urine.

    Certainly a test looking for multiple drug-specific compounds would be higher quality as it reduces the chance of a false positive. That said a well picked single ion transition should still be suitably selective. Their test certainly seems to be built around multiple compounds but whether one of them is the parent compound is unclear, as is their criteria for declaring a positive test.

    Not necessarily. Standard cannabis testing looks for the 9-carboxy-THC metabolite rather than parent drug, because it's much more abundant in urine. As long as they can demonstrate the test has suitably specificity.

    Of course in the first couple of years of the test it may become apparent that certain substances cause false positives. I'd imagine if those substances are also synthetic cannabinoids then Redwood will just add them to the tested substances list rather than re-design the test to avoid flagging them up.
     
  16. fatal

    fatal Newbie

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    What are Ki values for CB1, CB2, and GPR?
     
  17. Shampoo

    Shampoo entity of sorts Staff Member

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    Ki data for this compound has not been determined, outside of brief in silico predictions-- though these are generally vague.

    Length of the n-alkyl chain has a positive effect on CB1r Ki, so it is possible that the minor extension of the fluoropentyl chain will increase CB1r binding, but this is speculation-- the steric properties of the fluorine may cause this relationship to be nullified (the relationship was determined with unsubstituted alkyl chain lengths).

    GPR(55, I assume- please be specific as orphan GPRs represent a whole family of proteins without endogenous ligands) has shown a relationship with at least one AM molecule (AM-251), though the structure of this is quite far from AM-2201. Structurally and sterically, AM-2201 is more closely related to the napthoylindoles of the JWH family, including at least one (with a shorter alkyl chain and no terminal flourine) which has been tested at GPR55, only to confirm that it has no affinity. It is unlikely that AM-2201 shows any effect at GPR55.
     
  18. fatal

    fatal Newbie

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    That would explain why I was having trouble finding the data. ;) Yes GPR55 was what I meant. oops. :eek: This compound seems to be worth investingating. Hopefully swim will do some AMXXXX assays in the coming month and get back to me with results.


    :joint:
     
  19. shepj

    shepj Newbie

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    Regardless of the potency, are the effects similar to JWH-018?
     
  20. shaitand

    shaitand Newbie

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    AFOAF received a gram of this research chem today. Initial testing by dusting a tiny unmeasured quantity over a bowl of herb had extremely positve results. Extremely potent. Reported effects include a buzz similar to that of JWH-018 with improved pain relieving effects. Side effects included appetite stimulation which my friend did not report with JWH-018 and dry mouth. I suspect the dry mouth is part of the reason for the earlier reports of throat constriction and suspect that was the result of extreme od.

    I have a question about this chem for others though. JWH-018 requires acetone but at least one source recommended dissolving AM-2201 in distilled water. Would this work?