Introduction to 5-MeO-DIPT

5-MeO-DIPT (N,N-diisopropyl-5-methoxy-tryptamine, "Foxy") is an N,N-disubstituted tryptamine. It is very closely structurally related to 5-MeO-DMT, 5-MeO-MiPT, and 5-MeO-DALT. They differ only in their respective N-substituents; 5-MeO-DMT has two N-methyl substituents, while 5-MeO-DIPT has two N-isopropyl substituents; 5-MeO-MiPT has one N-isopropyl substituent and one N-methyl substituent; 5-MeO-DALT has two N-allyl substituents

Using 5-MeO-DIPT

5-MeO-DIPT is active parenterally and enterally. Oral dosage is generally higher than that for insufflation or inhalation. Oral administration provides a longer but less intense experience. The comeup is about 10-60 minutes, and the plateau lasts about 2-5 hours, followed by a 3-5 hour comedown. Lingering after effects can last up to 24 hours [1]. Unlike most smokable tryptamines, 5-MeO-DIPT freebase produces an experience that comes on slowly and can last several hours, versus, for example, the extremely rapid onset and short experience of smoking DMT freebase.

Ways of administration

Oral

5-MeO-DIPT is most commonly administered orally. It has a very offputting taste so is generally consumed in capsules

5-MeO-DIPT Oral Dosage [1][2]
Threshold	3 mg
Light	5-10 mg
Common	8-15mg
Strong	15-30 mg

Insufflation

Insufflation of a 5-MeO-DIPT salt produces a quicker onset, and a shorter and more intense experience as compared to oral ingestion.

Inhalation

Effects of 5-MeO-DIPT

As is expected of molecule closely resembling other psychedelic tryptamine analogues, 5-MeO-DIPT has hallucinogenic properties.

Physiological

Some prominent physiological effects include euphoria, empathy, enhancement of the senses - most notably tactile, visual, and auditory. Intestinal discomfort resulting in nausea, vomiting or diarrhea, or undesirable stimulation and tension are not entirely uncommon. It has also been noted by users and by Alexander Shulgin, it's first synthesizer, to enhance sexuality [3,4,15].

Opinions of drugs-forum users

A member of drugs-forum collected surveys about unresearched compounds from users of drugs-forum and other internet boards, and here is some of the information he summarized concerning the effects of 5-MeO-DIPT:

Here are some snippets from user reports:

General effects

A bullet list of effects compiled from experience threads and literature [2][3][1]:
Pyrexia (increase in body temperature above the normal range of 98-100F)
Perspiration
Nausea/vomiting (common)
Diarrhea
Mydriasis (dose dependent)
Muscle contraction/stiffness/twitching
Tremors
Anxiety
Strong body load/stimulation
Increased libido
Auditory distortions (pitch distortions reminiscent of the demethoxyl analogue, DIPT)
Visual distortions ("sharpness" of objects, light and color enhancement, shaking or vibrations)
Open eyed visuals (morphing, fractals, trails)
Closed eyed visuals
Increased aesthetic appreciation
Changes in perception (simple or profound - feeling reborn, detached from body, deep thought or introspection, oneness)
Social lubrication
Pronounced tactile enhancement (pleasurable or tingling feeling)
Time distortion
Synathesia
Headache
Chest pain
Abdominal pain
General physical discomfort

Combinations with 5-MeO-DIPT

Marijuana

GHB

2C-B

Different Uses for 5-MeO-DIPT

Chemistry of 5-MeO-DIPT

5-MeO-DIPT is a methoxylated tryptamine. Probably the most common of its "class" is dimethyltryptamine. 5-MeO-DIPT has a methoxy group on the fifth position of the molecule and in place of two N-methyl groups it has two isopropyl groups. This feature inhibits rapid metabolism which allow for its uncommon oral activity [4].

Synonyms: N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-propan-2-ylpropan-2-amine; 5-methoxy-N,N-bis(1-methylethyl)-1H-Indole-3-ethanamine;
Molecular Formula: C17H26N2O
Molecular Weight: 274.4011 g/mol
m.p.: 181 C
CAS #: 4021-34-5
PubChem ID: 151182



5-MeO-DIPT Electron Impact Mass Spectra and m/z ratios[5]


Gas Chromatography/Mass Spectrum [5]

Pharmacology of 5-MeO-DIPT

Often psychedelic tryptamines need to be administered parenterally in order to be active, as if they are taken orally they are rapidly metabolized to inactive metabolites, for example by oxidative deamination to give an indole-3-acetic acid [4]. The addition of bulky alkyl groups (the two isopropyl groups of 5-MeO-DIPT) cause steric hindrance which inhibits this reaction, making enteral administration viable.

In vitro, 5-MeO-DIPT has shown affinity for the 5-HT1A receptor. One study has shown that it does have affinity for the 5HT2A and 5HT-2C receptors, although much less relative to 5-HT1A [6]. However, pretreatment with a 5-HT2A antagonist before administration of 5-MeO-DIPT completely inhibited behavioral responses (in rats). In addition, pretreatment with a 5-HT1A antagonist did not significantly inhibit responses. Even though the Ki for 5-MeO-DIPT at the 5-HT1A receptor is significantly lower than at 5-HT2A and 5-HT2C, the attenuation of response as a result of a 5-HT2A antagonist, some generalization of LSD to 5-MeO-DIPT (rats), and the affinity of close structural analogues for the 5-HT2A receptor lend support to the effects of 5-MeO-DIPT being mainly a result of action at the 5-HT2A receptor.

Sogawa et al. [7] also showed that 5-MeO-DIPT is a competitive SERT (the serotonin reuptake transporter) inhibitor.
This finding is supported by Nagai et al. [8], who showed that 5-MeO-DIPT inhibits reuptake of dopamine, serotonin and norepinephrine with IC50 values (the concentration of a drug required to inhibit a biological process by 50%) of 6.5x10^-5M, 2.2x10^-6M and 8.2x10^-6M, respectively (as compared to that of cocaine and methamphetamine, which had IC50 values for dopamine, 5-HT and norepinephrine of 8.5x10^-7M, 2.1x10^-6 and 3.4x10^-7M, respectively, and 3.7x10^-7M, 4.0x10^-6M and 2.0x10^-7M, respectively. It did not show significant monoamine releasing activity, especially as compared to a close structural analogue, 5-MeO-AMT. A comparison of IC50 and EC50 (related to IC50--EC50 is the concentration required to produce a response halfway between baseline and maximum response) values of other drugs to that of 5-MeO-DIPT can be seen below.




Wilson et al. [9] reports that the primary metabolic pathway of 5-MeO-DIPT includes oxidative deamination to give the indole-3-acetic acid, 5-MeO-IAA. Urine samples also indicated the presence of 5-MeO-DIPT and 5-MeO-DIPT-N'-oxide. This study also indicated the presence of an unexpectedly hight amount of the metabolite 5-OH-DIPT relative to 5-MeO-DIPT/DIPT-N'-oxide. A previous subject had no 5-OH-DIPT but much higher levels of the former two [10]. It has not been concluded whether 5-OH-DIPT is a metabolite of 5-MeO-DIPT. For the subject studied by Wilson et al., urine concentration of 5-MeO-DIPT was 1.6ug/ml (as compared to 1.7ug/mL [10]); 5-MeO-IPT, ~0.1 ug/mL (as compared to 2ug/mL [10]; 5-MeO-DIPT-N'-oxide, ~0.1ug/mL (as compared to 0.1ug/mL [10]); 5-OH-DIPT, ~1.6ug/mL (as compared to none [10]). This may indicate metabolic differences as a result of genetics, as the expression of the enzymes involved in the different metabolic reactions is known to vary genetically [9]. A table containing results from urinalysis of two different subjects can be seen below.




N-dealkylation of 5-MeO-DIPT is catalyzed by the enzymes CYP1A2, CYP3A4 and CYP2C19. O-demethylation is catalyzed by CYP2D6 [11]. Narimatsu et al. report that O-demethylation is the primary metabolic pathway of 5-MeO-DIPT when substrate concentration is low, but N-dealkylation increases when substrate concentrations are higher. A comparison of metabolic reactions can be seen below [11]:




Kamata et al. [12] and Narimatsu et al. [11] provide useful depictions of the metabolic pathways and activities for 5-MeO-DIPT in vivo:

The dangers of 5-MeO-DIPT

These are the dangers common to all psychedelic drugs:

Accidental injury. When on a psychedelic drug, it is easier to accidentally injure yourself. Also because of the disorientating and potentially delusion inspiring nature of the experience, you could be lead to inflict harm on others or yourself. People have fallen off rooftops, run into traffic, attempted to throw people off rooftops as 'sacrifices', drowned, and so on. The best way of protecting against this is to have a friend with you who is sober to look after you and handle any negative situation that might arise.

Bad trips. A bad trip is a negative psychedelic experience. It can range from a mildly negative feeling of anxiety/discomfort, to full-blown psychosis. Bad trips usually ruin a psychedelic experience for the tripper and everyone else. Most bad trips are manageable, just very uncomfortable and difficult. Some are extreme and unmanageable though. It's not uncommon for a bad trip to result in lingering psychological issues. Usually just a few days of negative emotions and anxiety. Sometimes, however, a week or so of serious anxiety, destabilized mental state and impaired functioning is possible. On very rare occasions, a month or two of severely diminished functioning, traumatized mental state, depression & crippling anxiety can occur. More information on bad trips can be found here. The best way of avoiding a bad trip is having the correct set and setting.

Permanent psychosis. Psychedelics are believed by researchers not to cause permanent psychosis, however they could trigger a latent mental illness in someone who was already predisposed to it, or make existing mental illnesses worse. If there is a history of mental illness in your family, you are more likely to be predisposed. Everyone is at some risk, however.

PTSD, anxiety disorder, depression & depersonalization. There are anecdotal reports of the trauma inflicted by some bad trips leading to depression and anxiety which while usually temporary, could potentially develop into lasting disorders. While no different to the potential of any traumatic event to cause lasting disorders, nonetheless this is a danger of psychedelic drug use.

MAOI's and 5-MeO-DIPT

As a tryptamine, the metabolism of 5-MeO-DIPT can be heavily influenced by the presence of monoamine oxidase inhibitors (MAOI) which prevent the breakdown of monoamine neurotransmitters as well as tryptamines themselves. Because 5-MeO-DIPT affects the normal homeostasis of monoamine neurotransmitter systems, combining the drug with an MAOI could result in potentiation of the drug to the point where it can become physiologically dangerous or psychologically overwhelming. Some antidepressants, antibiotics, and antihypertensives are MAOI's so caution must be exerted.

HPPD, flashbacks and other psychological problems

As a psychedelic, use of 5-MeO-DIPT could potentially contribute to psychological issues. There has been at least one report of flashbacks attributed to the use of 5-MeO-DIPT [13]. Hallucinogen Persisting Perception Disorder is a disorder characterized by persistence of flashbacks (which are normally transient) or other psychological disturbances after use of a psychedelic is terminated. The symptoms of HPPD can adversely affect everyday life [14].

As with any drug which induces temporary psychological changes, 5-MeO-DIPT can induce anxiety, confusion, unwanted hallucinations, etc. Situations, locations or events which might overwhelm the user can contribute to these adverse psychological disturbances. Users who wound up in an emergency room or a poison control center have reported feelings of formication (bugs crawling on the skin) and paranoia, hypertension, tachycardia and agitation. Seizures and tremors, although rare, have also been reported [9].

Overdose

There has been at least one fatal overdose of 5-MeO-DIPT published in the literature [15]. After rectal administration of a 5-MeO-DIPT solution, a 29 year old male died about 3.5 hours later. No other drugs were found in the urine or serum. The autopsy revealed periarteritis nodosa (swelling and damaging of small and medium arteries which leads to tissue damage due to lack of proper circulation) in the heart and liver, an ischemic lesion in the myocardium (probably due to lack of proper blood flow), abnormally high white blood cell count (leukocytosis), pulmonary edema (fluid in lungs), hemorraghing of the pulmonary aveoli, and periprostatic (around the prostate) bleeding. The subject had a serum level of 5-MeO-DIPT about 4 times higher than that of the subject studied by Wilson et al. [9], a level of 5-OH-DIPT over 15 times that of [9], and 3 times the level of 5-MeO-NIPT. 5-OH-DIPT and 5-MeO-NIPT were also found in the subjects serum, whereas in other case studies these metabolites were only discovered in the urine. The cause of death was published as "acute cardiac failure due to neurotoxicity resulting from an overdose of 5-MeO-DIPT" [15].

Producing 5-MeO-DIPT

5-MeO-DIPT can be produced a variety of ways. Shulgin starts with 5-methoxytryptamine or perhaps N-acetyl-5-methoxytryptamine (melatonin) in sulfolane (or another suitable solvent) to which is added diisopropylethylamine and 2-iodopropane. The mixture is heated in a steam bath and shaken often for 3 hrs. The mixture was allowed to cool to room temperature and then stirred for 16 hrs. Volatiles removed under vacuum, gave a residue which was diluted with dH2O so as to give a clear solution. Washed with aqueous NaOH produces a cloudy solution which is extracted with hexane 3 times. Extracts were pooled and the solvent was removed to give an almost colorless oil. Distillation (@0.1mm Hg) - at 100 C comes over mostly residual sulfofane. At 140-150 C comes most of the product, a viscous white oil (5-MeO-DIPT freebase). The oil is dissolved in IPA and HCl was added to neutralize. A small portion of anhydrous diethyl ether was added to induce crystallization of the salt. The product is removed by filtration, washed with IPA/diethylether mixture, dried. mp 181-182C [16].

Forms of 5-MeO-DIPT

Appearance

5-MeO-DIPT HCl is a fine, white crystal [16]. It has also been discovered as a tan powder although this is likely an indication of impurity. It smells of indole (a fecal odor).

Images of 5-MeO-DIPT

A capsule of 5-MeO-DIPT seized by the DEA [17].


A tablet of 5-MeO-DIPT sent to the Oregon State Police Forensic Laboratory [18].


1 gram of 5-MeO-DIPT (presumably a salt) from a vendor, courtesy of Erowid [19].

Legal status of 5-MeO-DIPT [20]

United Nations

USA

5-MeO-DIPT is a Schedule I drug since 2004 as a result of the Controlled Substances Act.

EU

Other Countries

Canada

5-MeO-DIPT is not explicitly outlawed in Canada.

Denmark

5-MeO-DIPT is illegal in Denmarkas of 2004.

Greece

Germany

5-MeO-DIPT is Schedule I in Germany as of 1999.

History of 5-MeO-DIPT

More 5-MeO-DIPT Sections

5-MeO-DiPT (Foxy) Trip Reports
5-MeO-DiPT (Foxy) Drug Info

The latest 5-MeO-DIPT threads

References

1. ^ a bErowid. Erowid 5-MeO-DIPT Vault : Effects. http://www.erowid.org/chemicals/5meo..._effects.shtml
2. ^ a b cSurvey on 10 Tryptamines from 6 forums circa 2006
3. ^ a b c5-MeO-DIPT (Foxy) Trip Reports
4. ^ a bShulgin et al. N, N-Diisopropyltryptamine (DIPT) and 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT). Two orally active tryptamine analogs with CNS activity. Communications in Psychopharmacology, 1980.
5. ^ a bTakahashi et al. Analysis of phenethylamines and tryptamine designers drugs with gas chromatography-mass spectrometry. Journal of Health Science 2008.
6. ^Fantegrossi et al. Hallucinogen-Like Actions of 5-MeO-DIPT in Mice and Rats (2006). Pharmacology Biochemistry and Behaviour 2006.
7. ^Sogawa et al. 5-Methoxy-N,N-diisopropyltryptamine (Foxy), a selective and high affinity inhibitor of serotonin transporter (2007). Toxicology Letters 2007.
8. ^Nagai et al. The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain, European Journal of Pharmacology (2006).
9. ^ a b c d eWilson et al. A Foxy Intoxication (2005). Forensic Science International, 2005.
10. ^ a b c d eMeatherall et al. Foxy, a designer tryptamine hallucinogen. Journal of Analytical Toxicology, 2003.
11. ^ a b cNarimatsu et al. Oxidation of 5-methoxy-N,N-diisopropyltryptamine in rat liver microsomes and recombinant cytochrome P450 enzymes. Biochemical Pharmacology 2008.
12. ^Kamata et al. Metabolism of the psychotomimetic tryptamine derivative 5-methoxy-N,N-diisopropyltryptamine in humans: identification and quantification of its urinary metabolites (2005). Drug Metabolism and Disposition 2006.
13. ^Ikeda et al. 5-Methoxy-N,N-Diisopropyltryptamine-Induced Flashbacks (2005). American Journal of Psychiatry 2005
14. ^DSM IV-R
15. ^ a bTanaka et al. A fatal poisoning with 5-MeO-DIPT, foxy (2006). Forensic Science International 2006.
16. ^ a bTIHKAL #37 5-MeO-DIPT
17. ^"5-MeO-DIPT tablet." https://drugs-forum.com/photopost...g0803_fig4.jpg. 2009. DEA Microgram. 13 August 2010. <https://drugs-forum.com>
18. ^"5-MeO-DIPT capsule." https://drugs-forum.com/photopost...mg0308_008.jpg. 2009. DEA Microgram. 13 August 2010. <https://drugs-forum.com/>
19. ^Murple. "5-MeO-DIPT." https://drugs-forum.com/photopost...5meo_DIPT2.jpg. 2002. Erowid. 13 August 2010. <http://www.erowid.org/>
20. ^Erowid. Erowid 5-MeO-DIPT Vault : Legal Status. http://www.erowid.org/chemicals/5meo...DIPT_law.shtml. 1999. Erowid. 14 August 2010. <http://www.erowid.org/>