5-Methoxy-N,N-diisopropyltryptamine

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5-Methoxy-N,N-diisopropyltryptamine
5-MeO-DiPT.svg
5-MeO-DiPT-3d-sticks.png
Legal status
Legal status
  • DE:Anlage I, In general

/ Unscheduled unless that it was for human consumption. / Illegal in Sweden, Denmark, Greece, Japan, Singapore and China.

Contents

Identifiers
  • 3-[2-(Diisopropylamino)ethyl]-5-methoxyindole
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
Formula C17H26N2O
Molar mass 274.408 g·mol−1
3D model (JSmol)
Melting point 181 °C (358 °F)
  • CC(C)N(C(C)C)CCC1=C[NH]C(C=C2)=C1C=C2OC
  • InChI=1S/C17H26N2O/c1-12(2)19(13(3)4)9-8-14-11-18-17-7-6-15(20-5)10-16(14)17/h6-7,10-13,18H,8-9H2,1-5H3 Yes check.svgY
  • Key:DNBPMBJFRRVTSJ-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)
5-MeO-DiPT tablets from Salem, Oregon 5meodipt.jpg
5-MeO-DiPT tablets from Salem, Oregon

5-Methoxy-N,N-diisopropyltryptamine (5-MeO-DiPT, sometimes called foxy methoxy or simply foxy [1] ) is a psychedelic tryptamine and the methoxy derivative of diisopropyltryptamine (DiPT).

Pharmacology

The mechanism that produces the purported hallucinogenic and entheogenic effects of 5-MeO-DiPT is thought to result primarily from 5-HT2A receptor agonism, although additional mechanisms of action such as monoamine oxidase inhibition (MAOI) may be involved also. [2] The strongest receptor binding affinity for 5-MeO-DiPT is at the 5-HT1A receptor. [3]

5-MeO-DiPT is neurotoxic in rats. [4]

Overdose

Excessive doses have caused clinical intoxication, characterized by nausea, vomiting, agitation, hypotension, mydriasis, tachycardia and hallucinations, in a number of young adults. A number of these overdoses are attributed to the drug’s extended onset of action, where first time users, who were unfamiliar with the drug, administered a second dose after initially feeling no effects. Rhabdomyolysis and renal failure occurred in one young man and another one died 3–4 hours after an apparent rectal overdose. [5] At least one death has been attributed to consumption of 5-MeO-DiPT. [6]

Drug prohibition laws

China

As of October 2015 5-MeO-DiPT is a controlled substance in China. [7]

Denmark

Illegal since February 2004.

Germany

Illegal since September 1999.

Greece

Illegal since February 2003.

Japan

Illegal since April 2005.

Singapore

Illegal since early 2006.

Sweden

Sveriges riksdags health ministry Statens folkhälsoinstitut classified 5-MeO-DiPT as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Oct 1, 2004, in their regulation SFS 2004:696 listed as 5-metoxi-N,N-diisopropyltryptamin (5-MeO-DIPT), making it illegal to sell or possess. [8]

United States

On April 4, 2003, the United States DEA added both 5-MeO-DiPT and alpha-methyltryptamine (AMT) to Schedule I of the Controlled Substances Act under "emergency scheduling" procedures. The drugs were officially placed into Schedule I on September 29, 2004. Prior to its prohibition in the U.S., 5-MeO-DiPT was sold online alongside psychoactive analogues such as DiPT, and DPT, neither of which have yet been expressly outlawed.

See also

Related Research Articles

<i>alpha</i>-Methyltryptamine Chemical compound

α-Methyltryptamine is a psychedelic, stimulant, and entactogen drug of the tryptamine class. It was originally developed as an antidepressant by workers at Upjohn in the 1960s, and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued.

<span class="mw-page-title-main">Dipropyltryptamine</span> Chemical compound

N,N-Dipropyltryptamine (DPT) is a psychedelic entheogen belonging to the tryptamine family. Use as a designer drug has been documented by law enforcement officials since as early as 1968. However, potential therapeutic use was not investigated until the 1970s. It is found either as a crystalline hydrochloride salt or as an oily or crystalline base. It has not been found to occur endogenously. It is a close structural homologue of dimethyltryptamine and diethyltryptamine.

<span class="mw-page-title-main">2C-T-2</span> Chemical compound

2C-T-2 is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin, and rated by him as one of the "magical half-dozen" most important psychedelic phenethylamine compounds. The drug has structural and pharmacodynamic properties similar to those of 2C-T-7.

<span class="mw-page-title-main">5-MeO-DMT</span> Chemical compound

5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine) or O-methyl-bufotenin is a psychedelic of the tryptamine class. It is found in a wide variety of plant species, and also is secreted by the glands of at least one toad species, the Colorado River toad. Like its close relatives DMT and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include Five-methoxy, The power, and Toad venom.

<span class="mw-page-title-main">5-MeO-aMT</span> Chemical compound

5-MeO-aMT or 5-methoxy-α-methyltryptamine, α,O-Dimethylserotonin (Alpha-O) is a potent psychedelic tryptamine. It is soluble in ethanol.

<span class="mw-page-title-main">4-HO-DiPT</span> Chemical compound

4-Hydroxy-N,N-diisopropyltryptamine is a synthetic psychedelic drug. It is a higher homologue of psilocin, 4-HO-DET, and is a positional isomer of 4-HO-DPT and has a tryptamine molecular sub-structure.

<span class="mw-page-title-main">Diisopropyltryptamine</span> Chemical compound

Diisopropyltryptamine is a psychedelic hallucinogenic drug of the tryptamine family that has a unique effect. While the majority of hallucinogens affect the visual sense, DiPT is primarily aural.

<span class="mw-page-title-main">5-MeO-MiPT</span> Chemical compound

5-MeO-MiPT is a psychedelic and hallucinogenic drug, used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs 5-MeO-DiPT, DiPT, and MiPT. It is commonly used as a "substitute" for 5-MeO-DiPT because of the very similar structure and effects.

<span class="mw-page-title-main">5-MeO-DALT</span> Chemical compound

5-MeO-DALT or N,N-di allyl-5-methoxy tryptamine is a psychedelic tryptamine first synthesized by Alexander Shulgin.

<span class="mw-page-title-main">5-MeO-DET</span> Chemical compound

5-MeO-DET or 5-methoxy-N,N-diethyltryptamine is a hallucinogenic tryptamine.

<span class="mw-page-title-main">5-MeO-DPT</span> Chemical compound

5-MeO-DPT, is a psychedelic and entheogenic designer drug.

A serotonin releasing agent (SRA) is a type of drug that induces the release of serotonin into the neuronal synaptic cleft. A selective serotonin releasing agent (SSRA) is an SRA with less significant or no efficacy in producing neurotransmitter efflux at other types of monoamine neurons.

<span class="mw-page-title-main">5-Ethoxy-DMT</span> Chemical compound

5-Ethoxy-DMT is a tryptamine derivative which has been previously synthesized as a chemical intermediate, but has not been studied to determine its pharmacology.

<span class="mw-page-title-main">5-HO-DiPT</span> Chemical compound

5-HO-DiPT (5-hydroxy-N,N-di-iso-propyltryptamine) is a tryptamine derivative which acts as a serotonin receptor agonist. It is primarily known as a metabolite of the better known psychoactive drug 5-MeO-DiPT, but 5-HO-DiPT has also rarely been encountered as a designer drug in its own right. Tests in vitro show 5-HO-DiPT to have high 5-HT2A affinity and good selectivity over 5-HT1A, while being more lipophilic than the related drug bufotenine (5-HO-DMT), which produces mainly peripheral effects.

<span class="mw-page-title-main">5-Chloro-αMT</span> Chemical compound

5-Chloro-α-methyltryptamine (5-Chloro-αMT), also known as PAL-542, is a tryptamine derivative related to α-methyltryptamine (αMT) and one of only a few known specific serotonin-dopamine releasing agents (SDRAs). It has been investigated in animals as a potential treatment for cocaine dependence. The EC50 values of 5-chloro-αMT in evoking the in vitro release of serotonin (5-HT), dopamine (DA), and norepinephrine (NE) in rat synaptosomes were reported as 16 nM, 54 nM, and 3434 nM, with an NE/DA ratio of 63.6 and a DA/5-HT ratio of 3.38, indicating that it is a highly specific and well-balanced SDRA. However, 5-chloro-αMT has also been found to act as a potent full agonist of the 5-HT2A receptor, with an EC50 value of 6.27 nM and an efficacy of 105%, and almost assuredly acts as a potent agonist of other serotonin receptors as well.

<span class="mw-page-title-main">5-MeO-MALT</span> Chemical compound

5-MeO-MALT (5-methoxy-N-methyl-N-allyltryptamine) is a lesser-known psychedelic drug that is closely related to 5-MeO-DALT and has been sold online as a designer drug.

<span class="mw-page-title-main">5-MeO-MET</span> Chemical compound

5-MeO-MET (5-Methoxy-N-methyl-N-ethyltryptamine) is a relatively rare designer drug from the substituted tryptamine family, related to compounds such as N-methyl-N-ethyltryptamine and 5-MeO-DMT. It was first synthesised in the 1960s and was studied to a limited extent, but was first identified on the illicit market in June 2012 in Sweden. It was made illegal in Norway in 2013, and is controlled under analogue provisions in numerous other jurisdictions.

<span class="mw-page-title-main">MALT (psychedelic drug)</span> Chemical compound

MALT is a lesser-known drug from the tryptamine family. It is a novel compound with very little history of human use. It is closely related to methylpropyltryptamine (MPT), as well as N-methyltryptamine. It has been sold online as a designer drug. Very little information on the pharmacology or toxicity of MALT is available.

References

  1. ↑ Narimatsu S, Yonemoto R, Saito K, Takaya K, Kumamoto T, Ishikawa T, et al. (April 2006). "Oxidative metabolism of 5-methoxy-N,N-diisopropyltryptamine (Foxy) by human liver microsomes and recombinant cytochrome P450 enzymes". Biochemical Pharmacology. 71 (9): 1377–1385. doi:10.1016/j.bcp.2006.01.015. PMID   16510126.
  2. ↑ Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID   17223101.
  3. ↑ Ray TS (February 2010). "Psychedelics and the human receptorome". PLOS ONE. 5 (2): e9019. Bibcode:2010PLoSO...5.9019R. doi: 10.1371/journal.pone.0009019 . PMC   2814854 . PMID   20126400.
  4. ↑ Noworyta-Sokołowska K, Kamińska K, Kreiner G, Rogóż Z, Gołembiowska K (November 2016). "Neurotoxic Effects of 5-MeO-DIPT: A Psychoactive Tryptamine Derivative in Rats". Neurotoxicity Research. 30 (4): 606–619. doi:10.1007/s12640-016-9654-0. PMC   5047954 . PMID   27461536.
  5. ↑ Baselt R (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. pp. 975–976.
  6. ↑ Tanaka E, Kamata T, Katagi M, Tsuchihashi H, Honda K (November 2006). "A fatal poisoning with 5-methoxy-N,N-diisopropyltryptamine, Foxy". Forensic Science International. 163 (1–2): 152–154. doi:10.1016/j.forsciint.2005.11.026. PMID   16406422.
  7. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  8. ↑ "notisum.se" (PDF). Archived (PDF) from the original on 2013-09-29. Retrieved 2013-09-06.
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