5-Methoxy-N,N-diisopropyltryptamine

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).

5-Methoxy-N,N-diisopropyltryptamine
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.

Identifiers
IUPAC name
  • 3-[2-(Diisopropylamino)ethyl]-5-methoxyindole
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H26N2O
Molar mass274.408 g·mol−1
3D model (JSmol)
Melting point181 °C (358 °F)
SMILES
  • CC(C)N(C(C)C)CCC1=C[NH]C(C=C2)=C1C=C2OC
InChI
  • 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 Y
  • Key:DNBPMBJFRRVTSJ-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)
5-MeO-DiPT tablets from Salem, Oregon

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

References
  1. Narimatsu, Shizuo; Yonemoto, Rei; Saito, Keita; Takaya, Kazuo; Kumamoto, Takuya; Ishikawa, Tsutomu; Asanuma, Masato; Funada, Masahiko; Kiryu, Kimio; Naito, Shinsaku; Yoshida, Yuzo; Yamamoto, Shigeo; Hanioka, Nobumitsu (2006). "Oxidative metabolism of 5-methoxy-N,N-diisopropyltryptamine (Foxy) by human liver microsomes and recombinant cytochrome P450 enzymes". Biochemical Pharmacology. 71 (9): 1377–85. 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): 132–7. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
  3. Ray TS (2 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, Karolina; Kamińska, Katarzyna; Kreiner, Grzegorz; Rogóż, Zofia; Gołembiowska, Krystyna (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. ISSN 1029-8428. PMC 5047954. PMID 27461536.
  5. R. Baselt (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. pp. 975–976.
  6. Tanaka, Einosuke; Kamata, Tooru; Katagi, Munehiro; Tsuchihashi, Hitoshi; Honda, Katsuya (2006). "A fatal poisoning with 5-methoxy-N,N-diisopropyltryptamine, Foxy". Forensic Science International. 163 (1–2): 152–4. 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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