5-MeO-DiPT

5-Methoxy-N,N-diisopropyltryptamine
Clinical data
Trade names	Foxy, Foxy Methoxy
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); CA: Unscheduled; DE: Anlage I, In general; / Unscheduled unless that it was for human consumption. UK: Class A; US: Schedule I; UN: Unscheduled; / Illegal in Sweden, Denmark, Greece, Japan, Singapore and China.
Identifiers
	IUPAC name 3-[2-(Diisopropylamino)ethyl]-5-methoxyindole;
CAS Number	4021-34-5 ;
PubChem CID	151182;
DrugBank	DB01441 ;
ChemSpider	133247 ;
UNII	12D06G8W8E;
KEGG	C22724 ;
ChEBI	CHEBI:48282 ;
CompTox Dashboard (EPA)	DTXSID00193209 ;
Chemical and physical data
Formula	C17H26N2O
Molar mass	274.408 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	181 °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 ; Key:DNBPMBJFRRVTSJ-UHFFFAOYSA-N ;
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5-Methoxy-N,N-diisopropyltryptamine (5-MeO-DiPT, sometimes called foxy methoxy or simply foxy^[2]) is a psychedelic tryptamine and the methoxy derivative of diisopropyltryptamine (DiPT).

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Thumb — 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-HT_2A receptor agonism, although additional mechanisms of action such as monoamine oxidase inhibition (MAOI) may be involved also.^[3] The strongest receptor binding affinity for 5-MeO-DiPT is at the 5-HT_1A receptor.^[4]

5-MeO-DiPT is neurotoxic in rats.^[5]^[6]^[7]

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.^[8] At least one death has been attributed to consumption of 5-MeO-DiPT.^[9]

Drug prohibition laws

China

As of October 2015 5-MeO-DiPT is a controlled substance in China.^[10]

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.^[11]

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.

References

[1]
Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
[2]
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.
[3]
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.
[4]
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.
[5]
Gołembiowska, Krystyna (2022). "Pharmacology and Neurotoxicity of 5-MeO-DIPT". Handbook of Neurotoxicity. Cham: Springer International Publishing. p. 1403–1414. doi:10.1007/978-3-031-15080-7_207. ISBN 978-3-031-15079-1.
[6]
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.
[7]
Noworyta-Sokołowska K, Kamińska K, Rzemieniec J, Wnuk A, Wojcieszak J, Górska AM, Kreiner G, Kajta M, Gołembiowska K (2019). "Effects of exposure to 5-MeO-DIPT during adolescence on brain neurotransmission and neurotoxicity in adult rats". Forensic Toxicol. 37 (1): 45–58. doi:10.1007/s11419-018-0433-x. PMC 6315008. PMID 30636982.
[8]
Baselt R (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. pp. 975–976.
[9]
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.
[10]
"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.
[11]
"notisum.se" (PDF). Archived (PDF) from the original on 2013-09-29. Retrieved 2013-09-06.

External links

[1] [1]
Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[2] [2]
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.

[pmid17223101-3] [3]
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.

[4] [4]
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.

[Gołembiowska2022-5] [5]
Gołembiowska, Krystyna (2022). "Pharmacology and Neurotoxicity of 5-MeO-DIPT". Handbook of Neurotoxicity. Cham: Springer International Publishing. p. 1403–1414. doi:10.1007/978-3-031-15080-7_207. ISBN 978-3-031-15079-1.

[Noworyta-SokołowskaKamińskaKreiner2016-6] [6]
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.

[Noworyta-SokołowskaKamińskaRzemieniec2019-7] [7]
Noworyta-Sokołowska K, Kamińska K, Rzemieniec J, Wnuk A, Wojcieszak J, Górska AM, Kreiner G, Kajta M, Gołembiowska K (2019). "Effects of exposure to 5-MeO-DIPT during adolescence on brain neurotransmission and neurotoxicity in adult rats". Forensic Toxicol. 37 (1): 45–58. doi:10.1007/s11419-018-0433-x. PMC 6315008. PMID 30636982.

[8] [8]
Baselt R (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. pp. 975–976.

[9] [9]
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.

[10] [10]
"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.

[11] [11]
"notisum.se" (PDF). Archived (PDF) from the original on 2013-09-29. Retrieved 2013-09-06.

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