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5-MeO-DiPT

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5-MeO-DiPT
Clinical data
Other names5-Methoxy-N,N-diisopropyltryptamine; Foxy; Foxy Methoxy
Routes of
administration		Oral, intranasal[1]
Drug classSerotonin receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status
Pharmacokinetic data
Onset of action20–30 minutes[3]
Duration of action4–8 hours[4]
Identifiers
  • 3-[2-(Diisopropylamino)ethyl]-5-methoxyindole
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H26N2O
Molar mass274.408 g·mol−1
3D model (JSmol)
Melting point181 °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 checkY
  • Key:DNBPMBJFRRVTSJ-UHFFFAOYSA-N checkY
  (verify)

5-MeO-DiPT, also known as 5-methoxy-N,N-diisopropyltryptamine and sometimes as foxy methoxy or simply foxy, is a psychedelic drug of the tryptamine and 5-methoxytryptamine families.[1][4][5] It is the 5-methoxy derivative of diisopropyltryptamine (DiPT).[4]

Dosage

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In TiHKAL and other publications, Alexander Shulgin reported the dosage of 5-MeO-DiPT to be 6 to 12 mg orally, its onset to be 20 to 30 minutes, its time to peak effects to be 1 to 1.5 hours, and its duration to be 4 to 8 hours.[4][3][6][7] The drug can also be used intranasally.[1]

Effects

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The effects of 5-MeO-DiPT are reported to include psychedelic-like effects and pro-sexual effects, among others.[4] It is said to be associated with relatively few visual changes.[4][3] Only at higher doses have closed-eye visuals occurred.[3] On the other hand, 5-MeO-DiPT is said to produce some of the auditory distortions that DiPT is associated with.[4] 5-MeO-DiPT is reported to be more like a stimulant, party drug, and sexual enhancer than a psychedelic.[5] Other effects include somatic sensual activation, talkativeness, disinhibition, and emotional enhancement, easier emotional expression and communication, and intellectual activation.[3] The emotional enhancement is described as similar to that of entactogens like MDMA.[3]

Side effects

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Side effects of 5-MeO-DiPT include slight mydriasis (pupil dilation) among others.[3]

Overdose

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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]

Interactions

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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5-MeO-DiPT activities
Target Affinity (Ki, nM)
5-HT1A 15.8–132.4 (Ki)
>10,000 (EC50Tooltip half-maximal effective concentration)
5-HT1B 5,137
5-HT1D 1,718
5-HT1E >10,000
5-HT1F ND
5-HT2A 399–>10,000 (Ki)
6.21–946 (EC50)
99–124% (EmaxTooltip maximal efficacy)
5-HT2B 163
5-HT2C >10,000 (Ki)
73.5–393 (EC50)
100% (Emax)
5-HT3 >10,000
5-HT4 ND
5-HT5A >10,000
5-HT6 >10,000
5-HT7 1,231
α1A >10,000
α1B >10,000
α1D ND
α2A >10,000
α2B 5,293
α2C 2,865
β1 >10,000
β2 >10,000
β3 ND
D1 >10,000
D2 >10,000
D3 >10,000
D4 >10,000
D5 >10,000
H1–H4 >10,000
M1–M5 >10,000
I1 760
σ1 9,443
σ2 3,002
TAAR1Tooltip Trace amine-associated receptor 1 ND
SERTTooltip Serotonin transporter 1,618–2,531 (Ki)
646–24,215 (IC50Tooltip half-maximal inhibitory concentration)
>100,000 (EC50) (rat)
NETTooltip Norepinephrine transporter >10,000 (Ki)
8,200–>10,000 (IC50)
>100,000 (EC50) (rat)
DATTooltip Dopamine transporter >10,000 (Ki)
65,000 (IC50)
>100,000 (EC50) (rat)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [10][11][12][13][14][15][16]

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.[17] The strongest receptor binding affinity for 5-MeO-DiPT is at the 5-HT1A receptor.[1][11][18][19]

5-MeO-DiPT produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[20][18][1][21][15][19] This is blocked by serotonin 5-HT2A receptor antagonists such as volinanserin.[21][19] The drug produces a relatively weak head–twitch response, much lower in magnitude than that produced by for example 5-MeO-DMT or DOM.[15][19] 5-MeO-DiPT also produces hypolocomotion and hypothermia in rodents.[15] It partially substitutes for LSD in rodent drug discrimination tests (52–75% responding at different doses).[19] This could be completely blocked by by volinanserin, whereas the serotonin 5-HT1A receptor antagonist WAY-100635 had no effect on the stimulus properties of 5-MeO-DiPT.[19]

5-MeO-DiPT is a weak serotonin reuptake inhibitor.[22][23] The elevations in serotonin levels caused by its serotonin reuptake inhibition are limited by its concomitant serotonin 5-HT1A receptor agonism, serotonin 5-HT1A receptors serve as inhibitory autoreceptors that limit serotonin release.[22]

5-MeO-DiPT has been reported to be neurotoxic in rats.[24][25][26][1]

Pharmacokinetics

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The pharmacokinetics and metabolism of 5-MeO-DiPT have been studied.[1][27][28][29]

Chemistry

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Analogues of 5-MeO-DiPT include 5-MeO-DiBF, 5-MeO-DMT, 5-MeO-DPT, 5-MeO-AMT, and 5-MeO-MiPT, as well as DMT, DPT, AMT, DIPT, and MIPT, among others.

History

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5-MeO-DiPT was discovered in the 1970s and was first described by Alexander Shulgin and colleagues in 1980.[5][3] It started to be encountered as a novel recreational and designer drug in 1999.[1] The drug becamed a controlled substance in the United States in 2003.[1]

Society and culture

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5-MeO-DiPT tablets seized from Salem, Oregon.

Recreational use

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Use of 5-MeO-DiPT has been found to be particularly prevalent among gay men who use drugs.[1]

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China

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As of October 2015 5-MeO-DiPT is a controlled substance in China.[30]

Denmark

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Illegal since February 2004.[citation needed]

Germany

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Illegal since September 1999.[citation needed]

Greece

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Illegal since February 2003.[citation needed]

Japan

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Illegal since April 2005.[citation needed]

Singapore

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Illegal since early 2006.[citation needed]

Sweden

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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.[31]

United States

[edit]

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

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  1. ^ a b c d e f g h i j Araújo AM, Carvalho F, Bastos Mde L, Guedes de Pinho P, Carvalho M (August 2015). "The hallucinogenic world of tryptamines: an updated review" (PDF). Arch Toxicol. 89 (8): 1151–1173. doi:10.1007/s00204-015-1513-x. PMID 25877327.
  2. ^ 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.
  3. ^ a b c d e f g h Shulgin AT, Carter MF (1980). "N, N-Diisopropyltryptamine (DIPT) and 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT). Two orally active tryptamine analogs with CNS activity". Commun Psychopharmacol. 4 (5): 363–369. PMID 6949674.
  4. ^ a b c d e f g Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  5. ^ a b c Palamar JJ, Acosta P (January 2020). "A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines". Hum Psychopharmacol. 35 (1): e2719. doi:10.1002/hup.2719. PMC 6995261. PMID 31909513. 5-MeO compounds were less prevalent in this sample of experienced tryptamine users. We received few comments about the effects of individual compounds in this subclass, and these compounds tended to be described as being more sexual than other compounds. One participant also pointed out that 5-Meo-DIPT ("Foxy Methoxy" or "Foxy") gained notoriety in the United States as a sexual enhancement drug. [...]
  6. ^ Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Retrieved 1 February 2025.
  7. ^ Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Res Monogr. 146: 74–91. PMID 8742795.
  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. ^ "Kᵢ Database". PDSP. 26 March 2025. Retrieved 26 March 2025.
  11. ^ a b 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.
  12. ^ Rickli A, Moning OD, Hoener MC, Liechti ME (August 2016). "Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens" (PDF). European Neuropsychopharmacology. 26 (8): 1327–1237. doi:10.1016/j.euroneuro.2016.05.001. PMID 27216487. S2CID 6685927.
  13. ^ Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes" (PDF). Psychopharmacology (Berl). 231 (21): 4135–4144. doi:10.1007/s00213-014-3557-7. PMC 4194234. PMID 24800892.
  14. ^ Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". Eur J Pharmacol. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
  15. ^ a b c d Puigseslloses P, Nadal-Gratacós N, Ketsela G, Weiss N, Berzosa X, Estrada-Tejedor R, Islam MN, Holy M, Niello M, Pubill D, Camarasa J, Escubedo E, Sitte HH, López-Arnau R (August 2024). "Structure-activity relationships of serotonergic 5-MeO-DMT derivatives: insights into psychoactive and thermoregulatory properties" (PDF). Mol Psychiatry. 29 (8): 2346–2358. doi:10.1038/s41380-024-02506-8. PMC 11412900. PMID 38486047.
  16. ^ Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (April 2016). "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1". J Pharmacol Exp Ther. 357 (1): 134–144. doi:10.1124/jpet.115.229765. PMID 26791601.
  17. ^ 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.
  18. ^ a b Nichols DE (April 2016). "Psychedelics" (PDF). Pharmacol Rev. 68 (2): 264–355. doi:10.1124/pr.115.011478. PMC 4813425. PMID 26841800. Ikeda et al. (2005) reported flashbacks after use of 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT) by a 35-year-old man without a previous psychiatric history. He had used the substance six or seven times over 5 months but discontinued it after he had a bad trip, with anxiety, palpitations, auditory oversensitiveness, and visual distortions. Treatment with oral risperidone ameliorated his symptoms. [...] Fantegrossi et al. (2006) demonstrated that 5-MeODIPT induced the head twitch in mice, and the effect was antagonized by pretreatment with the 5-HT2A– selective antagonist M100907. The affinity of 5-MeO-DIPT was measured at rat 5-HT1A, 5-HT2A, and 5-HT2C receptors using antagonist radioligands, with Ki values determined to be 35 nM, 5620 nM, and 1700 nM, respectively. Thus, despite the higher affinity for 5-MeO-DIPT at the 5-HT1A receptor, the head twitch was mediated through the 5-HT2A receptor.
  19. ^ a b c d e f Fantegrossi WE, Harrington AW, Kiessel CL, Eckler JR, Rabin RA, Winter JC, Coop A, Rice KC, Woods JH (January 2006). "Hallucinogen-like actions of 5-methoxy-N,N-diisopropyltryptamine in mice and rats". Pharmacol Biochem Behav. 83 (1): 122–129. doi:10.1016/j.pbb.2005.12.015. PMID 16460788.
  20. ^ Halberstadt AL, Geyer MA (2018). "Behavioral Neurobiology of Psychedelic Drugs: Effect of Hallucinogens on Unconditioned Behavior" (PDF). Curr Top Behav Neurosci. Current Topics in Behavioral Neurosciences. 36: 159–199. doi:10.1007/7854_2016_466. ISBN 978-3-662-55878-2. PMC 5787039. PMID 28224459. Likewise, the HTR is induced by ring-substituted tryptamines, including psilocin, psilocybin, 5-MeO-DMT, and 5-MeO-DIPT (Corne and Pickering 1967; Bedard and Pycock 1977; Fantegrossi et al. 2006; González-Maeso et al. 2007; Halberstadt et al. 2011).
  21. ^ a b Halberstadt AL, Geyer MA (September 2011). "Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens". Neuropharmacology. 61 (3): 364–381. doi:10.1016/j.neuropharm.2011.01.017. PMC 3110631. PMID 21256140. Certain indolealkylamines, including DMT, N,N-dipropyltryptamine (DPT), 5-MeO-DMT, and 5-methoxy-N,Ndiisopropyltryptamine (5-MeO-DIPT) block 5-HT uptake at micromolar concentrations (Nagai et al., 2007; Sogawa et al., 2007; Cozzi et al., 2009) and serve as substrates for the 5-HT transporter (Cozzi et al., 2009). [...] Likewise, HTR induced by DPT, 5-MeO-DIPT, and TCB-2 in mice is blocked by M100,907 and MDL 11,939 (Fantegrossi et al., 2006, 2008; Fox et al., 2009). [...] Fantegrossi and colleagues have reported that the HTR induced by DOI, 2C-T-7, DPT, and 5-MeO-DIPT in NIH Swiss and Swiss-Webster mice typically follows an inverted U-shaped dose–response function (Fantegrossi et al., 2005, 2006, 2008, 2010).
  22. ^ a b Hagino Y, Hall FS, Uhl GR, Sora I, Ikeda K (March 2021). "Dual actions of 5-MeO-DIPT at the serotonin transporter and serotonin 5-HT1A receptor in the mouse striatum and prefrontal cortex". Neuropsychopharmacol Rep. 41 (1): 91–101. doi:10.1002/npr2.12161. PMC 8182963. PMID 33547882.
  23. ^ Sogawa C, Sogawa N, Tagawa J, Fujino A, Ohyama K, Asanuma M, Funada M, Kitayama S (April 2007). "5-Methoxy-N,N-diisopropyltryptamine (Foxy), a selective and high affinity inhibitor of serotonin transporter". Toxicol Lett. 170 (1): 75–82. doi:10.1016/j.toxlet.2007.02.007. PMID 17382495.
  24. ^ 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.
  25. ^ 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.
  26. ^ 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.
  27. ^ Yu AM (June 2008). "Indolealkylamines: biotransformations and potential drug-drug interactions". AAPS J. 10 (2): 242–253. doi:10.1208/s12248-008-9028-5. PMC 2751378. PMID 18454322.
  28. ^ Kamata T, Katagi M, Kamata HT, Miki A, Shima N, Zaitsu K, Nishikawa M, Tanaka E, Honda K, Tsuchihashi H (February 2006). "Metabolism of the psychotomimetic tryptamine derivative 5-methoxy-N,N-diisopropyltryptamine in humans: identification and quantification of its urinary metabolites". Drug Metab Dispos. 34 (2): 281–287. doi:10.1124/dmd.105.005835. PMID 16280455.
  29. ^ Narimatsu S, Yonemoto R, Saito K, Takaya K, Kumamoto T, Ishikawa T, Asanuma M, Funada M, Kiryu K, Naito S, Yoshida Y, Yamamoto S, Hanioka N (April 2006). "Oxidative metabolism of 5-methoxy-N,N-diisopropyltryptamine (Foxy) by human liver microsomes and recombinant cytochrome P450 enzymes". Biochem Pharmacol. 71 (9): 1377–1385. doi:10.1016/j.bcp.2006.01.015. PMID 16510126.
  30. ^ "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.
  31. ^ "notisum.se" (PDF). Archived (PDF) from the original on 2013-09-29. Retrieved 2013-09-06.
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