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5-MeO-DiPT

From Wikipedia, the free encyclopedia
(Redirected from5-Methoxy-N,N-diisopropyltryptamine)
Psychedelic tryptamine
Pharmaceutical compound
5-MeO-DiPT
Clinical data
Other names5-OMe-DiPT; 5-Methoxy-N,N-diisopropyltryptamine; Foxy; Foxy Methoxy
Routes of
administration
Oral, others[1][2][3][4][5]
Drug classNon-selectiveserotonin receptor agonist;Serotonin5-HT2A receptoragonist;Serotonergic psychedelic;Hallucinogen;Entactogen;Stimulant
Legal status
Legal status
Pharmacokinetic data
Onset of action20–30 min or ≤1 hour[1][2][4]
Duration of action3–6 hours or 4–8 hours[1][2][4]
Identifiers
  • 3-[2-(Diisopropylamino)ethyl]-5-methoxyindole
CAS Number
PubChemCID
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 as5-methoxy-N,N-diisopropyltryptamine and sometimes asfoxy methoxy or simplyfoxy, is an atypicalpsychedelic drug of thetryptamine and5-methoxytryptamine families.[1][3][7] It has unique and distinct effects from otherserotonergic tryptamines, including somestimulant- andentactogen-like effects, robusttactile andsexual enhancement, and only lighthallucinogenic effects.[1][2][7][4][8] The drug is usually takenorally, but may also be used by otherroutes.[1][2][3][4][5]

It acts as anon-selectiveserotonin receptor agonist, including of theserotonin5-HT1A and5-HT2A receptors among others.[9][10][11][12][13] Uniquely among most tryptamines, the drug has been found to produceserotonergic neurotoxicity and associatedcognitive deficits in rodents reminiscent of but distinct from those observed withMDMA.[3][14][15] Various severe and/orfatalintoxications associated with 5-MeO-DiPT have been reported in humans.[3][12][13] It is the 5-methoxyderivative ofdiisopropyltryptamine (DiPT) and is ananalogue of other psychedelic tryptamines like4-HO-DiPT,5-MeO-DMT, and5-MeO-MiPT.[1]

5-MeO-DiPT was first described in the literature byAlexander Shulgin and colleagues in 1980.[7][16][1][2] Subsequently, Shulgin described 5-MeO-DiPT in further detail in his 1997 bookTiHKAL (Tryptamines I Have Known and Loved).[1] The drug was first encountered as a noveldesigner drug in 1999.[3][4] It is usedrecreationally as a "party drug" andsexual enhancer, with notable use amonggay men andtransgender women as part of "chemsex", although its use in general has declined over time and is rare.[7][4][3][17] 5-MeO-DiPT became acontrolled substance in theUnited States in 2003.[3][18][19] The closely related drug5-MeO-MiPT (moxy) has similar effects as 5-MeO-DiPT, remains legal in the United States and many other countries, and is often used as a substitute for 5-MeO-DiPT.[7][1][20][21][22]

Use and effects

[edit]

In his bookTiHKAL (Tryptamines I Have Known and Loved) and other publications,Alexander Shulgin reported thedose of 5-MeO-DiPT to be 6 to 12 mgorally, itsonset to be 20 to 30 minutes or within 1 hour, its time to peak effects to be 1 to 1.5 hours, and itsduration to be 4 to 8 hours.[1][2][23][24][8][4] However, in other publications besidesTiHKAL he gave a dose range of 6 to 10 mg[2][8] or a dose range of 8 to 12 mg.[23][24][8] According to Shulgin, testing of 5-MeO-DiPT started at a dose of 0.1 mg and gradually titrated up in 10 human volunteers, with threshold effects occurring at a dose of 4 mg orally and full effects occurring at doses of 6 mg or more.[2][8] The drug's has been described as "fast-acting" and its duration has also been reported to be "short-lived" and as brief as 3 to 6 hours.[1][2][7][8][4] In addition to oral administration, 5-MeO-DiPT has been reported to be used less commonly bysmoking,insufflation, orintravenous injection.[4][3][5] Forms known to be used includepowder,tablets, andcapsules.[4]

Thepsychedelic orperceptual effects of 5-MeO-DiPT have been reported to include colors on edges of eyesight, color contrasts and sparkle, altered facial perception,sensory distortion, few if anyvisual enhancements, someclosed-eye imagery but only at high doses, feelings of strangeness, objects having special significance, somemusicalsound distortions reminiscent of those ofDiPT,music sounding strange and fake,time dilation, having only mildhallucinogenic effects, outgoing rather than inwardly reflective intellectual activation, lack ofintuitive leaps, and a wave-like experience wherein the effects "waved in and out".[1][2][7][4][8] Affective and behavioral effects have includedstimulation, someentactogen-like effects,talkativeness,disinhibition, emotional enhancement, opening of affect, easy emotional expression, easy communication with others, reduced guards and reservations,relaxation, feeling happy, mildeuphoria, and mellowness.[1][2][7][4][8] In addition, the drug has been reported to produce tactile or sensual enhancement, one's body feeling alive and alert, feeling like waves are passing back and forth over one's body, awareness of vibrations, feelingsexually aroused, and "dramatic"erotic or sexual enhancement.[1][2][7][4][8]

Negative emotional and behavioral effects have included uncomfortableness,agitation, feelingunnerved,paranoia, andsocial avoidance, but nohangover.[1][2][8] 5-MeO-DiPT has been described as having minimal physicalside effects and as being relatively free ofautonomic side effects and indicators oftoxicity.[1][2] Reported physical side effects have includedbody load and discomfort, slightpupil dilation, mildnausea, somemuscular hyperreflexia,muscle contractions andspasms,gastrointestinal disturbances,hypertension, and little change inappetite orsleep disruption.[1][2][8] The effects of 5-MeO-DiPT have been described as either being "positive" or a "mixed bag".[1][2] User responses are said to vary dramatically, with some people finding it appealing, sexual, invigorating, interesting, and enjoyable, and others finding itnauseating, annoying,diarrhea-inducing, and generally unpleasant.[4]

5-MeO-DiPT has been described asLSD-like in some ways but as being quite different from other psychedelics.[1][2][7] Descriptions have included the drug never being psychedelic in the way of classical psychedelics like LSD andpsilocybin, there being an absence of intensesensory disturbances or hallucinogenic effects as with other psychedelics likedimethyltryptamine (DMT) and psilocybin, never feeling as though one was having apsychedelic experience, and being able to function normally on a social level including at public events even at high doses.[1][2][7] However, one user who took a high dose described reaching a "plus-three" on theShulgin Rating Scale in a very LSD-like manner but without the visuals.[1] Higher doses may produce more psychedelic effects, but the drug is still described as not that psychedelic even at such doses.[7] Despite its lack of robust hallucinogenic effects at typical doses, 5-MeO-DiPT is described as nonetheless producing quite profound emotional and intellectual modifications.[2]

5-MeO-DiPT is reported to differ in its subjective effects from thestructurally related DiPT in most respects but to share someauditory effects with this drug.[2][1] In terms of these effects, whereas DiPT causedharmonic distortion of heard sounds, 5-MeO-DiPT caused changes in musical character and interpretation without apparent changes in harmonic structure.[1] As such, while both produced auditory effects, DiPT and 5-MeO-DiPT caused different distortions of musical interpretation.[1] 5-MeO-DiPT has been described as a "psychedelicstimulant" and has a reputation as a "sexual enhancer" or "aphrodisiac".[7][4] Among its effects, the pro-sexual effects of 5-MeO-DiPT have been especially highlighted, with these effects being present at low doses.[1] Users have remarked that it took them to a "marvelous sexy place", that "everything [was] shaded with eroticism", that the "erotic world was fantastic, explosive, almost scary", and that the drug may vie with2C-B as a sexual enhancer or that it left 2C-B "in the dust" in this regard.[1][7]

5-MeO-DiPT has been described as having effects similar to those of5-MeO-MiPT and these drugs as having unique and distinct effects from those of other psychedelic tryptamines.[7][22] They are reported to be very pro-sexual, much more stimulant, and more likeparty drugs than other tryptamines.[7][3][22] While 5-MeO-DiPT and 5-MeO-MiPT are described as pro-sexual, they may not be innately aphrodisiac but instead may produce tactile enhancement in a way that lends itself to sex.[7] The tactile enhancement and "body high" with 5-MeO-DiPT and 5-MeO-MiPT may in part be why they have been compared to entactogens likeMDMA.[7] 5-MeO-DiPT has been described as being closer to MDMA in its effects than to psychedelic tryptamines and that the effects are a "body high kind of thing".[7] The drug is also known to be combined with other drugs such as MDMA.[25]

Side effects

[edit]

Flashbacks have been reported with 5-MeO-DiPT.[26][27] There is a report of a prolongeddelusional state associated with 5-MeO-DiPT.[28]

Overdose

[edit]

Excessive doses oroverdose have caused clinicalintoxication, characterized bynausea,vomiting,agitation,hypotension,mydriasis,tachycardia, andhallucinations, in a number of young adults. A number of these overdoses are attributed to the drug's delayedonset of action, where first time users, who were unfamiliar with the drug, administered a second dose after initially feeling no effects.Rhabdomyolysis andrenal failure occurred in one young man and another one died 3 to 4 hours after an apparentrectal overdose.[29] There have been a number of published cases of severe and/or fatal intoxication with 5-MeO-DiPT.[3][12][13][8][30][31][32][33][34]

Interactions

[edit]
See also:Psychedelic drug § Interactions, andTrip killer § Serotonergic psychedelic antidotes

The effects of 5-MeO-DiPT may be potentiated when used in combination withcannabis.[8][1]

Pharmacology

[edit]

Pharmacodynamics

[edit]
5-MeO-DiPT activities
TargetAffinity (Ki, nM)
5-HT1A16–170 (Ki)
56–>10,000 (EC50Tooltip half-maximal effective concentration)
44–94% (EmaxTooltip maximal efficacy)
5-HT1B5,137–>10,000 (Ki)
85–170 (EC50)
100–134% (
Emax)
5-HT1D293–1,718 (Ki)
41–126 (EC50)
92–104% (
Emax)
5-HT1E>10,000 (Ki)
407–2,190 (EC50)
67–86% (
Emax)
5-HT1FND (Ki)
871–3,240 (
EC50)
53–83% (
Emax)
5-HT2A162–>10,000 (Ki)
6.2–946 (EC50)
99–124% (
Emax)
5-HT2B35–163 (Ki)
20–56 (EC50)
80–110% (
Emax)
5-HT2C1,740–>10,000 (Ki)
30–393 (EC50)
71–100% (
Emax)
5-HT3>10,000
5-HT4ND
5-HT5A>10,000 (Ki)
>10,000 (EC50)
ND (Emax)
5-HT62,190–>10,000 (Ki)
324 (EC50)
87% (
Emax)
5-HT71,231–>10,000 (Ki)
>10,000 (EC50)
ND (Emax)
α1A,α1B>10,000
α1DND
α2A>10,000
α2B5,293–>10,000
α2C2,865–3,081
β1,β2>10,000
β3ND
D1D5>10,000
H1H4>10,000
M1M5>10,000
I1760
σ19,443–>10,000
σ2291–3,002
TAAR1Tooltip Trace amine-associated receptor 1ND
SERTTooltip Serotonin transporter874–>10,000 (Ki)
239–24,215 (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 interacts with the site. All proteins are human unless otherwise specified.Refs:[35][36][9][10][37][38]
[11][39][12][13][40]

5-MeO-DiPT acts as anon-selectiveserotonin receptor agonist, including of theserotonin5-HT1A,5-HT1B,5-HT1D,5-HT2A,5-HT2B, and5-HT2C receptors, among others.[36][9][10][11][12][13] It has shown variably strong preference for the serotonin 5-HT1A receptor in terms ofbinding affinity, with 2-fold, 25-fold, >76-fold, and 161-fold higher for this receptor over the serotonin 5-HT2A receptor in different studies.[36][9][13][37][38][26][3] However, in terms ofreceptor activation, 5-MeO-DiPT showed similarpotency at the serotonin 5-HT1A receptor and the serotonin 5-HT2A receptor and had several-fold preference for these receptors over the serotonin 5-HT2C receptor.[12]

In addition to its directserotonin receptor interactions, 5-MeO-DiPT is aserotonin reuptake inhibitor with potency ranging from similar to its serotonin 5-HT2A receptor agonism to very low in different studies.[12][41][42][13] Conversely, it does not significantly affectdopamine ornorepinephrinereuptake and shows no activity as amonoamine releasing agent.[11][13][43][39][42] The drug can block the serotonin release induced bymethamphetaminein vitro.[43][42] 5-MeO-DiPT can elevate brain serotonin levels in rodents, presumably via its serotonin reuptake inhibition.[25][44] The elevations in serotonin levels caused by 5-MeO-DiPT may be limited by its concomitant serotonin 5-HT1A receptor agonism, as serotonin 5-HT1A receptors serve asinhibitoryautoreceptors that limit serotonin release.[41] By an unknown mechanism, but possibly serotonin 5-HT2A receptor agonism, 5-MeO-DiPT may also elevate braindopamine levels in rodents, including in theprefrontal cortex,striatum, and/ornucleus accumbens, although findings are mixed.[25][41][44] Themechanism of action of thepsychedelic effects of 5-MeO-DiPT is thought to be serotonin 5-HT2A receptor agonism, but its full mechanism of action is unclear and additional mechanisms may also be involved.[43][37][39]

5-MeO-DiPT produces thehead-twitch response, a behavioral proxy ofpsychedelic-like effects, in rodents.[45][26][3][46][13][47][37] As with many other psychedelics, this follows aninverted U-shapeddose–response curve.[46][37] The head-twitch response induced by 5-MeO-DiPT is blocked by serotonin 5-HT2A receptorantagonists such asvolinanserin.[46][37] 5-MeO-DiPT's head-twitch response is described as robust but also weak and much lower in magnitude than that produced by other serotonergic psychedelics such as5-MeO-DMT orDOM.[38][37][13] The serotonin 5-HT1A receptor agonism of 5-MeO-DiPT may inhibit its serotonin 5-HT2A receptor-mediated head-twitch response.[37] 5-MeO-DiPT partially substitutes forLSD in rodentdrug discrimination tests, with 52% responding at 1 mg/kg, 75% responding at 3 mg/kg, and behavioral disruption at higher doses.[37] In addition, it substitutes for DOM in rodent drug discrimination tests.[37][48] The stimulus properties of 5-MeO-DiPT in LSD substitution tests are completely and insurmountably blocked by the serotonin 5-HT2A receptor antagonist volinanserin.[38][37] Conversely, they are partially and surmountably blocked by the serotonin 5-HT1A receptor antagonistWAY-100635.[38][37] Besides psychedelic-like effects, 5-MeO-DiPT also produceshypolocomotion andhypothermia in rodents and potentiates the forepaw treading induced by the serotonin 5-HT1A receptor agonist8-OH-DPAT.[13][47][49][25]

5-MeO-DiPT has been reported to produceneurotoxicity in rodents.[50][43][25][51][3] Administration of 5-MeO-DiPT to adolescent rodents produced marked decreases inspatial navigation performance in adulthood that were suggestive of deficits incognitive flexibility,attention, and/orperseveration as well as othercognitive deficits.[3][52][14][53] This was associated withserotonergic neurotoxicity and substantial 26 to 49% reductions incortical andhippocampal serotonin levels that were analogous to those occurring withMDMA.[3][14] However, the neurotoxic effects of 5-MeO-DiPT are described as less severe than and distinct from those of MDMA.[14][15] The drug has also been reported to producecytotoxicity as well as neurotoxic effects on serotonergicneuronsex vivo.[43][51] The mechanisms underlying the serotonergic neurotoxicity of 5-MeO-DiPT are unknown.[43][14] The drug might also produce prolonged dopaminergic adaptations ordopaminergic neurotoxicity in rodents as evidenced by long-lasting decreases indopamine levels.[25][51] In addition, it has been associated with markedgenotoxicity oroxidativeDNA damage, which has also been seen with MDMA andmethamphetamine.[25][51] It is said to be the first knowntryptamine to be associated with such toxicity.[25]

Pharmacokinetics

[edit]

Thepharmacokinetics andmetabolism of 5-MeO-DiPT have been studied.[54][3][55][56][57]

Chemistry

[edit]

Properties

[edit]

Thelog P of 5-MeO-DiPT is 3.68.[13]

Synthesis

[edit]

Thechemical synthesis of 5-MeO-DiPT has been described.[1]

Analogues

[edit]

Analogues of 5-MeO-DiPT includediisopropyltryptamine (DiPT),4-HO-DiPT (iprocin),4-AcO-DiPT (ipracetin),4-MeO-DiPT,5-HO-DiPT,5-MeO-DMT,5-MeO-DET,5-MeO-DPT,5-MeO-DALT,5-MeO-MiPT,5-MeO-EiPT,5-MeO-PiPT,5-MeO-iPALT (ASR-3001), and5-MeO-DiBF, among others.[1]

Positional isomers

[edit]

4-MeO-DiPT, 6-MeO-DiPT, and 7-MeO-DiPT are knownpositional isomers of 5-MeO-DiPT.[1][24] 6-MeO-DiPT and 7-MeO-DiPT have been described byAlexander Shulgin as being inactive at doses of up to 50 mg and 70 mgorally, respectively, whereas 4-MeO-DiPT was not assessed.[1][24]

History

[edit]

5-MeO-DiPT was discovered in the 1970s and was first described byAlexander Shulgin and Michael Carter in 1980.[7][16][1][2] Shulgin tested it and discovered its effects starting in 1975.[58][59] The drug started to be encountered as a novelrecreational anddesigner drug in 1999.[3][4] 5-MeO-DiPT became a temporarilycontrolled substance in theUnited States in 2003 and a permanently controlled substance in 2004.[3][18][19] Therecreational use of 5-MeO-DiPT appears to have declined over time and its use is described as being not very prevalent.[4][7][3]

Society and culture

[edit]

Recreational use

[edit]
5-MeO-DiPT tablets seized fromSalem,Oregon.

Use of 5-MeO-DiPT has been found to be particularly prevalent amonggay men who usedrugs as part ofchemsex.[3][60][61] It is also seen intransgender women.[17][62] The drug is described as astimulant,sexual enhancer,party drug, and lightpsychedelic.[7] 5-MeO-DiPT has been associated with increased risk ofHIV diagnosis in multiple studies inAsia, perhaps due to risky sexual behavior involving the drug.[7][61][63][17]

Legal status

[edit]

Canada

[edit]

5-MeO-DiPT is not scheduled inCanada.[64]

China

[edit]

As of October 2015, 5-MeO-DiPT is a controlled substance in China.[65]

Denmark

[edit]

Illegal since February 2004.[citation needed]

Germany

[edit]

Illegal since September 1999.[citation needed]

Greece

[edit]

Illegal since February 2003.[citation needed]

Japan

[edit]

Illegal since April 2005.[3]

Singapore

[edit]

Illegal since early 2006.[citation needed]

Sweden

[edit]

Sveriges riksdags health ministryStatens folkhälsoinstitut classified 5-MeO-DiPT as "health hazard" under the actLagen om förbud mot vissa hälsofarliga varor (translatedAct 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.[66]

United States

[edit]

On April 4, 2003, theUnited StatesDEA added both 5-MeO-DiPT andα-methyltryptamine (AMT) to Schedule I of theControlled Substances Act under "emergency scheduling" procedures.[3] The drugs were officially placed into Schedule I on September 29, 2004.[3] Prior to its prohibition in the U.S., 5-MeO-DiPT was sold online alongside psychoactive analogues such asdiisopropyltryptamine (DiPT), anddipropyltryptamine (DPT), neither of which have yet been expressly outlawed.

See also

[edit]

References

[edit]
  1. ^abcdefghijklmnopqrstuvwxyzaaabacadaeafagShulgin, Alexander;Shulgin, Ann (September 1997).TiHKAL: The Continuation.Berkeley, California:Transform Press.ISBN 0-9630096-9-9.OCLC 38503252.https://www.erowid.org/library/books_online/tihkal/tihkal37.shtml
  2. ^abcdefghijklmnopqrstuvShulgin 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.
  3. ^abcdefghijklmnopqrstuvwxAraújo 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.Bibcode:2015ArTox..89.1151A.doi:10.1007/s00204-015-1513-x.PMID 25877327.
  4. ^abcdefghijklmnopqr"5-MeO-DiPT".АИПСИН (in Russian). Retrieved13 November 2025.
  5. ^abcMalaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA (December 2020)."Toxicology and Analysis of Psychoactive Tryptamines".Int J Mol Sci.21 (23): 9279.doi:10.3390/ijms21239279.PMC 7730282.PMID 33291798.
  6. ^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. Retrieved2023-08-27.
  7. ^abcdefghijklmnopqrstuvwPalamar 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.Other 5-MeO compounds 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. 5-Meo-DIPT, Foxy, or Moxy (5-Meo-MIPT) are tryptamines that are distinct. A lot of people I know that like them think they're very aphrodisiac and much more stimulant and a party drug. My opinion on 5-MeO-MIPT is that it was a very sexual chemical … it feels good to touch things, and that sort of sensation certainly lends itself to sex but I wouldn't call it innately an aphrodisiac. These increased sensations of touch are likely why some users compared the "body high" with the high associated with MDMA use. The effects of 5-MeO compounds were also described as being shorter lasting than other tryptamines. I would actually say that it is closer to MDMA in its effects. The whole series of 5-MeO and 4-MeO … they're both very closely related in their effects so it tends to be a body high kind of thing. At higher doses it can get more psychedelic, but it's not that psychedelic. [...] first discovered or first synthesized as early as [...] in the 1970s (e.g., 4-HO-MET and 5-MeO-DIPT). However, use does not appear to be very prevalent (Palamar & Le, 2019; Palamar, Martins, Su, & Ompad, 2015), and most of these compounds do not have much of a presence in the published literature. [...] Finally, 5-MeO-DIPT ("Foxy") was also used by a few of our participants, and they noted sexual effects of the drug. Although sometimes described as a sex drug on the internet, academic literature does not seem to describe sexual effects of the drug. However, multiple studies in Asia have linked use of 5-MeO-DIPT to increased risk for HIV diagnosis, likely due to risky sexual behavior involving the drug (Hayashi, Wakabayashi, Ikushima, & Tarui, 2017; Kuwahara et al., 2008; Shan et al., 2018).
  8. ^abcdefghijklmMeatherall R, Sharma P (2003). "Foxy, a designer tryptamine hallucinogen".J Anal Toxicol.27 (5):313–317.doi:10.1093/jat/27.5.313.PMID 12908946.Foxy is slang for 5-methoxy-N,N-diisopropyltryptamine. It has hallucinogenic properties, similar to other tryptamine compounds, and is mildly euphoric. [...] This case report describes a 21-year-old Caucasian man who ingested a pill called Foxy containing an unknown amount of drug. He was observed in hospital for 2 h, during which time he had mild hallucinations and could not move his limbs. [...] Clinically, the drug promotes emotional expression, a talkative uninhibited state (7), and visual and auditory sensory distortions (8). No other clinical studies appear in the medical literature. There are no reported pharmacological studies in humans. Some of the drug's physiological properties are also common to the recreational drug methylenedioxymethamphetamine (Ecstasy). Not surprisingly, 5-MeO-DIPT is a club drug (2) and has been substituted for Ecstasy on the street (3). [...] In 1980, Shulgin and Carter (7) described the administration of 5-MeO-DIPT to 10 human subjects. Each person received a 0.1mg oral dose which was then increased in increments of 30 to 50% in subsequent drug administrations. Threshold subjective effects were observed with a 4-mg dose. Effective doses were between 6 and 10 mg. The peak drug effect occurred at 1 to 1.5 h after ingestion, and recovery was observed after 3 h with no residual symptoms at 6 h. Subjects reported a relaxed feeling associated with emotional enhancement. They were frequently talkative and felt their conversations to be expressive and stimulating. Shulgin and Shulgin (8) later summarized the responses from an additional 10 human subjects upon administration of 6 to 12 mg of 5-MeO-DIPT. Most subjects reported auditory and visual distortions. Two indicated aphrodisiac tendencies; one experienced gastrointestinal emptying, muscle spasms, and agitation; and one indicated a synergistic effect with marijuana. [...] In our patient, the drug lasted 3.5 h. He said he felt "weird" (apprehensive) and saw symbols (visual hallucination) as opposed to being talkative or expressive of his emotions.
  9. ^abcdRay 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.
  10. ^abcRickli 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.
  11. ^abcdBlough 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.
  12. ^abcdefgKozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, Olson RJ, Janowsky A, Abbas AI (April 2023)."Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter".J Pharmacol Exp Ther.385 (1):62–75.doi:10.1124/jpet.122.001454.PMC 10029822.PMID 36669875.
  13. ^abcdefghijklPuigseslloses 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.
  14. ^abcdeCompton DM, Dietrich KL, Selinger MC, Testa EK (May 2011). "5-methoxy-N,N-di(iso)propyltryptamine hydrochloride (Foxy)-induced cognitive deficits in rat after exposure in adolescence".Physiol Behav.103 (2):203–209.doi:10.1016/j.physbeh.2011.01.021.PMID 21295050.
  15. ^abSkelton MR, Schaefer TL, Herring NR, Grace CE, Vorhees CV, Williams MT (June 2009)."Comparison of the developmental effects of 5-methoxy-N,N-diisopropyltryptamine (Foxy) to (+/-)-3,4-methylenedioxymethamphetamine (ecstasy) in rats".Psychopharmacology (Berl).204 (2):287–297.doi:10.1007/s00213-009-1459-x.PMC 2888297.PMID 19198809.
  16. ^abZamberlan F, Sanz C, Martínez Vivot R, Pallavicini C, Erowid F, Erowid E, Tagliazucchi E (2018)."The Varieties of the Psychedelic Experience: A Preliminary Study of the Association Between the Reported Subjective Effects and the Binding Affinity Profiles of Substituted Phenethylamines and Tryptamines".Front Integr Neurosci.12 54.doi:10.3389/fnint.2018.00054.PMC 6235949.PMID 30467466.5-MeO-DiPT (5-Methoxy-N,N-diisopropyltryptamine): substituted tryptamine, first synthesized and tested by Shulgin and Carter (1979).
  17. ^abcShan D, Yu MH, Yang J, Zhuang MH, Ning Z, Liu H, Liu L, Han MJ, Zhang DP (December 2018)."Correlates of HIV infection among transgender women in two Chinese cities".Infect Dis Poverty.7 (1) 123.doi:10.1186/s40249-018-0508-2.PMC 6276265.PMID 30509315.
  18. ^abDrug Enforcement Administration (Dea), Department of Justice (April 2003). "Schedules of controlled substances: temporary placement of alpha-methyltryptamine and 5-methoxy-N,N-diisopropyltryptamine into Schedule I. Final rule".Fed Regist.68 (65):16427–16430.PMID 12678045.
  19. ^abDrug Enforcement Administration (Dea), Department of Justice (September 2004). "Schedules of controlled substances: placement of alpha-methyltryptamine and 5-methoxy-N,N-diisopropyltryptamine into schedule I of the Controlled Substances Act. Final rule".Fed Regist.69 (188):58950–58953.PMID 15455477.
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  25. ^abcdefghNoworyta-Sokołowska K, Kamińska K, Kreiner G, Rogóż Z, Gołembiowska K (November 2016)."Neurotoxic Effects of 5-MeO-DIPT: A Psychoactive Tryptamine Derivative in Rats".Neurotox Res.30 (4):606–619.doi:10.1007/s12640-016-9654-0.PMC 5047954.PMID 27461536.
  26. ^abcNichols 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.
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  41. ^abcHagino 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.
  42. ^abcSogawa 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.Bibcode:2007ToxL..170...75S.doi:10.1016/j.toxlet.2007.02.007.PMID 17382495.
  43. ^abcdefNakagawa T, Kaneko S (January 2008). "Neuropsychotoxicity of abused drugs: molecular and neural mechanisms of neuropsychotoxicity induced by methamphetamine, 3,4-methylenedioxymethamphetamine (ecstasy), and 5-methoxy-N,N-diisopropyltryptamine (foxy)".J Pharmacol Sci.106 (1):2–8.doi:10.1254/jphs.fm0070141.PMID 18198474.
  44. ^abLi K, Li N, Chen Y, Li X, Qiao Y, Wang D, Di B, Xu P (July 2025)."A systematic study of changes in monoamine neurotransmitters in the rat brain following acute administration of alpha-methyltryptamine (AMT), 5-methoxy-alpha-methyltryptamine (5-MeO-AMT) and 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DiPT)".Neurosci Res.216 104903.doi:10.1016/j.neures.2025.04.006.PMID 40288614.
  45. ^Halberstadt AL, Geyer MA (2018). "Effect of Hallucinogens on Unconditioned Behavior".Behavioral Neurobiology of Psychedelic Drugs: Effect of Hallucinogens on Unconditioned Behavior(PDF). Current Topics in Behavioral Neurosciences. Vol. 36. pp. 159–199.doi:10.1007/7854_2016_466.ISBN 978-3-662-55878-2.PMC 5787039.PMID 28224459. Archived fromthe original(PDF) on 2017-08-29.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).{{cite book}}:|journal= ignored (help)
  46. ^abcHalberstadt 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).
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  50. ^Gołembiowska, Krystyna (2022). "Pharmacology and Neurotoxicity of 5-MeO-DIPT".Handbook of Neurotoxicity. Cham: Springer International Publishing. pp. 1403–1414.doi:10.1007/978-3-031-15080-7_207.ISBN 978-3-031-15079-1.
  51. ^abcdNoworyta-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.
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