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MiPT

From Wikipedia, the free encyclopedia
(Redirected fromMethylisopropyltryptamine)
Chemical compound
Not to be confused withMiPLA.
Pharmaceutical compound
MiPT
Clinical data
Other namesMiPT;N-Methyl-N-isopropyltryptamine
Routes of
administration		Oral[1]
Drug classSerotonin receptor modulator;Serotonin 5-HT2A receptor agonist;Serotonergic psychedelic;Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Onset of actionOral: 30 minutes[1]
Insufflation: <1 minute[1]
Duration of action3–4 hours[1]
Identifiers
  • N-[2-(1H-indol-3-yl)ethyl]-N-methylpropan-2-amine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC14H20N2
Molar mass216.328 g·mol−1
3D model (JSmol)
  • CC(C)N(C)CCc1c[nH]c2ccccc12
  • InChI=1S/C14H20N2/c1-11(2)16(3)9-8-12-10-15-14-7-5-4-6-13(12)14/h4-7,10-11,15H,8-9H2,1-3H3 checkY
  • Key:KTQJVAJLJZIKKD-UHFFFAOYSA-N checkY
  (verify)

Methylisopropyltryptamine (MiPT), also known asN-methyl-N-isopropyltryptamine, is apsychedelic drug of thetryptamine family related to other psychedelics likedimethyltryptamine (DMT) anddiisopropyltryptamine (DiPT).[1] It is takenorally.[1]

The drug acts as aserotonin receptor modulator, including as anagonist of theserotonin5-HT2A receptor.[2][3]Derivatives of MiPT include4-HO-MiPT (miprocin) and5-MeO-MiPT (moxy).[1]

MiPT was first described byDavid Repke and colleagues in 1981.[4][5][6][7] It was subsequently evaluated and described inAlexander Shulgin's 1997 bookTiHKAL (Tryptamines I Have Known and Loved).[1] MiPT was encountered as a noveldesigner drug by 2005.[8]

Use and effects

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In his bookTiHKAL (Tryptamines I Have Known and Loved),Alexander Shulgin lists MiPT's dose as 10 to 25 mgorally and itsduration as 3 to 4 hours.[1][9][10] A dose of 20 mg byinsufflation was also reported.[1] Itsonset orally was reported to be 30 minutes and peak effects occurred at 1 hour.[1] Conversely, its onset via insufflation was said to be immediate or less than 1 minute.[1] Oral doses of up to 20 mg were described as being relatively mild in their effects.[1] MiPT is notable in being the mostpotent of the simpleN,N-dialkyltryptamines, at least via oral administration.[1][9][10]

The effects of MiPT have been reported to include feeling "definitely psychedelic", being very "heady" (perhaps as in "psychedelic headspace"), effects onthoughts that were typically psychedelic, enhancement ofvisual field such as brighter colors and more clearly defined objects, vision tinted orange as if there was an orange overlay, an almost total absence of any othervisual effects (including nowave-forms, color distortion, object shape changes, orclosed-eyeimagery),auditory effects such as enhanced sound discrimination,hearing and skin being more sensitive, and minorsensory changes in general.[1] It was said to emphasize "psychedelic" effects over "hallucinogenic" effects.[1] Other effects includedfeeling good,excitement,stimulation,feeling alert,restlessness, and trailinginsomnia for 6 to 8 hours.[1] Physical effects includedpupil dilation,dizziness,dry mouth, andmuscle tension.[1]

Interactions

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

Pharmacology

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Pharmacodynamics

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MiPT acts as aserotonin receptor modulator.[2][3] It showsaffinity for theserotonin5-HT2A,5-HT1A, and5-HT2B receptors.[3] The drug acts as apotentpartial agonist of the serotonin 5-HT2A receptor.[2] It shows weak affinity for theserotonin transporter (SERT) andvesicular monoamine transporter 2 (VMAT2),[11] but does not act as amonoamine reuptake inhibitor orreleasing agent even at very high concentrations.[2]

Chemistry

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Properties

[edit]

MiPTbase, unlike many othertryptamines in theirfreebase form, does notdecompose rapidly in the presence oflight oroxygen.[citation needed]

Crystal structure

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In August 2019, Chadeayne et al. solved the crystal structure of fumarate salt of MiPT.[4]

Synthesis

[edit]

Thechemical synthesis of MiPT has been described.[1]

Analogues

[edit]

Analogues of MiPT include4-HO-MiPT,4-AcO-MiPT,5-MeO-MiPT,methylethyltryptamine (MET),methylpropyltryptamine (MPT),ethylisopropyltryptamine (EiPT),propylisopropyltryptamine (PiPT),dimethyltryptamine (DMT),diisopropyltryptamine (DiPT), andMiPBF, among others.[1]

History

[edit]

MiPT was firstsynthesized and described byDavid Repke and colleagues in 1981.[4][5][6][7] Subsequently, MiPT was further described byAlexander Shulgin in his 1997 bookTiHKAL (Tryptamines I Have Known and Loved).[1] The drug was encountered as a noveldesigner drug inEurope by 2005.[8]

Society and culture

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Legal status

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Canada

[edit]

MiPT is not acontrolled substance inCanada as of 2025.[12]

Sweden

[edit]

Sweden's public health agency suggested classifying MiPT as a hazardous substance, on May 15, 2019.[13][14]

United States

[edit]

In theUnited States, MiPT not an explicitlycontrolled substance.[15] However, as anisomer ofdiethyltryptamine (DET), it may be considered aSchedule I controlled substance similarly.[15] In addition, the purchase, sale, or possession for human consumption of MiPT could be prosecuted under theFederal Analogue Act.[16]

See also

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References

[edit]
  1. ^abcdefghijklmnopqrstuShulgin, 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/tihkal47.shtml
  2. ^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".Psychopharmacology (Berl).231 (21):4135–4144.doi:10.1007/s00213-014-3557-7.PMC 4194234.PMID 24800892.
  3. ^abcMcKenna DJ, Repke DB, Lo L, Peroutka SJ (March 1990). "Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes".Neuropharmacology.29 (3):193–198.doi:10.1016/0028-3908(90)90001-8.PMID 2139186.
  4. ^abcChadeayne AR, Pham DN, Golen JA, Manke DR (September 2019)."The fumarate salts of the N-isopropyl-N-methyl derivatives of DMT and psilocin".Acta Crystallographica Section E.75 (Pt 9):1316–1320.Bibcode:2019AcCrE..75.1316C.doi:10.1107/S2056989019011253.PMC 6727059.PMID 31523457.The synthesis of N-methyl-N-isopropyltryptamine (MiPT) was reported in 1981 (Repke et al., 1981). In 1985, Repke and co-workers reported that of the compounds in the series of N,N-dialkyl-4-hydroxytryptamines, the N-methyl-N-isopropyl derivative (4-HO-MiPT) is the most potent based upon qualitative effects on humans (Repke et al., 1985).
  5. ^abRepke DB, Ferguson WJ, Bates DK (1981). "Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-(N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols".Journal of Heterocyclic Chemistry.18 (1):175–179.doi:10.1002/jhet.5570180131.ISSN 0022-152X.
  6. ^abRepke DB, Grotjahn DB, Shulgin AT (July 1985). "Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents".J Med Chem.28 (7):892–896.doi:10.1021/jm00145a007.PMID 4009612.
  7. ^abGlennon RA, Jacyno JM, Young R, McKenney JD, Nelson D (January 1984). "Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines".Journal of Medicinal Chemistry.27 (1):41–45.doi:10.1021/jm00367a008.PMID 6581313.
  8. ^abhttps://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2005
  9. ^abShulgin 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. Archived fromthe original on 13 July 2025.
  10. ^abJacob P, Shulgin AT (1994)."Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". In Lin GC, Glennon RA (eds.).Hallucinogens: An Update(PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 146. National Institute on Drug Abuse. pp. 74–91.PMID 8742795. Archived fromthe original on 13 July 2025.
  11. ^Cozzi NV, Gopalakrishnan A, Anderson LL, Feih JT, Shulgin AT, Daley PF, Ruoho AE (December 2009). "Dimethyltryptamine and other hallucinogenic tryptamines exhibit substrate behavior at the serotonin uptake transporter and the vesicle monoamine transporter".J Neural Transm (Vienna).116 (12):1591–1599.doi:10.1007/s00702-009-0308-8.PMID 19756361.
  12. ^"Controlled Drugs and Substances Act".Department of Justice Canada. Retrieved19 January 2026.
  13. ^"Folkhälsomyndigheten föreslår att 20 ämnen klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 15 May 2019.
  14. ^"MIPT".АИПСИН (in Russian). Retrieved6 January 2026.
  15. ^abOrange Book: List of Controlled Substances and Regulated Chemicals (January 2026)(PDF),United States: U.S.Department of Justice:Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
  16. ^"21 U.S. Code § 841 - Prohibited acts A",LII / Legal Information Institute, retrieved2016-08-02

External links

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