Chemistry:MiPT

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Methylisopropyltryptamine (MiPT), also known as N-methyl-N-isopropyltryptamine, is a psychedelic drug of the tryptamine family related to other psychedelics like dimethyltryptamine (DMT) and diisopropyltryptamine (DiPT).[1] It is taken orally.[1]

The drug acts as a serotonin receptor modulator, including as an agonist of the serotonin 5-HT2A receptor.[2][3] Derivatives of MiPT include 4-HO-MiPT (miprocin) and 5-MeO-MiPT (moxy).[1]

MiPT was first described by David Repke and colleagues in 1981.[4][5][6][7] It was subsequently evaluated and described in Alexander Shulgin's 1997 book TiHKAL (Tryptamines I Have Known and Loved).[1] MiPT was encountered as a novel designer drug by 2005.[8]

Use and effects

In his book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin lists MiPT's dose as 10 to 25 mg orally and its duration as 3 to 4 hours.[1][9][10] A dose of 20 mg by insufflation was also reported.[1] Its onset 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 most potent of the simple N,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 on thoughts that were typically psychedelic, enhancement of visual 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 other visual effects (including no wave-forms, color distortion, object shape changes, or closed-eye imagery), auditory effects such as enhanced sound discrimination, hearing and skin being more sensitive, and minor sensory changes in general.[1] It was said to emphasize "psychedelic" effects over "hallucinogenic" effects.[1] Other effects included feeling good, excitement, stimulation, feeling alert, restlessness, and trailing insomnia for 6 to 8 hours.[1] Physical effects included pupil dilation, dizziness, dry mouth, and muscle tension.[1]

Interactions

Pharmacology

Pharmacodynamics

MiPT acts as a serotonin receptor modulator.[2][3] It shows affinity for the serotonin 5-HT2A, 5-HT1A, and 5-HT2B receptors.[3] The drug acts as a potent partial agonist of the serotonin 5-HT2A receptor.[2] It shows weak affinity for the serotonin transporter (SERT) and vesicular monoamine transporter 2 (VMAT2),[11] but does not act as a monoamine reuptake inhibitor or releasing agent even at very high concentrations.[2]

Chemistry

Properties

Crystal structure

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

Synthesis

The chemical synthesis of MiPT has been described.[1]

Analogues

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

History

MiPT was first synthesized and described by David Repke and colleagues in 1981.[4][5][6][7] Subsequently, MiPT was further described by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved).[1] The drug was encountered as a novel designer drug in Europe by 2005.[8]

Society and culture

Canada

MiPT is not a controlled substance in Canada as of 2025.[12]

Sweden

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

United States

In the United States, MiPT not an explicitly controlled substance.[15] However, as an isomer of diethyltryptamine (DET), it may be considered a Schedule I controlled substance similarly.[15] In addition, the purchase, sale, or possession for human consumption of MiPT could be prosecuted under the Federal Analogue Act.[16]

See also

References

  1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 1.12 1.13 1.14 1.15 1.16 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml.  https://www.erowid.org/library/books_online/tihkal/tihkal47.shtml
  2. ↑ 2.0 2.1 2.2 2.3 "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl) 231 (21): 4135–4144. October 2014. doi:10.1007/s00213-014-3557-7. PMID 24800892. 
  3. ↑ 3.0 3.1 3.2 "Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes". Neuropharmacology 29 (3): 193–198. March 1990. doi:10.1016/0028-3908(90)90001-8. PMID 2139186. 
  4. ↑ 4.0 4.1 4.2 "The fumarate salts of the N-isopropyl-N-methyl derivatives of DMT and psilocin". Acta Crystallographica Section E 75 (Pt 9): 1316–1320. September 2019. doi:10.1107/S2056989019011253. PMID 31523457. Bibcode: 2019AcCrE..75.1316C. "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. ↑ 5.0 5.1 "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. 1981. doi:10.1002/jhet.5570180131. ISSN 0022-152X. 
  6. ↑ 6.0 6.1 "Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents". J Med Chem 28 (7): 892–896. July 1985. doi:10.1021/jm00145a007. PMID 4009612. 
  7. ↑ 7.0 7.1 "Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines". Journal of Medicinal Chemistry 27 (1): 41–45. January 1984. doi:10.1021/jm00367a008. PMID 6581313. 
  8. ↑ 8.0 8.1 https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2005
  9. ↑ 9.0 9.1 "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://bibliography.maps.org/resources/download/12634. 
  10. ↑ 10.0 10.1 "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". Hallucinogens: An Update. National Institute on Drug Abuse Research Monograph Series. 146. National Institute on Drug Abuse. 1994. pp. 74–91. https://bibliography.maps.org/resources/download/11534. 
  11. ↑ "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. December 2009. doi:10.1007/s00702-009-0308-8. PMID 19756361. 
  12. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  13. ↑ "Folkhälsomyndigheten föreslår att 20 ämnen klassas som narkotika eller hälsofarlig vara" (in sv). Folkhälsomyndigheten. 15 May 2019. https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2019/maj/folkhalsomyndigheten-foreslar-att-20-amnen-klassas-som-narkotika-eller-halsofarlig-vara/. 
  14. ↑ "MIPT" (in ru). https://aipsin.com/newsubstance/151/. 
  15. ↑ 15.0 15.1 Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026, https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf 
  16. ↑ "21 U.S. Code § 841 - Prohibited acts A". https://www.law.cornell.edu/uscode/text/21/841. 



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