MiPT

Last updated
MiPT
MIPT.svg
Methylisopropyltryptamine.png
Clinical data
Other namesMiPT; N-Methyl-N-isopropyltryptamine
Routes of
administration 		Oral [1]
Drug class Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
  • AU:Unscheduled
  • CA:Unscheduled
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • US:Unscheduled
Pharmacokinetic data
Onset of action Oral: 30 minutes [1]
Insufflation: <1 minute [1]
Duration of action 3–4 hours [1]
Identifiers
  • N-[2-(1H-indol-3-yl)ethyl]-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C14H20N2
Molar mass 216.328 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 Yes check.svgY
  • Key:KTQJVAJLJZIKKD-UHFFFAOYSA-N Yes check.svgY
   (verify)

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]

Contents

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

MiPT base, unlike many other tryptamines in their freebase form, does not decompose rapidly in the presence of light or oxygen.[ citation needed ]

Crystal structure

In August 2019, Chadeayne et al. solved the crystal structure of fumarate salt of MiPT. [12]

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), and diisopropyltryptamine (DiPT), 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

Sweden

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

United States

In the United States, MiPT is unscheduled but purchase, sale, or possession for human consumption could be prosecuted under the Federal Analogue Act. [14]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 Shulgin, 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. 1 2 3 4 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". Psychopharmacology (Berl). 231 (21): 4135–4144. doi:10.1007/s00213-014-3557-7. PMC   4194234 . PMID   24800892.
  3. 1 2 3 McKenna 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. 1 2 Chadeayne AR, Pham DN, Golen JA, Manke DR (September 2019). "The fumarate salts of the N-isopropyl-N-methyl derivatives of DMT and psilocin". Acta Crystallogr E Crystallogr Commun. 75 (Pt 9): 1316–1320. 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. 1 2 Repke 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. 1 2 Repke 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. 1 2 Glennon 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. 1 2 https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2005
  9. 1 2 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. Archived from the original on 13 July 2025.
  10. 1 2 Jacob 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 from the 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. ↑ Chadeayne 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: Crystallographic Communications. 75 (Pt 9): 1316–1320. Bibcode:2019AcCrE..75.1316C. doi: 10.1107/S2056989019011253 . PMC   6727059 . PMID   31523457.
  13. ↑ "Folkhälsomyndigheten föreslår att 20 ämnen klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 15 May 2019.
  14. ↑ "21 U.S. Code § 841 - Prohibited acts A", LII / Legal Information Institute, retrieved 2016-08-02
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