Jump to content

MiPT

From Wikipedia, the free encyclopedia
(Redirected from Methylisopropyltryptamine)
MiPT
Clinical data
Other namesN-Methyl-N-isopropyltryptamine
ATC code
  • None
Legal status
Legal status
  • AU: Unscheduled
  • CA: Unscheduled
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • US: Unscheduled
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
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)

N-Methyl-N-isopropyltryptamine (MiPT) is a psychedelic tryptamine, closely related to DMT, DiPT and miprocin. It was first described by David Repke and colleagues in 1981[1][2][3][4] and was subsequently evaluated and described in Alexander Shulgin's 1997 book TiHKAL (Tryptamines I Have Known and Loved).[5]

Use and effects

[edit]

Moderate effects have been reported at 10 to 25 mg ingested orally, with effects lasting 4 to 8 hours. One of the test subjects in TiHKAL reported moderate effects at 20 mg ingested intranasally.[6]

In TiHKAL,[5] the subjective experience is reported to be biased towards mental (psychedelic/entheogenic) effects, with mild perceptual (sensory/hallucinogenic) alterations relative to other tryptamines.[6] Subjects reported enhancement of the visual field (brightened and modulated color perception) but a lack of visual distortion typical of tryptamines such as psilocin. Enhancement of auditory perception was also noted. Documented physical effects include stimulation, dry mouth, and muscle tension.

Interactions

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

Chemistry

[edit]

MiPT is the N-isopropyl analogue of DMT and the N-methyl analogue of DiPT.

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

In August 2019, Chadeayne et al. solved the crystal structure of fumarate salt of MiPT.[7]

History

[edit]

MiPT was first synthesized and described by David Repke and colleagues in 1981.[1][2][3][4]

Society and culture

[edit]
[edit]

Sweden

[edit]

Sweden's public health agency suggested classifying MiPT as a hazardous substance, on May 15, 2019.[8]

United States

[edit]

In the United States, MiPT is unscheduled but purchase, sale, or possession for human consumption could be prosecuted under the Federal Analogue Act.[9]

See also

[edit]

References

[edit]
  1. ^ a b 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).
  2. ^ a b 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.
  3. ^ a b 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.
  4. ^ a b 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.
  5. ^ a b Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  6. ^ a b Shulgin A, Shulgin A (September 1997). "#47 MIPT". Isomer Design. Transform Press. Retrieved 28 November 2023.
  7. ^ 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.
  8. ^ "Folkhälsomyndigheten föreslår att 20 ämnen klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 15 May 2019.
  9. ^ "21 U.S. Code § 841 - Prohibited acts A", LII / Legal Information Institute, retrieved 2016-08-02
[edit]
Retrieved from "https://en.wikipedia.org/w/index.php?title=MiPT&oldid=1317729616"