MiPT

Last updated
MiPT
MIPT.svg
Methylisopropyltryptamine.png
Clinical data
Other namesMiPT; N-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
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 was first described by David Repke and colleagues in 1981 [2] [3] [4] [5] and was subsequently evaluated and described in Alexander Shulgin's 1997 book TiHKAL (Tryptamines I Have Known and Loved). [6]

Contents

Use and effects

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. [1]

In TiHKAL, [6] the subjective experience is reported to be biased towards mental (psychedelic/entheogenic) effects, with mild perceptual (sensory/hallucinogenic) alterations relative to other tryptamines. [1] 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

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. [7]

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. [2] [3] [4] [5]

Society and culture

Sweden

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

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. [9]

See also

References

  1. 1 2 3 4 Shulgin A, Shulgin A (September 1997). "#47 MIPT". Isomer Design. Transform Press. Retrieved 28 November 2023.
  2. 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).
  3. 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.
  4. 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.
  5. 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.
  6. 1 2 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
  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
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.