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MiPT

Chemical compound


Chemical compound

FieldValue
verifiedrevid415855405
imageMIPT.svg
image_classskin-invert-image
width225px
image2Methylisopropyltryptamine.png
image_class2bg-transparent
width2225px
routes_of_administrationOral
classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC_prefixNone
legal_AUUnscheduled
legal_CAUnscheduled
legal_DENpSG
legal_UKClass A
legal_USUnscheduled
onsetOral: 30 minutes
Insufflation:
duration_of_action3–4 hours
CAS_number96096-52-5
PubChem29935323
ChemSpiderID_Ref
ChemSpiderID21106353
ChEMBL_Ref
ChEMBL353728
UNIIJO3SCR302A
synonymsMiPT; *N*-Methyl-*N*-isopropyltryptamine
IUPAC_name*N*-[2-(1*H*-indol-3-yl)ethyl]-*N*-methylpropan-2-amine
C14H = 20N = 2
SMILESCC(C)N(C)CCc1c[nH]c2ccccc12
StdInChI_Ref
StdInChI1S/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
StdInChIKey_Ref
StdInChIKeyKTQJVAJLJZIKKD-UHFFFAOYSA-N

Insufflation: | elimination_half-life =

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). It is taken orally.

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

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

Use and effects

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

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. It was said to emphasize "psychedelic" effects over "hallucinogenic" effects. Other effects included feeling good, excitement, stimulation, feeling alert, restlessness, and trailing insomnia for 6 to 8hours. Physical effects included pupil dilation, dizziness, dry mouth, and muscle tension.

Interactions

Pharmacology

Pharmacodynamics

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

Chemistry

Properties

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

Crystal structure

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

Synthesis

The chemical synthesis of MiPT has been described.

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.

History

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

Society and culture

Canada

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

Sweden

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

United States

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

References

References

  1. {{CiteTiHKAL https://www.erowid.org/library/books_online/tihkal/tihkal47.shtml
  2. (September 2019). "The fumarate salts of the N-isopropyl-N-methyl derivatives of DMT and psilocin". Acta Crystallographica Section E.
  3. (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.
  4. (July 1985). "Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents". J Med Chem.
  5. (January 1984). "Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines". Journal of Medicinal Chemistry.
  6. https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2005
  7. (2003). "Hallucinogens: A Forensic Drug Handbook". Elsevier Science.
  8. (1994). "Hallucinogens: An Update". National Institute on Drug Abuse.
  9. (March 1990). "Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes". Neuropharmacology.
  10. (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl).
  11. (December 2009). "Dimethyltryptamine and other hallucinogenic tryptamines exhibit substrate behavior at the serotonin uptake transporter and the vesicle monoamine transporter". J Neural Transm (Vienna).
  12. "Controlled Drugs and Substances Act".
  13. (15 May 2019). "Folkhälsomyndigheten föreslår att 20 ämnen klassas som narkotika eller hälsofarlig vara". Folkhälsomyndigheten.
  14. "MIPT".
  15. (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.
  16. "21 U.S. Code § 841 - Prohibited acts A".
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