MiPT

Not to be confused with MiPLA.

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]

MiPT

Clinical data
Other names	MiPT; 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
IUPAC name N-[2-(1H-indol-3-yl)ethyl]-N-methylpropan-2-amine
CAS Number	96096-52-5
PubChem CID	29935323
ChemSpider	21106353 Y
UNII	JO3SCR302A
ChEMBL	ChEMBL353728 Y
CompTox Dashboard (EPA)	DTXSID901024777
Chemical and physical data
Formula	C14H20N2
Molar mass	216.328 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)N(C)CCc1c[nH]c2ccccc12
InChI 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 Y Key:KTQJVAJLJZIKKD-UHFFFAOYSA-N Y
(verify)

The drug acts as a serotonin receptor modulator, including as an agonist of the serotonin 5-HT_2A 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

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

Pharmacology

Pharmacodynamics

MiPT acts as a serotonin receptor modulator.^[2][3] It shows affinity for the serotonin 5-HT_2A, 5-HT_1A, and 5-HT_2B receptors.^[3] The drug acts as a potent partial agonist of the serotonin 5-HT_2A 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

Legal status

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

• Substituted tryptamine
• ASR-3001 (5-MeO-iPALT)
• 2C-T-17