4-HO-MPT

4-HO-MPT, also knwon as 4-hydroxy-N-methyl-N-propyltryptamine or as meprocin, is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families.^[1][2] It is a higher homologue of psilocin (4-HO-DMT) as well as the 4-hydroxyl analogue of N-methyl-N-propyltryptamine (MPT).^[1][2] The drug is taken orally.^[1][2]

4-HO-MPT

Clinical data
Other names	4-OH-MPT; 4-Hydroxy-N-methyl-N-propyltryptamine; Meprocin
Routes of administration	Oral[1][2]
Drug class	Non-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Identifiers
IUPAC name 3-[2-[methyl(propyl)amino]ethyl]-1H-indol-4-ol
CAS Number	763035-03-6 Y (free base) 77872-42-5 (hydrochloride)
PubChem CID	21786584
ChemSpider	10513074 Y
UNII	37A55H0XW4
CompTox Dashboard (EPA)	DTXSID90904008
Chemical and physical data
Formula	C14H20N2O
Molar mass	232.327 g·mol−1
3D model (JSmol)	Interactive image
SMILES OC1=CC=CC2=C1C(CCN(C)CCC)=CN2
InChI InChI=1S/C14H20N2O/c1-3-8-16(2)9-7-11-10-15-12-5-4-6-13(17)14(11)12/h4-6,10,15,17H,3,7-9H2,1-2H3 Y Key:XFQDDPQGBLSNCN-UHFFFAOYSA-N Y
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It acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT_2A receptor.^[3][4] The drug produces psychedelic-like effects in animals.^[2][3]

4-HO-MPT has been encountered as a novel designer drug.^[5]

Use and effects

The dose and duration of 4-HO-MPT are listed as "unknown" in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved).^[1] In more recent publications, the dose has been reported to be 20 to 30 mg orally, with a mean dose of 25 mg.^[2] In a single trial of 8 mg 4-HO-MPT hydrochloride orally from TiHKAL, it was described as producing visual distortion, vertigo, and slight insomnia.^[1]

Interactions

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

Pharmacology

Pharmacodynamics

4-HO-MPT acts as a potent agonist of the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors.^[3][4] It is a full agonist of the serotonin 5-HT_2A receptor, a moderate-efficacy partial agonist of the serotonin 5-HT_2B receptor, and a high-efficacy partial agonist of the serotonin 5-HT_2C receptor.^[3] The drug has more than an order of magnitude higher potency as an agonist of the serotonin 5-HT_2A and 5-HT_2B receptors than as an agonist of the serotonin 5-HT_2C receptor.^[3] It also interacts with other serotonin receptors and targets.^[4] 4-HO-MPT produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.^[2][3]

History

4-HO-MPT was first described in the scientific literature by David Repke and colleagues in 1981.^[6] Subsequently, its effects in humans were described by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved).^[1]

Society and culture

Legal status

International

4-HO-MPT is not scheduled by the United Nations' Convention on Psychotropic Substances.^[7]

United States

4-HO-MPT is not scheduled at the federal level in the United States,^[8] but it is possible that 4-HO-MPT could legally be considered an analog of psilocin, in which case, sales or possession with intent for human consumption could potentially be prosecuted under the Federal Analogue Act.^[9]

See also

• Substituted tryptamine