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4-HO-MPT
| Field | Value | |||
|---|---|---|---|---|
| Verifiedfields | verified | |||
| Watchedfields | verified | |||
| verifiedrevid | 477222052 | |||
| image | 4-HO-MPT.svg | |||
| image_class | skin-invert-image | |||
| width | 200px | |||
| image2 | 4-HO-MPT 3D.png | |||
| image_class2 | bg-transparent | |||
| width2 | 200px | |||
| routes_of_administration | Oral | |||
| class | Non-selective serotonin receptor agonist; Serotonin [5-HT2A receptor](5-ht2a-receptor) agonist; Serotonergic psychedelic; Hallucinogen | |||
| ATC_prefix | None | |||
| CAS_number_Ref | ||||
| CAS_number | 763035-03-6 | |||
| CAS_supplemental | (free base) | |||
| 77872-42-5 (hydrochloride) | ||||
| PubChem | 21786584 | |||
| ChemSpiderID_Ref | ||||
| ChemSpiderID | 10513074 | |||
| UNII | 37A55H0XW4 | |||
| synonyms | 4-OH-MPT; 4-Hydroxy-*N*-methyl-*N*-propyltryptamine; Meprocin | |||
| IUPAC_name | 3-[2-[methyl(propyl)amino]ethyl]-1*H*-indol-4-ol | |||
| C | 14 | H=20 | N=2 | O=1 |
| SMILES | OC1=CC=CC2=C1C(CCN(C)CCC)=CN2 | |||
| StdInChI_Ref | ||||
| StdInChI | 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 | |||
| StdInChIKey_Ref | ||||
| StdInChIKey | XFQDDPQGBLSNCN-UHFFFAOYSA-N |
| Drugs.com =
| elimination_half-life =
77872-42-5 (hydrochloride)
4-HO-MPT, also known as 4-hydroxy-N-methyl-N-propyltryptamine or as meprocin, is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families. It is a higher homologue of psilocin (4-HO-DMT) as well as the 4-hydroxyl analogue of N-methyl-N-propyltryptamine (MPT). The drug is taken orally.
It acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor. The drug produces psychedelic-like effects in animals.
4-HO-MPT was first described in the scientific literature by 1981. It was encountered as a novel designer drug by 2021.
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). In more recent publications, the dose has been reported to be 20 to 30mg orally, with a mean dose of 25mg. In a single trial of 8mg 4-HO-MPT hydrochloride orally from TiHKAL, it was described as producing visual distortion, vertigo, and slight insomnia.
Interactions
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| [5-HT1A](5-ht1a-receptor) | 106–910 (Ki) |
| 490 () | |
| 90% () | |
| [5-HT1B](5-ht1b-receptor) | 224 |
| [5-HT1D](5-ht1d-receptor) | 170 |
| [5-HT1E](5-ht1e-receptor) | 246 |
| [5-HT2A](5-ht2a-receptor) | 71–114 (Ki) |
| 3.8–64a (EC50) | |
| 53%a–98% (Emax) | |
| [5-HT2B](5-ht2b-receptor) | 8 (Ki) |
| 3.4 (EC50) | |
| 58% (Emax) | |
| [5-HT2C](5-ht2c-receptor) | 150–203 (Ki) |
| 46–66a (EC50) | |
| 83–100%a (Emax) | |
| [5-HT5A](5-ht5a-receptor) | 664 |
| [5-HT6](5-ht6-receptor) | 48 |
| [5-HT7](5-ht7-receptor) | 99 |
| α2A | 3,625 |
| α2B | 1,844 |
| α2C | IA |
| D2 | IA |
| D3 | 921 |
| D4, D5 | IA |
| H1 | 92 |
| H2 | IA |
| M4 | IA |
| σ1 | 891 |
| σ2 | 1,166 |
| KOR | IA |
| NR2B | 3,658 |
| 910–1,180 (Ki) | |
| 575 () | |
| IA | |
| **Notes:** The smaller the value, the more avidly the drug binds to the site. **Footnotes:** a = Stimulation of formation. **Sources: ** |
4-HO-MPT acts as a potent agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. It is a partial or full agonist of the serotonin 5-HT2A receptor, a moderate-efficacy partial agonist of the serotonin 5-HT2B receptor, and a high-efficacy partial agonist of the serotonin 5-HT2C receptor.**** The drug has more than an order of magnitude higher potency as an agonist of the serotonin 5-HT2A and 5-HT2B receptors than as an agonist of the serotonin 5-HT2C receptor. It also interacts with other serotonin receptors such as 5-HT6 and 5-HT7 receptors with high affinity and non-serotonergic targets. Additionally it inhibits serotonin transporter.****
4-HO-MPT produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.
Chemistry
Synthesis
The chemical synthesis of 4-HO-MPT has been described.
Analogues
Analogues of 4-HO-MPT include methylpropyltryptamine (MPT), 4-AcO-MPT, 5-MeO-MPT, psilocin (4-HO-DMT), 4-HO-DET (ethocin), 4-HO-DPT (deprocin), 4-HO-MET (metocin), and 4-HO-PiPT (iprocin), among others.
History
4-HO-MPT was first described in the scientific literature by David Repke and colleagues in 1981. Subsequently, its effects in humans were described by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved). The drug was encountered as a novel designer drug by 2021.
Society and culture
Legal status
International
4-HO-MPT is not scheduled by the United Nations' Convention on Psychotropic Substances.
Canada
4-HO-MPT is not an explicitly nor implicitly controlled substance in Canada as of 2025.
United States
4-HO-MPT is not scheduled at the federal level in the United States, 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.
References
References
- (2021). "Identification of six tryptamine derivatives as designer drugs in illegal products". Forensic Toxicology.
- (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species". Neuropharmacology.
- (April 2023). "Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter". The Journal of Pharmacology and Experimental Therapeutics.
- (April 2021). "Investigation of the Structure-Activity Relationships of Psilocybin Analogues". ACS Pharmacology & Translational Science.
- (April 2023). "Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice". ACS Pharmacology & Translational Science.
- (April 2023). "Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter". The Journal of Pharmacology and Experimental Therapeutics.
- (April 2023). "Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter". The Journal of Pharmacology and Experimental Therapeutics.
- (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.
- [https://www.erowid.org/library/books_online/tihkal/tihkal23.shtml 4-HO-MPT Entry in ''TIHKAL'' @ Erowid.org]
- "Convention on Psychotropic Substances, 1971".
- (5 December 2025). "Controlled Drugs and Substances Act".
- "§1308.11 Schedule I.".
- [https://www.erowid.org/psychoactives/law/analog/analog_info1.shtml Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary]
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