4-HO-MPT
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| 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 |
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| Formula | C14H20N2O |
| Molar mass | 232.327 g·mol−1 |
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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.[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]
It acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor.[3][4] The drug produces psychedelic-like effects in animals.[2][3]
4-HO-MPT was first described in the scientific literature by 1981.[5] It was encountered as a novel designer drug by 2021.[6]
Use and effects
[edit]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
[edit]Pharmacology
[edit]Pharmacodynamics
[edit]| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 106–910 (Ki) 490 (EC50) 90% (Emax) |
| 5-HT1B | 224 |
| 5-HT1D | 170 |
| 5-HT1E | 246 |
| 5-HT2A | 71–114 (Ki) 3.8–64a (EC50) 53%a–98% (Emax) |
| 5-HT2B | 8 (Ki) 3.4 (EC50) 58% (Emax) |
| 5-HT2C | 150–203 (Ki) 46–66a (EC50) 83–100%a (Emax) |
| 5-HT5A | 664 |
| 5-HT6 | 48 |
| 5-HT7 | 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 |
| SERT | 910–1,180 (Ki) 575 (IC50) |
| DAT | IA |
| Notes: The smaller the value, the more avidly the drug binds to the site. Footnotes: a = Stimulation of IP1 formation. Sources: [3][4][7] | |
4-HO-MPT acts as a potent agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[3][4] 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.[3][8] 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.[3] It also interacts with other serotonin receptors such as 5-HT6 and 5-HT7 receptors with high affinity and non-serotonergic targets.[4] Additionally it inhibits serotonin transporter.[9]
4-HO-MPT produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[2][3]
Chemistry
[edit]Synthesis
[edit]The chemical synthesis of 4-HO-MPT has been described.[1]
Analogues
[edit]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.[1]
History
[edit]4-HO-MPT was first described in the scientific literature by David Repke and colleagues in 1981.[5] Subsequently, its effects in humans were 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 by 2021.[6]
Society and culture
[edit]Legal status
[edit]International
[edit]4-HO-MPT is not scheduled by the United Nations' Convention on Psychotropic Substances.[10]
United States
[edit]4-HO-MPT is not scheduled at the federal level in the United States,[11] 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.[12]
See also
[edit]References
[edit]- ^ a b c d e f g h i 4-HO-MPT Entry in TIHKAL @ Erowid.org
- ^ a b c d e f g Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF). Neuropharmacology. 167 107933. doi:10.1016/j.neuropharm.2019.107933. PMC 9191653. PMID 31917152.
Table 4 Human potency data for selected hallucinogens. [...]
- ^ a b c d e f g Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, et al. (April 2021). "Investigation of the Structure-Activity Relationships of Psilocybin Analogues". ACS Pharmacology & Translational Science. 4 (2): 533–542. doi:10.1021/acsptsci.0c00176. PMC 8033608. PMID 33860183.
- ^ a b c d Glatfelter GC, Naeem M, Pham DN, Golen JA, Chadeayne AR, Manke DR, et al. (April 2023). "Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice". ACS Pharmacology & Translational Science. 6 (4): 567–577. doi:10.1021/acsptsci.2c00222. PMC 10111620. PMID 37082754.
- ^ a b 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. Retrieved 9 October 2025.
- ^ a b Tanaka R, Kawamura M, Hakamatsuka T, Kikura-Hanajiri R (2021). "Identification of six tryptamine derivatives as designer drugs in illegal products". Forensic Toxicology. 39 (1): 248–258. doi:10.1007/s11419-020-00556-5. ISSN 1860-8965. Retrieved 9 October 2025.
- ^ Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, et al. (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. 385 (1): 62–75. doi:10.1124/jpet.122.001454. PMC 10029822. PMID 36669875.
- ^ Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, et al. (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. 385 (1): 62–75. doi:10.1124/jpet.122.001454. PMC 10029822. PMID 36669875.
- ^ Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, et al. (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. 385 (1): 62–75. doi:10.1124/jpet.122.001454. PMC 10029822. PMID 36669875.
- ^ "Convention on Psychotropic Substances, 1971". Archived from the original on 2022-01-19. Retrieved 2016-06-10.
- ^ "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2016-06-10.
- ^ Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary