Chemistry:4-HO-MPT

From HandWiki

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]

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 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

Pharmacology

Pharmacodynamics

4-HO-MPT acts as a potent agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[3][4] It is a 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] 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 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

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

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 4-HO-MPT Entry in TIHKAL @ Erowid.org
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species". Neuropharmacology 167. May 2020. doi:10.1016/j.neuropharm.2019.107933. PMID 31917152. PMC 9191653. http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf. "Table 4 Human potency data for selected hallucinogens. [...]". 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 "Investigation of the Structure-Activity Relationships of Psilocybin Analogues". ACS Pharmacology & Translational Science 4 (2): 533–542. April 2021. doi:10.1021/acsptsci.0c00176. PMID 33860183. 
  4. ↑ 4.0 4.1 4.2 "Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice". ACS Pharmacology & Translational Science 6 (4): 567–577. April 2023. doi:10.1021/acsptsci.2c00222. PMID 37082754. 
  5. ↑ "Identification of six tryptamine derivatives as designer drugs in illegal products". Forensic Toxicology 39 (1): 248–258. 2021. doi:10.1007/s11419-020-00556-5. ISSN 1860-8965. http://link.springer.com/10.1007/s11419-020-00556-5. Retrieved 9 October 2025. 
  6. ↑ "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. 1981. doi:10.1002/jhet.5570180131. ISSN 0022-152X. https://onlinelibrary.wiley.com/doi/10.1002/jhet.5570180131. Retrieved 9 October 2025. 
  7. ↑ "Convention on Psychotropic Substances, 1971". https://www.unodc.org/unodc/en/commissions/CND/conventions.html. 
  8. ↑ "§1308.11 Schedule I.". http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm. 
  9. ↑ Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary

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