Wikipedia

4-HO-MPT

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]

4-HO-MPT
Clinical data
Other names4-OH-MPT; 4-Hydroxy-N-methyl-N-propyltryptamine; Meprocin
Routes of
administration		Oral[1][2]
Drug classNon-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 3-[2-[methyl(propyl)amino]ethyl]-1H-indol-4-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H20N2O
Molar mass232.327 g·mol−1
3D model (JSmol)
  • OC1=CC=CC2=C1C(CCN(C)CCC)=CN2
  • 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 checkY
  • Key:XFQDDPQGBLSNCN-UHFFFAOYSA-N checkY
  (verify)

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

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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

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Pharmacology

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Pharmacodynamics

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4-HO-MPT activities
TargetAffinity (Ki, nM)
5-HT1A106–910 (Ki)
490 (EC50Tooltip half-maximal effective concentration)
90% (EmaxTooltip maximal efficacy)
5-HT1B224
5-HT1D170
5-HT1E246
5-HT2A71–114 (Ki)
3.8–64a (EC50)
53%a–98% (Emax)
5-HT2B8 (Ki)
3.4 (EC50)
58% (Emax)
5-HT2C150–203 (Ki)
46–66a (EC50)
83–100%a (Emax)
5-HT5A664
5-HT648
5-HT799
α2A3,625
α2B1,844
α2C IA
D2IA
D3921
D4, D5IA
H192
H2IA
M4IA
σ1891
σ2 1,166
KOR IA
NR2B 3,658
SERTTooltip Serotonin transporter910–1,180 (Ki)
575 (IC50Tooltip half-maximal inhibitory concentration)
DATTooltip Dopamine transporterIA
Notes: The smaller the value, the more avidly the drug binds to the site. Footnotes: a = Stimulation of IP1Tooltip inositol phosphate 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][7] 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.[7]

4-HO-MPT produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[2][3]

Chemistry

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Synthesis

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The chemical synthesis of 4-HO-MPT has been described.[1]

Analogues

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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

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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

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International

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4-HO-MPT is not scheduled by the United Nations' Convention on Psychotropic Substances.[8]

Canada

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4-HO-MPT is not an explicitly nor implicitly controlled substance in Canada as of 2025.[9]

United States

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4-HO-MPT is not scheduled at the federal level in the United States,[10] 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.[11]

See also

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References

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  1. 1 2 3 4 5 6 7 8 9 4-HO-MPT Entry in TIHKAL @ Erowid.org
  2. 1 2 3 4 5 6 7 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. [...]
  3. 1 2 3 4 5 6 7 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.
  4. 1 2 3 4 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.
  5. 1 2 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.
  6. 1 2 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.
  7. 1 2 3 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.
  8. ↑ "Convention on Psychotropic Substances, 1971". Archived from the original on 2022-01-19. Retrieved 2016-06-10.
  9. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. 5 December 2025. Retrieved 20 January 2026.
  10. ↑ "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2016-06-10.
  11. ↑ Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary
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