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4-HO-MPMI

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4-HO-MPMI
Clinical data
Other names4-Hydroxy-N-methyl-(α,N-trimethylene)tryptamine; Lucigenol
ATC code
  • None
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Identifiers
  • 3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indol-4-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H17N2O
Molar mass229.303 g·mol−1
3D model (JSmol)
  • CN1CCCC1CC2=CNC3=C2C(=CC=C3)O
  • InChI=1S/C14H18N2O/c1-16-7-3-4-11(16)8-10-9-15-12-5-2-6-13(17)14(10)12/h2,5-6,9,11,15,17H,3-4,7-8H2,1H3 ☒N
  • Key:XYRKPZYRLSWABB-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

4-HO-MPMI, also known as 4-hydroxy-N-methyl-(α,N-trimethylene)tryptamine or as lucigenol, is a psychedelic drug of the pyrrolidinylmethylindole and cyclized tryptamine families.[1]

Interactions

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

Pharmacology

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Pharmacodynamics

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(R)-4-HO-MPMI.

The affinity (Ki) of 4-HO-MPMI for the serotonin 5-HT2A receptor has been found to be 13 nM.[1] It produces psychedelic-appropriate responding in animal tests with similar potency as DOI.[1] The drug has two enantiomers, with only the (R)-enantiomer being active.[1]

Chemistry

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Analogues

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Analogues of 4-HO-MPMI include MPMI, 5-MeO-MPMI, 5F-MPMI, CP-135,807, 4-HO-McPeT, 4-HO-pyr-T, and SN-22, among others.

History

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4-HO-MPMI was developed by the team led by David E. Nichols from Purdue University in the late 1990s.[1]

Society and culture

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Canada

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4-HO-MPMI is not a controlled substance in Canada as of 2025.[2]

See also

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References

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  1. ^ a b c d e Gerasimov M, Marona-Lewicka D, Kurrasch-Orbaugh DM, Qandil AM, Nichols DE (1999). "Further studies on oxygenated tryptamines with LSD-like activity incorporating a chiral pyrrolidine moiety into the side chain". Journal of Medicinal Chemistry. 42 (20): 4257–4263. CiteSeerX 10.1.1.690.4941. doi:10.1021/jm990325u. PMID 10514296.
  2. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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