Edge Rewrite
restyle Source code View original
// HTMLRewriter · presentation

This page was redesigned at the edge.

Cloudflare fetched the original article and streamed it through HTMLRewriter to apply an entirely new visual system without rebuilding the source page.

Jump to content

4-HO-MPMI

From Wikipedia, the free encyclopedia
(Redirected from Lucigenol)
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 X markN
  • Key:XYRKPZYRLSWABB-UHFFFAOYSA-N X markN
 X markNcheckY (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

[edit]

Pharmacology

[edit]

Pharmacodynamics

[edit]
(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

[edit]

Analogues

[edit]

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

[edit]

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

Society and culture

[edit]
[edit]

Canada

[edit]

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

See also

[edit]

References

[edit]
  1. 1 2 3 4 5 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.
[edit]
Retrieved from "https://en.wikipedia.org/w/index.php?title=4-HO-MPMI&oldid=1338242489"