4-HO-MPMI

4-HO-MPMI

Clinical data
Other names	4-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
IUPAC name 3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indol-4-ol
CAS Number	250672-65-2 Y
PubChem CID	53441196
ChemSpider	21376515 N
UNII	46OU9HLZ35
CompTox Dashboard (EPA)	DTXSID80440389
Chemical and physical data
Formula	C14H17N2O
Molar mass	229.303 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN1CCCC1CC2=CNC3=C2C(=CC=C3)O
InChI 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
NY (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

The affinity (K_i) of 4-HO-MPMI for the serotonin 5-HT_2A 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

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.

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

4-HO-MPMI is not a controlled substance in Canada as of 2025.²