4-HO-MPMI

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]

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 (R)-3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole
CAS Number	250672-65-2 Y
PubChem CID	10466404
ChemSpider	8641815 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 OC1=C2C(C[C@@]3([H])CCCN3C)=CNC2=CC=C1
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/t11-/m1/s1 N Key:XYRKPZYRLSWABB-LLVKDONJSA-N N
NY (what is this?)  (verify)

Interactions

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

Pharmacology

Pharmacodynamics

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]

Chemistry

Analogues

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

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

See also

• Pyrrolidinylmethylindole
• Cyclized tryptamine