4-HO-MPMI

4-Hydroxy-N-methyl-(α,N-trimethylene)tryptamine
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 ;
PubChem CID	10466404;
ChemSpider	8641815 ;
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 ; Key:XYRKPZYRLSWABB-LLVKDONJSA-N ;
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4-HO-MPMI (also known as 4-Hydroxy-N-methyl-(α,N-trimethylene)-tryptamine or lucigenol) is a tryptamine derivative that is a psychedelic drug. It was developed by the team led by David Nichols from Purdue University in the late 1990s. This compound produces hallucinogen-appropriate responding in animal tests with a similar potency to the amphetamine-derived psychedelic DOI, and has two enantiomers, with only the (R)-enantiomer being active.^[1]

The binding affinity for 5-HT2A receptor is 13 ± 2 nM (Ki [125I]DOI). It is reported at doses starting at 0.5 mg and 1.0-1.5 mg seem to be psychedelic doses. The duration it is reported between six and eight hours. Available (anecdotal) data on subjective effects report open- and closed-eye visuals, sedation, and anxiety.^[2]

References

^ 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.
^ "Lucigenol Info - Hip Forums". Archived from the original on 2011-07-11. Retrieved 2010-08-02.