{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 449774285 | drug_name = | image = Lucigenol (4-HO-MPMI).svg | image_class = skin-invert-image | width = 185px | image2 = 4-HO-MPMI 3D.png | image_class2 = bg-transparent | width2 = 225px
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<!-- Legal status --> | legal_AU = | legal_CA = | legal_DE = NpSG | legal_UK = Class A | legal_US = | legal_status =
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<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 250672-65-2 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 46OU9HLZ35 | PubChem = 53441196 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 21376515 | synonyms = 4-Hydroxy-''N''-methyl-(α,''N''-trimethylene)tryptamine; Lucigenol
<!-- Chemical data --> | IUPAC_name = 3-[(1-methylpyrrolidin-2-yl)methyl]-1''H''-indol-4-ol | C=14 | H=17 | N=2 | O=1 | SMILES = CN1CCCC1CC2=CNC3=C2C(=CC=C3)O | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = XYRKPZYRLSWABB-UHFFFAOYSA-N
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'''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.<ref name="GerasimovMarona-LewickaKurrasch-Orbaugh1999" />
==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
==Pharmacology== ===Pharmacodynamics=== thumb|left|150px|class=skin-invert-image|(''R'')-4-HO-MPMI.
The affinity (K<sub>i</sub>) of 4-HO-MPMI for the serotonin 5-HT<sub>2A</sub> receptor has been found to be 13{{nbsp}}nM.<ref name="GerasimovMarona-LewickaKurrasch-Orbaugh1999" /> It produces psychedelic-appropriate responding in animal tests with similar potency as DOI.<ref name="GerasimovMarona-LewickaKurrasch-Orbaugh1999" /> The drug has two enantiomers, with only the (''R'')-enantiomer being active.<ref name="GerasimovMarona-LewickaKurrasch-Orbaugh1999">{{cite journal | doi = 10.1021/jm990325u | vauthors = Gerasimov M, Marona-Lewicka D, Kurrasch-Orbaugh DM, Qandil AM, Nichols DE | title = Further studies on oxygenated tryptamines with LSD-like activity incorporating a chiral pyrrolidine moiety into the side chain | journal = Journal of Medicinal Chemistry | year = 1999 | volume = 42 | issue = 20 | pages = 4257–4263 | pmid = 10514296| citeseerx = 10.1.1.690.4941 }}</ref>
==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.<ref name="GerasimovMarona-LewickaKurrasch-Orbaugh1999" />
==Society and culture== ===Legal status=== ====Canada==== 4-HO-MPMI is not a controlled substance in Canada as of 2025.<ref name="CDSA">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=19 January 2026}}</ref>
==See also== * Pyrrolidinylmethylindole * Cyclized tryptamine * MSP-2020
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/5376 Lucigenol (4-HO-MPMI) – Isomer Design] * [https://web.archive.org/web/20110711171020/http://www.hipforums.com/newforums/showthread.php?t=315326 Lucigenol Info - Hip Forums]
{{Psychedelics}} {{Serotonin receptor modulators}} {{Tryptamines}}
{{DEFAULTSORT:4-HO-MPMI}}
Category:Alpha-Alkyltryptamines Category:David E. Nichols Category:Designer drugs Category:N,N-Dialkyltryptamines Category:4-Hydroxytryptamines Category:Pyrrolidinylmethylindoles Category:Psychedelic tryptamines