4-Hydroxy-N-methyl-(α,N-trimethylene)tryptamine

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IUPAC_name = (R)-3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole


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PubChem = 10466404
C=14 | H=17 | N=2 | O=1
molecular_weight = 229.297 g/mol
smiles = c3ccc2ncc(c2c3O)CC1CCCN1C
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4-Hydroxy-N-methyl-(α,N-trimethylene)tryptamine (also known as (R)-3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole and Lucigenol) is a tryptamine derivative that is a hallucinogenic 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 hallucinogen DOI, and has two enantiomers, with only the (R) enantiomer being active. [Gerasimov M, Marona-Lewicka D, Kurrasch-Orbaugh DM, Qandil AM, Nichols DE. Further studies on oxygenated tryptamines with LSD-like activity incorporating a chiral pyrrolidine moiety into the side chain. "Journal of Medicinal Chemistry". 1999 Oct 7;42(20):4257-63. PMID 10514296]

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