5-Methoxy-N-methyl-(α,N-trimethylene)tryptamine

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IUPAC_name = (R)-3-(N-methylpyrrolidin-2-ylmethyl)-5-methoxyindole


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PubChem = 9881324
C=15 | H=19 | N=2 | O=1
molecular_weight = 243.323 g/mol
smiles = CN2CCCC2Cc(c1cc3OC)cnc1cc3
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5-Methoxy-N-methyl-(α,N-trimethylene)tryptamine (also known as (R)-3-(N-methylpyrrolidin-2-ylmethyl)-5-methoxyindole) is a tryptamine derivative that is a hallucinogenic drug. It was first developed by the team led by JE Macor in 1992, [Macor JE, Blake J, Fox CB, Johnson C, Koe BK, Lebel LA, Morrone JM, Ryan K, Schmidt AW, Schulz DW, et al. Synthesis and serotonergic pharmacology of the enantiomers of 3- [(N-methylpyrrolidin-2-yl)methyl] -5-methoxy-1H-indole: discovery of stereogenic differentiation in the aminoethyl side chain of the neurotransmitter serotonin. "Journal of Medicinal Chemistry". 1992 Nov 13;35(23):4503-5. PMID 1447752] and subsequently investigated 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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