The allylbenzene 5-allyl-1-methoxy-2,3-dihydroxybenzene is the main metabolite of myristicin created in vivo after oral or topical use.[1]


This compound is not an alkaloid and is believed to have no psychedelic action in man. However, being an allylbenzene, this metabolite of myristicin may possibly be metabolized further into an alkaloid in vivo as has been proven for myristicin and other similar allylbenzenes. The predicted activity for this compound's theoretical alkaloid metabolites is stimulation without psychedelic action because it lacks a methoxy group on the 3 position (the middle position) on the benzene ring.

In vitro tests indicate that this metabolite is created primarily by the P450 enzyme CYP3A4.[1] The P450 enzyme CYP1A2 plays a minor role in its formation in vitro.[1] CYP2A6, CYP2C19, CYP2D6, and CYP2E1 appear to play no role in creating this metabolite in vitro.[1]

Chemical Properties

PubChem Compound ID: 11389746
Molecular Weight: 180.20048 [g/mol]
Molecular Formula: C10H12O3
XLogP3-AA: 2.3
IUPAC Name: 3-methoxy-5-prop-2-enylbenzene-1,2-diol
InChI: InChI=1S/C10H12O3/c1-3-4-7-5-8(11)10(12)9(6-7)13-2/h3,5-6,11-12H,1,4H2,2H3
Canonical SMILES: COC1=CC(=CC(=C1O)O)CC=C

1. Yun CH, Lee HS, Lee HY, Yim SK, Kim KH, Kim E, Yea SS, Guengerich FP
Department of Genetic Engineering, Pai-Chai University, 439-6 Doma-dong, Seo-ku, Taejon 302-735, South Korea. Toxicology Letters [2003, 137(3):143-150]; Roles of human liver cytochrome P450 3A4 and 1A2 enzymes in the oxidation of myristicin; DOI: 10.1016/S0378-4274(02)00397-1 PubMed PMID 12523956
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