1'-Oxoestragole is a phenyl vinyl ketone metabolite produced by rats fed 1'-hydroxyestragole (the 1'-hydroxy metabolite of the allylbenzene methyl chavicol). It has also been produced in vitro in human liver exposed to 1'-hydroxyestragole.
1'-Oxoestragole was found to have no carcinogenic potential in mice.
1'-Oxoestragole was found to form adducts with guanosine and 2′-deoxyguanosine in a direct reaction with these nucleosides. Regardless, 1′-oxoestragole was not found to be carcinogenic in vivo in mice . The lack of carcinogenicity is caused by extensive detoxification of 1′-oxoestragole via conjugation with glutathione, N-acetylcysteine, or endogenous amines (Fennell et al., 1984; Wislocki et al., 1977).
The 2',3'-double bond of 1'-oxoestragole may possibly react with amines such as dimethylamine, piperidine, and pyrrolidine at room temperature without enzymes to form the corresponding 3'-addition products leading to alkaloids of potential psychoactivity. This is proven to be the case for the closely related 1'-oxosafrole.
Psychedelic Alkaloid Metabolites
1'-Oxoestragole is capable of forming adducts with endogenous amines. This action is believed to be responsible for the psychedelic effects methyl chavicol is capable of producing in humans under certain conditions.
The alkaloids in this section are all adducts of 1'-oxoestragole (a metabolite of methyl chavicol) and endogenous amines. Similar endogenous amine adducts are proven to form from myristicin, elemicin, and other similar allylbenzenes.
1-(4-methoxyphenyl)-3-(piperidin-1-yl)propan-1-one is an adduct of 1'-oxoestragole and piperidine.
PubChem Compound ID: 24017
Molecular Weight: 162.1852 [g/mol]
Molecular Formula: C10H10O2
H-Bond Donor: 0
H-Bond Acceptor: 2
IUPAC Name: 1-(4-methoxyphenyl)prop-2-en-1-one
Canonical SMILES: COC1=CC=C(C=C1)C(=O)C=C