1'-Oxosafrole, which is electrophilic, has little or no carcinogenic activity in rats and mice.
Giving 1'-oxosafrole to rats and mice produced 3'-(glutathion-S-yl)-1'-oxo-2',3'-dihydrosafrole and 3'-(N-acetylcystein-S-yl)-1'-oxo-2',3'-dihydrosafrole as metabolites. These conjugates could be synthesized in a lab by non-enzymatic reaction of 1'-oxosafrole with glutathione and N-acetylcysteine at pH 8.
The 2',3'-double bond of 1'-oxosafrole reacts with amines such as dimethylamine, piperidine, and pyrrolidine at room temperature without enzyme catalysts to form the corresponding 3'-addition products leading to alkaloids of potential psychoactivity.
The 2',3'-double bond of 1'-oxosafrole reacts with glutathione and N-acetylcysteine at pH 8 without enzyme catalysts to form the corresponding conjugates 3'-(glutathion-S-yl)-1'-oxo-2',3'-dihydrosafrole and 3'-(N-acetylcystein-S-yl)-1'-oxo-2',3'-dihydrosafrole.
Safrole is proven to produce dimethylamine, piperidine, and pyrrolidine alkaloids as very minor metabolites after oral or topical use. They are believed to be adducts that form as 3'-addition products of 1'-oxosafrole and the endogenous amines dimethylamine, piperidine, and pyrrolidine. They are presumed to be psychoactive, and to contribute to the effects of nutmeg as sassafras.
3-N,N-Dimethylamino-1-(3,4-methylenedioxyphenyl)-1-propanone is the dimethylamine adduct of 1'-oxosafrole.
3-Piperidino-1-(3,4-methylenedioxyphenyl)-1-propanone is the piperidine adduct of 1'-oxosafrole.
3-Pyrrolidino-1-(3,4-methylenedioxyphenyl)-1-propanone is the pyrrolidine adduct of 1'-oxosafrole.
Synonyms: 3,4-Methylenedioxyphenyl vinyl ketone; 1'-ketosafrole; 3,4-Methylenedioxyphenylvinyl ketone; 5-Acryloyl-1,3-benzodioxole; 1-(1,3-Benzodioxol-5-yl)-2-propen-1-one;
PubChem Compound ID: 160188
Molecular Weight: 176.16872 [g/mol]
Molecular Formula: C10H8O3
H-Bond Donor: 0
H-Bond Acceptor: 3
IUPAC Name: 1-(1,3-benzodioxol-5-yl)prop-2-en-1-one
Canonical SMILES: C=CC(=O)C1=CC2=C(C=C1)OCO2
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