3-Piperidino-1-(3,4-methylenedioxyphenyl)-1-propanone, referfed to as 1'-oxosafrole-piperidine in this article, is a very minor metabolite that forms after the oral ingestion or topical use of safrole.[1] It's an adduct of 1'-oxosafrole and piperidine.

This piperidine based alkaloid metabolite of safrole is presumed to be partially responsible for the psychedelic effects of nutmeg and the rare psychedelic effects attributed to sassafras. This alkaloid has not been tested in man.

Instability and Decomposition

1'-oxosafrole-piperidine is not very stable. Its prone to decomposition, and easily decomposes during analysis. However it decomposes less rapidly than the corresponding 1'-oxoelemicin-piperidine adduct. Prolonged exposure to air, alkali, silica gel or heat decomposes 1'-oxosafrole-piperidine into an allylic ketone and piperidine.[2]

Dopamine D3 Interaction

In vitro tests show that 1'-oxosafrole-piperidine antagonizes human dopamine D3 receptor sites.[3]

Chemical Properties

Synonyms: Safrole II; 1'-oxosafrole-piperidine
PubChem Compound ID: 147354
Molecular Weight: 261.31626 [g/mol]
Molecular Formula: C15H19NO3
XLogP3-AA: 2.2
IUPAC Name: 1-(1,3-benzodioxol-5-yl)-3-piperidin-1-ylpropan-1-one
InChI: InChI=1S/C15H19NO3/c17-13(6-9-16-7-2-1-3-8-16)12-4-5-14-15(10-12)19-11-18-14/h4-5,10H,1-3,6-9,11H2
Canonical SMILES: C1CCN(CC1)CCC(=O)C2=CC3=C(C=C2)OCO3

See Also

1. E.O. Oswald, L. Fishbein, B.J. Corbett, M.P. Walker. Identification of tertiary aminomethylenedioxy-propiophenones as urinary metabolites of safrole in the rat and guinea pig. Biochimica et Biophysica Acta (BBA) - General Subjects, Volume 230, Issue 2, 23 February 1971, Pages 237-247 (web link)
2. E.O. Oswald, L. Fishbein, B.J. Corbett, M.P. Walker. Metabolism of naturally occuring propenylbenzene derivatives : II. Separation and identification of tertiary aminopropiophenones by combines gas—liquid chromatography and chemical ionization mass spectrometry. Journal of Chromatography A, Volume 73, Issue 1, 8 November 1972, Pages 43-57 (web link)
(Download Attached PDF Document) PubMed PMID 5081654
3. qHTS of D3 Dopamine Receptor Antagonist: qHTS - BioAssay Summary
PubChem AID: 652054
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