1'-Oxomyristicin

1'-Oxomyristicin is a phenyl vinyl ketone believed to be an intermediate metabolite that forms from 1'-hydroxymyristicin, a metabolite of myristicin.[4]

Corresponding 1'-oxo metabolites have been found for the closely related 1'-hydroxy metabolites of safrole[4][3], methyl eugenol[5], and methyl chavicol[2].

Alkaloid Metabolites Created In Vivo

1'-Oxomyristicin is believed to be the primary myristicin metabolite that leads to the creation of 2 alkaloids found in vivo after the ingestion of myristicin.[1] These alkaloids are believed to be responsible for the psychedelic activity of myristicin.[1]

3-piperidyl-1-(3'methoxy-4',5'-methylenedioxyphenyl)-1-propanone

This is the piperidine alkaloid metabolite of myristicin. See the article on 3-piperidyl-1-(3'methoxy-4',5'-methylenedioxyphenyl)-1-propanone for more details on this alkaloid metabolite.

3-pyrrolidinyl-1-(3'methoxy-4',5'-methylenedioxyphenyl)-1-propanone

This is the pyrrolidine alkaloid metabolite of myristicin.

Note that dimethylamine alkaloid metabolites of myristicin have not been found, but have been found for several other related allylbenzenes.^[1]

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Chemical Properties

Canonical SMILES: COC1=CC(=CC2=C1OCO2)C(C=C)=O

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See Also

• Myristicin
• Nutmeg
• Oilahuasca Activation

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Bibliography

1. E.S. Oswald, L. Fishbein, B.J. Corbett, M.P. Walker.

Urinary excretion of tertiary amino methoxy methylenedioxy propiophenones as metabolites of myristicin in the rat and guinea pig; Biochimica et Biophysica Acta (BBA) - General Subjects, Volume 244, Issue 2, 19 August 1971, Pages 322-328; DOI: 10.1016/0304-4165(71)90233-9. ISSN: 0304-4165; PubMed PMID: 5125615 (web link) (Download Attached PDF Document)

2. Use of physiologically based biokinetic (PBBK) modeling to study estragole bioactivation and detoxification in humans as compared with male rats.

Punt A, Paini A, Boersma MG, Freidig AP, Delatour T, Scholz G, Schilter B, van Bladeren PJ, Rietjens IM. PubMed PMID: 19447879

3. Physiologically based biokinetic (PBBK) modeling of safrole bioactivation and detoxification in humans as compared with rats.

Martati E, Boersma MG, Spenkelink A, Khadka DB, van Bladeren PJ, Rietjens IM, Punt A. PubMed PMID: 22588462

4. Safrole and Its Alkenylbenzene Congeners: Safrole, Estragole, and Related Compounds: Carcinogenicity and Structure Activity Relationships: Other Biological Properties: Metabolism: Environmental Significance

Yin-Tak Woo, Ph.D., D.A.B.T., David Y. Lai, Ph.D; June 1986; Page 376 (Download Attached PDF Document)

5. Metabolism of methyleugenol in liver microsomes and primary hepatocytes: pattern of metabolites, cytotoxicity, and DNA-adduct formation.

Cartus AT, Herrmann K, Weishaupt LW, Merz KH, Engst W, Glatt H, Schrenk D. PubMed PMID: 22610610