Methoxyeugenol
Methoxyeugenol.gif

Methoxyeugenol (also known as O-demethyl elemicin) is a metabolite present in human urine that forms after the ingestion elemicin.[1]

Methoxyeugenol is predicted to produce stimulant action without psychedelic action when properly activated using Oilahuasca Activation techniques.


Direct Metabolism by UGT and SULT

Unlike the psychedelic allylbenzenes (elemicin, myristicin, etc.) methoxyeugenol contains a hydoxy group. Because of methoxyeugenol's hydroxy group on the 3 position of the benzene it is a direct substrate of glucuronosyltransferase (UGT) and sulfotransferase (SULT). Inhibiting UGT and SULT could theoretically greatly increase the potency of methoxyeugenol.

Glucuronosyltransferase (UGT) readily attacks methoxyeugenol (a metabolite of elemicin) on the 4 hydroxy position of the benzene ring producing methoxyeugenol-O-glucuronide. This action reduces the lipid solubility from methoxyeugenol's XLogP3-AA of 2.6 down to methoxyeugenol-O-glucuronide's XLogP3 of 1.02.

Substrate UGT End Product
Methoxyeugenol Methoxyeugenol-O-glucuronide
Methoxyeugenol.gif methoxyeugenol-O-glucuronide.png
Cofactor Byproduct
UDPglucuronate UDP

Sulfotransferase (SULT) readily attacks methoxyeugenol (a metabolite of elemicin) on the 4 hydroxy position of the benzene ring producing methoxyeugenol-O-sulfate. This action reduces the lipid solubility from methoxyeugenol's XLogP3-AA of 2.6 down to methoxyeugenol-O-sulfate's XLogP3 of 1.61.

Substrate SULT End Product
Methoxyeugenol Methoxyeugenol-O-sulfate
Methoxyeugenol.gif Methoxyeugenol-O-sulfate.png
Cofactor Byproduct
3'-phosphoadenylylsulfate adenosine 3',5'-bisphosphate

Chemical Properties

Synonyms: 5-Methoxyeugenol; 4-allyl-2,6-dimethoxyphenol; 2,6-dimethoxy-4-prop-2-enylphenol; 4-Hydroxy-3,5-dimethoxyallylbenzene; O-demethyl elemicin
PubChem Compound ID: 226486
Molecular Weight: 194.22706 [g/mol]
Molecular Formula: C11H14O3
XLogP3-AA: 2.6
H-Bond Donor: 1
H-Bond Acceptor: 3
IUPAC Name: 2,6-dimethoxy-4-prop-2-enylphenol
InChI: InChI=1S/C11H14O3/c1-4-5-8-6-9(13-2)11(12)10(7-8)14-3/h4,6-7,12H,1,5H2,2-3H3
InChIKey: FWMPKHMKIJDEMJ-UHFFFAOYSA-N
Canonical SMILES: COC1=CC(=CC(=C1O)OC)CC=C


See Also


References
1. Ther Drug Monit. 2006 Aug;28(4):568-75.
Abuse of nutmeg (Myristica fragrans Houtt.): studies on the metabolism and the toxicologic detection of its ingredients elemicin, myristicin, and safrole in rat and human urine using gas chromatography/mass spectrometry. Beyer J, Ehlers D, Maurer HH; Department of Experimental and Clinical Toxicology, Institute of Experimental and Clinical Pharmacology and Toxicology, University of Saarland, Homburg (Saar), Germany; PubMed PMID: 16885726
Unless otherwise stated, the content of this page is licensed under Creative Commons Attribution-ShareAlike 3.0 License