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 | |
|
 |
|
| 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 | |
|
 |
|
| 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
- Elemicin
- Glucuronosyltransferase (UGT)
- Methoxyeugenol-O-glucuronide
- Methoxyeugenol-O-sulfate
- Oilahuasca Activation
- Sulfotransferase (SULT)