Chavicol is an allylbenzene found in bay leaf and betel leaf essential oils.
Fresh betel leaf essential oil contains 30-40% chavicol.[1] Its commonly used as a mild stimulant. Essential oil from dried leaves can contain methyl chavicol in amounts of 70-75%.[1]
Chavicol is also the O-demethyl metabolite of methyl chavicol.
When activated using proper oilahuasca activation techniques chavicol has stimulant effects without psychedelic activity similar to its various corresponding alkaloid analogs (hordenine, tyramine, p-hydroxyamphetamine).
Sulfotransferase (SULT) readily attacks chavicol on the 4 hydroxy position of the benzene ring producing chavicol-O-sulfate. This action reduces the lipid solubility from chavicol's XLogP3 of 2.9 down to chavicol-O-sulfate's XLogP3 of 2.
Glucuronosyltransferase (UGT) readily attacks chavicol on the 4 hydroxy position of the benzene ring producing chavicol-O-glucuronide. This action reduces the lipid solubility from chavicol's XLogP3 of 2.9 down to chavicol-O-glucuronide's XLogP3 of 1.08.
Natural Sources
| Essential oil | Content |
|---|---|
| bay leaf essential oil | <0.01-15.51% |
| bay leaf essential oil clove | 17.1% |
| betel leaf essential oil | 30-40%[1] |
Alkaloids with similar structure
All of the alkaloids in this section are stimulants. None of these alkaloids have psychedelic activity.
Hordenine
Hordenine is the dimethylamine analog of chavicol. It is a short acting stimulant that's also a competitive MAO-B inhibitor.
Tyramine
Tyramine is the phenethylamine analog of chavicol. It is a very potent stimulant. Tyramine acts as a catecholamine (dopamine, noradrenaline, adrenaline) releasing agent. It's a primary substrate of MAO-A.
P-Hydroxyamphetamine
P-Hydroxyamphetamine is the amphetamine analog of chavicol. It is a stimulant found in Acacia berlandieri.
Synonyms: p-Hydroxyallylbenzene; 4-Allylphenol; p-Allylphenol; 4-prop-2-enylphenol
PubChem Compound ID: 68148 (On 2/1/2013 PubChem incorrectly identified this compound as estragole, which is methyl chavicol and not chavicol.)
Molecular Weight: 134.1751 [g/mol]
Molecular Formula: C9H10O
XLogP3: 2.9
H-Bond Donor: 1
H-Bond Acceptor: 1
IUPAC Name: 4-prop-2-enylphenol
InChI: InChI=1S/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7,10H,1,3H2
InChIKey: RGIBXDHONMXTLI-UHFFFAOYSA-N
Canonical SMILES: C=CCC1=CC=C(C=C1)O