Chavicol
chavicol.png

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.gif
Hordenine is the dimethylamine analog of chavicol. It is a short acting stimulant that's also a competitive MAO-B inhibitor.

Tyramine

Tyramine.png
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.png
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

Bibliography
1. Allen's commerical organic analysis, Volume 4.
W. A. Davis, G. C. Jones, Julian L. Baker, Emil Schlichting, Henry Leffmann, E. Frankland Armstrong, R. W. Sindall; 1915; ISBN-10: 1130539288; ISBN-13: 978-1130539288
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