ALPHA-(-)-THUJONE

Description

The monoterpene α-thujone [(+)-3-thujone], and its diastereomer, β-thujone, occur in several plants, such as arborvitae (genus Thuja), mugwort, common sage, wormwood, and some junipers. α-Thujone, and to a lesser extent the β-isomer, is a γ-aminobutyric acid (GABA) antagonist and can cause brain neurons to fire easily, causing muscle spasms and convulsions. It has been implicated in unusual behaviors attributed to the wormwood oil–flavored liqueur absinthe, but recent?studies?have shown that the thujone concentration in absinthe is too small to cause toxic effects.

Chemical properties

Colorless liquid. Insoluble in water; soluble in alcohol. Combustible.

The Uses of ALPHA-(-)-THUJONE

Solvent.

The Uses of ALPHA-(-)-THUJONE

α-Thujone is a GABA modulator and a genotoxic compound found in plants used in traditional medicines in developing countries.

What are the applications of Application

(?)-α-Thujone is a GABAA antagonist and chiral building block

Definition

ChEBI: The (1S,4R,5R)-stereoisomer of alpha-thujone.

General Description

(-)-α-Thujone, a monoterpene ketone found in the essential oil of Thuja occidentalis, shows potent antitumorigenic effect.

Hazard

Toxic by ingestion.

Biochem/physiol Actions

GABAA receptor antagonist.

Safety Profile

Poison by intravenous, intraperitoneal, and subcutaneous routes. Moderately toxic by ingestion. Serious physiological consequences from abuse of absinthe (mainly in France) led to its abolition in 1915. Wormwood is still used in concentrations of less than 10 ppm in flavored wines. Thujone at 30 mg/kg causes convulsions associated with lesions of the cerebral cortex. Little is known of thujone metabolism. Both forms occur in wormwood oil, oak moss. The a form is major constituent of cedar leaf oil or oil of thuja, sage. The p form occurs in tansy, yarrow. When heated to decomposition it emits acrid smoke and irritating fumes.