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Wormwood Chemistry
by Erowid

The active ingredients in wormwood are the volatile terpenes alpha- and beta-thujone, both of which are isomers of camphor.

NAME :alpha-thujone
CHEMICAL NAME :4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one; 3-thujanone
ALTERNATE CHEMICAL NAMES : (-)-Isothujone; (1S, 4R, 5R)-(-)-3-thujanone; thujon; thujone; (-)-thujone
CAS #546-80-5

Merck Entry
9533. Thujone.

4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one; 3-thujanone. .C10H16O; .mol wt 152.24. .C 78.90%, H 10.59%, O 10.51%. . A constituent of many essential oils; present in thuja, etc. Equilibrium mixture contains 33% .alpha.-thujone and 67% .beta.-thujone: Eastman, Winn, J. Am. Chem. Soc. 82, 5908 (1960). .alpha.- and .beta.-Thujones differ only in the stereochemistry of the 4- methyl group. Conformation: Hach et al., Tetrahedron Letters 1970, 3175. Chemistry: J. P. Kutney et al., Bioorg. Chem. 7, 289 (1978); eidem, Can. J. Chem. 57, 3145 (1979); 58, 2641 (1980). Toxicity study: K. C. Rice, R. S. Wilson, J. Med. Chem. 19, 1054 (l976). Review: J. L. Simonsen, The Terpenes vol. II (University Press, Cambridge, 1949) pp 32-52.

Colorless or almost colorless liquid. uv max (isooctane): 300 nm (.epsilon. 23). Practically insol in water. Sol in alc and many other organic solvents. LD50 s.c. in mice: 134.2 mg/kg (Rice, Wilson).

Caution: Ingestion may cause convulsions.

l-Form, ..alpha.-thujone.. ..bp17 83.8-84.1 deg. d425 0.9109. nD15 1.4490. [.alpha.]D20 -19.2 deg. LD50 s.c. in mice: 87.5 mg/kg (Rice, Wilson).

d-Form, .d-isothujone., .beta.-thujone.. ..bp17 85.7-86.2 deg. d425 0.9135. nD25 1.4500. [.alpha.]D15 +72.5 deg. LD50 s.c. in mice: 442.2 mg/kg (Rice, Wilson).


Chemistry & Pharmacology Info from a College Paper