Thujone

Thujone
(−)-α-Thujone	(+)-β-Thujone
	; Ball-and-stick model of (−)-α-thujone
Names
	IUPAC names α: (1S,4R,5R)-4-Methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one; β: (1S,4S,5R)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one
	Other names Bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-, [1S-(1α,4α,5α)]-; α-Thujone ; β-Thujone ; Thujone, cis; 3-Thujanone, (1S,4R,5R)-(-)-; Thujon; 3-Thujanone, (-)-; l-Thujone; 4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one-, (1S,4R,5R)-; 3-Thujone; cis-Thujone; (Z)-Thujone; (-)-Thujone; Bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1S,4R,5R)-; NSC 93742; 1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
Identifiers
CAS Number	76231-76-0 (α,β-thujone) ; 546-80-5 (α-thujone) ; 471-15-8 (β-thujone) ;
3D model (JSmol)	(α-thujone): Interactive image; (β-thujone): Interactive image;
Beilstein Reference	4660369
ChEBI	CHEBI:9577 ;
ChEMBL	ChEMBL1444078;
ChemSpider	229574 (α-thujone) ; 82583 (β-thujone) ;
ECHA InfoCard	100.013.096
EC Number	214-405-7;
IUPHAR/BPS	5344;
KEGG	C09906;
PubChem CID	261491; 11027;
UNII	86HK1QRJ4K (α,β-thujone) ; R0SQ9G0DU5 (α-thujone) ; 8ZI5R3T54Q (β-thujone) ;
CompTox Dashboard (EPA)	DTXSID20859476 ;
	InChI InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8-,10+/m1/s1 Key: USMNOWBWPHYOEA-MRTMQBJTSA-N ; InChI=1/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8-,10+/m1/s1 Key: USMNOWBWPHYOEA-MRTMQBJTBZ; InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8-,10+/m1/s1 Key: USMNOWBWPHYOEA-MRTMQBJTSA-N;
	SMILES (α-thujone): O=C1[C@H](C)[C@@H]2[C@](C(C)C)(C1)C2; (β-thujone): C[C@@H]([C@@H](C2)[C@]2([C@@H](C)C)C1)C1=O;
Properties
Chemical formula	C10H16O
Molar mass	152.237 g·mol−1
Density	0.92 g/cm3 (β-thujone); 0.9116 g/cm3 (α-thujone)
Melting point	<25 °C
Boiling point	203 °C (397 °F; 476 K) (alpha,beta-thujone)
Solubility in water	407 mg/L
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264, P270, P301+P312, P330, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Thujone (/ˈθuːdʒoʊn/ ^ⓘ) is a ketone and a monoterpene that occurs predominantly in two diastereomeric (epimeric) forms: (−)-α-thujone and (+)-β-thujone.

Though it is best known as a chemical compound in the spirit absinthe, it is unlikely to be responsible for absinthe's alleged stimulant and psychoactive effects due to the small quantities present. Thujone acts on the neurotransmitter gamma-aminobutyric acid (GABA) as an antagonist (opposite to the effects of alcohol, which is an agonist of GABA). As a competitive antagonist of GABA, thujone alone is considered to be convulsant, though by interfering with the inhibitory transmitter GABA, it may convey stimulating, mood-elevating effects at low doses. It is also found in perfumery as a component of several essential oils.

In addition to the naturally occurring (−)-α-thujone and (+)-β-thujone, two other forms are possible: (+)-α-thujone and (−)-β-thujone. In 2016, they were found in nature as well, in Salvia officinalis.

(−)-α-thujone
(+)-α-thujone
(+)-β-thujone
(−)-β-thujone

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