Compound: alpha-Thujone
SMILES: O=C1[C@@H]([C@H]2C[C@]2(C1)C(C)C)C
InChIKey: USMNOWBWPHYOEA-MRTMQBJTSA-N
Synonyms: alpha-Thujone, 546-80-5, THUJONE, (-)-alpha-thujone, l-Thujone, (-)-3-thujanone, R0SQ9G0DU5, 3-Thujanone, (1S,4R,5R)-(-)-, DTXSID3026148, (1S,4R,5R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one, (-)-Thujone, CHEBI:9577, DTXCID206148, (1S,4R,5R)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one, NSC-93742, 86HK1QRJ4K, CHEBI:50040, (1S,4R,5R)-4-methyl-1-(propan-2-yl)bicyclo(3.1.0)hexan-3-one, (1S,4R,5R)-4-methyl-1-propan-2-ylbicyclo(3.1.0)hexan-3-one, RefChem:50983, CHEBI:50042, 208-912-2, alpha-(-)-Thujone, Thujon, (-)-3-Isothujone, (1S,4R,5R)-thujan-3-one, (+-)-Isothujone, (1S,4R,5R)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-one, MFCD00001313, 59573-80-7, Bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1S,4R,5R)-, 3-Thujanone, (-)-, Bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1S,4R,5R)-, (1S,4R,5R)-(-)-3-thujanone, dl-Thujone, NSC 93742, racemic 3-Isothujone, .alpha.-Thujone, (-)-|A-Thujone, Absinthol, EINECS 208-912-2, UNII-R0SQ9G0DU5, 3-Thujanone, (+-)-, BRN 4660369, CCRIS 8582, L-alpha-Thujone, ??-Thujone, (-)-trans-Thujone, (-)-a-Thujone, ALFA-THUJONE, (?)-|A-Thujone, (-)- alpha -Thujone, a-(-)-THUJONE, THUJONE, .ALPHA.-, MLS001065588, SCHEMBL122447, .ALPHA.-THUJONE [MI], GTPL5344, orb1299134, CHEMBL1444078, USMNOWBWPHYOEA-MRTMQBJTSA-N, HMS3039B05, HMS6018B09, (1R,2R,5S)-5-isopropyl-2-methyl-bicyclo[3.1.0]hexan-3-one, Tox21_200868, (-)-Thujone ((-)-alpha-Thujone), MSK163943, (1S,4R,5R)- 3-THUJANONE, AKOS040759330, EBC-616778, LMPR0102120019, Bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1-alpha,4-alpha,5-alpha)-(+-)-, NCGC00091438-01, NCGC00091438-02, NCGC00164360-01, NCGC00258422-01, CAS-546-80-5, MS-22862, SMR000568469, (-)-alpha-Thujone, >=96.0% (GC), HY-121618, CS-0082886, NS00003614, C09906, Q421838, (1S,4R,5R)-1-isopropyl-4-methyl-bicyclo[3.1.0]hexan-3-one, (-)-alpha-Thujone, (1S,4R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one, [1S-(1alpha,4alpha,5alpha)]-4-methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one, 58501-78-3
Theoretical properties:
molecular_formula: C10H16O
molecular_weight: 152.23 g/mol
exact_mass: 152.120115130 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 1
heavy_atom_count: 11
topological_polar_surface_area: 17.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
boiling_point: 200.00 to 201.00 °C. @ 760.00 mm Hg
melting_point: < 25 °C
Descriptions:
pubchem: (-)-alpha-thujone is the (1S,4R,5R)-stereoisomer of alpha-thujone. It is an enantiomer of a (+)-alpha-thujone.
chebi: The (1S,4R,5R)-stereoisomer of α-thujone.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Thujone ( ) 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 only present in trace amounts and is unlikely to be responsible for the spirit's purported stimulant and psychoactive effects.
Thujone acts on the GABAA receptor as an antagonist. As a competitive antagonist of GABAA receptor, 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.