Dihydromethysticin

Names

[ CAS No. ]:
19902-91-1

[ Name ]:
Dihydromethysticin

[Synonym ]:
2H-Pyran-2-one, 6-[2-(1,3-benzodioxol-5-yl)ethyl]-5,6-dihydro-4-methoxy-, (6S)-
(6S)-6-[2-(1,3-Benzodioxol-5-yl)ethyl]-5,6-dihydro-4-methoxy-2H-pyran-2-one Dihydromethysticin
(6S)-6-[2-(1,3-Benzodioxol-5-yl)ethyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one
DIHYDROMETHYSTICIN

Biological Activity

[Description]:

Dihydromethysticin is one of the six major kavalactones found in the kava plant; has marked activity on the induction of CYP3A23.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

Natural Products >> Others

Research Areas >> Others

[References]

[1]. Ma Y, et al. Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23. Drug Metab Dispos. 2004 Nov;32(11):1317-24.

[2]. Walden J, et al. Effects of kawain and dihydromethysticin on field potential changes in the hippocampus. Prog Neuropsychopharmacol Biol Psychiatry. 1997 May;21(4):697-706.

[3]. Sarris J, et al. Kava: a comprehensive review of efficacy, safety, and psychopharmacology. Aust N Z J Psychiatry. 2011 Jan;45(1):27-35.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
476.1±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₅H₁₆O₅

[ Molecular Weight ]:
276.284

[ Flash Point ]:
214.1±28.8 °C

[ Exact Mass ]:
276.099762

[ PSA ]:
53.99000

[ LogP ]:
1.81

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.576

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UQ0516000

CHEMICAL NAME :: 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(3,4-(methylenedioxy)phenethy l)-, (S)-

CAS REGISTRY NUMBER :: 19902-91-1

LAST UPDATED :: 199206

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C15-H16-O5

MOLECULAR WEIGHT :: 276.31

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1050 mg/kg

TOXIC EFFECTS :: Behavioral - muscle weakness Behavioral - ataxia Lungs, Thorax, or Respiration - other changes

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 138,505,1962

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 420 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 26,283,1970

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >200 mg/kg

TOXIC EFFECTS :: Behavioral - muscle weakness Behavioral - muscle contraction or spasticity Gastrointestinal - nausea or vomiting

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 138,505,1962

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 300 mg/kg

TOXIC EFFECTS :: Behavioral - muscle weakness Behavioral - muscle contraction or spasticity Gastrointestinal - nausea or vomiting

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 138,505,1962

Safety Information

[ RIDADR ]:
NONH for all modes of transport