Sinomenine
Title: Sinomenine
CAS Registry Number: 115-53-7
CAS Name: (9a,13a,14a)-7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one
Additional Names: cucoline; coculine; kukoline
Molecular Formula: C19H23NO4
Molecular Weight: 329.39
Percent Composition: C 69.28%, H 7.04%, N 4.25%, O 19.43%
Literature References: An optical isomer of methoxythebainone. Configuration at the asymmetric centers, C9, C13, and C14, is the mirror image of those in morphine. From root of Sinomenium acutum (Thunb.) Rehd. & Wils. (Cocculus diversifolius DC.), Menispermaceae: Goto, J. Chem. Soc. Jpn. 44, 795 (1923), C.A. 18, 2710 (1924); Ohta, Kitasato Arch. Exp. Med. 6, 259 (1925), C.A. 21, 32332 (1927). Structure: Kondo, Ochiai, Ann. 470, 224 (1929); Sasaki, Yakugaku Zasshi 80, 270 (1960), C.A. 54, 11702g (1960). Biogenesis: Cohen, Chem. Ind. (London) 1956, 1391. Pharmacology: S. Fu et al., Yao Hsueh Hsueh Pao 10, 673 (1963), C.A. 60, 8525h (1964). Reviews: Holmes in R. H. F. Manske, H. L. Holmes, The Alkaloids vol. II (Academic Press, New York, 1952) pp 219-260; K. W. Bentley, The Chemistry of the Morphine Alkaloids (Oxford, 1954).
Properties: Clusters of needles from benzene, mp 161°. After melting once, the mp is raised to 182°. [a]D26 -71° (c = 2.1 in alc). Sol in alc, acetone, chloroform, dil alkali; slightly sol in water, ether, benzene. LD50 orally in mice: 580 mg/kg (Fu).
Melting point: mp 161°; mp is raised to 182°
Optical Rotation: [a]D26 -71° (c = 2.1 in alc)
Toxicity data: LD50 orally in mice: 580 mg/kg (Fu)
 
Derivative Type: Hydrochloride dihydrate
Molecular Formula: C19H24ClNO4.2H2O
Molecular Weight: 401.88
Percent Composition: C 56.78%, H 7.02%, Cl 8.82%, N 3.49%, O 23.89%
Properties: Long prisms from water, dec 231° when anhydr. [a]D17 -82° (c = 4.4). Sol in about 1.5 parts water.
Optical Rotation: [a]D17 -82° (c = 4.4)

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