8546. Sinomenine

Nomenclature

CAS number: 115-53-7
(9α,13α,14α)-7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one; cucoline; coculine; kukoline.
C19H23NO4; mol wt 329.39.
C 69.28%, H 7.04%, N 4.25%, O 19.43%.

Description and 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).

Chemical structure

Properties

Clusters of needles from benzene, mp 161°. After melting once, the mp is raised to 182°. [α]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).

Derivative

Hydrochloride dihydrate.
C19H24ClNO4.2H2O; mol wt 401.88.
C 56.78%, H 7.02%, Cl 8.82%, N 3.49%, O 23.89%.

Properties

Long prisms from water, dec 231° when anhydr. [α]D17 -82° (c = 4.4). Sol in about 1.5 parts water.