Mesembrine
Title: Mesembrine
CAS Registry Number: 24880-43-1
CAS Name: (3aS-cis)-3a-(3,4-Dimethoxyphenyl)octahydro-1-methyl-6H-indol-6-one
Additional Names: 3a-(3,4-dimethoxyphenyl)tetrahydro-1-methyl-6(3aH)-indolinone
Molecular Formula: C17H23NO3
Molecular Weight: 289.37
Percent Composition: C 70.56%, H 8.01%, N 4.84%, O 16.59%
Literature References: Alkaloid used in preparing Channa, a drug of Southwest Africa. Occurs naturally as the (-)-form. From Sceletium expansum L., S. tortuosum L., Aizoaceae: Hartwick, Zwicky, Apoth. Ztg. 29, 925 (1914); Rimington et al., J. Vet. Sci. Animal Ind. 9, 187 (1938), C.A. 32, 42799 (1938). Structure: Popelak et al., Naturwissenschaften 47, 156 (1960). Configuration: P. W. Jeffs et al., J. Am. Chem. Soc. 91, 3831 (1969). Synthesis of (±) form: Shamma, Rodriguez, Tetrahedron Lett. 1965, 4847; O. Hoshino et al., Heterocycles 10, 61 (1978); of (±)-form and trans isomer: Oh-Ishi, Kugita, Chem. Pharm. Bull. 18, 299 (1970). Synthesis of (+)-form: Yamada, Otani, Tetrahedron Lett. 1971, 1133; eidem, Chem. Pharm. Bull. 21, 2130 (1973). Stereoselective synthesis of (±)-form: Wijnberg, Speckamp, Tetrahedron Lett. 1975, 3963; eidem, Tetrahedron 34, 2579 (1978); S. F. Martin et al., J. Org. Chem. 44, 3391 (1979); S. Takano et al., Chem. Lett. 1981, 1385. Enantioselective synthesis of natural mesembrine: eidem, Tetrahedron Lett. 22, 4479 (1981). Biosynthesis: Jeffs et al., J. Am. Chem. Soc. 93, 3752 (1971); eidem, Chem. Commun. 1977, 60. Review of mesembrine alkaloids: A. Popelak, G. Lettenbauer in The Alkaloids vol. IX, R. H. F. Manske, Ed. (Academic Press, New York, 1967) pp 467-481; R. V. Stevens in The Total Synthesis of Natural Products vol. 3, J. ApSimon, Ed. (Wiley, New York, 1977) pp 443-453.
Properties: Pale yellow oil. bp0.3 186-190°. [a]D20 -55.4° (CH3OH). Freely sol in alcohol, chloroform, acetone; slightly sol in ether. Practically insol in benzene, petr ether, alkalies.
Boiling point: bp0.3 186-190°
Optical Rotation: [a]D20 -55.4° (CH3OH)
 
Derivative Type: Hydrochloride
Molecular Formula: C17H23NO3.HCl
Molecular Weight: 325.83
Percent Composition: C 62.67%, H 7.42%, N 4.30%, O 14.73%, Cl 10.88%
Properties: mp 205-206°. [a]D20 -8.4° (CH3OH).
Melting point: mp 205-206°
Optical Rotation: [a]D20 -8.4° (CH3OH)
 
Derivative Type: (+)-Form
Properties: (Partially optically active). Pale yellow oil. [a]D20 +16.1° (c = 1.32 in CH3OH).
Optical Rotation: [a]D20 +16.1° (c = 1.32 in CH3OH)
 
Derivative Type: (+)-Form hydrochloride
Molecular Formula: C17H23NO3.HCl
Molecular Weight: 325.83
Percent Composition: C 62.67%, H 7.42%, N 4.30%, O 14.73%, Cl 10.88%
Properties: Crystals from 2-propanol, mp 206.5-207.5°. [a]D20 +7.3° (c = 0.465 in CH3OH).
Melting point: mp 206.5-207.5°
Optical Rotation: [a]D20 +7.3° (c = 0.465 in CH3OH)
 
Derivative Type: (±)-Form
Properties: Colorless oil. bp0.07 178°.
Boiling point: bp0.07 178°
 
Derivative Type: (±)-Form hydrochloride
Molecular Formula: C17H23NO3.HCl
Molecular Weight: 325.83
Percent Composition: C 62.67%, H 7.42%, N 4.30%, O 14.73%, Cl 10.88%
Properties: mp 179-181°.
Melting point: mp 179-181°

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