Title: Chonemorphine
CAS Registry Number: 4282-07-9
CAS Name: (3b,5a,20S)-N20,N20-Dimethylpregnane-3,20-diamine
Additional Names: 3b-amino-20a-dimethylamino-5a-pregnane
Molecular Formula: C23H42N2
Molecular Weight: 346.59
Percent Composition: C 79.70%, H 12.21%, N 8.08%
Literature References: Antiamebic principle from bark and leaves of Chonemorpha macrophylla G. Don, Ch. fragrans Alston, and Ch. penangensis Ridl., Apocynaceae: Greshoff, Ber. 23, 3545 (1890); Das, Pillay, J. Sci. Ind. Res. 13B, 602, 701 (1954); Chatterjee, Das, Chem. Ind. (London) 1959, 1445. Structure and synthesis: eidem, ibid. 1960, 290; Janot et al., Bull. Soc. Chim. Fr. 1962, 111. Stereochemistry: Chien et al., J. Org. Chem. 29, 315 (1964).
Properties: Bitter crystals, mp 149°. [a]D +25° (chloroform). Sol in chloroform, ether.
Melting point: mp 149°
Optical Rotation: [a]D +25° (chloroform)
Derivative Type: N-Benzilidenechonemorphine
Molecular Formula: C30H46N2
Molecular Weight: 434.70
Percent Composition: C 82.89%, H 10.67%, N 6.44%
Properties: Crystals, mp 182-183°. [a]D +36°. uv max: 248, 277, 287 nm.
Melting point: mp 182-183°
Optical Rotation: [a]D +36°
Absorption maximum: uv max: 248, 277, 287 nm
Derivative Type: N-Acetylchonemorphine
Molecular Formula: C25H44N2O
Molecular Weight: 388.63
Percent Composition: C 77.26%, H 11.41%, N 7.21%, O 4.12%
Properties: Crystals, mp 262-265°. [a]D +17°.
Melting point: mp 262-265°
Optical Rotation: [a]D +17°
Status: This monograph has been retired and is no longer subject to revision or update. |