Aspidospermine

Title: Aspidospermine
CAS Registry Number: 466-49-9
CAS Name: 1-Acetyl-17-methoxyaspidospermidine
Molecular Formula: C22H30N2O2
Molecular Weight: 354.49
Percent Composition: C 74.54%, H 8.53%, N 7.90%, O 9.03%
Literature References: In Aspidosperma quebracho-blanco Schlect., Vallesia dichotoma Ruiz & Pav., and Vallesia glabra (Cav.) Link, Apocynaceae: G. Fraude, Ber. 11, 2189 (1878); Hesse, Ann. 211, 249 (1882); Ewins, J. Chem. Soc. 105, 2738 (1914); Deulofeu et al., ibid. 1940, 1051; Holker et al., J. Org. Chem. 24, 314 (1959). Structure: Conroy et al., Tetrahedron Lett. no. 11, 4 (1959). Crystal structure: Mills, Nyburg, J. Chem. Soc. 1960, 1458. Stereochemistry: Smith, Wrobel, ibid. 1463; Craven, Zacharias, Experientia 24, 770 (1968). Biogenesis: Robinson, Tetrahedron Lett. no. 18, 1F4 (1959). Synthesis of dl-form: Stork, Dolfini, J. Am. Chem. Soc. 85, 2872 (1963); Ban et al., Tetrahedron Lett. 1965, 2261; Stevens et al., Chem. Commun. 1971, 857; S. F. Martin et al., J. Am. Chem. Soc. 102, 3294 (1980). Aspidospermine has been reported as having a wide variety of pharmacological properties, including diuretic and respiratory stimulant activity. Biological and phytochemical evaluation: R. L. Lyon et al., J. Pharm. Sci. 62, 218 (1973). Microbial transformation: S. K. Lin et al., ibid. 64, 2021 (1975). NMR study: W. E. Campbell et al., Spectrosc. Lett. 26, 707 (1993). Isoln: H. F. Deutsch et al., J. Pharm. Biomed. Anal. 12, 1283 (1994). Acute toxicity data: V. Plzak, J. Doull, Further Survey of Compounds for Radiation Protection (AD691490, USAF Radiation Lab., 1969) 82 pp.
Properties: Needles or prisms from alc, needles from petr ether. mp 208°. Sublimes 180°. bp2 220°. [a]D15 -100.2° (alc); [a]D -93° (chloroform). uv max (methanol): 218, 255, 280-290 nm (log e 4.52, 4.04, 3.53-3.40). One gram dissolves in 60 ml water, 50 ml alc, 100 ml ether. Also sol in benzene, chloroform, petr ether. LD50 i.p. in mice: 40 mg/kg (Plzak, Doull).
Melting point: mp 208°
Boiling point: bp2 220°
Optical Rotation: [a]D15 -100.2° (alc); [a]D -93° (chloroform)
Absorption maximum: uv max (methanol): 218, 255, 280-290 nm (log e 4.52, 4.04, 3.53-3.40)
Toxicity data: LD50 i.p. in mice: 40 mg/kg (Plzak, Doull)
Derivative Type: N-Formyl-N-deacetylaspidospermine
Additional Names: Vallesine
Molecular Formula: C21H28N2O2
Molecular Weight: 340.46
Percent Composition: C 74.08%, H 8.29%, N 8.23%, O 9.40%
Properties: Structure: Taylor et al., Helv. Chim. Acta 42, 2750 (1959). Long, fine needles from acetone, mp 154-156°. [a]D24 -91 ± 2° (c = 1.814 in abs alc). uv max: 211, 250 nm (log e 4.47, 3.94).
Melting point: mp 154-156°
Optical Rotation: [a]D24 -91 ± 2° (c = 1.814 in abs alc)
Absorption maximum: uv max: 211, 250 nm (log e 4.47, 3.94)
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