Psychotrine
Title: Psychotrine
CAS Registry Number: 7633-29-6
CAS Name: 1¢,15-Didehydro-7¢,10,11-trimethoxyemetan-6¢-ol
Molecular Formula: C28H36N2O4
Molecular Weight: 464.60
Percent Composition: C 72.38%, H 7.81%, N 6.03%, O 13.77%
Literature References: Minor alkaloid found in ipecac, the ground roots of Uragoga ipecacuanha (Brot.) Baill. [Cephaelis ipecacuanha (Brot.) A. Rich.], Rubiaceae: F. H. Carr, F. L. Pyman, J. Chem. Soc. 105, 1591 (1914); O. Hesse, Ann. 405, 1 (1914). Structure and stereochemistry: A. R. Battersby et al., J. Chem. Soc. 1959, 2704, 3512. Mass spectrum: H. Budzikiewicz et al., Tetrahedron 20, 399 (1964); 1H,13C-NMR of O-methylpsychotrine: T. Fujii et al., Chem. Pharm. Bull. 30, 598 (1982); 13C-NMR of psychotrine: eidem, ibid. 31, 2583 (1983). Proposed alternate structure with exocyclic double bond: E. E. van Tamelen et al., J. Am. Chem. Soc. 79, 4817 (1957); C. Schuij et al., J. Chem. Soc. Perkin Trans. 1 1979, 970. Review: M. Janot in Manske, Holmes, The Alkaloids vol. 3 (Academic Press, New York, 1953) pp 363-394.
 
Derivative Type: Tetrahydrate
Properties: Yellow prisms with blue fluorescence from dil acetone or alcohol. Very bitter taste, produces nausea instantly. The anhydr material sinters at 120°, becomes transparent at 120-126° and melts completely at 128°. [a]D15 +69.3° (c = 2 in alcohol, calcd as the tetrahydrate). Sparingly sol in water, benzene, petr ether, ether. More sol in alcohol, acetone, chloroform. uv max (0.1N HCl): 240, 288, 306, 356 nm (e 13900, 5700, 6250, 6800).
Optical Rotation: [a]D15 +69.3° (c = 2 in alcohol, calcd as the tetrahydrate)
Absorption maximum: uv max (0.1N HCl): 240, 288, 306, 356 nm (e 13900, 5700, 6250, 6800)
 
Derivative Type: Sulfate trihydrate
Molecular Formula: C28H36N2O4.H2SO4.3H2O
Molecular Weight: 616.72
Percent Composition: C 54.53%, H 7.19%, N 4.54%, O 28.54%, S 5.20%
Properties: Pale yellow scales from water, dec 214-217° when anhydr. [a]D20 +39.2°.
Optical Rotation: [a]D20 +39.2°
 
Derivative Type: O-Methylpsychotrine
Properties: Has a methoxy group in place of the hydroxyl group. mp 123-124°. [a]D20 +43.2° (alc). uv max (water) pH 1: 241.5, 288.5, 305, 354 (log e 4.26, 3.86, 3.92, 3.91); pH 13: 226, 278.5, 307 (log e 4.43, 3.96, 3.77).
Melting point: mp 123-124°
Optical Rotation: [a]D20 +43.2° (alc)
Absorption maximum: uv max (water) pH 1: 241.5, 288.5, 305, 354 (log e 4.26, 3.86, 3.92, 3.91); pH 13: 226, 278.5, 307 (log e 4.43, 3.96, 3.77)

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