Evodiamine
Title: Evodiamine
CAS Registry Number: 518-17-2
CAS Name: 8,13,13b,14-Tetrahydro-14-methylindolo[2¢,3¢:3,4]pyrido[2,1-b]quinazolin-5(7H)-one
Molecular Formula: C19H17N3O
Molecular Weight: 303.36
Percent Composition: C 75.23%, H 5.65%, N 13.85%, O 5.27%
Literature References: From Evodia rutaecarpa Hook. & Thoms and bark of Zanthoxylum rhetsa DC., Rutaceae: Y. Asahina, K. Kashiwaki, J. Pharm. Soc. Jpn. 1915, 1293, C.A. 10, 607 (1916); Gopinath et al., Tetrahedron 8, 293 (1960). Structure: Y. Asahina J. Pharm. Soc. Jpn. 1924, 1; Ohta, J. Pharm. Soc. Jpn. 65, 15 (1945), C.A. 45, 5697 (1951). Synthesis: Asahina, Ohta, Ber. 61B, 319 (1928); T. Kametani et al., J. Am. Chem. Soc. 98, 6186 (1976); eidem, Heterocycles 4, 23 (1976). Biosynthesis: M. Yamazaki et al., Tetrahedron Lett. 1966, 3221; 1967, 3317. Mass spec.: J. Tamas et al., Acta Chim. Acad. Sci. Hung. 89, 85 (1976).
Properties: Yellow plates from alc, mp 278°. [a]D15 +352° (acetone); [a]D +440° (chloroform). uv max (acetonitrile): 272, 280, 291, 335 nm (log e 4.06, 4.02, 3.90, 3.30). Sol in acetone; slightly sol in alcohol, ether, chloroform. Practically insol in water, petr ether, benzene. Does not seem to form salts.
Melting point: mp 278°
Optical Rotation: [a]D15 +352° (acetone); [a]D +440° (chloroform)
Absorption maximum: uv max (acetonitrile): 272, 280, 291, 335 nm (log e 4.06, 4.02, 3.90, 3.30)

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