6218. Mitragynine

Nomenclature

CAS number: 4098-40-2
(16E,20β)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester; (E)-16,17-didehydro-9,17-dimethoxy-17,18-seco-20α-yohimban-16-carboxylic acid methyl ester; 9-methoxycorynantheidine.
C23H30N2O4; mol wt 398.50.
C 69.32%, H 7.59%, N 7.03%, O 16.06%.

Description and references

Major alkaloid of Mitragyna speciosa Korth., Rubiaceae: Field, J. Chem. Soc. 119, 887 (1921); Ing, Raison, ibid. 1939, 986. Structural studies: Hendrickson, Chem. Ind. (London) 1961, 713; Joshi et al., ibid. 1963, 573. Revised structure: Zacharias et al., Acta Crystallogr. 18, 1039 (1965). Pharmacology: Macko et al., Arch. Int. Pharmacodyn. Ther. 198, 145 (1972).

Chemical structure

Properties

White, amorphous powder, mp 102-106°. bp5 230-240°. [α]D +39° (chloroform). uv max: 226, 292 nm (ε 41,150, 6600). Soluble in alcohol, chloroform, acetic acid.