2462. Codamine

Nomenclature

CAS number: 21040-59-5
(1S)-1-[(3,4-Dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6-methoxy-2-methyl-7-isoquinolinol; 1,2,3,4-tetrahydro-6-methoxy-2-methyl-1-veratryl-7-isoquinolinol.
C20H25NO4; mol wt 343.42.
C 69.95%, H 7.34%, N 4.08%, O 18.64%.

Description and references

Minor opium alkaloid. Constitutes about 0.003% of Turkish opium. Isoln: Hesse, Ann. 282, 213 (1894). Structure: Sp"ath, Epstein, Ber. 59B, 2791 (1926). Synthesis: Sch"opf, Thierfelder, Ann. 537, 143 (1939); Billek, Monatsh. Chem. 87, 106 (1956).

Chemical structure

Derivative

dl-Form.

Properties

Large, six-sided prisms from ether, mp 127°. Very sol in alcohol, chloroform. Somewhat sol in boiling water. In soln codamine reacts strongly basic. The salts are bitter in taste, whereas the base is said to be tasteless.