2608. Cryptopine

Nomenclature

CAS number: 482-74-6
4,6,7,13-Tetrahydro-9,10-dimethoxy-5-methylbenzo[e]-1,3-dioxolo[4,5-l][2]benzazecin-12(5H)-one; cryptocavine.
C21H23NO5; mol wt 369.41.
C 68.28%, H 6.28%, N 3.79%, O 21.66%.

Description and references

Occurs in opium (0.003-0.03%). Has been found in Corydalis sempervirens (L.) Pers., and in Dicentra spp., Fumariaceae: Manske, Can. J. Res. 8, 407 (1933); 7, 265 (1932); 15B, 274 (1937). Structure: Perkin, J. Chem. Soc. 115, 713 (1919). Synthesis: Haworth, Perkin, ibid. 1926, 1769. Crystal structure: S. R. Hall, F. R. Ahmed, Acta Crystallogr. B24, 346 (1968).

Chemical structure

Properties

Crystallizes as six-sided prisms or plates from benzene, mp 220-221°. d 1.35. Almost insol in water and ether. Soluble in chloroform, acetic acid. One part dissolves in 455 parts alc or 80 parts boiling alc. Sparingly sol in most other organic solvents. May be crystallized from hot alc, benzene, petr ether, methyl ethyl ketone, isoamyl alcohol, acetophenone, pyridine, or an alcohol-pyridine mixture. The salts tend to oil out, but can be crystallized by warming, redissolving, and slow cooling.