4788. Hydrocotarnine

Nomenclature

CAS number: 550-10-7
5,6,7,8-Tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinoline; 8-methoxy-5,6-methylenedioxy-2-methyl-1,2,3,4-tetrahydroisoquinoline.
C12H15NO3; mol wt 221.25.
C 65.14%, H 6.83%, N 6.33%, O 21.69%.

Description and references

Found in mother liquors from morphine extraction. It is not certain whether it is formed from narcotine during the extraction or whether it exists in the poppy plant. May also be prepd by reduction of cotarnine: Topchiev, J. Appl. Chem. USSR 6, 529 (1933), C.A. 28, 2718 (1934); Schneider, Müller, Ann. 615, 34 (1958); Knabe, Arch. Pharm. 292, 652 (1959). Reduction of hydrocotarnine with sodium in alcohol leads to replacement of the methoxyl group by hydrogen, with formation of hydrohydrastinine. Review and bibliography: Small, Lutz, “Chemistry of the Opium Alkaloids,” Suppl. No. 103, Public Health Reports, Washington (1932).

Chemical structure

Derivative

Hemihydrate.

Properties

Plates from petr ether, mp 56°. Loses water of crystn at 60°. May be distilled with little decompn at 100°: Hesse, Ber. 4, 693 (1871). Absorption spectrum: Hantzsch, Ber. 44, 1816 (1911); Steiner, Compt. Rend. 176, 244, 1379 (1923); Csokán, Z. Anal. Chem. 124, 344 (1942). Almost insol in water, alkaline solns; sol in alcohol, acetone, chloroform, benzene, ether.

Derivative

Hydrochloride monohydrate.

Properties

Prisms; sol in water.

Derivative

Hydrobromide.

Properties

Crystals, mp 237°; sparingly sol in water.

Derivative

Hydriodide.

Properties

Needles from methanol, mp 196°; sol in hot water.

Derivative

Methiodide.

Properties

Needles from water, plates from alc, mp 206°.

Derivative

Methobromide.

Properties

Needles from chloroform, dec 221°.