Hydrocotarnine
Title: Hydrocotarnine
CAS Registry Number: 550-10-7
CAS Name: 5,6,7,8-Tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinoline
Additional Names: 8-methoxy-5,6-methylenedioxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
Molecular Formula: C12H15NO3
Molecular Weight: 221.25
Percent Composition: C 65.14%, H 6.83%, N 6.33%, O 21.69%
Literature 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).
 
Derivative Type: 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.
Melting point: mp 56°
 
Derivative Type: Hydrochloride monohydrate
Properties: Prisms; sol in water.
 
Derivative Type: Hydrobromide
Properties: Crystals, mp 237°; sparingly sol in water.
Melting point: mp 237°
 
Derivative Type: Hydriodide
Properties: Needles from methanol, mp 196°; sol in hot water.
Melting point: mp 196°
 
Derivative Type: Methiodide
Properties: Needles from water, plates from alc, mp 206°.
Melting point: mp 206°
 
Derivative Type: Methobromide
Properties: Needles from chloroform, dec 221°.

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