N-Methylconanin-5-en-3β-amine

Description

A pregnene type alkaloid found in the bark and seeds of Holarrhena antidysenterica Wall., the base yields a hydrate, m.p. 88-92°C and has [α]²⁵_D + 30.0° (aqueous EtOH). It is freely soluble in most organic solvents. It yields a series of crystalline salts and derivatives, e.g. the hydrochloride, m.p. 334-335°C (dec.); hydrobromide, m.p. 344°C; hydriodide, m.p. 316°C; platinichloride, m.p. 285°C (dec.); methiodide, m.p. 290°C (dec.) and the picrate, m.p. 198-200°C. The N-acetyl derivative has also been prepared, m.p. 161°C yielding a hydrochloride, m.p. 325-6°C, as has the benzoyl compound, m.p. l59-l60°C, also forming a hydrochloride, m.p. 325-6°C (dec.).
On methylation, the alkaloid yields conessine and heating with dilute H2S04 isomerizes the base to isonorisoconessine, [0:]5S + 101 ° (EtOH), furnishing a hydriodide, m.p. 289°C (dec.) and a picrate, m.p. 166°C.

References

Siddiqui.,J. Ind. Chern. Soc., 11,283 (1934) Siddiqui, Siddiqui., ibid, 11,787 (1934) Haworth, McKenna, Whitfield.,J. Chern. Soc., 1102 (1953)