467-51-6

This pentacyclic alkaloid also occurs in the skin secretion of Salamandra species, particularly S. atra and S. maculosa. It forms colourless crystals from a variety of solvents but when crystallized from MeOH contains solvent of crystallization. The solutions are strongly alkaline and the base is dextrorotatory with [α]¹⁷_D + 43.7°. Two bridge methyl groups, a non-phenolic hydroxyl group and a methylimino group are present in the molecule. Several crystalline derivatives have been prepared including the hydrochloride, m.p. 32l-2°C; the O,N-diacetyl derivative, m.p. l67-8°C; the monoformyl compound, m.p. l48-ISOoC; diformyl derivative, m.p. 2S6-g0C; N-nitroso compound, m.p. 164-5°C and the N-methyl derivative which is characterized as the hydrochloride, m.p. 300-2°C (dec.) and the methiodide, m.p. 27l-2°C.

ChEBI: Samandarine is a steroid alkaloid fundamental parent.

Schopf, Braun., Annalen., 514,69 (1934)
Schopf, Koch., ibid, 552,62 (1942)
Wolfeletal., Ber., 94, 2361 (1961)