SAMANDARINE Property

Melting point:

187-188°

alpha 

D17 +43.3° (acetone)

Boiling point:

427.9±40.0 °C(Predicted)

Density 

1.111±0.06 g/cm3(Predicted)

pka

15.26±0.60(Predicted)

optical activity

+43.317 (c 0.842, acetone)

Hazard and Precautionary Statements (GHS)

SAMANDARINE Chemical Properties,Usage,Production

Description

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.

Definition

ChEBI: Samandarine is a steroid alkaloid fundamental parent.

References

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