Samandarine
Title: Samandarine
CAS Registry Number: 467-51-6
CAS Name: 1a,4a-Epoxy-3-aza-A-homoandrostan-16b-ol
Molecular Formula: C19H31NO2
Molecular Weight: 305.45
Percent Composition: C 74.71%, H 10.23%, N 4.59%, O 10.48%
Literature References: Constitutes together with samandarone approx 75% of the alkaloid content in the skin glands of the European fire and Alpine salamanders: Salamandra maculosa resp. atra Laur., Salamandridae. Isoln: Schöpf, Braun, Ann. 514, 69 (1934). Structure and configuration: Wölfel et al., Ber. 94, 2361 (1961).
Properties: Needles from abs methanol or 50% acetone, mp 187-188°. Solvated crystals from dil methanol. [a]D17 +43.3° (acetone). Freely sol in most organic solvents. Practically insol in water and NaOH solns.
Melting point: mp 187-188°
Optical Rotation: [a]D17 +43.3° (acetone)
 
Derivative Type: Hydrochloride
Molecular Formula: C19H31NO2.HCl
Molecular Weight: 341.92
Percent Composition: C 66.74%, H 9.43%, N 4.10%, O 9.36%, Cl 10.37%
Properties: Crystals from methanol, mp 312-313°; from water, mp 321-322° (monohydrate).
Melting point: mp 312-313°; mp 321-322° (monohydrate)
 
Derivative Type: Samandarone
Molecular Formula: C19H29NO2
Molecular Weight: 303.44
Percent Composition: C 75.21%, H 9.63%, N 4.62%, O 10.55%
Literature References: ketone corresponding to the secondary alcohol in samandarine. Synthesis: Hara, Oka, J. Am. Chem. Soc. 89, 1041 (1967).
Properties: Needles from methyl ethyl ketone, mp 191-192°; from 35% acetone, mp 189-191°. [a]D21 -115.7° (acetone).
Melting point: mp 191-192°; mp 189-191°
Optical Rotation: [a]D21 -115.7° (acetone)

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