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467-51-6
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SAMANDARINE
???(??):
Samandarin;SAMANDARINE;1α,4α-Epoxy-3-aza-A-homo-5β-androstan-16β-ol;2,5-Epoxycyclopenta[5,6]naphth[1,2-d]azepin-9-ol, octadecahydro-5a,7a-dimethyl-, (2S,5R,5aS,5bS,7aR,9S,10aS,10bS,12aR)-
CBNumber:
CB21432361
???:
C19H31NO2
??? ??:
305.45
MOL ??:
467-51-6.mol

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187-188°
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D17 +43.3° (acetone)
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427.9±40.0 °C(Predicted)
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1.111±0.06 g/cm3(Predicted)
?? ?? (pKa)
15.26±0.60(Predicted)
optical activity
+43.317 (c 0.842, acetone)

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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]17D + 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.

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

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