Samandarin

Samandarin
Names
Preferred IUPAC name
(2S,5R,5aS,5bS,7aR,9S,10aS,10bS,12aR)-5a,7a-Dimethyloctadecahydro-2,5-epoxycyclopenta[5,6]naphtho[1,2-d]azepin-9-ol
Other names
Samandarine
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C19H31NO2/c1-18-6-5-14-13(15(18)8-12(21)9-18)4-3-11-7-17-20-10-16(22-17)19(11,14)2/h11-17,20-21H,3-10H2,1-2H3/t11-,12+,13-,14+,15+,16+,17+,18-,19+/m1/s1 checkY
    Key: HJCSQOSWSRPBOU-XTXNWKRWSA-N checkY
  • InChI=1S/C19H31NO2/c1-18-6-5-14-13(15(18)8-12(21)9-18)4-3-11-7-17-20-10-16(22-17)19(11,14)2/h11-17,20-21H,3-10H2,1-2H3/t11-,12+,13-,14+,15+,16+,17+,18-,19+/m1/s1
    Key: HJCSQOSWSRPBOU-XTXNWKRWBO
  • Key: HJCSQOSWSRPBOU-XTXNWKRWSA-N
  • O[C@H]5C[C@@H]2[C@](C)(CC[C@@H]1[C@@]3(C)[C@@H]4CN[C@H](C[C@H]3CC[C@H]12)O4)C5
Properties
C19H31NO2
Molar mass 305.462 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Samandarin or Samandarine is the main steroidal alkaloid secreted by the fire salamander (Salamandra salamandra).[1] The compound is extremely toxic (LD50 = 70 μg/kg in mice).[2] Poisoning can cause convulsions, respiratory paralysis, and eventual death.[3] Samandarin is also believed to be the active ingredient in Salamander brandy, a Slovenian traditional medicinal alcoholic drink with purported hallucinogenic and aphrodisiac effects.[4]

  1. ^ Cite error: The named reference best was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference daly was invoked but never defined (see the help page).
  3. ^ Blyth, A. W. (1895). Poisons, Their Effects and Detection (4 ed.). London: Charles Griffin and Company, Limited. pp. 483–484.
  4. ^ Cite error: The named reference kozorog was invoked but never defined (see the help page).