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Samandarin information


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
CAS Number
  • 467-51-6 ☒N
3D model (JSmol)
  • Interactive image
3DMet
  • L04227
ChEBI
  • CHEBI:36324 checkY
ChemSpider
  • 16736008 checkY
KEGG
  • C19950 checkY
PubChem CID
  • 9548773
UNII
  • IJN7TXF3HK
CompTox Dashboard (EPA)
  • DTXSID80894040
InChI
  • 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
SMILES
  • 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
Chemical formula
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 ?)
Infobox references

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 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).

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Samandarin

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Samandarin or Samandarine is the main steroidal alkaloid secreted by the fire salamander (Salamandra salamandra). The compound is extremely toxic (LD50...

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Fish

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Cinobufagin Marinobufagin Epibatidine Histrionicotoxin Pumiliotoxin 251D Samandarin Samandaridine Tarichatoxin Zetekitoxin AB Reptile/ Snake venom: Bungarotoxin...

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Fire salamander

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involved in cave adaptation. The fire salamander's primary alkaloid toxin, samandarin, causes strong muscle convulsions and hypertension combined with hyperventilation...

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Steroidal alkaloid

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some other organisms at all. Samandarin possesses a distinctive oxazolidine structure within the A ring. Besides samandarin, there are several other steroid...

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Samandaridine

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extremely toxic alkaloid produced by the skin glands of various salamanders. Samandarin Schöpf, C.; Koch, K. (1942). "Über Samandaron und Samandaridin, Nebenalkaloide...

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Botulinum toxin

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Cinobufagin Marinobufagin Epibatidine Histrionicotoxin Pumiliotoxin 251D Samandarin Samandaridine Tarichatoxin Zetekitoxin AB Reptile/ Snake venom: Bungarotoxin...

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Poison dart frog

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Ricin

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Cinobufagin Marinobufagin Epibatidine Histrionicotoxin Pumiliotoxin 251D Samandarin Samandaridine Tarichatoxin Zetekitoxin AB Reptile/ Snake venom: Bungarotoxin...

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Exotoxin

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Ciguatera fish poisoning

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Cinobufagin Marinobufagin Epibatidine Histrionicotoxin Pumiliotoxin 251D Samandarin Samandaridine Tarichatoxin Zetekitoxin AB Reptile/ Snake venom: Bungarotoxin...

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Aflatoxin

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Toxin

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Aflatoxin B1

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Neurotoxin

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Lipopolysaccharide

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Cardiotoxicity

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Muscimol

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Virulence factor

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Snake venom

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Tetanus toxin

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Shiga toxin

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Clostridium perfringens

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Ochratoxin

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Mycotoxin

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Clostridium botulinum

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Enterotoxin

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Bufotoxin

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Fumonisin

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Cinobufagin Marinobufagin Epibatidine Histrionicotoxin Pumiliotoxin 251D Samandarin Samandaridine Tarichatoxin Zetekitoxin AB Reptile/ Snake venom: Bungarotoxin...

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