ساماندارین

Also known as (1R,2S,3S,6R,8S,10S,11S,14R,16S)-2,6-dimethyl-19-oxa-17-azapentacyclo[14.2.1.02,14.03,11.06,10]nonadecan-8-ol

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

Chemical data

Formula: C19H31NO2
Molecular weight: 305.5 g/mol
IUPAC name: (1R,2S,3S,6R,8S,10S,11S,14R,16S)-2,6-dimethyl-19-oxa-17-azapentacyclo[14.2.1.02,14.03,11.06,10]nonadecan-8-ol
SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@@H](C2)O)CC[C@H]4[C@@]3([C@@H]5CN[C@H](C4)O5)C
InChIKey: HJCSQOSWSRPBOU-XTXNWKRWSA-N
XLogP: 3.7
Polar surface area: 41.5 Å²
H-bond donors: 2
H-bond acceptors: 3
Formal charge: 0

via PubChem

Wikidata facts

Mass: 305.235479232

Show 5 more facts

chemical formula: C₁₉H₃₁NO₂
found in taxon: corroboree frog
Commons category: Samandarin
isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@@H](C2)O)CC[C@H]4[C@@]3([C@@H]5CN[C@H](C4)O5)C
canonical SMILES: OC1CC2C3CCC4CC5OC(CN5)C4(C)C3CCC2(C)C1

Sources (2)

via Wikidata · CC0