Samandarin

Structural formula
General
Surname	Samandarin
other names	(1α, 4α, 5β, 16β) -1,4-epoxy-3-aza-A-homoandrostan-16-ol; (2 S , 5 R , 5a S , 5b S , 7a R , 9 S , 10a S , 10b S , 12a R ) -Octadecahydro-5a, 7a-dimethyl-2,5-epoxycyclopenta [5,6] naphth [1 , 2-d] azepin-9-ol;
Molecular formula	C 19 H 31 NO 2
External identifiers / databases
PubChem	120690
ChemSpider	16736008
Wikidata	Q425064
properties
Molar mass	305.46 g · mol -1
Physical state	firmly
Melting point	187-188 ° C
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
Toxicological data	1.5 mg kg −1 ( LD 50 , mouse , sc ) ; 1 mg kg −1 ( LD 50 , rabbit , iv ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Samandarin is a chemical compound from the group of oxazolidine derivatives that occurs naturally as a skin poison in the salamandra genera (including fire salamander ( S. salamandra ) and alpine salamander ( S. atra )) and Lycia salamandra . The complex structure of this compound could only be deciphered after extensive crystallographic investigations. The structure of the molecule with four linked rings is very similar to steroids ; the basic structure of the four-ring system is 3- aza- A-homo-5β-androstane . Due to the presence of a nitrogen atom in one of the rings, samandarin is one of the alkaloids , more precisely to the salamander alkaloids .

The biosynthesis of samandarin starts from cholesterol ; the nitrogen atom comes from glutamine .

Fire salamander ( Salamandra salamandra ).

Samandarin causes respiratory inhibition, high blood pressure, arrhythmias of the heart and hemolysis in humans . It is a highly effective local anesthetic , but is unsuitable for medical use due to its high toxicity. The physiological effect of samandarin depends on both the amount and the concentration. According to certain signs, it makes a difference whether the salamander is actively spraying its venom into the area or releasing it into the environment in a flowing burst. Studies have shown that from a certain amount of poison the toxic effects of samandarin no longer increase (so-called over-maximum dose).

Individual evidence

^ Brockhaus ABC Chemie , VEB FA Brockhaus Verlag Leipzig 1965, page 1222.
↑ ^a ^b ^c ^d ^e entry on salamander alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on September 6, 2013.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ ^a ^b Entry on Samandarin in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ Miguel Vences, Eugenia Sanchez, J. Susanne Hauswaldt, Daniel Eikelmann, Ariel Rodríguez, Salvador Carranza, David Donaire, Marcelo Gehara, Véronique Helfer, Stefan Lötters, Philine Werner, Stefan Schulz, Sebastian Steinfartz: Nuclear and mitochondrial multilocus phylogeny and survey of alkaloid content in true salamanders of the genus Salamandra (Salamandridae). Molecular Phylogenetics and Evolution, January 2014, doi: 10.1016 / j.ympev.2013.12.009 .

[ABC_Chemie-1] Brockhaus ABC Chemie , VEB FA Brockhaus Verlag Leipzig 1965, page 1222.

[roempp-2] ↑ ^a ^b ^c ^d ^e entry on salamander alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on September 6, 2013.

[NV-3] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[ChemIDplus-4] Entry on Samandarin in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[5] Miguel Vences, Eugenia Sanchez, J. Susanne Hauswaldt, Daniel Eikelmann, Ariel Rodríguez, Salvador Carranza, David Donaire, Marcelo Gehara, Véronique Helfer, Stefan Lötters, Philine Werner, Stefan Schulz, Sebastian Steinfartz: Nuclear and mitochondrial multilocus phylogeny and survey of alkaloid content in true salamanders of the genus Salamandra (Salamandridae). Molecular Phylogenetics and Evolution, January 2014, doi: 10.1016 / j.ympev.2013.12.009 .