Samandarin

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.

Samandarine family

Samandarin belongs to a family of toxic compounds called samandarines. Samandarines are biologically active, lipid-soluble steroidal alkaloids. They all contain a 7-6-6-5 fused ring system. Nine structures in this family have been characterized. Samandarines are exclusively produced and secreted by the fire salamander through their parotoid glands (20 mg/gland). Samandarin is the main component of these glandular secretions, although the precise ratio of alkaloids can vary from species to species and individual to individual. Fire salamanders are indigenous to central Europe and reside in deciduous forests. Salamander secretions have been shown to be toxic and distasteful to mammals, birds, fishes, and even other amphibians. It has also been suggested that samandarines help to prevent the salamander from contracting bacterial and fungal infections.

History

Discovery Early descriptions of salamander poisonings were found in the writings of many physicians and philosophers in Classical antiquity and the Middle Ages. Little was known about the toxic compounds, but the recorded symptoms from poisonings were consistent with what is known today. The ancient healers also had some interesting theories about how one contracted poison from the salamander. They believed that the mere sighting of the black and yellow spotted animal or ingestion of salamander ashes would lead to sickness and death. It was not until 1768 when Laurentius, a physician, discovered that the secretions from the skin glands of the salamander were the source of the poison. In 1866, Zalesky performed more studies on the toxicology of samandarines. He was able to isolate the family of alkaloids (believing they were one compound) and tested their toxicity on a variety of animals. He also found that the salamander could be poisoned by its own venom if it entered the salamander's bloodstream. Samandarin was the first in the family of compounds to be isolated. In 1899, Faust purified samandarin as a crystalline sulfate salt by killing the salamanders with chloroform, mincing their corpses, and performing a number of acid-base extractions. In 1926, the pharmacology of samandarin was further examined by Gessner who administered the poison to animals and dissected their corpses. He determined that the poison primarily affected the central nervous system and spinal cord. Most studies on samandarin and other samandarine alkaloids were performed in the mid-1900s by German scientists Schöpf and Habermehl. They were able to elucidate the structures of nine samandarines and found that samandarin was the main alkaloid in the salamander's secretions. The structure and stereochemistry of samandarin was confirmed in 1961 using X-ray crystallography. In 1968, Habermehl and Haaf also investigated biosynthesis of samandarines with in vitro and in vivo experiments, finding that the compounds originate from a cholesterol precursor.

Use in Salamander Brandy It is believed that the samandarine family of compounds is the active ingredient in an indigenous Slovenian drink called Salamander brandy. Salamander brandy was first brought to attention in 1995 by an article published in the Slovenian magazine Mladina, describing the hallucinogenic and intensely aphrodisiac effects of the drink. Ogorevc, the author of the article, writes about his first-hand experience of obtaining and experimenting with Salamander brandy. In the excerpt below, Ogorevc describes his intoxication with Salamander brandy:

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