Samandarines

There are in total nine naturally occurring samandarines.  The first alkaloid to be synthesized was samandarone, but samandinine, samandenone and isocycloneosamandaridine, have not been synthesised. The name cycloneosamandaridine is used for the synthetically obtained  material. 

Two further samandarines have been synthesised samane (deoxysamanine) and 17(i-hydroxysamane), neither of which have been detected in Nature.

Chemically the samandarines have a modified steroidal A-ring containing a ring-nitrogen and in most cases an oxygen-bridge that forms an oxazolidine ring.

Samandarines are potent local anaesthetics.

Samandarines are potentially highly toxic with an injected lethal dose in a mouse being about 70 jig...

When ingested they cause strong muscle convulsions and hypertension combined with hyperventilation..  But as far as I can ascertain no memory  effects are experienced.

They are known only from salamanders of the Eurasian genus Salamandra, where they occur in parotoid glands. The parotoid glands of each fire salamander  contains about 20 mg of samandarine, while the glands of each alpine salamander  contain about 5 mg. A closely related salamander of Italy, Salamandrina terdigitata, has not been investigated because of strict animal protection laws. Remarkably, the fire salamander is sensitive to the toxic effects of samandarine.

The paratoid glands of the Fire Salamander are concentrated in certain areas of the body, especially around the head and the dorsal skin surface. The colored portions of the animal's skin usually coincide with these glands. It is believed that these secretions “might be effective against bacterial and fungal infections of the epidermis”, which is a different reason for excretion from the toxins produced by, for example newts.

The fire salamander appears to synthesize the samandarine alkaloids , since there was no change in alkaloid content of parotoid glands over three generations reared in captivity.

References

• “Salamander alkaloids. II. Samandarone and samandaridine, secondary alkaloids in the poison of the fire and alpine salamanders." Schopf, C.; Koch, K. Ann. (1942)”

•  Variability of alkaloids in the skin secretion of the European fire salamander (Salamandra salamandra terrestris) - Mebs D Pogoda W - Zentrum der Rechtsmedizin, University of Frankfurt, Kennedyallee 104, D-60596 Frankfurt, Germany