Samandarine | CAS#467-51-6 | steroidal alkaloid

MedKoo Cat#: 461739 | Name: Samandarine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Samandarine is the main steroidal alkaloid secreted by the fire salamander (Salamandra salamandra). The compound is extremely toxic and causes convulsions, respiratory paralysis, and eventual death.

Chemical Structure

Samandarine

CAS#467-51-6

Theoretical Analysis

MedKoo Cat#: 461739

Name: Samandarine

CAS#: 467-51-6

Chemical Formula: C19H31NO2

Exact Mass: 305.2355

Molecular Weight: 305.46

Elemental Analysis: C, 74.71; H, 10.23; N, 4.59; O, 10.48

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Samandarine;

IUPAC/Chemical 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

InChi Key

HJCSQOSWSRPBOU-XTXNWKRWSA-N

InChi Code

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

SMILES Code

C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@@H](C2)O)CC[C@@H]4C[C@H]5NC[C@@H]([C@]34C)O5

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 305.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Oka K, Hara S. Stereoselective synthesis of samandarine nucleus. Tetrahedron Lett. 1969 May;(24):1987-90. PubMed PMID: 5790176. 2: Franke H, Partch R. The chemistry of samandarine model compounds. J Med Chem. 1966 Jul;9(4):643-4. PubMed PMID: 5968049. 3: Vences M, Sanchez E, Hauswaldt JS, Eikelmann D, Rodríguez A, Carranza S, Donaire D, Gehara M, Helfer V, Lötters S, Werner P, Schulz S, Steinfartz S. Nuclear and mitochondrial multilocus phylogeny and survey of alkaloid content in true salamanders of the genus Salamandra (Salamandridae). Mol Phylogenet Evol. 2014 Apr;73:208-16. doi: 10.1016/j.ympev.2013.12.009. Epub 2014 Jan 8. PubMed PMID: 24412216. 4: Mebs D, Pogoda W. Variability of alkaloids in the skin secretion of the European fire salamander (Salamandra salamadra terrestris). Toxicon. 2005 Apr;45(5):603-6. PubMed PMID: 15777956. 5: Daly JW, Myers CW, Whittaker N. Further classification of skin alkaloids from neotropical poison frogs (Dendrobatidae), with a general survey of toxic/noxious substances in the amphibia. Toxicon. 1987;25(10):1023-95. Review. PubMed PMID: 3321567.