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Properties of substance:

batrachotoxin



skc-file

Group of substances:

organic

Physical appearance:

crystals

Empirical formula (Hill's system for organic substances):

C31H44N2O6

Molar/atomic mass: 540.69

CAS №: 23509-16-2

Solubility (g/100 g of solvent):

water: insoluble [Ref.]

Synthesis 1:

Reference: Journal of the American Chemical Society. - 1969. - Vol. 91, No. 14 pp. 3938

Eighteen milligrams of batrachotoxinin A and 170 mg of anhydride 2,4-dimethylpyrrole-3-carboxylic acid and ethyl Carbonic acid (8.2 molar excess) were dissolved in 3 ml of chloroform and stirred vigorously with 3.0 ml of 0.2 N potassium hydroxide solution for 5 hr at room temperature. The chloroform layer was separated and extracted with 0.3 N hydrochloric acid. The aqueous phase was made basic with ammonia and was extracted with chloroform. The chloroform was removed in vacuo and the 16 mg of basic products was purified over a column containing 14 g of silica gel (height 18 cm). The eluting solvent consisted of a mixture of chloroform and methanol, 9: 1. Each fraction consisted of 1.1 ml. Synthetic batrachotoxin (5 mg) appeared in fractions 21-24 and unreacted batrachotoxinin A (8 mg) was isolated after fraction 50. The synthetic batrachotoxin was identified by tlc, mass spectrometry, and nmr in deuteriochloroform and deuteriobenzene and by its unique toxicity, LD50 2 mcg/kg in mice.

LD50 (mg/kg):

0.002 (mice, subcutaneous)

References:

  1. Buckingham J. B., Baggaley K. H., Roberts A. D., Szabo L. F. Dictionary of Alkaloids. - 2 ed. - CRC Press, 2010. - pp. 267
  2. Journal of Toxicology - Toxin Reviews. - 1982. - Vol. 1, №1. - pp. 33-43
  3. Lewis R.J. Sax's Dangerous Properties of Industrial Materials. - 11ed. - Wiley-interscience, 2004. - pp. 347
  4. Potential military chemical/biological agents and compounds. - Washington: Departament of the Army, 1990. - pp. 79
  5. Science. - 1971. - Vol. 172, No. 3987. - pp. 995-1002
  6. Science. - 2016. - Vol. 354, No. 6314. - pp. 865-869
  7. The Merck Index 11th ed., Merck & Company, 1989. - pp. 157
  8. Орлов Б.Н., Гелашвили Д.Б. Зоотоксинология: ядовитые животные и их яды. - М.: Высшая школа, 1985. - pp. 190-192 [Russian]
  9. Химическая энциклопедия. - Т. 5. - М.: Советская энциклопедия, 1999. - pp. 526 [Russian]
  10. Турсунходжаева Ф.М., Джахангиров Ф.Н., Салимов Б.Т. Антидотное действие дитерпеноидных алкалоидов при отравлении нейротоксинами типа аконитина. Взаимосвязь структура-активность / Химия природных соединений. - 2016. - №5. - pp. 725-727 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru