9558. Toxiferine I

Nomenclature

CAS number: 6888-23-9
C-Toxiferine I.
[C40H46N4O2]2+.

Description and references

Naturally occurring neuromuscular blocker. From calabash curare: Schmid, Karrer, Helv. Chim. Acta 30, 1162 (1947); from Strychnos toxifera Schomb., Loganiaceae: Wieland et al., Ann. 547, 156 (1941); King, J. Chem. Soc. 1949, 3263. Identity with toxiferine V and toxiferine XI: Battersby et al., ibid. 1960, 1848. Structure: Arnold et al., Helv. Chim. Acta 44, 620 (1961). Synthesis: Berlage et al., ibid. 42, 394 (1959); Grdinic et al., J. Am. Chem. Soc. 86, 3357 (1964). Pharmacokinetics: P. G. Waser, J. Reller, Agents Actions 2, 170 (1972). 13C-NMR study: E. Wenkert et al., J. Org. Chem. 43, 1099 (1978).

Chemical structure

Derivative

Dichloride.
C40H46Cl2N4O2; mol wt 685.72.
C 70.06%, H 6.76%, Cl 10.34%, N 8.17%, O 4.67%.

Properties

Crystals. [α]D22 546° (c = 0.30). uv max (ethanol): 292 nm (log ε 4.62). Sol in water.

Derivative

C-Toxiferine II.

Nomenclature

CAS number: 7257-29-6
C-Calebassine; C-strychnotoxine.
[C40H48N4O2]2+.

Description and references

From calabash-curare: Karrer, Schmidt, Helv. Chim. Acta 29, 1853 (1946); Zürcher et al., J. Am. Chem. Soc. 80, 1500 (1958). Identity as C-toxiferine II and C-strychnotoxine: Wieland, Merz, Ber. 85, 731 (1952). Structure: Hesse et al., Helv. Chim. Acta 44, 2211 (1961); Fehlmann et al., ibid. 48, 303 (1965).