CAS Registry Number: 59392-53-9
Additional Names: MTX
Molecular Formula: C164H256Na2O68S2
Molecular Weight: 3425.86
Percent Composition: C 57.50%, H 7.53%, Na 1.34%, O 31.76%, S 1.87%
Literature References: Polycyclic ether toxin involved in ciguatera fish poisoning of humans. From the Tahitian for the surgeon fish (maito) from which it was orginally isolated; later found to be a product of the dinoflagellate, Gamberdiscus toxicus. One of the most toxic and the largest (mol wt 3422 Da) natural products known to date besides the biopolymers. Isoln from surgeon fish: T. Yasumoto et al., Bull. Jpn. Soc. Sci. Fish. 42, 359 (1976); from dinoflagellate: idem et al., "A New Toxic Dinoflagellate Found in Association with Ciguatera" in Toxic Dinoflagellate Blooms, D. L. Taylor, H. Seliger, Eds. (Elsevier/North Holland, Inc., NY, 1979) pp 65-70. Toxicity and channel activation: M. Takahashi et al., J. Biol. Chem. 257, 7287 (1982). Structure: M. Murata et al., J. Am. Chem. Soc. 115, 2060 (1993); and stereochemistry: L. R. Cook et al., ibid. 119, 7928 (1997). Use as activator of calcium influx: J. W. Daly et al., Biochem. Pharmacol. 50, 1187 (1995); H. M. Brereton et al., Biochim. Biophys. Acta 1540, 107 (2001); as receptor differentiator: P. M. Lundy et al., Eur. J. Pharmacol. 487, 17 (2004). Effect of cations on MTX response: V. Morales-Tlalpan, L. Vaca, Toxicon 40, 493 (2002). Determn by capillary zone electrophoresis: N. Bouaïcha et al., ibid. 35, 955 (1997). Review of use as tool for calcium flux: F. Gusovsky, J. W. Daly, Biochem. Pharmacol. 39, 1633-1639 (1990); of mechanism of action and pharmacology: M. Estacion, Food. Sci. Technol. 103, 473-503 (2000).
Properties: Sol in water, methanol, ethanol, 1-butanol saturated with water. Insol in diethyl ether, acetone and chloroform.
Use: Calcium channel activator; research tool for ion flux.