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Science 23 June 1967:
Vol. 156. no. 3782, pp. 1625 - 1627
DOI: 10.1126/science.156.3782.1625
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Articles

Potency Difference between the Zwitterion Form and the Cation Forms of Tetrodotoxin

George Camougis 1, Bertil H. Takman 1, J. Rene 1, and P. Tasse 1

1 Laboratory of Biological Research, Astra Pharmaceutical Products, Inc., Worcester, Massachusetts 01606

Tetrodotoxin can exist as a zwitterion or two different cations in aqueous solutions. The cation forms are more potent in nerve block. Thus the lactone-hemilactal configuration of tetrodotoxin influences potency. Electrostatic attraction, hydrogen bonding, and intermolecular hemilactal formation are possible mechanisms of interaction with membrane receptors.

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Science. ISSN 0036-8075 (print), 1095-9203 (online)