Tetraethylammonium Derivatives

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Abstract
Derivatives of tetraethylammonium ion (TEA+) were synthesized in which one ethyl group was replaced by a C6, C8, C10, C12, C14 or C16 side chain. These TEA+ derivatives were tested for duration of sensory block of the rat infraorbital (trigeminal) nerve. The duration of sensory anesthesia increased exponentially from 1.2 h to 388 h as chain length increased from C2-C12, while C12, C14, and C16 all produced a similar reversible block of 17-20 days. The block duration of C12 was correlated with C12 bound to the infraorbital nerve; C12 not bound by the nerve was quantitatively excreted by the kidneys. These data, along with the lack of observable microscopic toxicity, suggest that TEA+ derivatives may be a useful new class of ultralong-acting local anesthetics.