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[3H]imidacloprid: Synthesis of a candidate radioligand for the nicotinic acetylcholine receptor

✍ Scribed by Bachir Latli; John E. Casida

Publisher
John Wiley and Sons
Year
1992
Tongue
French
Weight
192 KB
Volume
31
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Imidacloprid is an exceptionally potent insecticide known from physiological studies to act at the nicotinic acetylcholine receptor. To prepare [^3^H]imidacloprid as a candidate radioligand, 6‐chloronicotinoyl chloride was reduced with NaB^2^H~4~ (in model studies) or NaB^3^H~4~ in absolute ethanol to 2‐chloro‐5‐pyridinylmethanol which was transformed to 2‐chloro‐5‐chloromethylpyridine on refluxing with thionyl chloride. Coupling with 4,5‐dihydro‐N‐nitro‐1H‐imidazol‐2‐amine then gave [^2^H~2~]imidacloprid incorporating about 95% of the deuterium or [^3^H~2~]imidacloprid (25 Ci/mmol) in 80% radiochemical yield. In studies not detailed here [^3^H]imidacloprid was found to undergo high affinity, specific and saturable binding to a site in insect brain.

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