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A short synthesis of [14C]-labelled levamisole and its major metabolite

✍ Scribed by Cor G.M. Janssen; Jos B.A. Thijssen; Willy L.M. Verluyten

Publisher
John Wiley and Sons
Year
2002
Tongue
French
Weight
109 KB
Volume
45
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Levamisole (I) is the levo isomer of tetramisole. It is a broad spectrum anthelmintic which is used extensively as a veterinary drug for food producing animals. Metabolism and environmental studies necessitated the synthesis of ^14^C‐labelled levamisole (6) and of its major metabolite (12).

^14^C‐Tetramisole was obtained in two steps from ^14^C‐thiourea. Resolution via salt formation and crystallization afforded ^14^C‐levamisole and ^14^C‐dexamisole. Racemisation followed again by resolution made it possible to improve the over‐all radiochemical yield of ^14^C‐levamisole to 51.0%. The compound had a specific activity of 73.6 MBq/mmol, a HPLC purity of 99.8% and an enantiomeric excess of 99.4%.

The ^14^C‐labelled metabolite of levamisole (II) was obtained from ^14^C‐potassium cyanate in 4 consecutive steps. Resolution via chiral HPLC afforded the desired compound in a 16.2% overall radiochemical yield. It had a specific activity of 895 MBq/mmol, a HPLC purity of 98.7% and an enantiomeric excess of 100%. Copyright © 2002 John Wiley & Sons, Ltd.

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