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Synthesis of deuterium and tritium labelled m-aminolevamisole and levamisole

✍ Scribed by Nicholas C. Sangster; Ernest Lacey; Chit Than; Mervyn A. Long

Publisher
John Wiley and Sons
Year
1989
Tongue
French
Weight
349 KB
Volume
27
Category
Article
ISSN
0022-2135

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✦ Synopsis

Levamisole (LEV) i s a w i d e l y used a n t i -p a r a s i t i c agent. I n o r d e r t o c h a r a c t e r i s e t h e biochemical pharmacology o f LEV i n p a r a s i t i c nematodes, [3H]LEV and a more a c t i v e analogue [3H]m-aminolevamisole (MAL) have been prepared. Label1 i n g was accomplished by t r i t i a t e d water exchange o f MAL under a c i d c o n d i t i o n s . M u l t i p l e s i t e l a b e l l i n g was achreved i n t h e p o s i t i o n s ortho and p a r a t o t h e amino group o f MAL. T r i t i a t i o n o f MAL HC1 i n C3H],0 was achieved a t 103°C f o r 23 h. Crude [3H]MAL was d i a z o t i s e d ( h y d r o c h l o r i c a c i d and sodium n i t r i t e ) and deaminated (hypophosphorous acid) t o e f f e c t t h e synthesis o f [3H]LEV. Products o f both r e a c t i o n s were p u r i f i e d by p r e p a r a t i v e h.p.1 .c. and c h a r a c t e r i s e d by h.p.1 .c., t.1.c. and mass spectrometry. (Radiochemical y i e l d was about 15% and p u r i t y >go%.) S p e c i f i c a c t i v i t i e s o f 39 Ci/mmol f o r [3H]MAL and 37 Ci/mmol f o r [3H]LEV were obtained.

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