Abstract
In order to trace the loss of N τ-methylhistamine, a principal metabolite of histamine, during extraction and purification from human plasma and urine samples, N τ-[ 3H]methylhistamine was prepared in two steps from N α t-butoxycarbonylhistamine (II). In the first step, compound II was deprotonated with NaH in an aprotic solvent and treated with [ 3H]methyl iodide. The products, N αt- butoxycarbonyl-N τ-[ 3 H]methylhistamine (III) and N αt- butoxycarbonyl-N π-[ 3 H] methylhistamine (IV), were then hydrolysed with iodotrimethylsilane under mild and short reaction conditions. Facile purification with Sep-Pak™ silica cartridges gave the combined two isomers of N τ[ 3H]methylhistamine and N τ[ 3H]methylhistamine in 10.7% radiochemical yield with a radiochemical purity of >94% and a ratio of approximately 2:1. Improvements in the extraction of methylhistamine using chromatography on Sep-Pak silica cartridges led to an overall recovery of 82.5±0.3% ( n = 3) based upon total [ 3H]methylhistamine from normal human plasma.
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