Van Vunakis H, Farrow J T, Gjika H B, Levine L
Proc Natl Acad Sci U S A. 1971 Jul;68(7):1483-7. doi: 10.1073/pnas.68.7.1483.
Antibodies to D-lysergic acid have been produced in rabbits and guinea pigs and a radioimmunoassay for the hapten was developed. The specificity of this lysergamide-antilysergamide reaction was determined by competitive binding with unlabeled lysergic acid diethylamide (LSD), psychotomimetic drugs, neurotransmitters, and other compounds with diverse structures. LSD and several related ergot alkaloids were potent competitors, three to seven times more potent than lysergic acid itself. The N,N-dimethyl derivatives of several compounds, including tryptamine, 5-hydroxytryptamine, 4-hydroxytryptamine, 5-methoxytryptamine, tyramine, and mescaline, were only about ten times less effective than lysergic acid, even though these compounds lack some of the ring systems of lysergic acid. The pattern of inhibition by related compounds with various substituents suggests that the antibody receptor site recognizes structural features resembling the LSD molecule. In particular, the aromatic nucleus and the dimethylated ethylamine side chain in phenylethylamine and tryptamine derivatives may assume in solution a conformation resembling ring A and the methylated nitrogen in ring C of LSD. Among the tryptamine derivatives, a large percentage of the most potent competitors are also psychotomimetic compounds.
已在兔和豚鼠体内产生了针对D - 麦角酸的抗体，并开发了一种针对该半抗原的放射免疫测定法。通过与未标记的麦角酸二乙酰胺（LSD）、拟精神病药物、神经递质及其他结构各异的化合物进行竞争性结合，确定了这种麦角酰胺 - 抗麦角酰胺反应的特异性。LSD和几种相关的麦角生物碱是强效竞争者，其效力比麦角酸本身高3至7倍。包括色胺、5 - 羟色胺、4 - 羟色胺、5 - 甲氧基色胺、酪胺和三甲氧苯乙胺在内的几种化合物的N，N - 二甲基衍生物，其效力仅比麦角酸低约十分之一，尽管这些化合物缺乏麦角酸的一些环系。具有各种取代基的相关化合物的抑制模式表明，抗体受体位点识别类似于LSD分子的结构特征。特别是，苯乙胺和色胺衍生物中的芳香核和二甲基化乙胺侧链在溶液中可能呈现出类似于LSD的A环和C环中甲基化氮的构象。在色胺衍生物中，大部分最强效的竞争者也是拟精神病化合物。
