Sango K, Maruyama W, Matsubara K, Dostert P, Minami C, Kawai M, Naoi M
Department of Applied Chemistry, Nagoya Institute of Technology, Nagoya, Japan.
Neurosci Lett. 2000 Apr 14;283(3):224-6. doi: 10.1016/s0304-3940(00)00963-0.
Tetrahydropapaveroline is an endogenous complex alkaloid derived from dopamine through the oxidation by monoamine oxidase. This alkaloid is considered to be involved in the pathogenesis of alcoholism and to act as a false neurotransmitter. Recently the (S) enantiomer was proposed to be a precursor of morphine biosynthesis in the opium poppy. In this paper stereo-chemical characteristic of tetrahydropapaveroline in human brains was examined. In all four control human brains examined, only the (S)-tetrahydropapaveroline was detected. The concentrations were 0.12-0.22 pmol/g wet weight of brain tissue, and the presence of alcohol in blood did not affect the concentration. The results suggest that (S)-tetrahydropapaveroline may be enantio-selectively synthesized in human brain and it may be an intermediate of the de novo synthesis of morphine analogues.
四氢罂粟碱是一种内源性复合生物碱，由多巴胺经单胺氧化酶氧化产生。这种生物碱被认为与酒精中毒的发病机制有关，并作为一种假性神经递质起作用。最近，有人提出（S）对映体是罂粟中吗啡生物合成的前体。本文研究了人脑四氢罂粟碱的立体化学特征。在所检测的4例对照人脑中，仅检测到（S）-四氢罂粟碱。浓度为脑组织湿重0.12 - 0.22 pmol/g，血液中酒精的存在不影响该浓度。结果表明，（S）-四氢罂粟碱可能在人脑中以对映体选择性方式合成，并且可能是吗啡类似物从头合成的中间体。
