O'Brien E M, Tipton K F, Strolin Benedetti M, Bonsignori A, Marrari P, Dostert P
Department of Biochemistry, Trinity College, Dublin, Ireland.
Biochem Pharmacol. 1991 Jun 1;41(11):1731-7. doi: 10.1016/0006-2952(91)90177-7.
The anticonvulsant drug milacemide (2-n-pentylaminoacetamide) is known to be oxidized by monoamine oxidase-B to yield glycinamide which then breaks-down to give glycine. It has been postulated that it is this liberation of glycine in the brain that accounts for the anticonvulsant effects. In order to test this hypothesis, and since amines bearing a methyl-group in the alpha-position have been shown to be resistant to oxidation by monoamine oxidase, the effects of milacemide were compared with those of alpha-methyl-milacemide. Although the latter compound was found to be toxic at higher concentrations, it was found to antagonize bicuculline-induced convulsions in mice. When milacemide was administered to mice (0.5 mmol/kg, p.o.) there was a substantial increase in urinary glycinamide excretion. No such increase was observed after the administration of the same dose of alpha-methyl-milacemide. Furthermore, alpha-methyl-milacemide was not oxidized by either monoamine oxidase-A or -B in vitro to any detectable extent, although it was a competitive inhibitor of both forms of the enzyme. The findings that alpha-methyl-milacemide has anticonvulsant properties in the bicuculline test but is not a substrate for monoamine oxidase or a source of urinary glycinamide cast doubt on the importance of the oxidation or milacemide to form glycinamide as a major factor in its anticonvulsant action.
抗惊厥药物米拉酰胺(2-正戊基氨基乙酰胺)已知可被单胺氧化酶-B氧化生成甘氨酰胺,然后甘氨酰胺分解产生甘氨酸。据推测,正是大脑中甘氨酸的这种释放导致了抗惊厥作用。为了验证这一假设,并且由于已表明在α位带有甲基的胺对单胺氧化酶的氧化具有抗性,因此将米拉酰胺的作用与α-甲基米拉酰胺的作用进行了比较。尽管发现后一种化合物在较高浓度下有毒,但发现它能拮抗小鼠中荷包牡丹碱诱导的惊厥。当给小鼠口服米拉酰胺(0.5 mmol/kg)时,尿中甘氨酰胺排泄量大幅增加。给予相同剂量的α-甲基米拉酰胺后未观察到这种增加。此外,α-甲基米拉酰胺在体外未被单胺氧化酶-A或 -B氧化到任何可检测的程度,尽管它是这两种形式酶的竞争性抑制剂。α-甲基米拉酰胺在荷包牡丹碱试验中具有抗惊厥特性,但不是单胺氧化酶的底物或尿中甘氨酰胺的来源,这一发现使人怀疑米拉酰胺氧化形成甘氨酰胺作为其抗惊厥作用的主要因素的重要性。