Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites by gas chromatography/mass spectrometry.
Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites by gas chromatography/mass spectrometry.
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采用气相色谱/质谱法对 3,4-亚甲二氧基甲基苯丙胺及其主要代谢物进行立体化学分析。
DOI：
10.1002/rcm.919
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发表时间：
2003
期刊：
影响因子：
--
通讯作者：
R. de la Torre
中科院分区：
文献类型：
--
作者：
N. Pizarro;A. Llebaria;Silvia Cano;J. Joglar;M. Farré;J. Segura;R. de la Torre
3,4-Methylenedioxymethamphetamine (MDMA, ecstasy) is consumed as the racemate but some metabolic steps are enantioselective. In addition, chiral properties are preserved during MDMA biotransformation. A quantitative analytical methodology using gas chromatography/mass spectrometry (GC/MS) to determine enantioselective disposition in the body of MDMA and its main metabolites including 3,4-methylenedioxyamphetamine (MDA), 4-hydroxy-3-methoxymethamphetamine (HMMA), and 4-hydroxy-3-methoxyamphetamine (HMA) was developed. Plasma and urine samples were collected from a male volunteer. The analysis of MDMA, MDA, and 4-hydroxy-3-methoxy metabolites by GC/MS required a two-step derivatization procedure. The first step consisted of derivatization of the amine with enantiomerically pure Mosher's reagent ((R)-MTPCl). Triethylamine was used as a base to neutralize hydrochloric acid formed during the reaction allowing quantitative derivatization, which resulted in a substantial improvement in the sensitivity of the method compared with other previously described techniques. Further treatment with ammonium hydroxide was required since both amine and hydroxyl groups underwent derivatization in the reaction. Ammonium hydroxide breaks bonds formed with hydroxyl groups without affecting amine derivatives. The second derivatization step using hexamethyldisilazane was needed for metabolites containing phenol residues. This derivatization method permitted the stereochemically specific study of MDMA and its main monohydroxylated metabolites by GC/MS. A detailed study of the chemical reactions involved in the derivatization steps was indispensable to develop a straightforward, sensitive, and reproducible method for the analysis of the parent drug compound and its metabolites.
全血中 3,4-亚甲二氧基苯丙胺和 3,4-亚甲二氧基甲基苯丙胺对映体的测定。
DOI：
10.1016/s0378-4347(00)82761-9
发表时间：
1989
期刊：
Journal of chromatography
影响因子：
--
作者：
Fitzgerald,RL;Blanke,RV;Glennon,RA;Yousif,MY;Rosecrans,JA;Poklis,A
通讯作者：
Poklis,A
3,4-亚甲二氧基甲基苯丙胺体内和体外代谢的立体化学差异：药代动力学分析。
DOI：
--
发表时间：
1990
期刊：
Drug metabolism and disposition: the biological fate of chemicals
影响因子：
--
作者：
Cho,AK;Hiramatsu,M;Distefano,EW;Chang,AS;Jenden,DJ
通讯作者：
Jenden,DJ
细胞色素 P450-2B 和 -2D 同工酶参与大鼠亚甲二氧基甲基苯丙胺对映体的去甲基化。
影响因子：
3.6
作者：
Kumagai,Y;Lin,LY;Hiratsuka,A;Narimatsu,S;Suzuki,T;Yamada,H;Oguri,K;Yoshimura,H;Cho,AK
通讯作者：
Cho,AK