Synthesis of 2,3- and 3,4-methylenedioxyphenylalkylamines and their regioisomeric differentiation by mass spectral analysis using GC-MS-MS

3,4-methylenedioxyamphetamine (MDA) derivatives are increasingly abused central nervous system stimulants with neurotoxic properties. In recent years a number of controlled substance analogs (designer drugs) with high structural variety reached the illegal market making their identification an arduous task. The underivatized compounds give very similar or even virtually identical electron impact mass spectra containing mainly intense C(n)H(2n+2)N(+) immonium ions. Using tandem mass spectrometry (MS-MS) the additional structural information contained in the collision induced dissoziation (CID) mass spectra of molecular ions using electron impact (EI) and especially chemical ionization (CI) allowed an unequivocal differentiation of 18 studied regioisomeric 1-(methylenedioxyphenyl)-2-propanamines and 1-(methylenedioxyphenyl)-2-butanamines.Further synthetic methods are presented for 1-(3,4-methylenedioxyphenyl)-N-propyl-2-butanamine, N-isopropyl-1-(3,4-methylenedioxyphenyl)-2-butanamine and four 1-(2, 3-methylenedioxyphenyl)-2-butanamines. N-alkylated 1-(3, 4-methylenedioxyphenyl)-2-butanamine compounds (e.g. MBDB) are also known to be abused psychoactive agents (entactogenes) without the sympatomimetic effects of the 3,4-methylenedioxyamphetamines.     

The incorporation of dyes into hair as a model for drug binding

The binding of charged substances from external aqueous media to hair has been investigated through the use of fluorescence microscopy. Eleven hair samples, reflecting various ethnic groups and cosmetic treatments, were tested. Rhodamine 6G, a cationic dye representative of drugs such as cocaine and opiates, showed incorporation throughout the hair of all samples except one. In contrast, fluorescein, an anionic dye representative of drugs such as THC carboxylic acid, was not readily incorporated. The incorporation of rhodamine 6G was faster for chemically 'straightened' and bleached African-American female hair than for untreated hair. Incorporation of rhodamine 6G followed a pH dependence, but an ionic strength dependence could not be established. These studies support three postulates: (1) electrostatic interactions explain the preferential binding of cationic drugs of abuse to hair; (2) the hair matrix, or the non-helical portion of hair, is accessible to external solutions and thus subject to contamination; and (3) cosmetic treatments may alter the helical portion of hair thereby increasing its accessibility to external contamination.     

同一个体发毛角蛋白电泳谱型的分析

用SDS -PAGGE对收集到的 2 0例人体表毛发 (头发、阴毛、腋毛、腿毛 )角蛋白组分进行了分析。结果表明 ,同一个体毛发角蛋白电泳谱型基本相同 ,用激光光密度仪对电泳凝胶板扫描后证实 ,同一个体毛发角蛋白组分相对百分含量也无明显差异 ;人头部不同部位 (顶部、左侧、右侧、额部、枕部 )头发角蛋白的电泳谱型和角蛋白组分相对百分含量也基本相同。同一个体毛发角蛋白组分的分析 ,可为法医物证学鉴定中的毛发个人识别提供重要的依据。