摘要
甲基苯丙胺(MAMP)分子结构中含有1个手性碳原子,因此存在1对对映异构体,即S-MAMP和R-MAMP。S-MAMP和R-MAMP的许多物理化学性质非常相近,但两者的药理、毒理作用却差异巨大。S-(+)-MAMP是目前成瘾性毒品"冰毒"的主要成分,它严重影响着人体健康与公共安全,对其分离分析及毒性作用机制的探讨是目前研究热点。如何有效快速地区分它们依然是个没有完全解决的难题。用密度泛函理论(DFT)和方法(B3LYP/6-31+G(d,p)),优化了手性MAMP分子的结构,比较了R-MAMP和S-MAMP分子的红外光谱(IR)、拉曼光谱(Raman)和振动园二色谱(VCD)及其紫外-可见吸收光谱(UV-Vis)、电子圆二色谱(ECD)和氢原子和碳原子的核磁共振吸收光谱。此外还采用信息理论(IT)方法,对比分析了2种苯丙胺类毒品的5种原子信息熵值与其半致死致量IE50的关系。理论模拟研究结果显示,R和S型手性MAMP分子的红外吸收、拉曼吸收、H和C原子核磁共振吸收及其紫外-可见吸收光谱峰型是完全相同的;而它们的VCD吸收谱和ECD吸收谱峰形则完全相反;S-MAMP中的手性碳原子Parr信息熵(Gs)与IE50的线性相关性最佳(y8=-28.96+5.10x8,R2=0.89)。提出了用手性原子的信息熵值及其VCD(ECD)吸收峰来快速区分和识别手性冰毒毒品,这一方法将为法医学研究和应用提供了有益的参考数据。
There is a chiral carbon atom in the structure of methamphetamine(MAMP),there is a pair of enantiomers,namely S-(+)-methamphetamine and R-(-)-methamphetamine.The physical and chemical properties of R-methamphetamine and S-methamphetamine are similar,but their pharmacological and toxicological effects are quite different.S-(+)-MAMP is the main component of the addictive drug"methamphetamine",which has a serious impact on human health and public safety.Its separation analysis and toxic mechanism are the current hot research content.In this paper,the structure of chiral methamphetamine(MAMP)was optimized by density functional theory(DFT)and method(B3 LYP/6-31+G(d,p)).The IR,Raman,VCD,UV Vis,ECD and NMR spectra of R-MAMP and S-MAMP were compared.In addition,the information theory(IT)method was used to compare and analyze the relationship between 5 types of atomic information entropy values and the semi-lethal IE50 of 2 kinds of amphetamine drugs.The results showed that the infrared absorption,Raman absorption,nuclear magnetic resonance absorption and UV-Vis absorption spectra of the two chiral molecules were identical,while their VCD and ECD spectra were completely opposite;The linear correlation between chiral carbon atom Parr information entropy(Gs)in S-MAMP and IE50 was the best(y8=-28.96+5.10 x8,R2=0.89).This theoretical method can be used for the detection and recognition of chiral drugs.
作者
崔露丹
CUI Lu-dan(Food and Drug Inspection and Testing Center of Xianju County,Taizhou 317326,China)
出处
《当代化工》
CAS
2020年第9期1859-1862,1866,共5页
Contemporary Chemical Industry
作者简介
崔露丹(1985-),女,浙江省台州市人,工程师,硕士学位,2012年毕业于浙江工业大学工业催化专业,研究方向:食品药品检测。E-mail:jelly.34132353@163.com。
