Enantioresolution of Amphetamine, Metamphetamine, and Deprenyl ( Selegiline) by LC, GC, and CE การแยก enantiomeric ( R, S, (+), (-) form) ของ amphetamine,methamphetamine, และ selegiline ด้วยวิธี LC, GC และ CE นำเสนอโดย น. ส. อรทัย กฤษณานุวัฒน์ รหัส นักศึกษา

จุดประสงค์ของงานวิจัย

Enantiomer ? - Sterioisomer - Isomer are two or more compounds with the same molecular composition but different Structures result in different properties Example of structural isomer (a) butane and (b) isobutane

*Stereoisomers describes compounds with the same Molecular formula and chemical structure but the atom are orientated in different direction. *There are two isomer each a mirror image of the other call enantiomers These two molecules are stereoisomer or enantiomer

*The mean of d-,l-, (+), (-), R- and S- - if an isomer rotates the plane clockwise label (+) termed d - its counter is label (-) termed l Structures of enantiomers of amphetamine and methamphetamine l-Methamphetamine H CH 3 NH CH 3 l-Amphetamine H2NH2N CH 3 H d-Amphetamine NH 2 CH 3 H d-Methamphetamine H NHCH 3 CH 3

* Amphetamine, methamphetamine and selegiline are chiral compound

* The legimate uses of amphetamine and methamphetamine hyperactivity and treatment of exogenous obesity * The rapid and effective enantioresolution is important for pharmacological, toxicological, forensic studies and product quality control * Capillary electrophoresis (CE) may be the best for the rapid analysis of small amounts of pure compound * Greater sensitivity and reproducibility of GC or LC may be needed when analyzing low levels of a compound

*Materials And Method - LC and CE Fisher Scientific - LC  Cyclobond  2000 LC column  Cyclobond  2000 RSP LC column  Cyclobond  2000 DMPLC column  Cyclobond  2000 RN LC column  Cyclobond  2000 SN LC column - GC  Chiraldex  - DM capillary GC column  Chiraldex G-PN GC column

Result and Discussion  Derivatized cyclodextrin chiral stationary phase ephedrine amphetamine methamphetamine pseudoephedrine Chiraldex G-PN column

Chiraldex  - DM column Selegiline

* The ability to rapid determine enantiomeric rations of methamphetamine and its possible precursors in a single run can be useful for forensic identification * IT is not necessary for routine pharmaceutical analyses

LC CE AM MA AM MA

Selegiline

- o-phthaldehyde (OPA) - naphthalene- dialdehyde (NDA) - aromatic anhydrides (AA) - 9- fluorenylmethylchloroformate (FMOC) - 6- aminoquinolyl-N-hydroxysuccinimidyl carbamate (AQC) - For chiral amines and amino acid where enantioseparations are also involved AQC, AA and FMOC Fluorescent tagging agent

- LC enantiomeric separation of AQC-amphetamine tagging agent Reversed- organic mode Polar- organic mode

- LC separation of AQC-methamphetamine

- Clearly, different approaches are useful for biological assay, forensic assays and QC of a pharmaceutical product - One chiral separation method may be superior to another