Enantioresolution of Amphetamine, Metamphetamine, and Deprenyl

( Selegiline) by LC, GC, and CE

การแยก enantiomeric (R, S, (+), (-) form) ของ amphetamine,methamphetamine,และ selegiline ด้วยวธิ ี LC, GC และ CE

นำาเสนอโดย

น.ส. อรทัย กฤษณานุวฒัน์ รหัสนักศึกษา 51312336

จุดประสงค์ของงานวจิยั

• Enantiomer ? - Sterioisomer - Isomer are two or more compounds with the same molecular composition but differentStructures 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

HCH3NH

CH3

l-Amphetamine

H2N

CH3

H

d-Amphetamine

NH2

CH3

H

d-Methamphetamine

H NHCH3

CH3

* 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

AMMA

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