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