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17th Iranian Chemistry Congress Vali-e-Asr University of Rafsanjan 1-3 september 2014

The impurity characteristics of seized in Iran

Nafiseh Shekaria, Maryam Vosoughb*

a Chemistry and Chemical Engineering Research Center of Iran, P.O. Box 14335-186 Tehran, Iran, Email:[email protected] b Chemistry and Chemical Engineering Research Center of Iran, P.O. Box 14335-186 Tehran, Iran, Email: [email protected]

Background: Methamphetamine hydrochloride (MA) is one of the most widely used illicit in Iran. Impurity profiling and classification of seized MA may play an important role in the determination of the synthetic method, and the criminal investigations of traffic routes. There are two distinct synthetic procedures for the preparation of MA: one is synthesis from 1-phenyl-2-propanone (P2P), which is a precursor for the Leuckart method or reductive amination, and the other is synthesis from l- or d- via Birch reduction, the Nagai method, or Emde method [1].

Methods: Herein, the identification of impurities in seized MA samples using GC-MS by head space liquid-liquid extraction (HS-LLE) and solid phase micro extraction (SPME) is described.

Results: LLE method is reproducible, but it suffers from the high concentration of MA that co- extracts. Besides, SPME is suitable for volatile impurities and limits methamphetamine interference [1]. So it seemed beneficial to apply LLE along with SPME. The following impurities were detected in seized samples by LLE: P2P, , trans-2,3-dimethyl-1-phenylmethyl-aziridine, MA, dimethylamphetamine, , (+)-, chlordiazepoxide, n-formylmethamphetamine and n-acetyl-methamphetamine. On the other hand, benzyl choloride, 2-phenyl-aziridine, P2P, MA, n- benzyl-2-methylaziridine, dimethylamphetamine, n-methyl-benzamide, phenmetrazine, n- formylmethamphetamine, 1,2-dimethyl-3-phenyl-aziridine and benzylamphetamine were detected by HS- SPME.

Conclusion: Detected aziridine derivatives can be regarded as marker compounds indicating the synthesis method of seized MA samples is probably based on ephedrine (or pseudoephedrine) as a starting material. The aziridines can be reduced to form methamphetamine or react to form other impurities. It's the first report on the presence of phendimetrazine, trans-2,3-dimethyl-1-phenylmethyl-aziridine and chlordiazepoxide in seized methamphetamine samples all over the world. By increasing the number of MA samples a classification technique would be applied to discriminate the samples and determining their origin.

Keywords: Methamphetamine, Liquid–liquid extraction, Solid-phase microextraction, Impurity profiling

References

[1] Lee J., Park Y., Yang W., Chung H., Choi W., Inoue H., Kuwayama K., Park J., Forensic Science International, 2012, 215, 175–178.

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