The characterisation of two halogenated cathinone analogues: 3,5- Difluoromethcathinone and 3,5-dichloromethcathinone  Sean Davis, Karen Rands-Trevor, Sue Boyd, Methsiri Edirisinghe  Forensic Science International  Volume 217, Issue 1, Pages 139-145 (April 2012) DOI: 10.1016/j.forsciint.2011.10.042 Copyright © 2011 Elsevier Ireland Ltd Terms and Conditions

Fig. 1 Analogues of cathinone: 4-methylmethcathinone 1 3-fluoromethcathinone 2 3,4-methylenedioxymethcathinone 3 cathinone 4 3,5-difluoromethcathinone 5 3,5-dichloromethcathinone 6 and bupropion 7. Forensic Science International 2012 217, 139-145DOI: (10.1016/j.forsciint.2011.10.042) Copyright © 2011 Elsevier Ireland Ltd Terms and Conditions

Fig. 2 Electron impact mass spectrum for (a) 3,5-difluoromethcathinone (b) suspected 3,5-difluoromethcathinone (c) N-acetyl-3,5-difluoromethcathinone (d) suspected N-acetyl-3,5-difluoromethcathinone. Forensic Science International 2012 217, 139-145DOI: (10.1016/j.forsciint.2011.10.042) Copyright © 2011 Elsevier Ireland Ltd Terms and Conditions

Fig. 3 Major EIMS fragmentations for 5 and 6. Forensic Science International 2012 217, 139-145DOI: (10.1016/j.forsciint.2011.10.042) Copyright © 2011 Elsevier Ireland Ltd Terms and Conditions

Fig. 4 3-Fluoro-isomethcathinone 8 iso-mephedrone 9 iso-ethcathinone 10 and 3,5-difluoro-isomethcathinone 11. Forensic Science International 2012 217, 139-145DOI: (10.1016/j.forsciint.2011.10.042) Copyright © 2011 Elsevier Ireland Ltd Terms and Conditions

Fig. 5 EIMS for (a) compound tentatively identified as 3,5-difluoro-isomethcathinone (b) sample containing compound tentatively identified as 3,5-difluoro-isomethcathinone and the N-acetyl derivatives (c) and (d), respectively. Forensic Science International 2012 217, 139-145DOI: (10.1016/j.forsciint.2011.10.042) Copyright © 2011 Elsevier Ireland Ltd Terms and Conditions

Fig. 6 EIMS for (a) 3,5-dichloromethcathinone (b) suspected 3,5-dichloromethcathinone (c) N-acetyl-3,5-dichloromethcathinone and (d) suspected N-acetyl-3,5-dichloromethcathinone. Forensic Science International 2012 217, 139-145DOI: (10.1016/j.forsciint.2011.10.042) Copyright © 2011 Elsevier Ireland Ltd Terms and Conditions

Fig. 7 ATR-FTIR spectra for (a) 3,5-difluoromethcathinone hydrochloride (b) suspected 3,5-difluoromethcathinone hydrochloride and the compound tentatively identified as 11 (c) 3,5-dichloromethcathinone hydrochloride and (d) suspected 3,5-dichloromethcathinone hydrochloride. Forensic Science International 2012 217, 139-145DOI: (10.1016/j.forsciint.2011.10.042) Copyright © 2011 Elsevier Ireland Ltd Terms and Conditions

Fig. 8 Vapour phase infrared spectra for (a) 3,5-difluoromethcathinone, (b) suspected 3,5-difluoromethcathinone, (c) 3,5-dichloromethcathinone and (d) suspected 3,5-dichloromethcathinone. Forensic Science International 2012 217, 139-145DOI: (10.1016/j.forsciint.2011.10.042) Copyright © 2011 Elsevier Ireland Ltd Terms and Conditions

Scheme 1 Formation of 3,5-difluoromethcathinone hydrochloride. a. Br2, CH2Cl2, RT, 30min, 95%; b. CH3NH2, RT, 2h, 27%. Forensic Science International 2012 217, 139-145DOI: (10.1016/j.forsciint.2011.10.042) Copyright © 2011 Elsevier Ireland Ltd Terms and Conditions

Scheme 2 Formation of 3,5-dichloromethcathinone hydrochloride. a. EtMgBr, THF, RT, 18h, 64%; b. Br2, CH2Cl2, RT, 18h, 45%; c. CH3NH2, THF, RT, 1h, 17%. Forensic Science International 2012 217, 139-145DOI: (10.1016/j.forsciint.2011.10.042) Copyright © 2011 Elsevier Ireland Ltd Terms and Conditions

Forensic Science International 2012 217, 139-145DOI: (10. 1016/j Forensic Science International 2012 217, 139-145DOI: (10.1016/j.forsciint.2011.10.042) Copyright © 2011 Elsevier Ireland Ltd Terms and Conditions