PMID- 10955507
OWN - NLM
STAT- MEDLINE
DCOM- 20000901
LR  - 20190513
IS  - 0021-9665 (Print)
IS  - 0021-9665 (Linking)
VI  - 38
IP  - 8
DP  - 2000 Aug
TI  - Chromatographic and mass spectral methods of identification for the side-chain 
      and ring regioisomers of methylenedioxymethamphetamine.
PG  - 329-37
AB  - The popular drug of abuse 3,4-methylenedioxymethamphetamine (MDMA) is one of a 
      total of 10 regioisomeric 2,3- and 3,4-methylenedioxyphenethylamines of MW 193 
      that yields regioisomeric fragment ions with equivalent mass (m/z 58 and 135/136) 
      in the electron-impact (EI) mass spectrum. Thus, these 10 
      methylenedioxyphenethylamines are uniquely isomeric; they have the same molecular 
      weight and equivalent major fragments in their mass spectra. The specific 
      identification of one of these compounds (i.e., Ecstasy or 3,4-MDMA) in a 
      forensic drug sample depends upon the analyst's ability to eliminate the other 
      regioisomers as possible interfering or coeluting substances. This study reports 
      the synthesis, chemical properties, spectral characterization, and 
      chromatographic analysis of these 10 unique regioisomers. The ten 2,3- and 
      3,4-regioisomers of MDMA are synthesized from commercially available precursor 
      chemicals. In the EI mass spectra, the side-chain regioisomers show some 
      variation in the relative intensity of the major ions, with the exception of only 
      one or two minor ions that might be considered side-chain specific fragments. The 
      position of substitution for the methylenedioxy ring is not easily determined by 
      mass spectral techniques, and the ultimate identification of any one of these 
      amines with the elimination of the other nine must depend heavily upon 
      chromatographic methods. The chromatographic separation of these 10 uniquely 
      regioisomeric amines are studied using reversed-phase liquid chromatographic 
      methods with gradient elution and gas chromatographic techniques with temperature 
      program optimization.
FAU - Aalberg, L
AU  - Aalberg L
AD  - Department of Pharmacal Sciences, School of Pharmacy, Auburn University, AL 
      36849, USA.
FAU - DeRuiter, J
AU  - DeRuiter J
FAU - Noggle, F T
AU  - Noggle FT
FAU - Sippola, E
AU  - Sippola E
FAU - Clark, C R
AU  - Clark CR
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - United States
TA  - J Chromatogr Sci
JT  - Journal of chromatographic science
JID - 0173225
RN  - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine)
SB  - IM
MH  - Chromatography/*methods
MH  - Chromatography, High Pressure Liquid
MH  - Gas Chromatography-Mass Spectrometry
MH  - Isomerism
MH  - Mass Spectrometry/*methods
MH  - Molecular Structure
MH  - N-Methyl-3,4-methylenedioxyamphetamine/*analysis/*chemistry
MH  - *Substance Abuse Detection
EDAT- 2000/08/24 11:00
MHDA- 2000/09/09 11:01
CRDT- 2000/08/24 11:00
PHST- 2000/08/24 11:00 [pubmed]
PHST- 2000/09/09 11:01 [medline]
PHST- 2000/08/24 11:00 [entrez]
AID - 10.1093/chromsci/38.8.329 [doi]
PST - ppublish
SO  - J Chromatogr Sci. 2000 Aug;38(8):329-37. doi: 10.1093/chromsci/38.8.329.