Fingerprinting of 3,4-Methylenedioxymethamphetamine Markers by Desorption/Ionization on Porous Silicon

Abstract

Desorption/ionization on porous silicon (DIOS) is a method which extends the application range of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. This technique eliminates matrix background in the low mass range; DIOS is especially advantageous in research on small organic molecules and their metabolites in biological samples. DIOS mass spectrometry was applied for 3, 4-methylenedioxymethamphetamine, (MDMA, Ecstasy) impurities identification. Trace component profiling enables the identification of by-product characteristics for the synthesis route of MDMA. Ecstasy, a synthetic psychoactive drug, is highly popular among young people, and often used as a recreational drug, most commonly during disco parties. MDMA enhances feeling of euphoria by increasing the level of neurotransmitters such as serotonin, dopamine and norepinephrine and causes acute behavioral and psychological effects. MDMA is almost exclusively produced illegally, primarily in Western Europe. The new method for MDMA impurities profiling has been developed to trace the origin of MDMA pills. For comparison and classification of the impurity profiles, principal components analysis was used.

Keywords

Ecstasy MDMA impurities profiling DIOS MALDI ToF principal components analysis mass spectrometry substances of abuse

Get full access to this article

View all access options for this article.

References

Parrott

A.C.

, “Is ecstasy MDMA? A review of the proportion of ecstasy tablets containing MDMA, their dosage levels, and the changing perceptions of purity,” Psychopharmacology 173, 234 (2004). doi: 10.1007/s00213-003-1712-7

Morgan

M.J.

, “Ecstasy (MDMA): A review of its possible persistent psychological effects,” Psychopharmacology 152, 230 (2000). doi: 10.1007/s002130000545

Świst

Wilamowski

and Parczewski

, “Basic and neutral route specific impurities in MDMA prepared by different synthesis methods. Comparison of impurity profiles,” Forensic Sci. Int. 155, 100 (2005). doi: 10.1016/j.forsciint.2004.11.003

Świst

Wilamowski

and Parczewski

, “Determination of synthesis method of ecstasy based on the basic impurities,” Forensic Sci. Int. 152, 175 (2005). doi: 10.1016/j.forsciint.2004.08.003

Ballany

Caddy

Cole

Finnon

Aalberg

Janhunen

Sippola

Andersson

Bertler

Dahlen

Kopp

Dujourdy

Lock

Margot

Huizer

Poortman

Kaa

and Lopes

, “Development of a harmonised pan-European method for the profiling of amphetamines,” Sci. Justice 41, 193 (2001).

Palhol

Boyer

Naulet

and Chabrillat

, “Impurity profiling of seized MDMA tablets by capillary gas chromatography,” Anal. Bioanal. Chem. 374, 274 (2002). doi: 10.1007/s00216-002-1477-6

Tanaka

Ohmori

Inoue

and Seta

, “Impurity Profiling Analysis of Illicit Methamphetamine by Capillary Gas Chromatography,” J. Forensic Sci. 39, 500 (1994).

Jonson

C.S.L.

and Strömberg

, “Computer Aided Retrieval of Common-Batch Members in Leuckart Amphetamine Profiling,” J. Forensic Sci. 38, 1472 (1993).

Świst

Wilamowski

Zuba

Kochana

and Parczewski

, “Determination of synthesis route of 1-(3,4-methylenedioxyphenyl)-2-propanone (MDP-2-P) based on impurity profiles of MDMA,” Forensic Sci. Int. 149, 181 (2005). doi: 10.1016/j.forsciint.2004.06.016

10.

Verweij

A.M.A.

, “Impurities in illicit drug preparations: Amphetamine and methamphetamine,” Forensic Sci. Rev. 1, 1 (1989).

11.

Kram

T.C.

and Kruegel

, “The identification of impurities in illicit methamphetamine exhibits by gas chromatography/mass spectrometry and nuclear magnetic resonance spectroscopy,” J. Forensic Sci. 22, 40 (1977).

12.

Lekskulchai

Carter

Poklis

and Soine

, “GC-MS analysis of methamphetamine impurities: Reactivity of (+)- or (–)-chloroephedrine and cis- or trans-1,2-dimethyl-3-phenylaziridine,” J. Anal. Toxicol. 24, 602 (2000).

13.

Verweij

A.M.A.

, “Clandestine manufacture of 3,4-methylenedioxymethylamphetamine (MDMA) by low pressure reductive amination. A mass spectrometric study of some reaction mixtures,” Forensic Sci. Int. 45, 91 (1990). doi: 10.1016/0379-0738(90)90225-N

14.

Noggle

F.T.

Clark

C.R.

Andurkar

and DeRuiter

, “Methods for the analysis of 1-(3,4-methylenedioxyphenyl)-2-butanamine and N-methyl-1-(3,4-methylenedioxyphenyl)-2-propanamine (MDMA),” J. Chromatogr. Sci. 29, 103 (1991).

15.

Noggle

F.T.

Clark

C.R.

and DeRuiter

, “Liquid chromatographic and mass spectral analysis of 1-(3,4-methylenedioxyphenyl)-3-butanamines, homologues of 3,4-methylenedioxyamphetamines,” J. Chromatogr. Sci. 27, 240 (1989).

16.

Bohn

and Blaschke

, “Synthesis markers in illegally manufactured 3,4-methylenedioxyamphetamine and 3,4-methylenedioxymethamphetamine,” Int. J. Leg. Med. 106, 19 (1993). doi: 10.1007/BF01225019

17.

Renton

R.J.

Cowie

J.S.

and Oon

M.C.H.

, “A study of the precursors, intermediates and reaction by-products in the synthesis of 3,4-methylenedioxymethylamphetamine and its application to forensic drug analysis,” Forensic Sci. Int. 60, 189 (1993). Doi: 10.1016/0379-0738(93)90238-6

18.

Gimeno

Besacier

and Chaudron-Thozet

, “A contribution to the chemical profiling of 3,4-methylenedioxymethamphetamine (MDMA) tablets”, Forensic Sci. Int. 127, 1 (2002).

19.

Lurie

I.S.

Bailey

C.G.

Anex

D.S.

Bethea

M.J.

McKibben

T.D.

and Casale

J.F.

, “Profiling of impurities in illicit methamphetamine by high-performance liquid chromatography and capillary electrochromatography,” J. Chromatogr. A 870, 53 (2000). Doi: 10.1016/S0021-9673(99)00849-3

20.

Wei

Buriak

J.M.

and Siuzdak

, “Desorption-ionization mass spectrometry on porous silicon,” Nature 399, 243 (1999). doi: 10.1038/20400

21.

Kraj

Dylag

Gorecka-Drzazga

Bargiel

Dziuban

and Silberring

, “Desorption/ionization on silicon for small molecules: A promising alternative to MALDI ToF,” Acta Biochim. Pol. 50, 783 (2003).

22.

Thomas

J.J.

Shen

Crowell

J.E.

Finn

M.G.

and Siuzdak

, “Desorption/ionization on silicon (DIOS): A diverse mass spectrometry platform for protein characterization,” P. Natl. Acad. Sci. USA 98, 4932 (2001). doi: 10.1073/pnas.081069298