Analysis of 3,4-methylenedioxy-N-methylamphetamine (MDMA) in 'Ecstasy' tablets by 13C solid state nuclear magnetic resonance (NMR) spectroscopy

Garry S.H. Lee, Don C. Craig, G. S.Kamali Kannangara, Michael Dawson, Costa Conn, James Robertson, Michael A. Wilson

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The solution and solid state NMR spectra of 3,4-methylenedioxy-N- methylamphetamine hydrochloride (MDMA. HCl) and a number of illicitly manufactured tablets containing this material and marketed as 'Ecstasy' have been obtained. We show solid state NMR to be a useful technique for the analysis of the impurities and excipients in 'Ecstasy' tablets and with further development may be used quantitatively for determining the percentage carbon which is MDMA. Excipients detected include lactose, cellulose, stearate salts, sucrose, starch, polyvinylpyrrolidone and sodium croscarmellose. Two samples were found to contain 3,4-methylenedioxy-N- ethylamphetamine (MDEA), rather than MDMA. Some interesting conformational infirmation is also observed. Differences in the chemical shifts of C-8 and C-10 carbons for 3,4-methylenedioxy-N-methylamphetamine hydrochloride in solution and solid state and in different 'Ecstasy' samples are attributed to conformational freezing and hydrogen bonding. In the solid state, carbons 8 and 10 are restricted from free rotation and the methyl groups at carbon 10 and carbon 11 are held only in trans conformation unlike in solution. These results were confirmed by a crystal structure analysis. When excipients capable of hydrogen bonding are physically mixed with MDMA · HCl, the chemical shifts of carbons 8 and 10 in the resulting mixture changes such that they more closely resemble the shifts observed in solution.

Original languageEnglish
Pages (from-to)761-771
Number of pages11
JournalJournal of Forensic Sciences
Volume44
Issue number4
DOIs
Publication statusPublished - 1 Jan 1999
Externally publishedYes

Fingerprint

Methamphetamine
Tablets
Magnetic Resonance Spectroscopy
Carbon
Excipients
Hydrogen Bonding
Povidone
Carboxymethylcellulose Sodium
Lactose
Cellulose
Starch
Freezing
Salts

Cite this

Lee, Garry S.H. ; Craig, Don C. ; Kannangara, G. S.Kamali ; Dawson, Michael ; Conn, Costa ; Robertson, James ; Wilson, Michael A. / Analysis of 3,4-methylenedioxy-N-methylamphetamine (MDMA) in 'Ecstasy' tablets by 13C solid state nuclear magnetic resonance (NMR) spectroscopy. In: Journal of Forensic Sciences. 1999 ; Vol. 44, No. 4. pp. 761-771.
@article{1d857274f506402faf2ea2e997531a9d,
title = "Analysis of 3,4-methylenedioxy-N-methylamphetamine (MDMA) in 'Ecstasy' tablets by 13C solid state nuclear magnetic resonance (NMR) spectroscopy",
abstract = "The solution and solid state NMR spectra of 3,4-methylenedioxy-N- methylamphetamine hydrochloride (MDMA. HCl) and a number of illicitly manufactured tablets containing this material and marketed as 'Ecstasy' have been obtained. We show solid state NMR to be a useful technique for the analysis of the impurities and excipients in 'Ecstasy' tablets and with further development may be used quantitatively for determining the percentage carbon which is MDMA. Excipients detected include lactose, cellulose, stearate salts, sucrose, starch, polyvinylpyrrolidone and sodium croscarmellose. Two samples were found to contain 3,4-methylenedioxy-N- ethylamphetamine (MDEA), rather than MDMA. Some interesting conformational infirmation is also observed. Differences in the chemical shifts of C-8 and C-10 carbons for 3,4-methylenedioxy-N-methylamphetamine hydrochloride in solution and solid state and in different 'Ecstasy' samples are attributed to conformational freezing and hydrogen bonding. In the solid state, carbons 8 and 10 are restricted from free rotation and the methyl groups at carbon 10 and carbon 11 are held only in trans conformation unlike in solution. These results were confirmed by a crystal structure analysis. When excipients capable of hydrogen bonding are physically mixed with MDMA · HCl, the chemical shifts of carbons 8 and 10 in the resulting mixture changes such that they more closely resemble the shifts observed in solution.",
keywords = "3,4-methylenedioxy-N-methyl amphetamine, Crystal structure, Ecstasy, Forensic science, Identification systems, MDMA, NMR, Solid state nuclear magnetic resonance",
author = "Lee, {Garry S.H.} and Craig, {Don C.} and Kannangara, {G. S.Kamali} and Michael Dawson and Costa Conn and James Robertson and Wilson, {Michael A.}",
year = "1999",
month = "1",
day = "1",
doi = "10.1520/JFS14550J",
language = "English",
volume = "44",
pages = "761--771",
journal = "Journal of forensic Science",
issn = "0022-1198",
publisher = "Wiley-Blackwell",
number = "4",

}

Analysis of 3,4-methylenedioxy-N-methylamphetamine (MDMA) in 'Ecstasy' tablets by 13C solid state nuclear magnetic resonance (NMR) spectroscopy. / Lee, Garry S.H.; Craig, Don C.; Kannangara, G. S.Kamali; Dawson, Michael; Conn, Costa; Robertson, James; Wilson, Michael A.

In: Journal of Forensic Sciences, Vol. 44, No. 4, 01.01.1999, p. 761-771.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Analysis of 3,4-methylenedioxy-N-methylamphetamine (MDMA) in 'Ecstasy' tablets by 13C solid state nuclear magnetic resonance (NMR) spectroscopy

AU - Lee, Garry S.H.

AU - Craig, Don C.

AU - Kannangara, G. S.Kamali

AU - Dawson, Michael

AU - Conn, Costa

AU - Robertson, James

AU - Wilson, Michael A.

PY - 1999/1/1

Y1 - 1999/1/1

N2 - The solution and solid state NMR spectra of 3,4-methylenedioxy-N- methylamphetamine hydrochloride (MDMA. HCl) and a number of illicitly manufactured tablets containing this material and marketed as 'Ecstasy' have been obtained. We show solid state NMR to be a useful technique for the analysis of the impurities and excipients in 'Ecstasy' tablets and with further development may be used quantitatively for determining the percentage carbon which is MDMA. Excipients detected include lactose, cellulose, stearate salts, sucrose, starch, polyvinylpyrrolidone and sodium croscarmellose. Two samples were found to contain 3,4-methylenedioxy-N- ethylamphetamine (MDEA), rather than MDMA. Some interesting conformational infirmation is also observed. Differences in the chemical shifts of C-8 and C-10 carbons for 3,4-methylenedioxy-N-methylamphetamine hydrochloride in solution and solid state and in different 'Ecstasy' samples are attributed to conformational freezing and hydrogen bonding. In the solid state, carbons 8 and 10 are restricted from free rotation and the methyl groups at carbon 10 and carbon 11 are held only in trans conformation unlike in solution. These results were confirmed by a crystal structure analysis. When excipients capable of hydrogen bonding are physically mixed with MDMA · HCl, the chemical shifts of carbons 8 and 10 in the resulting mixture changes such that they more closely resemble the shifts observed in solution.

AB - The solution and solid state NMR spectra of 3,4-methylenedioxy-N- methylamphetamine hydrochloride (MDMA. HCl) and a number of illicitly manufactured tablets containing this material and marketed as 'Ecstasy' have been obtained. We show solid state NMR to be a useful technique for the analysis of the impurities and excipients in 'Ecstasy' tablets and with further development may be used quantitatively for determining the percentage carbon which is MDMA. Excipients detected include lactose, cellulose, stearate salts, sucrose, starch, polyvinylpyrrolidone and sodium croscarmellose. Two samples were found to contain 3,4-methylenedioxy-N- ethylamphetamine (MDEA), rather than MDMA. Some interesting conformational infirmation is also observed. Differences in the chemical shifts of C-8 and C-10 carbons for 3,4-methylenedioxy-N-methylamphetamine hydrochloride in solution and solid state and in different 'Ecstasy' samples are attributed to conformational freezing and hydrogen bonding. In the solid state, carbons 8 and 10 are restricted from free rotation and the methyl groups at carbon 10 and carbon 11 are held only in trans conformation unlike in solution. These results were confirmed by a crystal structure analysis. When excipients capable of hydrogen bonding are physically mixed with MDMA · HCl, the chemical shifts of carbons 8 and 10 in the resulting mixture changes such that they more closely resemble the shifts observed in solution.

KW - 3,4-methylenedioxy-N-methyl amphetamine

KW - Crystal structure

KW - Ecstasy

KW - Forensic science

KW - Identification systems

KW - MDMA

KW - NMR

KW - Solid state nuclear magnetic resonance

UR - http://www.scopus.com/inward/record.url?scp=0033060726&partnerID=8YFLogxK

U2 - 10.1520/JFS14550J

DO - 10.1520/JFS14550J

M3 - Article

VL - 44

SP - 761

EP - 771

JO - Journal of forensic Science

JF - Journal of forensic Science

SN - 0022-1198

IS - 4

ER -