Abstract
A number of analogues of phenethylamine and tryptamine, which are prepared by modification of the chemical structures, are being developed for circulation on the black market. Often called “designer drugs,” they are abused in many countries, and cause serious social problems in many parts of the world. Acute deaths have been reported after overdoses of designer drugs. Various methods are required for screening and routine analysis of designer drugs in biological materials for forensic and clinical purposes. Many sample preparation and chromatographic methods for analysis of these drugs in biological materials and seized items have been published. This review presents various colorimetric detections, gas chromatographic (GC)–mass spectrometric, and liquid chromatographic (LC)–mass spectrometric methods proposed for designer drug analyses. Basic information on extractions, derivatizations, GC columns, LC columns, detection limits, and linear ranges is also summarized.
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Abbreviations
- AA:
-
Acetic anhydride
- ACN:
-
Acetonitrile
- N-Ac-2′-FMC:
-
N-Acetyl-2′-fluoromethacathinone
- N-Ac-3′-FMC:
-
N-Acetyl-3′-fluoromethacathinone
- N-Ac-4′-FMC:
-
N-Acetyl-4′-fluoromethacathinone
- 4-AcO-DIPT:
-
4-Acetoxy-N,N-diisopropyltryptamine
- ALEPH:
-
2,5-Dimethoxy-4-methylthioamphetamine
- ALEPH-2:
-
2,5-Dimethoxy-4-ethylthioamphetamine
- ALEPH-5:
-
2,5-Dimethoxy-4-cyclohexylthioamphetamine
- ALEPH-7:
-
2,5-Dimethoxy-4-(n)-propylthioamphetamine
- AMT:
-
α-Methyltryptamine
- AP:
-
Amphetamine
- BDB:
-
2-Amino-1-(3,4-methylenedioxyphenyl)butane
- 4-Brom-2,5-dimethoxy-BZP:
-
4-Bromo-2,5-dimethoxybenzylpiperazine
- 2-Brom-4,5-dimethoxy-BZP:
-
2-Bromo-4,5-dimethoxybenzylpiperazine
- 5-Brom-2,4-dimethoxy-BZP:
-
5-Bromo-2,4-dimethoxybenzylpiperazine
- BZP:
-
N-Benzylpiperazine
- 2C-B:
-
2,5-Dimethoxy-4-bromophenethylamine
- 2C-B-DragonFLY:
-
1-(8-Bromobenzo[1,2-b;4,5-b′]difuran-4-yl)-2-aminoethane
- 2C-B-FLY:
-
1-(8-Bromo-2,3,6,7-tetrahydrobenzo[1,2-b;4,5-b′]difuran-4-yl)-2-aminoethane
- 2C-C:
-
2,5-Dimethoxy-4-chlorophenethylamine
- 2C-D:
-
2,5-Dimethoxy-4-methyl-phenethylamine
- CE:
-
Capillary electrophoresis
- 2C-E:
-
2,5-Dimethoxy-4-ethylphenethylamine
- 2C-H:
-
2,5-Dimethoxyphenethylamine
- 2C-I:
-
2,5-Dimethoxy-4-iodophenethylamine
- 2C-N:
-
2,5-Dimethoxy-4-nitrolphenethylamine
- 2-CPP:
-
1-(2-Chlorophenyl)piperazine
- 3-CPP:
-
1-(3-Chlorophenyl)piperazine, mCPP
- 4-CPP:
-
1-(4-Chlorophenyl)piperazine
- 2C series:
-
4-Substituted 2,5-dimethoxy phenethylamines
- 2C-T:
-
2,5-Dimethoxy-4-methylthiophenethylamine
- 2C-T-2:
-
2,5-Dimethoxy-4-ethylthiophenethylamine
- 2C-T-4:
-
2,5-Dimethoxy-4-isopropylthiophenethylamine
- 2C-T-5:
-
2,5-Dimethoxy-4-cyclohexylthiophenethylamine
- 2C-T-7:
-
2,5-Dimethoxy-4-(n)-propylthiophenethylamine
- DIPT:
-
N,N-Diisopropyltryptamine
- 2,5-DMA:
-
2,5-Dimethoxyamphetamine
- DMT:
-
N,N-Dimethyltryptamine
- DOB:
-
2,5-Dimethoxy-4-bromoamphetamine
- DOB-DragonFLY:
-
1-(8-Bromobenzo[1,2-b;4,5-b′]difuran-4-yl)-2-aminopropane
- DOB-FLY:
-
1-(8-Bromo-2,3,6,7-tetrahydrobenzo[1,2-b;4,5-b′]difuran-4-yl)-2-aminopropane
- DOC:
-
2,5-Dimethoxy-4-chloroamphetamine
- DOET:
-
2,5-Dimethoxy-4-ethylamphetamine
- DOI:
-
2,5-Dimethoxy-4-iodoamphetamine
- DOM:
-
2,5-Dimethoxy-4-methyl-amphetamine
- DOPR:
-
2,5-Dimethoxy-4-propylamphetamine
- DPT:
-
N,N-Dipropyltryptamine
- EAMP:
-
Ethylamphetamine
- ECF:
-
Ethyl chloroformate
- EP:
-
Ephedrine
- 2′-FMC:
-
2′-Fluoromethacathinone
- 3′-FMC:
-
3′-Fluoromethacathinone
- 4′-FMC:
-
4′-Fluoromethacathinone
- 4-FMP:
-
4-Fluoro-α-methyl-phenethylamine
- GC:
-
Gas chromatography
- HFBA:
-
Heptafluorobutyric anhydride
- HMMA:
-
4-Hydroxy-3-methoxymethamphetamine
- HMMA-Glu:
-
4-Hydroxy-3-methoxy-methamphetamine-glucuronide
- HMMA-Sul:
-
4-Hydroxy-3-methoxy-methamphetamine-sulfate
- 5-HT:
-
5-Hydroxytryptamine, serotonin
- IS:
-
Internal standard
- JWH-018:
-
1-Naphthalenyl(1-pentyl-1H-indol-3-yl)methanone
- LC:
-
Liquid chromatography
- LLE:
-
Liquid–liquid extraction
- LOD:
-
Limit of detection
- LOQ:
-
Limit of quantitation
- LSD:
-
Lysergic acid diethylamide
- MA:
-
Methamphetamine
- MBDB:
-
N-Methyl-benzodioxolylbutanamine
- bk-MBDB:
-
2-Methylamino-1-(3,4-methylenedioxyphenyl)-butan-1-one, butylone
- MBTFA:
-
N-Methylbis-(trifluoroacetamide)
- MBZP:
-
1-Benzyl-4-methyl-piperazine
- MDA:
-
3,4-Methylenedioxy-amphetamine
- MDBZP:
-
1-(3,4-Methylenedioxybenzyl)-piperazine
- bk-MDDMA:
-
2-Dimethylamino-1-(3,4-methylenedioxyphenyl)-propan-1-one
- MDEA:
-
3,4-Methylenedioxy-N-ethylamphetamine
- bk-MDEA:
-
2-Ethylamino-1-(3,4-methylenedioxyphenyl)-propan-1-one, ethylone
- MDMA:
-
3,4-Methylenedioxymeth-amphetamine
- bk-MDMA:
-
2-Methylamino-1-(3,4-methylenedioxyphenyl)-propan-1-one, methylone
- MDPPP:
-
R,S-3′,4′-Methylenedioxy-α-pyrrolidinopropiophenone
- MDPV:
-
3,4-Methylenedioxy-pyrovalerone
- ME:
-
Methylephedrine
- N-Me-DOB-DragtonFLY:
-
1-(8-Bromobenzo[1,2-b;4,5-b′]difuran-4-yl)-2-methylaminopropane
- N-Me-DOB-FLY:
-
1-(8-Bromo-2,3,6,7-tetrahydrobenzo[1,2-b;4,5-b′]difuran-4-yl)-2-methylaminopropane
- N-Me-4-FMP:
-
1-(4-Fluorophenyl)-N-methylpropan-2-amine
- 5-MeO-AMT:
-
5-Methoxy-α-methyltryptamine
- 5-MeO-DALT:
-
N,N-Diallyl-5-methoxytryptamine
- 5-MeO-DET:
-
5-Methoxy-N,N-diethyltryptamine
- 5-MeO-DIPT:
-
5-Methoxy-N,N-diisopropyltryptamine
- 5-MeO-DMT:
-
5-Methoxy-N,N-dimethyltryptamine
- 5-MeO-DPT:
-
5-Methoxy-N,N-di-n-propyltryptamine
- 5-MeO-EIPT:
-
5-Methoxy-N-ethyl-N-isopropyltryptamine
- 5-MeO-EPT:
-
N-Ethyl-5-methoxy-N-propyltryptamine
- MeOH:
-
Methanol
- 5-MeO-MIPT:
-
N-Isopropyl-5-methoxy-N-methyltryptamine
- MeOPP:
-
1-(4-Methoxyphenyl)piperazine
- MIPT:
-
N-Methyl-N-isopropyltryptamine
- MMDA:
-
3-Methoxy-4,5-methylenedioxyamphetamine
- MOPPP:
-
R,S-4′-Methoxy-α-pyrrolidinopropiophenone
- MPBP:
-
4′-Methyl-α-pyrrolidinobutyrophenone
- MPHP:
-
4′-Methyl-α-pyrrolidinohexanophenone
- 2-MPP:
-
1-(2-Methoxyphenyl)piperazine
- 3-MPP:
-
1-(3-Methoxyphenyl)piperazine
- 4-MPP:
-
1-(4-Methoxyphenyl)piperazine
- MPPP:
-
R,S-4′-Methyl-α-pyrrolidinopropiophenone
- MRM:
-
Multiple reaction monitoring
- MS:
-
Mass spectrometry
- MSTFA:
-
N-Methyl-N-trimethylsilyltri-fluoroacetamide
- 4-MTA:
-
4-Methylthioamphetamine
- 4-OH-DIPT:
-
4-Hydroxy-N,N-diisopropyltryptamine
- 4-OH-DMT:
-
4-Hydroxy-N,N-dimethyltryptamine
- p-OH-MA:
-
4-Hydroxymethamphetamine
- p-OH-MA-Glu:
-
4-Hydroxymethamphetamine-glucuronide
- p-OH-MA-Sul:
-
4-Hydroxymethamphetamine-sulfate
- N-OH-MDA:
-
N-Hydroxy-3,4-methylenedioxyamphetamine
- N-OH-MDMA:
-
N-Hydroxy-3,4-methylenedioxy-methamphetamine
- 3-OH-4-MeO-MA:
-
3-Hydroxy-4-methoxymethamphetamine
- PCEEA:
-
N-(1-Phenylcyclohexyl)-2-ethoxyethanamine
- PCMEA:
-
N-(1-Phenylcyclohexyl)-2-methoxyethanamine
- PCMPA:
-
N-(1-Phenylcyclohexyl)-3-methoxypropanamine
- PCPR:
-
N-(1-Phenylcyclohexyl)-propanamine
- PDMS:
-
Polydimethylsiloxane
- PEA:
-
β-Phenethylamine
- PFPA:
-
Pentafluoropropionic anhydride
- PMA:
-
p-Methoxyamphetamine
- PMEA:
-
p-Methoxyethylamphetamine
- PMMA:
-
p-Methoxymethamphetamine
- PPA:
-
Phenylpropanolamine
- PPP:
-
R,S-α-Pyrrolidinopropiophenone
- PVP:
-
1-Phenyl-2-pyrrolidin-1-ylphentan-1-one, α-pyrrolidinovaleophenone
- SERT:
-
Serotonin transporter
- SIM:
-
Selected ion monitoring
- SPDE:
-
Solid-phase dynamic extraction
- SPE:
-
Solid-phase extraction
- SPME:
-
Solid-phase microextraction
- TFA:
-
Trifluoroacetic acid
- TFAA:
-
Trifluoroacetic anhydride
- TFMPP:
-
1-(3-Trifluoromethyl)-piperazine
- TFAP:
-
S-(−)-N-(Trifluoroacetyl)propyl chloride
- TLC:
-
Thin-layer chromatography
- TMA-1:
-
3,4,5-Trimethoxyamphetamine
- TMA-2:
-
2,4,5-Trimethoxyamphetamine
- TMA-3:
-
2,3,4-Trimethoxyamphetamine
- TMA-4:
-
2,3,5-Trimethoxyamphetamine
- TMA-5:
-
2,3,6-Trimethoxyamphetamine
- TMA-6:
-
2,4,6-Trimethoxyamphetamine
- TMF:
-
3-Methylfentanyl
- TMSCI:
-
Trimethylsilylchloride
- TOFMS:
-
Time-of-flight mass spectrometry
- TPC:
-
Trifluoroacetyl-l-propylchloride
- UPLC:
-
Ultra performance liquid chromatography
- UV:
-
Ultraviolet
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Acknowledgments
The authors thank Dr. Kunio Gonmori, Hamamatsu University School of Medicine, Hamamatsu, Japan, for his technical support and Professor Osamu Suzuki, Chief Editor of Forensic Toxicology, for providing the opportunity to write this review.
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Namera, A., Nakamoto, A., Saito, T. et al. Colorimetric detection and chromatographic analyses of designer drugs in biological materials: a comprehensive review. Forensic Toxicol 29, 1–24 (2011). https://doi.org/10.1007/s11419-010-0107-9
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DOI: https://doi.org/10.1007/s11419-010-0107-9