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Derivatization

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Principles of Forensic Toxicology

Abstract

Gas chromatography-mass spectrometry (GC-MS) is still one of the most widely used analytical techniques in the forensic toxicology laboratory. Chemical derivatization is used to enhance the volatility, temperature stability, and detectability of drugs. It is an unavoidable requirement for some drugs and metabolites, particularly those with polar functional groups. Although chemical derivatization is an additional sample preparation step, chromatographic characteristics, stability, and overall improvements in detectability and specificity can be achieved. The most common derivatization techniques include silylation, acylation, and alkylation. A wide variety of derivatization reagents can be employed for this purpose. Approaches to derivatization are discussed for drugs of forensic interest, including amphetamines, benzodiazepines, cocaine metabolites, and opiates.

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Abbreviations

BF3:

Boron trifluoride

BSA:

N,O-bis(trimethylsilyl)acetamide

BSTFA:

O,N-bis(trimethylsilyl)fluoroacetamide

HFBA or HFAA:

Heptafluorobutyric acid anhydride

HFBI:

Heptafluorobutyrylimidazole

HFIP:

1,1,1,3,3,3-hexafluoroisopropanol

l-TPC:

l-N-trifluoracetyl-prolyl chloride

MBTFA:

N-methyltrifluoroacetamide

MSTFA:

N-methyl-N-trimethylsilyltrifluoroacetamide

MTBSTFA:

N-methyl-N-(tert-butyldimethylsilyl)-trifluoroacetamide

MTPA:

(R)-(-)methoxytrifluoromethylphenylacetic acid

PFBBr:

Pentafluorobenzyl bromide

PFPA or PFAA:

Pentafluoropropionic acid anhydride

PFPI:

Pentafluoropropany limidazole

PFPOH:

2,2,3,3,3-Pentafluoro-1-propanol

TBDMDMCS:

Tert-butyldimethylchlorosilane

TFAA:

Trifluoroacetic acid anhydride

TFAI:

Trifluoroacetylimidazole

TMCS:

Trimethylchlorosilane

TMS:

Trimethylsilyl

TMSI:

Trimethylsilylimidazole

Further Reading

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Correspondence to Lindsay Glicksberg .

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Glicksberg, L., Kerrigan, S. (2020). Derivatization. In: Levine, B.S., KERRIGAN, S. (eds) Principles of Forensic Toxicology. Springer, Cham. https://doi.org/10.1007/978-3-030-42917-1_12

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