Abstract

The most common means of identification of gamma-hydroxybutyrate (NaGHB) involves using Fourier transform infrared spectroscopy (FTIR) or gas chromatography-mass spectrometry (GC-MS) of a suitable derivative. However, these methods may be complicated by possible shifts in chemical equilibrium between gamma-hydroxybutyric acid (GHB), GHB salts and the precursor lactone, gamma-butyrolactone (GBL). This paper addresses the technique of proton and carbon nuclear magnetic resonance spectroscopy (1H and 13C NMR) for the direct and accurate identification of GHB and GBL. The application of 1H NMR for GHB quantitation is also discussed.

References

1.
Lewis
A
,
Smith
E
.
Gamma-hydroxybutyrate: From the 60s to the present
.
Proceedings of the American Academy of Forensic Sciences
2000
;
6
:43.
2.
Duchaine
D
.
Underground steroid handbook (II)
. Update: 1992,
Golden, CO
:
Mile High Publishing
,
1992
.
3.
Phillips
WN
.
Anabolic reference guide
, 6th ed.
Golden, CO
:
Mile High Publishing
,
1991
.
4.
Auerbach
SB
.
Multistate outbreak of poisonings associated with illicit use of gamma hydroxybutyrate
.
MMWR
1999
;
Nov 39
(
47
):
861
3
.
5.
Drug Enforcement Administration
.
Gamma hydroxybutyric acid
.
Washington, D.C.
:
Press Release
March, 2000.
6.
Substance Abuse and Mental Health Services Administration, Office of Applied Sciences
.
The Dawn Report, Club Drugs
,
12
2000
(Updated).
7.
Morris
JA
.
Extraction of GHB for FTIR analysis and a new color test for gamma-butyrolactone (GBL)
.
Microgram
1999
;
32
(
8
):215.
8.
Krawczeniuk
A
.
The occurrence of gamma-hydroxybutyric acid (GHB) in a steroid seizure
.
Microgram
1993
;
26
(
7
):
160
6
.
9.
Blackledge
RD
,
Miller
MD
.
The identification of GHB
.
Microgram
1991
;
24
(
7
):
172
9
.
10.
Blair
S
,
Song
M
,
Hall
B
,
Brodbelt
J
.
Determination of gamma-hydroxybutyrate in water and human urine by solid phase microextraction—gas chromatography/quadrupole ion trap spectrometry
.
J Forensic Sci
 0022-1198
2001
;
46
(
3
):688.
11.
Ciolino
LA
.
Bridging the gap between GHB and GBL
.
Proceedings of American Academy of Forensic Sciences Meeting
2000
;
6
:44.
12.
Mesmer
MZ
,
Satzger
RD
.
Determination of gamma-hydroxybutyrate (GHB) and gamma-butyrolactone (GBL) by HPLC/UV-VIS spectrophotometry and HPLC/thermospray mass spectrometry
.
J Forensic Sci
 0022-1198
1998
;
43
(
3
):
489
92
.
13.
Chew
SL
.
Identification and quantitation of GHB by nuclear magnetic resonance spectroscopy
.
Proceedings of the American Academy of Forensic Sciences
,
1999
;
5
:41.
14.
Lettieri
JT
,
Fung
H
.
Evaluation and development of gas chromatographic procedures for the determination of gamma-hydroxybutyric acid and gamma-butyrolactone in plasma
.
Biochem Med
 0006-2944
1978
;
(
20
):
70
80
.
15.
Krawczeniuk
A
.
Direct detection of gamma hydroxybutyrate (GHB): A new recreational drug via free zone capillary electrophoresis
.
Proceedings of American Academy of Forensic Sciences
.
1998
;
4
:34.
16.
Garcia
AD
,
Lurie
IS
,
Hulett
L
,
Almirall
JR
.
Quantitation of gammahydroxybutyric acid and gamma-butyrolactone using capillary electrophoresis and high performance liquid chromatography
.
Proceedings of the American Academy of Forensic Sciences
.
2001
;
7
:28.
17.
Beyerle
TH
.
Optimum high performance liquid chromatography parameters for the quantitation of gamma-hydroxybutyrate and gammabutyrolactone
.
Proceedings of American Academy of Forensic Sciences
.
2000
;
6
:44.
18.
Aue
WP
,
Bartholdi
E
,
Ernst
RR
.
Two-dimensional spectroscopy: Applications to nuclear magnetic resonance
.
J Chem Phys
 0021-9606 https://doi.org/10.1063/1.432450
1976
;
64
:
2229
46
.
19.
Bax
A
,
Morris
GA
.
An improved method for heteronuclear chemical shift correlation by two dimensional NMR
.
J Magn Reson
 1090-7807
1981
;
42
:
501
5
.
20.
Stortz
CA
,
Maier
MS
.
Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modeling
.
Perkin Trans
2 2000;
9
:
1832
6
.
21.
Jaime
C
,
Segura
C
.
Substituted γ-lactones with vicinal hydrogen atoms: conformational study by MM2 calculations and coupling constant analysis
.
J Org Chem
 0022-3263
1993
;
58
(
1
):
154
8
.
22.
Thomas
SA
,
Agbaji
EB
.
Molecular conformation of γ-lactone rings from crystal structure data
.
J Crystallogr Spectrosc Res
 0277-8068
1989
;
19
(
1
):
3
23
.
23.
Jaime
C
,
Ortuno
RM
,
Font
J
.
Di- and trisubstituted γ-lactones. Conformational study by molecular mechanics calculations and coupling constant analysis
.
J Org Chem
 0022-3263
1986
;
51
(
21
):
3946
51
.
24.
Lere-Porte
JP
,
Galsomias
J
,
Petrissans
J
,
Brianso
MC
.
Substituents effects on the conformation of γ-lactones. I. γ-Butyrolactone derivatives
.
J Molec Struct
 0022-2860
1984
;
118
(
3–4
):
277
92
.
25.
Pihlaja
K
,
Kleinpeter
E
.
Carbon-13 NMR chemical shifts in structural and stereochemical analysis
.
VCH
,
New York, NY
,
1994
.
26.
Croasmun
WR
,
Carlson
RM
.
Two-dimensional NMR spectroscopy
.
Applications for chemists and biochemists, 2nd edition
.
VCH
,
New York, NY
,
1994
.
27.
Martin
GE
,
Zektzer
AS
.
Two-dimensional NMR methods for establishing molecular connectivity
.
VCH
,
New York, NY
,
1988
.
28.
Abraham
RJ
,
Fisher
J
,
Loftus
P
.
Introduction to NMR spectroscopy
.
John Wiley & Sons
,
New York, NY
,
1988
.
29.
Becker
ED
.
High resolution NMR, 2nd edition
.
Academic Press
,
New York, NY
,
1980
.
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