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Lecture 4
Organic Compounds
Toxicological Drug
Analysis
HPLC
AN/water 1:1
Barbituric acid
H
O
N
R5a
O
Some common barbiturates:
N
R5b
H
O
Drug
R5a
R5b
Amobarbital ethyl isopentyl
Butabarbital ethyl sec-Butyl
Butalbital
allyl isobutyl
Phenobarbital ethyl phenyl
…………………………….
UV@254nm
Marijuana
H
Major metabolic route:
OH
H
OH
H
O
H
OH
O
H
OH
Primary active
H
O
COOH
Primary inactive
H
H
Tetrahydrocannabinol
O
OH
HPLC acetonitrile/phosphate buffer
1-THC acid
2-Tetrahydrocannabinol
H
N
methamphetamine
NH2
amphetamine
O
Amphetamines
O
Ritalin
H
N
Methamphetamine (50%)
H
N
H
N
15%
HO
NH2
NH2
4-7%
HO
O
OH
OH
NH2
NH2
HO
COOH
Norephedrine 2%
3%
Metabolism of methamphetamine
Amphetamine and Methamphetamine (TFAA Derivatives)
Chiral GC separation
Phencyclidine
N
pKa=8.5
Analogs:
N
S
N
Solid Phase Extraction:
@strong cation exchange
column
Elution: 2% NH3 in Ethyl Acetate
H
N
Determination: GC/MS
NH2
O
Mescaline
O
O
psilocybin
psilocin
Gamma-Hydroxybutyric acid (GHB)
O
OH
Very unstable in vivo
HO
γ-butyrolactone
O
O
OH
1,4-butanediol
HO
Headspace GC
1. -hydroxybutyrate (GHB) / -butyrolactone (GBL)
2. -methylene- -butyrolactone (AMGBL)
10μg/mL each in water
O
O
CH2
AMGBL
4. 1,4-butanediol
5. γ-butyrolactone
naloxene