Lecture 4

Organic CompoundsToxicological Drug

Analysis

Barbituric acid

N

NO O

O

R5a

R5b

H

H Drug R5a R5b

Amobarbital ethyl isopentylButabarbital ethyl sec-ButylButalbital allyl isobutylPhenobarbital ethyl phenyl…………………………….

Some common barbiturates:

HPLCAN/water 1:1

UV@254nm

O

OH

H

H

O

OH

H

H

O

OH

H

H

O

OH

H

H

COOH

OH

Tetrahydrocannabinol

Major metabolic route:

Primary active

Primary inactive

Marijuana

HPLC acetonitrile/phosphate buffer

1-THC acid2-Tetrahydrocannabinol

HN

NH2

methamphetamine

amphetamine

HN

O ORitalin

Amphetamines

HN

NH2

HN

HO

NH2

HO

NH2

HO

OH

NH2

OHO

COOH

Norephedrine 2%

Methamphetamine (50%)

4-7%

15%

3%

Metabolism of methamphetamine

Amphetamine and Methamphetamine (TFAA Derivatives)

Chiral GC separation

NPhencyclidine

N

HN

NS

Analogs:

pKa=8.5

Solid Phase Extraction:@strong cation exchangecolumn

Elution: 2% NH3 in Ethyl Acetate

Determination: GC/MS

NH2

O

O

O

Mescaline

psilocybin

psilocin

Gamma-Hydroxybutyric acid (GHB)

HO

OHO

O O

γ-butyrolactone

1,4-butanediol

HO

OH

Very unstable in vivo

1. -hydroxybutyrate (GHB) / -butyrolactone (GBL)

2. -methylene- -butyrolactone (AMGBL)

Headspace GC

O CH2OAMGBL

10μg/mL each in water

4. 1,4-butanediol5. γ-butyrolactone

naloxene