60
Methods for impurity profiling of heroin and cocaine
(b)
Cocaine trace-level impurities
Typical source
Heptadienoylecgonine methyl ester
Coca leaf
Cis-3-heptenoylecgonine methyl ester
Coca leaf
Trans-3-heptenoylecgonine methyl ester
Coca leaf
Trans-,
trans-2,4-hexadienoylecgonine methyl ester
Coca leaf
Hexanoylecgonine methyl ester
Coca leaf
Trans-2-hexenoylecgonine methyl ester
Coca leaf
Trans-3-hexenoylecgonine methyl ester
Coca leaf
Trans-4-hexenoylecgonine methyl ester
Coca leaf
2’-Hydroxybenzoylpseudotropine
Coca leaf
1-Hydroxycocaine
Coca leaf
3’-Hydroxycocaine
Coca leaf; no 2’ or 4’ isomers detected
4"-Hydroxycocaine
Coca leaf
4$-Hydroxycocaine
Coca leaf
5-Hydroxycocaine
Coca leaf
6-endo-Hydroxycocaine
Coca leaf
6-exo-Hydroxycocaine
Coca leaf
7-endo-Hydroxycocaine
Coca leaf
7-exo-Hydroxycocaine
Coca leaf
1-Hydroxytropacocaine
Coca leaf
6-exo-Hydroxytropacocaine
Coca leaf
Isobutyroylecgonine methyl ester
Coca leaf
Isovaleroylecgonine methyl ester
Coca leaf
Nicotinoylecgonine methyl ester
Coca leaf
3"-Phenylacetoxytropane
Coca leaf
Pseudococaine
Coca leaf
Pseudoecgonine
Hydrolysis of pseudococaine
Pseudoecgonine methyl ester
GC: solvent MeOH + trace bicarbonate (crack)
Hydrolysis and epimerization of cocaine (the
very low levels of pseudococaine in sample
make it an unlikely co-source)
Propionoylecgonine methyl ester
Coca leaf
2’-Pyrroloylecgonine methyl ester
Coca leaf
Senecioylecgonine methyl ester
Coca leaf
Tigloylecgonine methyl ester
Coca leaf
3’,4’,5’-Trimethoxybenzoyltropine
Coca leaf
Cis-3’,4’,5’-trimethoxycinnamoylcocaine
Coca leaf
Trans-3’,4’,5’-trimethoxycinnamoylcocaine
Coca leaf
Trans-3’,4’,5’-trimethoxycinnamoylpseudotropine
Coca leaf
Trans-3’,4’,5’-trimethoxycinnamoyltropine
Coca leaf
3’,4’,5’-Trimethoxycocaine
Coca leaf
3’,4’,5’-Trimethoxytropacocaine
Coca leaf
Tropacocaine
Coca leaf (levels higher than 1% relative to
cocaine may indicate addition of the com-
mercially available product)
Tropacocalline
Coca leaf: presence in leaf not confirmed.
16 theoretical diastereomers–10 observed.
a
O
2
= oxidation.
Table 4.
Alkaloidal impurities in cocaine and their sources (continued)
Annex II
61
Table 5.
Cocaine: adulterants
(non-coca-related cutting agents with pharmacological effects)
Allobarbital
Ephedrine
Nicotinamide
Amphetamine
Fentanyl
Nitrazepam
Antipyrine
Flunitrazepam
Paracetamol (acetaminophen)
Aspirin
Flurazepam
Phenacetin
Atropine
Lidocaine (lignocaine)
Phenobarbital
Benzocaine
MDEA
a
Piracetam
Benzoic acid
MDMA
b
Procaine
Caffeine
Methadone
Quinine
Diazepam
Methamphetamine
Tetracaine
Dipyrone
Methaqualone Theophylline
a
3,4-Methylenedioxyethylamphetamine.
b
3,4-Methylenedioxymethamphetamine.
Table 6.
Cocaine: diluents (cutting agents to dilute the sample)
Ascorbic acid
Inositol
Mannitol
Citric acid
Lactose
Mannose
Fructose Lysine
Sorbitol
Glucose
Maltose
Sucrose
ANNEX III
REFERENCE CHROMATOGRAMS AND
PEAK IDENTIFICATION TABLES
Figure I. Capillary gas chromatograms of illicit heroin samples
63
Peaks:
1 = nicotinamide-TMS
2 = meconin
3 = caffeine
4 = glucose-TMS
5 = phenobarbital-TMS
6 = methaqualone
7 = acetylcodeine
8 = acetylthebaol
9 = morphine-TMS
10 = 6-O-acetylmorphine-TMS
11 = diacetylmorphine
12 = papaverine
13 = phenolphthalein-TMS
14 = narcotine
S = n-tetracosane
(internal standard)
Note: TMS =
trimethylsilyl derivative.
(Top = uncut heroin sample; bottom = cut heroin sample)
Conditions: Fused silica capillary column 25 m x 0.32 mm i.d. coated with OV-1 cross-
linked; carrier gas 0.7 bar hydrogen, split 20 ml/min; make-up gas 18 ml argon/min; oven
temperature programme 150° C to 280° C at 9° C/min, then 0.5 min isothermal; and injec-
tor/detector (FID) temperatures 250° C/280° C.
Source: Reprinted from
Forensic Science International, vol. 44, No. 1, H. Neumann, “Comments on the
routine profiling of illicit heroin samples”, pp. 85-87. Copyright 1990, with permission from Elsevier.