Methods for impurity profiling of heroin and cocaine



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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.




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