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Annex II 59 B. Impurities in cocaine and their sources Detailed information on the primary alkaloidal constituents of cocaine is available in the United Nations manual Recommended Methods for Testing Cocaine: Manual for Use by National Narcotics Laboratories (ST/NAR/7). In the tables below, major components are > 1% by weight (w/w); minor components are usually < 1% w/w; and trace components are usually < 0.1% w/w (typically requiring an extraction step). Table 4. Alkaloidal impurities in cocaine and their sources (a) Major and minor components Typical source Anhydroecgonine Gas chromatography (GC) artefact Anhydroecgonine methyl ester GC artefact Benzoic acid Hydrolysis of cocaine Benzoylecgonine Hydrolysis of cocaine, also found in coca leaf but thought not to be extracted in the clandestine process Trans-cinnamic acid Hydrolysis of cis- and trans-cinnamoylcocaine Cis-cinnamoylecgonine (often at trace level) Hydrolysis of cis-cinnamoylcocaine Trans-cinnamoylecgonine (often at trace level) Hydrolysis of trans-cinnamoylcocaine Cis-cinnamoylcocaine Coca leaf Trans-cinnamoylcocaine Coca leaf Ecgonine Hydrolysis of cocaine, also found in coca leaf, but thought not to be extracted in the clandestine process Ecgonine methyl ester Found in coca leaf and occurs due to cocaine hydrolysis; most probably is not extracted in the clandestine process N-formyl-cocaine O 2 , a not present in coca leaf Norcocaine O 2 , not known to be present in coca leaf Pseudoecgonine methyl ester GC artefact: direct injection in MeOH of cocaine base (crack) containing traces of NaHCO 3 Truxillic acid(s) Hydrolysis of truxillines Truxillines Coca leaf, the total content of all isomers can be more than 10% of an unadulterated cocaine sample. 11 theoretical diastereomers– 11 observed. Truxinic acid(s) Hydrolysis of truxillines (b) Cocaine trace-level impurities Typical source Acetoxyecgonine methyl ester Coca leaf N-Benzoylnorcocaine Possibly a GC artefact 6-exo-Benzoyloxytropine Coca leaf Benzoyltropine Coca leaf Butyroylecgonine methyl ester Coca leaf Cis-cinnamoyltropacocaine Coca leaf Trans-cinnamoyltropacocaine Coca leaf 2’-Furanoylecgonine methyl ester Coca leaf 3’-Furanoylecgonine methyl ester Coca leaf
60 Methods for impurity profiling of heroin and cocaine Table 4. Alkaloidal impurities in cocaine and their sources (continued) (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 commercially available product) Tropacocalline Coca leaf: presence in leaf not confirmed. 16 theoretical diastereomers–10 observed. a O2 = oxidation.
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METHODS FOR IMPURITY PROFILING OF H
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Note Operating and experimental con
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Contents page I. Introduction. . .
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I. INTRODUCTION A. Background In or
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Introduction 3 on the detection and
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II. ASPECTS OF DRUG CHARACTERIZATIO
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Aspects of drug characterization an
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