Ecgonin methyl ester

Thus the ecgonin methyl ester fragment J ean elearly be reeognised only the link to the O atom still remains to be established. The attaehment of the O atom is identified by the large ehemieal shift value (Sfj = 5.59) of the proton on the same earbon atom. The parts A and J then give the skeleton K of eoeaine. 

The isomeric -cinnamylcocaine (methylcinnamoyl-d- -ecgonine) prepared by Einhorn and Deckers by the action of cinnamoyl chloride at 150-60° on d-i/r-ecgonine methyl ester, crystallises in prisms, m.p. 68°, [ Id + 2° (EtOH). The hydrochloride, B. HCl, forms needles, m.p. 186° the platinichloride, needles, m.p. 208°, and the aurichloride orange needles, m.p. 164°. 

Alkaloids, e.g. cocaine, ecgonine, benzoylecgonine, ecgonine methyl ester 280 °C, 8 min or 260°C, 10-30 min Pale blue induced fluorescence (Xn > 390 nm, cut off filter), fluorescence amplification by a factor of 2 on dipping in liquid paraffin solution detection limits <10 ng. [13]... 

Cocaine, ecgonine, ecgonine methyl ester, benzoylecgonine ... 

Fig. I Fluorescence scan of a chromatogram zone with 300 ng each of ecgonine methyl ester (1), cocaine (2), ecgonine (3) and benzoylecgonine (4) per chromatogram zone.

Phthalate esters are widespread contaminants and the dialkyl phthalates are hydrolyzed before degradation of the resulting phthalate (Eaton and Ribbons 1982), which is discussed in Chapter 8, Part 3. For dimethyl phthalate, dimethyl terephthalate, and dimethyl isophthalate only partial hydrolysis may take place (Li et al. 2005). Cocaine is hydrolyzed to benzoate and ecgonine methyl ester by a strain of Pseudomonas maltophilia (Britt et al. 1992). 

However, there are some data on interactions of phosphate esters with other compounds. Cocaine undergoes metabolism by three major routes one of these routes involves hydrolysis by liver and plasma cholinesterases to form ecgonine methyl ester. It has been suggested that cocaine users with serious complications tend to have lower plasma cholinesterase levels. Thus, it is possible that individuals with decreased plasma cholinesterase levels (such as resulting from organophosphate ester exposure) may be highly sensitive to cocaine (Cregler and Mark 1986 Hoffman et al. 1992). However, there are no experimental data to support this hypothesis. 

S. M. Roberts, R. D. Harbison, R. C. James, Inhibition by Ethanol of the Metabolism of Cocaine to Benzoylecgonine and Ecgonine Methyl Ester in Mouse and Human Liver , Drug Metab. Dispos. 1993, 21, 537-541. 

Electrode mechanism and analytical determination of cocaine and its metaboKtes, such as benzoylecgonine, ecgonine, and ecgonine methyl ester have been studied [192] at HMDE. These compounds were adsorbed at the electrode. Adsorption of benzoylecgonine was stronger than that of cocaine. Consequently, adsorptive stripping voltammetric method for the determination of cocaine was based on reduction of benzoylecgonine. 

In humans, the principal route of metabolism of cocaine is by hydrolysis of the ester linkages. Pseudocholinesterase and liver esterases produce the inactive metabolite, ecgonine methyl ester (EME) (Figure 4.5). The second major metabolite, BE, is formed spontaneously at physiological pH. In addition, there is evidence that BE may be formed enzymatically from cocaine by liver carboxylesterases. N-Demethylation of BE produces benzoylnorecgonine. Further metabolism of EME and BE produces ecgonine. Further hydrolysis of cocaine and BE produces minor metabolites, meta- and para-hydroxy-cocaine and -BE. The proportion of each metabolite produced and the activity of the individual metabolites have yet to be completely determined. 

In contrast to TA of the Solanaceae family cocaine from Erythroxylaceae coca contains a substituted 3(1 -hydroxytropanc (3(i-tropinc, pseudotropine) skeleton (ecgonine methyl ester) (Fig. 1). 

Cocaine easily passes the blood brain barrier and the plasma levels are detectable for about 4-6 h after nasal ingestion it is rapidly metabolized into inactive metabolites benzoylecgonine (BEG), ecgonine methyl ester (EME), and ecgonine [12], These molecules are biomarkers for the identification of cocaine abuse due to their higher biological half-life with respect to cocaine (about fivefold). 

Quintela O, Lendoiro E, Cruz A, de Castro A, Quevedo A, Jurado C, Lopez-Rivadulla M (2010) Hydrophilic interaction liquid chromatography-tandem mass spectrometry (HILIC-MS/MS) determination of cocaine and its metabolites benzoylecgonine, ecgonine methyl ester, and cocaethylene in hair samples. Anal Bioanal Chem 396(5) 1703-1712. doi 10.1007/s00216-009-3393-5... 

Springfield, A. C., CartmeU, L. W., Aufderheide, A. C., Buikstra, J., and Ho, J., Cocaine and metabolites in the hair of ancient Peruvian coca leaf chewers. Forensic Sci. Int., 63, 269, 1993. Baumgartner, W. A. and HiU, V. A., Sample preparation techniques. Forensic Sci. Int., 63,121,1993. Nakahara, Y. and Kikura, R., Hair analysis for drugs of abuse. VII. The incorporation rates of cocaine, benzoylecgonine cmd ecgonine methyl ester into rat hair and hydrolysis of cocaine in rat hair. Arch. Toxicol, 68, 54,1994. 

Benzoylecgonine Ecgonine methyl ester Cocaine SDS-MeOH EN-SPE MTBSTFA... 

Benzoylecgonine Benzoylnorecgonine Cocaethylene N orcocaethylene Ecgonine methyl ester Benzoylecgonine Cocaine CH2CI2 MeOH HY-EX EH -SPE BSTFA BSTFA... 

Moeller, M. R., Fey, P., Rimbach, S., Identification and Quantitation of Cocaine and Its Metabolites, Benzoylecgonine and Ecgonine Methyl Ester, in Hair of Bohvian Coca Chewers by Gas Chromatography-Mass Spectrometry, /. Anal. Toxicol., 16, 291,1992. 

Nakahara, Y., Ochiai, T., Kikura, R., Hair analysis for drugs of abuse. V. The facility in incorporation of cocaine into hair over its major metabolites, benzoylecgonine and ecgonine methyl ester. Arch. Toxicol, 66, 446-449, 1992. 

The metabolic scheme of cocaine analytes in hair. (Abbreviations COC, cocaine BE, benzoylecgonine EME, ecgonine methyl ester ECG, ecgonine CE, cocaethylene NCOC, norcocaine NCE, norcocaethylene and AEME, anhydroecgonine methyl ester). 

Cone et al. Cocaine users 6.4-19.2 0.3-2.5 0-1.9 (ecgonine methyl ester) 0-2.6 (cocaethylene) 0-0.7 (norcocaine) 0-trace (norcocaethylene) 1... 

---