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'Crack' and Cocaine Hydrochloride

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'Crack' and Cocaine Hydrochloride Joumal of Analytical Toxicology, VoL 15, May/June 1991 Inhalation Efficiencyof Free-Base Cocaine by Pyrolysis of 'Crack' and Cocaine Hydrochloride Yuji Nakahara* and Akiko Ishigami National Institute of Hygienic Sciences, Tokyo 158, Japan Materials and Methods Abstract t The Inhalation efficiency and pyrolysis products of cocaine by Reagent and chemicals the pyrolysis of crack and cocaine hydrochlorlde at various Chemical reagents used in this study were of reagent grade, temperatures are described. The Inhalation efficiency of Cocaine hydrochloride was purchased from Takeda Pharma- cocaine by the pyrolysis of crack was 73 + 9% and 62 :J: 11% at ceutical Co. (Osaka, Japan). Benzoylecgonine and ecgonine 170~ and 220~ respectively. When crack was heated at over were prepared by the method of Bell et al. (6). The mixture of a, 225~ the higher temperature resulted In a lower Inhalatlbn r, 7, and ~-carbomethoxycycloheptatriene (CMCHT) were syn- efficiency of cocaine. In that case, more methylecgon|dlne wee thesized by the method of Grundman (7) and methylation with produced. Furthermore, In the pyrolysis of crack, the lower diazomethane. concentration of cocaine In crack resulted in a lower Inhalation efficiency of cocaine. The major pyrolysis product of cocaine Preparation of crack HCI was a mixture of ~ ,8, 7, and ~-carbomethoxycyclo- To three 5-mL aliquots of 34-mg/mL cocaine hydrochloride heptstrlanes, and the malor pyrolysis product of crack was aqueous solution were added 1.5, 3, and 4.5 g of sodium bicar- methylecgonldlne. This study proposes a new method of bonate, The mixtures in beakers were warmed on a hot plate for discrimination between cocaine HCl and crack by GC or 1 h to remove water and prepare three types of white masses of GC/MS with a curie point pyrolyzer. crack (cocaine-sodium bicarbonate 1:10, 1:20, and 1:30). Pyroty$|s o'/crack The pyrolysis of crack was carried out in a glass oven (Shibata GTO-350 RS, Tokyo, Japan) as shown in Figure 1. 200 mg of Introduction crack was put in the sample round bottle (3 mL) joined with two cooling glass valves as shown in Figure 1. The sample bottle was Smoking free-base cocaine ("crack") is a serious drug abuse put into the oven and heated with rotation for 10 min under problem. This potent, highly addictive form is more dangerous 400--500 mm Hg suction from an aspirator. The oven tempera- than the old manner of cocaine use. Because this is a new method tures were set at 170, 220, 270, 320, 370, and 420~ The volatile for the self-administration of cocaine, there have been few substances were collected on the glass filter (GA-400). After studies (1-4) concerning the characterization of pyrolyzates pro- cooling, the glass filter trapping tar was extracted with 10 mL of duced by smoking crack. methanol three times. The combined extracts plus one drop of c- Crack is made by mixing cocaine hydrochloride and sodium HC1 were evaporated to dryness. The residue was dissolved in bicarbonate. Cocaine base is easily evaporated by heating and 0.1 mL of methanol and 1 laL was injected into the GC/MS may be directly inhaled to cause rapid stimulant effects. How- column. ever, the inhalation efficiency of cocaine, along with species and quantities of pyrotyzates produced by smoking crack, remain unclear, though thermal degradation of free-base cocaine has been reported to form benzoic acid and methylecgonidine (3-5), ~m as well as methyl-4-(3-pyridinyl)butyrate (2). This paper describes the inhalation efficiency and pyrolysis products of cocaine by pyrolysis experiments of crack at various temperatures. Furthermore, we report a method of discriminating between cocaine hydrochloride and crack. * Address requests for repdnts or additional information: Dr. Y. Nakahara,National Institute of Hygienic Sciences, 1-18-1, Kamiyoga,Setagaya-ku, Tokyo 158, Japan. ucts of crack, Reproduction(photocopying) of editorial content of this journal is prohibited without publisher's permission. 1 05 Journal of Analytical Toxicology,Vol. 15, May/June 1991 The substances that passed through the filter were trapped zene, applied on silica gel (10 g), and eluted with benzene (30 into an ether solution and analyzed, but there were no detectable mL), chloroform (50 mL), chloroform-methanol (9:1) (50 mL), compounds in the ether solution. and methanol (50 mL), respectively. As a result, cocaine (180 mg) was recovered in the chloroform fraction, in the mixture of Pyrolysls-GC and pyrolyals-GC/MS cocaine and pyrolysis product (P-X:150 mg) in the chloro- Pyrolysis gas chromatography (GC) was carried out with a form-methanol fraction and P-X (82 mg) in methanol. The chlo- Hewlett-Packard 5890 instrument using a fused-silica capillary roform-methanol fraction was reanalyzed to give 66 mg of P-X. column (Gaskuro Kogyo OV-1 bonded, 0.3-I.tm film thickness, P-X was characterized as follows: oil, MS(%); m/z 181(30), 25 m x 0.25 mm i.d.) with a JHP-3 curie point pyrolyzer (Nihon 152(100), 138(9), 122(13), 120(10), 82 (16), and 42 (55). Bunseki Kogyo Co., Tokyo, Japan). The GC parameters were as NMR(CDCI3)ppm: 1.52 (C-6en, 1H, m), 1.8-1.88 (C-4 en, 07 follows: injection port, 150~ oven temperature, 150~ for 0.5 en, 2H, m), 2.1-2.2 (C-6ex, C-7ex, 2H, m), 2.35 (3H, s, NCH3), min, ramp to 250~ at 6~ carrier gas, nitrogen at KPa = 6 2.63 ( 1 H, d, J = 0.007 Hz, C-4ex), 3.25 ( 1 H, t, J = 0.02 Hz, C- psi; and detector, FID. 5), 3.74 (3H, s, COOCH3), 3.79 (1H, D, J = 0.02 Hz), 6.82 Pyrolysis GC/mass spectrometry (GC/MS) was carried out (vinyl proton, 1H, t, J= 0.01 Hz). P-X was identical to methylec- with a Hewlett-Packard 5890 GC/5970 mass selective detector gonidine (1,3) in all aspects. using the same fused-silica capillary column and curie point py- rolyzer as in the GC analysis. The GC parameters were the same Identification of carbomethoxycycloheptatrlene (CMCHT) as above GC conditions except for the carrier gas, which was As shown in Figure 2, the mass chromatogram (0-16 rain) of helium at KPa = 5 psi. pyrolysis products of cocaine hydrochloride by curie-point py- A small amount of crack sample was wrapped with the pyro- rolysis at 315~ showed the four main peaks at 9.41, 10.57, foils (175, 192, 205,225,235,255, 315,333, 356, 396, 423, 445, 11.05, and l 1.25 rain which were identical with those of the 500, 590, 650, and 740~ set in the sample holder, and in- GC/MS chromatogram of synthetic mixture of tx, fl, 1/and 5-car- serted into the oven. The pyrolysis time was 3 s, injection tem- bomethoxycycloheptatriene (CMCHT). perature was 150~ and needle temperature was 200~ Isolation of the major pyrolysis product Crack prepared with cocaine hydrochloride (0.59 g) and sodium bicarbonate (3 g) by using the above method was heated Results and Discussion in a flask of the pyrolysis apparatus at 250~ for 30 min. After cooling, the products were extracted with 30 mL of methanol three times, and the extracts with hydrochloric acid added were Pyrolysis of crack evaporated. The residue was dissolved in diluted HCl and the so- The inhalation experiment of crack (cocaine-sodium bicar- lution was washed with ether. The aqueous layer was made al- bonate 1:20), by the method of trapping cocaine and its pyrolysis kaline with ammonia and extracted with ether. After evaporation, products on the glass filter, was found to produce mainly cocaine the residue (455 mg) was dissolved in a small volume of ben- and methylecgonidine (MEc). The volatilization and pyrolysis of TIC of V3:COCR 315.0 o 1 . 8E6 P-3 p-q c 73 c 5 . E)E5 ] P-I P~=2 _(3 E E~ i i i 8 12 14 16 Time (min.) Scan 904 (11.249 min) o9 V3:COCR 315.D 4 . E)E5 p-q 3 , E~E5 2. E~E5 B5 1 18 15E~ E / ] 185 77 _o 1 . E~E5 / E i I I ..... , j ,,,I. I, .... Ii I J ; j . , J ..... i ........ i 9 9 9 i , 7E~ BE) 9~ IE)E~ i IE) 12E) 13E) 14E) 15E~ Mass/Charse Figure 2. (A) Mass chromatogram (0-16 min) of pyrolysis products of cocaine hydrochloride by curie point pyrolyzer at 315~ and (B) mass spectrum of P-4. 106 Journal of AnalyticalToxicology, Vol. 15, May/June1991 Table I. Effect of Temperature on the Volatilization cocaine in crack depended on the heating temperatures as shown and Pyrolysis of Cocaine in Crack (Cocaine-Sodlum in Table I. Ratios of 1:10, 1:20, and 1:30 of cocaine-sodium bi- Blcarbonate 1:20)* carbonate produced relative abundances of 49 + 12, 37 + 8, and PyrolysisTemperature (~ 35 + 9% of cocaine and 45 + 16, 63 + 19, and 59 + 21% of methylecgonidine, respectively at a pyrolysis temperature of Substance 170 220 270 320 370 420 270~ Cocaine 73+9 62+11 37+7 30+8 28• 21• In the pyrolysis of crack, the higher temperature and the lower Methylecgonidine 1• 18• 63• 68• 58• 55• ratio of cocaine, the more pyrolysate (MEc) is produced. *n=3 Major pyrolysis products of crack and cocaine HCI Methylecgonidine (MEc). T. Lukaszewski et al. (1) reported that methylecgonidine was formed from cocaine as the result of TIC of V3 : CCN NR.D (A) thermal elimination of benzoic acid. B.R. Martin et al. (5) also re- e 4"OEGI ported that the conversion from cocaine to MEc was predominant at over 400~ and 89% of cocaine was converted to MEc by py- onc 3 OEG 1 rolysis of free base cocaine at 650~ and a flow rate of 400 3c 2 OEG 1 mL/min.
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