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38749096817
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note
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Synthesis of compound 1 (lidocaine hydrochloride) and its analogues (28-40). Aniline 2-11 (0.25 M) in toluene (300 mL) and sodium carbonate (53 g, 0.50 M) at 20-30 °C were added little by little over 30 min to 2-chloroacetyl chloride or 3-chloropropionyl chloride (0.30 M). The mixture was stirred for one hour at room temperature, diluted with water (100 mL), and diethylamine (0.74 M) was added. The reaction mixture was refluxed for 6-10 h, the organic layer collected and washed three times with water (3 × 100 mL). The organic solvent was removed under vacuum to leave a crude product which was dissolved in acetone (100 mL), and charcoal (2.0 g) was added at room temperature. After 30 min under stirring the suspension was filtered. The solution was kept at 10-15 °C and a flux of HCl (g) was passed into the solution until pH = 2-3. The product was filtered and recrystallized from acetone to give the lidocaine hydrochloride or its analogues (28-40).
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13
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33845973344
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Costa J.C.S., Olsen P.C., Siqueira R.A., Carvalho V.F., Serra M.F., Alves L.A., Faria R.X., Xisto D.G., Rocco P.R.M., Cordeiro R.S., Silva P.M.R., and Martins M.A. J. Allergy Clin. Immunol. 119 (2007) 219
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Cordeiro, R.S.10
Silva, P.M.R.11
Martins, M.A.12
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14
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38749128553
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note
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15 All solutions of lidocaine and analogues were prepared using physiological saline (0.9% NaCl solution).
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17
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0025775776
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Mcmaster P.D., Noris V.J., Stankard C.E., Byrnes E.W., and Guzzo P.R. Pharm. Res. 8 (1991) 1013
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22
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24
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38749136031
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note
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27
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25
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38749089219
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note
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SYBYL, Tripos Associates, 1699 South Hanley Road, Suite 303, St. Louis, Missouri 63144.
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27
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38749116790
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BioByte Corp. 201 W. Fourth Street, Suite #204 Claremont, CA 91711-4707; USA.
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BioByte Corp. 201 W. Fourth Street, Suite #204 Claremont, CA 91711-4707; USA.
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38749128176
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note
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50 values ± standard error of the mean (SEM).
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34
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34447499150
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