519-09-5

Basic information

• Product Name: BENZOYLECGONINE
• Synonyms: BENZOYLECGONINE;1alphaH,5alphaH-Tropane-2beta-carboxylic acid, 3beta-hydroxy-, benzoate (ester);3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid;8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl;8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, [1R-(exo,exo)]-;Benzoylecogonine;Ecgonine benzoate;o-Benzoyl-(-)-ecgonine
• CAS NO: 519-09-5
• Molecular Formula: C₁₆H₁₉NO₄
• Molecular Weight: 289.33
• EINECS: 208-263-5
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;AlkaloidsAlphabetic;BA - BHDrugs of Abuse;Drugs of Abuse;EcgoninenForensic and Veterinary Standards;Neat Compounds;B;Chemical Structure;Drugs&Metabolites;Solutions;Aromatics
• Mol File: 519-09-5.mol

Chemical Properties

• Melting Point: 1950C (dec)
• Boiling Point: 431.49°C (rough estimate)
• Flash Point: 11 °C
• Appearance: Crystalline Solid
• Density: 1.1267 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: 2-8°C
• PKA: pKa 11.80 (Uncertain)
• CAS DataBase Reference: BENZOYLECGONINE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZOYLECGONINE(519-09-5)
• EPA Substance Registry System: BENZOYLECGONINE(519-09-5)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25-25
• Safety Statements: 16-36/37-45-7
• RIDADR: UN 1230 3/PG 2
• WGK Germany: 1
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 519-09-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
BENZOYLECGONINE is used as a controlled substance for its association with Cocaine. It serves as a crucial compound in the study and understanding of the metabolism and effects of Cocaine on the human body. This knowledge aids in the development of potential treatments and interventions for cocaine addiction and related health issues.
Used in Research and Development:
BENZOYLECGONINE is used as a research compound for studying the metabolic pathways of Cocaine and its potential implications on human health. This research can contribute to the development of new drugs, therapies, and diagnostic tools related to substance abuse and addiction.
Used in Forensic Science:
BENZOYLECGONINE is used as a forensic marker in the detection and analysis of Cocaine use. Its presence in biological samples can help in determining the consumption of Cocaine, which is valuable in legal investigations and criminal cases involving drug use.
Used in Drug Testing and Analysis:
BENZOYLECGONINE is used as a target analyte in drug testing and analysis, both for individual and workplace drug screening. Its detection in biological samples can confirm the use of Cocaine, which is essential for monitoring and ensuring compliance with drug policies and regulations.

InChI:InChI=1/C16H19NO4/c1-17-11-7-8-12(17)14(15(18)19)13(9-11)21-16(20)10-5-3-2-4-6-10/h2-6,11-14H,7-9H2,1H3,(H,18,19)/t11-,12+,13-,14+/m0/s1

Synthetic route

RTI-128 (155748-84-8) → benzylecgonine (519-09-5)

Conditions	Yield
With sodium nitrite In acetic anhydride; acetic acid 1.) 0 deg C, 16 h, 2.) room temperature, 8 h;	93%

(-)-cocaine hydrochloride (53-21-4) → benzylecgonine (519-09-5)

Conditions	Yield
With ammonia; water	86%
With dipotassium hydrogenphosphate; potassium dihydrogenphosphate In tetrahydrofuran; water at 80℃; for 3h;	83%
With sodium hydroxide for 12h; Heating; Yield given;

Cocaine (50-36-2) → benzylecgonine (519-09-5)

Conditions	Yield
With water for 24h; Reflux;	84%
With human carboxylesterase 1b, recombinant In aq. phosphate buffer at 37℃; for 1h; pH=7.4; Enzymatic reaction;
With water In 1,4-dioxane at 130℃; for 2h; Microwave irradiation;

benzoic acid anhydride (93-97-0) + ecgonine (481-37-8) → benzylecgonine (519-09-5)

Conditions	Yield
With acetone
With water at 100℃;

Cocaine (50-36-2) → methanol (67-56-1) + benzoic acid (65-85-0) + ecgonine (481-37-8) + methyl ecgonine (7143-09-1) + benzylecgonine (519-09-5)

Conditions	Yield
With hydrogenchloride In water at 70 - 90℃; Product distribution; Rate constant; Thermodynamic data; also in plasma and with other reagents ; ΔHa, ΔS(excit.), Arrhenius parameters;

Cocaine (50-36-2) → methyl ecgonine (7143-09-1) + benzylecgonine (519-09-5)

Conditions	Yield
at 37℃; Rate constant; various pH from 6.9 to 10.4; I=0.1 M;

water (7732-18-5) + benzoic acid anhydride (93-97-0) + ecgonine (481-37-8) → benzylecgonine (519-09-5)

Conditions	Yield
at 100℃;
at 100℃;

water (7732-18-5) + Cocaine (50-36-2) → benzylecgonine (519-09-5)

l-cocaine → benzylecgonine (519-09-5)

Conditions	Yield
With water

Cocaine (50-36-2) → methylecgonine benzoate + benzylecgonine (519-09-5)

Conditions	Yield
cocE-pIX Enzyme kinetics; Enzymatic reaction;
cocE-pIII Enzyme kinetics; Enzymatic reaction;
cocE Enzyme kinetics; Enzymatic reaction;

anhydroecgonine hydrochloride (74242-55-0) → benzylecgonine (519-09-5)

Conditions	Yield
Multi-step reaction with 13 steps 1: 93 percent / H2 / Pd/C / methanol / 6.5 h / 3102.9 Torr / Ambient temperature 2: 1.) (COCl)2, DMF, 2.) N-hydroxy-2-thiopyridone / 1.) CH2ClCH2Cl, room temperature, 12 h, 2.) CH2ClCH2Cl, room temperature, 1.5 h, 3.) CH2Cl2, irradiation, 0 deg C, 2 h 3: toluene / 24 h / Heating 4: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h 5: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 6: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 7: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 8: 80 percent / 0.67 h / 105 - 110 °C 9: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 10: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 11: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 12: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 13: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme
Multi-step reaction with 13 steps 1: 93 percent / H2 / Pd/C / methanol / 6.5 h / 3102.9 Torr / Ambient temperature 2: 1.) (COCl)2, DMF, 2.) N-hydroxy-2-thiopyridone / 1.) CH2ClCH2Cl, room temperature, 12 h, 2.) CH2ClCH2Cl, room temperature, 1.5 h, 3.) CH2Cl2, irradiation, 0 deg C, 2 h 3: toluene / 24 h / Heating 4: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h 5: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 6: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 7: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 8: 80 percent / 0.67 h / 105 - 110 °C 9: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 10: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 11: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 12: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 13: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme
Multi-step reaction with 13 steps 1: 93 percent / H2 / Pd/C / methanol / 6.5 h / 3102.9 Torr / Ambient temperature 2: 1.) (COCl)2, DMF, 2.) N-hydroxy-2-thiopyridone / 1.) CH2ClCH2Cl, room temperature, 12 h, 2.) CH2ClCH2Cl, room temperature, 1.5 h, 3.) CH2Cl2, irradiation, 0 deg C, 2 h 3: NaIO4 / H2O / 2 h / Ambient temperature 4: 57 percent / 75 °C / 0.08 - 0.1 Torr 5: 1.) 1-chloroethyl chloroformate, 3.) Et3N / 1.) toluene, reflux, 16 h, 2.) MeOH, reflux, 16 h, 3.) room temperature, 14 h 6: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 7: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 8: 80 percent / 0.67 h / 105 - 110 °C 9: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 10: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 11: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 12: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 13: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

(1R,5S)-8-Methyl-2-phenylselanyl-8-aza-bicyclo[3.2.1]octane → benzylecgonine (519-09-5)

Conditions	Yield
Multi-step reaction with 11 steps 1: toluene / 24 h / Heating 2: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h 3: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 4: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 5: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 6: 80 percent / 0.67 h / 105 - 110 °C 7: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 8: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 9: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 10: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 11: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme
Multi-step reaction with 11 steps 1: toluene / 24 h / Heating 2: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h 3: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 4: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 5: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 6: 80 percent / 0.67 h / 105 - 110 °C 7: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 8: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 9: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 10: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 11: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme
Multi-step reaction with 11 steps 1: NaIO4 / H2O / 2 h / Ambient temperature 2: 57 percent / 75 °C / 0.08 - 0.1 Torr 3: 1.) 1-chloroethyl chloroformate, 3.) Et3N / 1.) toluene, reflux, 16 h, 2.) MeOH, reflux, 16 h, 3.) room temperature, 14 h 4: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 5: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 6: 80 percent / 0.67 h / 105 - 110 °C 7: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 8: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 9: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 10: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 11: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

C14H19NOSe (208038-05-5) → benzylecgonine (519-09-5)

Conditions

Yield

Multi-step reaction with 10 steps 1: 57 percent / 75 °C / 0.08 - 0.1 Torr 2: 1.) 1-chloroethyl chloroformate, 3.) Et3N / 1.) toluene, reflux, 16 h, 2.) MeOH, reflux, 16 h, 3.) room temperature, 14 h 3: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 4: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 5: 80 percent / 0.67 h / 105 - 110 °C 6: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 7: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 8: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 9: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 10: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

(1R,5R)-8-Methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid; hydrochloride → benzylecgonine (519-09-5)

Conditions	Yield
Multi-step reaction with 12 steps 1: 1.) (COCl)2, DMF, 2.) N-hydroxy-2-thiopyridone / 1.) CH2ClCH2Cl, room temperature, 12 h, 2.) CH2ClCH2Cl, room temperature, 1.5 h, 3.) CH2Cl2, irradiation, 0 deg C, 2 h 2: toluene / 24 h / Heating 3: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h 4: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 5: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 6: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 7: 80 percent / 0.67 h / 105 - 110 °C 8: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 9: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 10: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 11: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 12: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme
Multi-step reaction with 12 steps 1: 1.) (COCl)2, DMF, 2.) N-hydroxy-2-thiopyridone / 1.) CH2ClCH2Cl, room temperature, 12 h, 2.) CH2ClCH2Cl, room temperature, 1.5 h, 3.) CH2Cl2, irradiation, 0 deg C, 2 h 2: toluene / 24 h / Heating 3: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h 4: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 5: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 6: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 7: 80 percent / 0.67 h / 105 - 110 °C 8: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 9: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 10: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 11: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 12: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme
Multi-step reaction with 12 steps 1: 1.) (COCl)2, DMF, 2.) N-hydroxy-2-thiopyridone / 1.) CH2ClCH2Cl, room temperature, 12 h, 2.) CH2ClCH2Cl, room temperature, 1.5 h, 3.) CH2Cl2, irradiation, 0 deg C, 2 h 2: NaIO4 / H2O / 2 h / Ambient temperature 3: 57 percent / 75 °C / 0.08 - 0.1 Torr 4: 1.) 1-chloroethyl chloroformate, 3.) Et3N / 1.) toluene, reflux, 16 h, 2.) MeOH, reflux, 16 h, 3.) room temperature, 14 h 5: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 6: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 7: 80 percent / 0.67 h / 105 - 110 °C 8: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 9: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 10: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 11: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 12: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

tropidine (208037-81-4) → benzylecgonine (519-09-5)

Conditions

Yield

Multi-step reaction with 9 steps 1: 1.) 1-chloroethyl chloroformate, 3.) Et3N / 1.) toluene, reflux, 16 h, 2.) MeOH, reflux, 16 h, 3.) room temperature, 14 h 2: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 3: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 4: 80 percent / 0.67 h / 105 - 110 °C 5: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 6: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 7: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 8: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 9: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

(1R,5S)-8-benzyl-8-azabicyclo[3.2.1]octan-2-one (208037-76-7) → benzylecgonine (519-09-5)

Conditions

Yield

Multi-step reaction with 11 steps 1: 96 percent / H2 / Pd/C / methanol / 5 h 2: 88 percent / methanol / 2 h / Ambient temperature 3: 70 percent / NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h 4: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 5: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 6: 80 percent / 0.67 h / 105 - 110 °C 7: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 8: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 9: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 10: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 11: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

(1R,5S)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester (208037-78-9) → benzylecgonine (519-09-5)

Conditions

Yield

Multi-step reaction with 8 steps 1: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 2: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 3: 80 percent / 0.67 h / 105 - 110 °C 4: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 5: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 6: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 7: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 8: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

(1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone (208037-77-8) → benzylecgonine (519-09-5)

Conditions

Yield

Multi-step reaction with 10 steps 1: 88 percent / methanol / 2 h / Ambient temperature 2: 70 percent / NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h 3: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 4: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 5: 80 percent / 0.67 h / 105 - 110 °C 6: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 7: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 8: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 9: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 10: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

(2R,5S)-5-[1'-(2'-methoxycarbonyl)ethyl]proline methyl ester (208037-73-4) → benzylecgonine (519-09-5)

Conditions	Yield
Multi-step reaction with 13 steps 1: 93 percent / Et3N / methanol / 14 h / Ambient temperature 2: 85 percent / KHMDS / tetrahydrofuran / 6 h / -78 °C 3: 87 percent / NaI / pyridine / 7.5 h 4: 88 percent / methanol / 2 h / Ambient temperature 5: 70 percent / NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h 6: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 7: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 8: 80 percent / 0.67 h / 105 - 110 °C 9: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 10: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 11: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 12: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 13: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme
Multi-step reaction with 14 steps 1: 96 percent / K2CO3 / acetonitrile / 14 h / Ambient temperature 2: 90 percent / KHMDS / tetrahydrofuran / 1 h / -78 °C 3: 90 percent / NaI / pyridine / 8 h / Heating 4: 96 percent / H2 / Pd/C / methanol / 5 h 5: 88 percent / methanol / 2 h / Ambient temperature 6: 70 percent / NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h 7: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 8: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 9: 80 percent / 0.67 h / 105 - 110 °C 10: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 11: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 12: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 13: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 14: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

(2R,5S)-5-(2-Carboxy-ethyl)-pyrrolidine-2-carboxylic acid tert-butyl ester (208037-72-3) → benzylecgonine (519-09-5)

Conditions	Yield
Multi-step reaction with 14 steps 1: 95 percent / AcCl / 14 h / Heating 2: 93 percent / Et3N / methanol / 14 h / Ambient temperature 3: 85 percent / KHMDS / tetrahydrofuran / 6 h / -78 °C 4: 87 percent / NaI / pyridine / 7.5 h 5: 88 percent / methanol / 2 h / Ambient temperature 6: 70 percent / NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h 7: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 8: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 9: 80 percent / 0.67 h / 105 - 110 °C 10: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 11: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 12: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 13: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 14: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme
Multi-step reaction with 15 steps 1: 95 percent / AcCl / 14 h / Heating 2: 96 percent / K2CO3 / acetonitrile / 14 h / Ambient temperature 3: 90 percent / KHMDS / tetrahydrofuran / 1 h / -78 °C 4: 90 percent / NaI / pyridine / 8 h / Heating 5: 96 percent / H2 / Pd/C / methanol / 5 h 6: 88 percent / methanol / 2 h / Ambient temperature 7: 70 percent / NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h 8: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 9: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 10: 80 percent / 0.67 h / 105 - 110 °C 11: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 12: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 13: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 14: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 15: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

(1R,2R,3S,5S)-2-cyano-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (208037-85-8) → benzylecgonine (519-09-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 2: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 3: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 4: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 5: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

methyl 8-benzyl-2-hydroxy-8-azabicyclo[3.2.1]oct-2-ene-3-carboxylate (208037-75-6) → benzylecgonine (519-09-5)

Conditions

Yield

Multi-step reaction with 12 steps 1: 90 percent / NaI / pyridine / 8 h / Heating 2: 96 percent / H2 / Pd/C / methanol / 5 h 3: 88 percent / methanol / 2 h / Ambient temperature 4: 70 percent / NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h 5: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 6: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 7: 80 percent / 0.67 h / 105 - 110 °C 8: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 9: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 10: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 11: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 12: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

Benzoic acid (1R,2R,3S,5S)-2-carbamoyl-8-aza-bicyclo[3.2.1]oct-3-yl ester (208037-88-1) → benzylecgonine (519-09-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 2: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

(1R,2R,3S,5S)-2-Carbamoyl-3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (208037-86-9) → benzylecgonine (519-09-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 2: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 3: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 4: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

(1R,2S,5S)-2-Phenylselanyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (208037-82-5) → benzylecgonine (519-09-5)

Conditions

Yield

Multi-step reaction with 9 steps 1: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 2: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 3: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 4: 80 percent / 0.67 h / 105 - 110 °C 5: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 6: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 7: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 8: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 9: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

(1R,2R,5S)-2-Phenylselanyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (208038-13-5) → benzylecgonine (519-09-5)

Conditions

Yield

Multi-step reaction with 9 steps 1: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 2: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 3: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 4: 80 percent / 0.67 h / 105 - 110 °C 5: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 6: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 7: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 8: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 9: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

(1R,2S,5S)-2-Phenylselanyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid 1-chloro-ethyl ester (208037-92-7) → benzylecgonine (519-09-5)

Conditions

Yield

Multi-step reaction with 10 steps 1: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h 2: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 3: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 4: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 5: 80 percent / 0.67 h / 105 - 110 °C 6: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 7: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 8: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 9: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 10: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

(1R,2R,5S)-2-Phenylselanyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid 1-chloro-ethyl ester → benzylecgonine (519-09-5)

Conditions

Yield

Multi-step reaction with 10 steps 1: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h 2: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 3: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 4: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 5: 80 percent / 0.67 h / 105 - 110 °C 6: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 7: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 8: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 9: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 10: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

(1R,5S)-2-Hydroxy-8-aza-bicyclo[3.2.1]oct-2-ene-3,8-dicarboxylic acid 8-tert-butyl ester 3-methyl ester (208037-90-5) → benzylecgonine (519-09-5)

Conditions

Yield

Multi-step reaction with 11 steps 1: 87 percent / NaI / pyridine / 7.5 h 2: 88 percent / methanol / 2 h / Ambient temperature 3: 70 percent / NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h 4: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 5: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 6: 80 percent / 0.67 h / 105 - 110 °C 7: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 8: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 9: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 10: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 11: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h View Scheme

diazomethane (186581-53-3, 908094-01-9) + benzylecgonine (519-09-5) → Cocaine (50-36-2)

Conditions	Yield
In dichloromethane	95%

benzylecgonine (519-09-5) + trimethyleneglycol (504-63-2) → 1-hydroxy-3-propyl benzoylecgonine

Conditions	Yield
Stage #1: benzylecgonine With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; Stage #2: trimethyleneglycol In DMF (N,N-dimethyl-formamide); dichloromethane at 20℃;	95%
Stage #1: benzylecgonine With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 24h; Stage #2: trimethyleneglycol In dichloromethane
Stage #1: benzylecgonine With 1,1'-carbonyldiimidazole In dichloromethane for 22h; Stage #2: trimethyleneglycol In dichloromethane at 20℃; for 6h;

propan-1-ol (71-23-8) + benzylecgonine (519-09-5) → RTI 13 (64091-46-9)

Conditions	Yield
With hydrogenchloride at 0℃; for 48h;	83%

ethyl iodide (75-03-6) + benzylecgonine (519-09-5) → cocaethylene (529-38-4)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine In dichloromethane for 72h; Ambient temperature;	72%
With ethanol at 100℃; im Rohr;

benzyl 6-bromohexanoate (78277-26-6) + benzylecgonine (519-09-5) → (1R,2R,3S,5S)-3-Benzoyloxy-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid 5-benzyloxycarbonyl-pentyl ester (173443-26-0)

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 80℃;	72%

6-amino-hexanoic acid benzyl ester toluene-4-sulfonic acid (5514-99-8) + benzylecgonine (519-09-5) → (1R,2R,3S,5S)-2-((6-(benzyloxy)-6-oxohexyl)carbamoyl)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl benzoate

Conditions	Yield
Stage #1: 6-amino-hexanoic acid benzyl ester toluene-4-sulfonic acid; benzylecgonine With dmap In dichloromethane for 1.5h; Inert atmosphere; Cooling with ice; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane for 96h; Inert atmosphere;	71%

t-butyl (RS)-phenylalaninate (16367-71-8) + benzylecgonine (519-09-5) → Benzoic acid (1R,2R,3S,5S)-2-(1-tert-butoxycarbonyl-2-phenyl-ethylcarbamoyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

Conditions	Yield
With benzotriazol-1-yl-oxy-tris-pyrrolidinophosphonium; triethylamine In dichloromethane for 12h; Ambient temperature;	65%

ethanol (64-17-5) + benzylecgonine (519-09-5) → cocaethylene (529-38-4)

Conditions	Yield
Stage #1: benzylecgonine With oxalyl dichloride at 20℃; for 0.333333h; Stage #2: ethanol at 20℃; for 12h;	60%
With hydrogenchloride
With hydrogenchloride at 0℃; for 48h;

diisopropyl-carbodiimide (693-13-0) + benzylecgonine (519-09-5) → Benzoic acid (1R,2R,3S,5S)-2-(N,N'-diisopropyl-carbamimidoyloxycarbonyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester + Benzoic acid (1R,2R,3S,5S)-2-(1-tert-butoxycarbonyl-2-phenyl-ethylcarbamoyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

Conditions	Yield
With t-butyl (RS)-phenylalaninate In dichloromethane Ambient temperature;	A 58% B 15%

t-butyl (RS)-phenylalaninate (16367-71-8) + benzylecgonine (519-09-5) → (S)-N-benzoylphenylalanine tert-butyl ester (109309-90-2)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;	34%

benzylecgonine (519-09-5) → 3β-(benzoyloxy)-2β-(hydroxymethyl)-8-methyl-8-azabicyclo<3.2.1>octane (137718-56-0)

Conditions	Yield
With B2H6-THF In tetrahydrofuran at 0 - 20℃; for 3h;	31%

methanol (67-56-1) + benzylecgonine (519-09-5) → Cocaine (50-36-2)

Conditions	Yield
With hydrogenchloride

Isobutyl iodide (513-38-2) + benzylecgonine (519-09-5) → (1R)-3exo-benzoyloxy-tropane-2exo-carboxylic acid isobutyl ester

Conditions	Yield
With 2-methyl-propan-1-ol at 95℃; im Rohr;

1-iodo-propane (107-08-4) + benzylecgonine (519-09-5) → RTI 13 (64091-46-9)

Conditions	Yield
With propan-1-ol at 95℃; im Rohr;

ethylene dibromide (106-93-4) + benzylecgonine (519-09-5) → 3-benzoyloxy-tropane-2-carboxylic acid-(2-bromo-ethyl ester)

Conditions	Yield
With ethanol at 95℃; im Rohr; O-benzoyl-l-ecgonine-<β-bromo-ethyl ester>;

benzylecgonine (519-09-5) + methyl iodide (74-88-4) → Cocaine (50-36-2)

Conditions	Yield
With methanol at 100℃; im Rohr;
With methanol; sodium methylate at 100℃; im Rohr;

benzylecgonine (519-09-5) → (+)-pseudoecgonine (481-38-9)

Conditions	Yield
With potassium hydroxide
With potassium hydroxide

benzylecgonine (519-09-5) → ecgonine (481-37-8)

Conditions	Yield
With hydrogenchloride

benzylecgonine (519-09-5) → 2-β-benzamido-3β-tropanol

Conditions	Yield
With thionyl chloride Behandeln des Reaktionsprodukts mit NaN3 in H2O, Erwaermen mit wss. HCl und anschliessendes Behandeln mit wss. NaOH;

benzylecgonine (519-09-5) → benzoylnorecgonine (41889-45-6)

Conditions	Yield
With potassium permanganate; sodium carbonate

2-(4-nitrophenyl)ethanol (100-27-6) + benzylecgonine (519-09-5) → 3β-(benzoyloxy)-8-methyl-8-azabicyclo<3.2.1>octane-2β-carboxylic acid (p-nitrophenyl)ethyl ester (137819-59-1)

Conditions	Yield
With 1,1'-carbonyldiimidazole 1.) CH2Cl2, RT, 6 h, 2.) acetone, reflux, 3 h; Yield given. Multistep reaction;

2-phenylethanol (60-12-8) + benzylecgonine (519-09-5) → RTI 53 (137718-50-4)

Conditions	Yield
With 1,1'-carbonyldiimidazole 1.) CH2Cl2, RT, 6 h, 2.) acetone, reflux, 3 h; Yield given. Multistep reaction;

methylamine (74-89-5) + benzylecgonine (519-09-5) → 3β-(benzoyloxy)-8-methyl-8-azabicyclo<3.2.1>octane-2β-carboxylic acid N-methylamide (137819-57-9)

Conditions	Yield
With 1,1'-carbonyldiimidazole 1.) CH2Cl2, RT, 1 h, 2.) CH2Cl2, 3 h; Yield given. Multistep reaction;

benzyl alcohol (100-51-6) + benzylecgonine (519-09-5) → RTI 52 (137718-48-0)

Conditions	Yield
With 1,1'-carbonyldiimidazole 1.) CH2Cl2, RT, 6 h, 2.) acetone, reflux, 3 h; Yield given. Multistep reaction;

benzylecgonine (519-09-5) → benzoylecgonine acid chloride (61194-36-3)

Conditions	Yield
With thionyl chloride
With thionyl chloride at 0℃; for 4h;
With oxalyl dichloride In dichloromethane for 1h; Ambient temperature;
With oxalyl dichloride for 0.25h; Substitution;

Upstream product

• 93-97-0 benzoic acid anhydride 
• 481-37-8 ecgonine 
• 50-36-2 Cocaine 
• 7732-18-5 water 
• 208037-81-4 tropidine 
• 208037-73-4 (2R,5S)-5-[1'-(2'-methoxycarbonyl)ethyl]proline methyl ester 
• 208038-13-5 (1R,2R,5S)-2-Phenylselanyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester 
• 208037-92-7 (1R,2S,5S)-2-Phenylselanyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid 1-chloro-ethyl ester 
• 208037-71-2 2-[(R)-1-Benzyl-5-tert-butoxycarbonyl-pyrrolidin-(2Z)-ylidene]-succinic acid dibenzyl ester 
• 74242-55-0 anhydroecgonine hydrochloride 
• 155748-84-8 RTI-128 
• 53-21-4 (-)-cocaine hydrochloride 
• 208037-91-6 (1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone p-tosylhydrazone 
• 208037-87-0 (1R,2R,3S,5S)-3-Benzoyloxy-2-carbamoyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester 

Downstream Products

• 50-36-2 Cocaine 
• 529-38-4 cocaethylene 
• 64091-46-9 RTI 13 
• 481-37-8 ecgonine 
• 41889-45-6 benzoylnorecgonine 
• 137718-56-0 3β-(benzoyloxy)-2β-(hydroxymethyl)-8-methyl-8-azabicyclo<3.2.1>octane 
• 61194-36-3 benzoylecgonine acid chloride 
• 65-85-0 benzoic acid 
• 109309-90-2 (S)-N-benzoylphenylalanine tert-butyl ester 
• 110-15-6 succinic acid 
• 481-38-9 (+)-pseudoecgonine 
• 137819-58-0 3β-(benzoyloxy)-2β-(acetoxymethyl)-8-methyl-8-azabicyclo<3.2.1>octane 
• 137819-55-7 RTI 14 
• 137819-56-8 RTI 15 

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Prediction of stability in pharmaceutical preparations. XX: Stability evaluation and bioanalysis of cocaine and benzoylecgonine by high-performance liquid chromatography

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