Cocaine
- Formula: C17H21NO4
- Molecular weight: 303.3529
- IUPAC Standard InChI: InChI=1S/C17H21NO4/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12?,13?,14-,15+/m0/s1
- IUPAC Standard InChIKey: ZPUCINDJVBIVPJ-PFSRBDOWSA-N
- CAS Registry Number: 50-36-2
- Chemical structure:
This structure is also available as a 2d Mol file - Stereoisomers:
- Other names: 8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, [1R-(exo,exo)]-; 1αH,5αH-Tropane-2β-carboxylic acid, 3β-hydroxy-, methyl ester, benzoate (ester); L-Cocaine; Benzoylmethylecgonine; Ecgonine, methyl ester, benzoate (ester); Neurocaine; 2β-Carbomethoxy-3β-benzoyloxytropane; 2β-Tropanecarboxylic acid, 3β-hydroxy-, methyl ester, benzoate (ester); 1-α-H,5-α-H-Tropane-2-β-carboxylic acid, 3-β-hydroxy-, methyl ester, benzoate; Bernice; Bernies; Burese; Cecil; Cholly; Coke; Corine; Ecgonine, methyl ester, benzoate; Eritroxilina; Erytroxylin; Girl; Gold dust; Happy dust; Kokain; Kokan; Kokayeen; Methyl 3-β-hydroxy-1-α-H,5-α-H-tropane-2-β-carboxylate benzoate; Star dust; 2-β-Tropanecarboxylic acid, 3-β-hydroxy-, methyl ester, benzoate; 3-Tropanylbenzoate-2-carboxylic acid methyl ester; Methyl 3β-hydroxy-1αH,5αH-tropane-2β-carboxylate benzoate (ester); 3β-Hydroxy-2β-tropanecarboxylic acid methyl ester, benzoate; 2-Methyl-3β-hydroxy-1αH,5αH-tropane-2β-carboxylate benzoate (ester); (1R,2R,3S,5S)-2-Methoxycarbonyltropan-3-yl benzoate
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Phase change data
Go To: Top, Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: William E. Acree, Jr., James S. Chickos
Enthalpy of sublimation
| ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 112.3 ± 2.8 | 304. | GS | Lawrence, Elias, et al., 1984 | Based on data from 294. to 314. K. |
Gas Chromatography
Go To: Top, Phase change data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | BP-1 | 200. | 2177. | Japp, Gill, et al., 1987 | 25. m/0.22 mm/0.25 μm, N2 |
| Capillary | BP-1 | 200. | 2184. | Japp, Gill, et al., 1987 | 25. m/0.53 mm/1. μm, N2 |
| Packed | SE-30 | 220. | 2185. | Musumarra, Scarlata, et al., 1987 | N2, 1% se-30 on Anachrom ABS(80-100mesh); Column length: 2. m |
| Capillary | SPB-1 | 250. | 2233. | Lora-Tamayo, Rams, et al., 1986 | He; Column length: 25. m; Column diameter: 0.20 mm |
| Packed | SE-30 | 220. | 2200. | Mari, Bertol, et al., 1984 | Anakrom ABS; Column length: 2. m |
| Packed | SE-30 | 260. | 2235. | Mari, Bertol, et al., 1984 | Anakrom ABS; Column length: 2. m |
| Packed | OV-1 | 200. | 2180. | Berninger and Möller, 1977 |
Kovats' RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SE-30 | 2191. | Schepers, Wijsbeek, et al., 1982 | 25. m/0.49 mm/1.14 μm, 100. C @ 2. min, 8. K/min, 275. C @ 15. min |
Kovats' RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Packed | SE-30 | 2180. | Moffat, Stead, et al., 1974 | Column length: 2. m; Program: not specified |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SPB-1 | 2186. | Christ, Noomano, et al., 1988 | 30. m/0.75 mm/1.0 μm, He, 10. K/min, 280. C @ 12. min; Tstart: 160. C |
| Capillary | DB-1 | 2175. | Perrigo, Peel, et al., 1985 | 15. m/0.32 mm/0.25 μm, He, 8. K/min, 280. C @ 5. min; Tstart: 120. C |
| Capillary | Methyl Silicone | 2176.0 | Newton and Foery, 1984 | 12. m/0.2 mm/0.33 μm, He, 50. C @ 1. min, 20. K/min, 300. C @ 3. min |
| Capillary | DB-1 | 2175. | Perrigo, Ballantyne, et al., 1984 | 15. m/0.25 mm/0.25 μm, He, 8. K/min, 280. C @ 5. min; Tstart: 120. C |
| Capillary | SE-30 | 2161. | Anderson and Stafford, 1983 | 15. m/0.25 mm/0.25 μm, He, 5. K/min; Tstart: 100. C; Tend: 295. C |
| Packed | SE-30 | 2190. | Perrigo and Peel, 1981 | N2, Chromosorb W, 130. C @ 2. min, 8. K/min, 290. C @ 8. min; Column length: 1.8 m |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | BP-1 | 2179. | Stowell and Wilson, 1987 | 12. m/0.22 mm/0.25 μm, He; Program: 120C => 8C/min => 270C => 25C/min => 300C |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Packed | Polydimethyl siloxane | 2187. | MHA, 9999 | Nitrogen; Column length: 2. m; Tstart: 100. C; Tend: 300. C |
| Packed | SE-30 | 2187. | MHA, 9999 | Nitrogen, Chromosorb G AW DMCS (80-100 mesh); Column length: 2. m; Tstart: 100. C; Tend: 300. C |
| Capillary | Polymethylsiloxane, (PMS-20000) | 2187. | Gambaro, Saligari, et al., 1997 | 12. m/0.20 mm/0.33 μm, He, 10. K/min; Tstart: 160. C; Tend: 300. C |
| Capillary | DB-5 | 2163. | Phillips, Logan, et al., 1990 | 15. m/0.25 mm/0.2 μm, He, 10. K/min; Tstart: 185. C; Tend: 270. C |
| Capillary | BP-1 | 2161. | Stowell and Wilson, 1985 | 12. m/0.22 mm/0.25 μm, He, 5. K/min; Tstart: 100. C; Tend: 295. C |
| Capillary | BP-1 | 2175. | Stowell and Wilson, 1985 | 12. m/0.22 mm/0.25 μm, He, 8. K/min; Tstart: 120. C; Tend: 280. C |
| Capillary | BP-1 | 2176. | Stowell and Wilson, 1985 | 12. m/0.22 mm/0.25 μm, He, 20. K/min; Tstart: 50. C; Tend: 300. C |
| Packed | OV-1 | 2190. | Marozzi, Gambaro, et al., 1982 | Gas Chrom P, 2.5 K/min; Column length: 2. m; Tstart: 120. C; Tend: 200. C |
| Packed | SE-30 | 2187. | Peel and Perrigo, 1976 | Nitrogen, Chromosorb W AW DMS (80-100 mesh), 130. C @ 2. min, 8. K/min, 290. C @ 8. min; Column length: 2. m |
| Packed | SE-30 | 2187. | Peel and Perrigo, 1975 | N2, Chromosorb W AW DMS, 130. C @ 2. min, 8. K/min, 290. C @ 8. min; Column length: 2. m |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Polymethylsiloxane, (PMS-20000) | 2182. | Gambaro, Saligari, et al., 1997 | 12. m/0.20 mm/0.33 μm, He; Program: not specified |
| Capillary | BP-1 | 2179. | Stowell and Wilson, 1985 | 12. m/0.22 mm/0.25 μm, He; Program: 120 0X 8 0C/min -> 270 0C 25 0C/min -> 300 0C (5 min) |
| Capillary | BP-1 | 2179. | Stowell and Wilson, 1985 | 12. m/0.22 mm/0.25 μm, He; Program: 120 0X 8 0C/min -> 270 0C 25 0C/min -> 300 0C (5 min) |
| Capillary | BP-1 | 2179. | Stowell and Wilson, 1985 | 12. m/0.22 mm/0.25 μm, He; Program: 120 0X 8 0C/min -> 270 0C 25 0C/min -> 300 0C (5 min) |
| Capillary | BP-1 | 2178. | Stowell and Wilson, 1985 | 12. m/0.22 mm/0.25 μm, He; Program: not specified |
| Capillary | BP-1 | 2178. | Stowell and Wilson, 1985 | 12. m/0.22 mm/0.25 μm, He; Program: not specified |
| Capillary | BP-1 | 2180. | Stowell and Wilson, 1985 | 12. m/0.22 mm/0.25 μm, He; Program: not specified |
| Capillary | BP-1 | 2182. | Stowell and Wilson, 1985 | 12. m/0.22 mm/0.25 μm, He; Program: not specified |
| Capillary | BP-1 | 2179. | Stowell and Wilson, 1985 | 12. m/0.22 mm/0.25 μm, He; Program: 120 0X 8 0C/min -> 270 0C 25 0C/min -> 300 0C (5 min) |
| Capillary | BP-1 | 2180. | Stowell and Wilson, 1985 | 12. m/0.22 mm/0.25 μm, He; Program: not specified |
| Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 2233. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
| Other | Methyl Silicone | 2187. | Ardrey and Moffat, 1981 | Program: not specified |
References
Go To: Top, Phase change data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Lawrence, Elias, et al., 1984
Lawrence, A.H.; Elias, L.; Authier-Martin, M.,
Determination of amphetamine, cocaine, and heroin vapour pressures using a dynamic gas blending system and gas chromatographic analysis,
Can. J. Chem., 1984, 62, 10, 1886-1888, https://doi.org/10.1139/v84-323
. [all data]
Japp, Gill, et al., 1987
Japp, M.; Gill, R.; Osselton, M.D.,
Comparison of drug retention indices determined on packed, wide bore capillary and narrow bore capillary columns,
J. Forensic Sci., 1987, 32, 6, 1574-1586. [all data]
Musumarra, Scarlata, et al., 1987
Musumarra, G.; Scarlata, G.; Romano, G.; Cappello, G.; Clementi, S.; Giulietti, G.,
Qualitative organic analysis. Part 2. Identification of drugs by principal components analysis of standardized TLC data in four eluent systems and of retention indices on SE 30,
J. Anal. Toxicol., 1987, 11, 4, 154-163, https://doi.org/10.1093/jat/11.4.154
. [all data]
Lora-Tamayo, Rams, et al., 1986
Lora-Tamayo, C.; Rams, M.A.; Chacon, J.M.R.,
Gas Chromatographic Data for 187 Nitrogen- or Phosphorus-Containing Drugs and Metabolites of Toxicological Interest Analysed on Methyl Silicone Capillary Columns,
J. Chromatogr., 1986, 374, 73-85, https://doi.org/10.1016/S0378-4347(00)83254-5
. [all data]
Mari, Bertol, et al., 1984
Mari, F.; Bertol, E.; Tosti, M.,
Benzoyltropeine, an unusual substance in street heroin samples,
Bull. Narc., 1984, 1, 59-67. [all data]
Berninger and Möller, 1977
Berninger, H.; Möller, M.R.,
Retentionsindices zur gaschromatographischen Identifizierung von Arzneimitteln,
Arch. Toxicol., 1977, 37, 4, 295-305, https://doi.org/10.1007/BF00330821
. [all data]
Schepers, Wijsbeek, et al., 1982
Schepers, P.; Wijsbeek, J.; Franke, J.P.; de Zeeuw, R.A.,
Applicability of capillary gas chromatography to substance identification in toxicology by means of retention indices,
J. Forensic Sci., 1982, 27, 1, 49-60. [all data]
Moffat, Stead, et al., 1974
Moffat, A.C.; Stead, A.H.; Smalldon, K.W.,
Optimum use of paper, thin-layer and gas-liquid chromatography for the identification of basic drugs. III. Gas-liquid chromatography,
J. Chromatogr., 1974, 90, 1, 19-33, https://doi.org/10.1016/S0021-9673(01)94770-3
. [all data]
Christ, Noomano, et al., 1988
Christ, D.W.; Noomano, P.; Rosas, M.; Rhone, D.,
Retention indices by wide-bore capillary gas chromatography with nitrogen-phosphorus detection,
J. Anal. Toxicol., 1988, 12, 2, 84-88, https://doi.org/10.1093/jat/12.2.84
. [all data]
Perrigo, Peel, et al., 1985
Perrigo, B.J.; Peel, H.W.; Ballantyne, D.J.,
Use of Dual-Column Fused-Silica Capillary Gas Chromatography in Combination with Detector Response Factors for Analytical Toxicology.,
J. Chromatogr., 1985, 341, 81-88, https://doi.org/10.1016/S0378-4347(00)84011-6
. [all data]
Newton and Foery, 1984
Newton, B.; Foery, R.F.,
Retention indices and dual capillary gas chromatography for rapid identification of sedative hypnotic drugs in emergency toxicology,
J. Anal. Toxicol., 1984, 8, 3, 129-134, https://doi.org/10.1093/jat/8.3.129
. [all data]
Perrigo, Ballantyne, et al., 1984
Perrigo, B.J.; Ballantyne, D.J.; Peel, H.W.,
Condierations in developing a data base for drugs on a DBI capillary column,
J. Can. Soc. Forensic Sci., 1984, 17, 2, 41-49, https://doi.org/10.1080/00085030.1984.10757360
. [all data]
Anderson and Stafford, 1983
Anderson, W.H.; Stafford, D.T.,
Applications of capillary gas chromatography in routine toxicological analyses,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1983, 6, 5, 247-254, https://doi.org/10.1002/jhrc.1240060506
. [all data]
Perrigo and Peel, 1981
Perrigo, B.J.; Peel, H.W.,
The use of retention indices and temperature-programmed gas chromatography in analytical toxicology,
J. Chromatogr. Sci., 1981, 19, 5, 219-226, https://doi.org/10.1093/chromsci/19.5.219
. [all data]
Stowell and Wilson, 1987
Stowell, A.; Wilson, L.W.,
A simple approach to the interlaboratory transfer of drug retention indices determined by temperature programmed capillary gas chromatography,
J. Forensic Sci., 1987, 32, 5, 1214-1220. [all data]
MHA, 9999
MHA, Directorate of ForensicScience.,
Forensic Toxicology, 9999. [all data]
Gambaro, Saligari, et al., 1997
Gambaro, V.; Saligari, E.; Froldi, R.; Bianchi, L.,
Analysis of street drugs by means of HRGC,
Bollettino Chimico Farmaceutica, 1997, 36, 4, 359-367. [all data]
Phillips, Logan, et al., 1990
Phillips, A.M.; Logan, B.K.; Stafford, D.T.,
Further applications for capillary gas chromatography in routine quantitative toxicological analyses,
J. Hi. Res. Chromatogr., 1990, 13, 11, 754-758, https://doi.org/10.1002/jhrc.1240131106
. [all data]
Stowell and Wilson, 1985
Stowell, A.; Wilson, L.,
Use of retention indices in drug screening by capillary gas chromatography, Rep. # CD 2362, Department of Scientific and Industrial Reseach, Chemistry Division, Lower Hutt, NZ, 1985, 32. [all data]
Marozzi, Gambaro, et al., 1982
Marozzi, E.; Gambaro, V.; Saligari, E.; Mariani, R.; Lodi, F.,
Use of the retention index in gas chromatographic studies of drugs,
J. Anal. Toxicol., 1982, 6, 4, 185-192, https://doi.org/10.1093/jat/6.4.185
. [all data]
Peel and Perrigo, 1976
Peel, H.W.; Perrigo, B.,
A practical gas chromatographic screening procedure for toxicological analysis,
Can. Soc. Forens. Sci. J., 1976, 9, 2, 69-74, https://doi.org/10.1080/00085030.1976.10757247
. [all data]
Peel and Perrigo, 1975
Peel, H.W.; Perrigo, B.,
A practical gas chromatographic screening procedure for toxicological analysis,
Can.Soc.Forens.Sci.J., 1975, 9, 2, 69-74, https://doi.org/10.1080/00085030.1976.10757247
. [all data]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]
Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C.,
Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase,
J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1
. [all data]
Notes
Go To: Top, Phase change data, Gas Chromatography, References
- Symbols used in this document:
ΔsubH Enthalpy of sublimation - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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