Amphetamine
- Formula: C9H13N
- Molecular weight: 135.2062
- IUPAC Standard InChIKey: KWTSXDURSIMDCE-UHFFFAOYSA-N
- CAS Registry Number: 300-62-9
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Stereoisomers:
- Other names: Adderal; Dexedrine; Benzeneethanamine, α-methyl-, (.+/-.)-; Phenethylamine, α-methyl-, (.+/-.)-; β-Aminopropylbenzene; (.+/-.)-α-Methylphenethylamine; (.+/-.)-α-Methylphenylethylamine; (.+/-.)-β-Phenylisopropylamine; (.+/-.)-Desoxynorephedrine; DL-α-Methylphenethylamine; Actedron; Adipan; Allodene; Anorexine; Benzebar; Benzedrine; Benzolone; Elastonon; Finam; Isoamyne; Isomyn; Mecodrin; Norephedrane; Novydrine; Oktedrin; Ortedrine; Percomon; Phenamine; Phenedrine; Phenylisopropylamine; Profamina; Propisamine; Raphetamine; Rhinalator; Simpatedrin; Simpatina; Sympamine; Sympatedrine; Weckamine; 1-Phenyl-2-aminopropane; Benzeneethanamine, α-methyl-, (±)-; dl-Amphetamine; Anorexide; (.+/-.)-Benzedrine; dl-Benzedrine; racemic-Desoxynor-ephedrine; Fenylo-izopropylaminyl; Isoamycin; α-Methylbenzeneethaneamine; Norephedrine, deoxy-; dl-1-Phenyl-2-aminopropane; Psychedrine; (±)-Desoxynorephedrine; (±)-β-Phenylisopropylamine; (±)-α-Methylphenethylamine; (±)-α-Methylphenylethylamine; Phenethylamine, α-methyl-, (±)-; 1-Methyl-2-phenylethylamine; Benzeneethanamine, α-methyl-; 1-Phenyl-2-propanamine; 1-Phenyl-2-propylamine; 3-Phenyl-2-propylamine; Amfetamine; Desoxynorephedrine; Fenopromin; Obesine; α-Methylbenzeneethanamine; 60-13-9; (.+/-.)-Amphetamine; Fenamin; Euphodyn; Fabedrine; Noclon; Oraldrina; Ortenal; Vapedrine; Zedrine; Stimulan; Sympametin; 96332-84-2; 60-15-1; 17108-96-2
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase ion energetics 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 as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.99 ± 0.06 | PE | Domelsmith and Houk, 1978 | Vertical value; LLK |
8.91 ± 0.14 | PE | Domelsmith, Munchausen, et al., 1977 | Vertical value; LLK |
Gas Chromatography
Go To: Top, Gas phase ion energetics 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 | 130. | 1119. | Japp, Gill, et al., 1987 | 25. m/0.22 mm/0.25 μm, N2 |
Capillary | BP-1 | 130. | 1122. | Japp, Gill, et al., 1987 | 25. m/0.53 mm/1. μm, N2 |
Packed | SE-30 | 140. | 1115. | Musumarra, Scarlata, et al., 1987 | N2, 1% se-30 on Anachrom ABS(80-100mesh); Column length: 2. m |
Packed | OV-101 | 120. | 1117. | Huber, Kenndler, et al., 1979 | N2; Column length: 2. m |
Packed | Apiezon L | 120. | 1132. | Huber, Kenndler, et al., 1979 | |
Packed | Apiezon L | 120. | 1132. | Donike and Stratmann, 1976 | Chromosorb W |
Kovats' RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-30 | 1105. | 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 | OV-101 | 1130. | McLinden and Stenhouse, 1979 | N2, Chromosorb W; Column length: 2. m; Program: not specified |
Packed | SE-30 | 1110. | Moffat, Stead, et al., 1974 | Column length: 2. m; Program: not specified |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | PEG-20M | 120. | 1581. | Huber, Kenndler, et al., 1979 | N2 |
Packed | PEG-20M | 120. | 1581. | Donike and Stratmann, 1976 | Chromosorb W |
Kovats' RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | Carbowax 20M | 1587. | Moffat, Stead, et al., 1974 | Column length: 1. m; Program: not specified |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | VF-5MS | 1136.2 | Tretyakov, 2014 | 30. m/0.25 mm/0.25 μm, He; Tstart: 60. C; Tend: 270. C |
Capillary | SPB-1 | 1123. | Christ, Noomano, et al., 1988 | 30. m/0.75 mm/1.0 μm, He, 10. K/min, 280. C @ 12. min; Tstart: 160. C |
Packed | Methyl Silicone | 1108. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
Packed | Methyl Silicone | 1110. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
Packed | Methyl Silicone | 1100. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
Packed | Methyl Silicone | 1105. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
Packed | Methyl Silicone | 1105. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
Packed | Methyl Silicone | 1100. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
Packed | Methyl Silicone | 1100. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
Packed | Methyl Silicone | 1105. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
Packed | Methyl Silicone | 1120. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
Packed | Methyl Silicone | 1110. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
Packed | Methyl Silicone | 1110. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
Packed | Methyl Silicone | 1110. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
Packed | Methyl Silicone | 1110. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
Packed | Methyl Silicone | 1112. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
Packed | Methyl Silicone | 1112. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
Packed | Methyl Silicone | 1115. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
Packed | Methyl Silicone | 1117. | Bogusz, Wijsbeek, et al., 1985 | 120. C @ 4. min, 7. K/min, 290. C @ 10. min |
Capillary | DB-1 | 1118. | 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 | DB-1 | 1118. | 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 | 1111. | 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 | 1120. | 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 | Methyl Silicone | 1125. | University Centre for Pharmacy, 2003 | 12.5 m/0.32 mm/1.5 μm; Program: 135C(4min) => 13C/min => 200C => 8C/min => 240C => 6C/min => 312C (6min) |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 1123. | MHA, 9999 | Nitrogen, Chromosorb G AW DMCS (80-100 mesh); Column length: 2. m; Tstart: 100. C; Tend: 300. C |
Capillary | Polymethylsiloxane, (PMS-20000) | 1125. | 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-1 | 1123. | Yashiki, Kojima, et al., 1995 | 30. m/0.25 mm/0.25 μm, He, 40. C @ 2. min, 25. K/min, 250. C @ 5. min |
Capillary | DB-5 | 1110. | Phillips, Logan, et al., 1990 | 15. m/0.25 mm/0.2 μm, He, 10. K/min; Tstart: 100. C; Tend: 150. C |
Packed | OV-1 | 1145. | 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 | 1120. | 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 | 1118. | 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 | 1118. | 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 | 5 % Phenyl methyl siloxane | 1129. | Grigoriev and Savchuk, 2010 | 25. m/0.20 mm/0.33 μm; Program: 50 0C (0.5 min) 99 0C/min -> 100 0C (1 min) 15 0C/min -> 280 0C (20 min) |
Capillary | 5 % Phenyl methyl siloxane | 1135. | Grigoriev and Savchuk, 2010 | 25. m/0.20 mm/0.33 μm; Program: 50 0C (0.5 min) 99 0C/min -> 100 0C (1 min) 15 0C/min -> 280 0C (20 min) |
Capillary | Polymethylsiloxane, (PMS-20000) | 1126. | Gambaro, Saligari, et al., 1997 | 12. m/0.20 mm/0.33 μm, He; Program: not specified |
Capillary | Polydimethyl siloxanes | 1118. | Zenkevich and Chupalov, 1996 | Program: not specified |
Other | Methyl Silicone | 1123. | Ardrey and Moffat, 1981 | Program: not specified |
References
Go To: Top, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Domelsmith and Houk, 1978
Domelsmith, L.N.; Houk, K.N.,
Photoelectron spectroscopic studies of hallucinogens: The use of ionization potentials in QSAR,
NIDA Res. Monogr., 1978, 22, 423. [all data]
Domelsmith, Munchausen, et al., 1977
Domelsmith, L.N.; Munchausen, L.L.; Houk, K.N.,
Photoelectron spectra of psychotropic drugs. 1. Phenethylamines, tryptamines, and LSD,
J. Am. Chem. Soc., 1977, 99, 4311. [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]
Huber, Kenndler, et al., 1979
Huber, J.F.K.; Kenndler, E.; Reich, G.,
Quantitation of the Information Content of Multi-Dimensional Gas Chromatography and Low- Resolution Mass Spectrometry in the Identification of Doping Drugs,
J. Chromatogr., 1979, 172, 1, 15-30, https://doi.org/10.1016/S0021-9673(00)90941-5
. [all data]
Donike and Stratmann, 1976
Donike, M.; Stratmann, D.,
Gas-chromatographische identifizierung von stimulantien der phenyläthylaminreihe mit hilfe der retnetions-indices,
Z. Anal. Chem., 1976, 279, 2, 129-131, https://doi.org/10.1007/BF00440798
. [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]
McLinden and Stenhouse, 1979
McLinden, V.J.; Stenhouse, A.M.,
A chromatography system for drug identification,
Forensic Sci. Int., 1979, 13, 71-79, https://doi.org/10.1016/0379-0738(79)90265-2
. [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]
Tretyakov, 2014
Tretyakov, K.V.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [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]
Bogusz, Wijsbeek, et al., 1985
Bogusz, M.; Wijsbeek, J.; Franke, J.P.; de Zeeuw, R.A.; Gierz, J.,
Impact of biological matrix, drug concentration, and method of isolation on detectability and variability of retention index values in gas chromatography,
J. Anal. Toxicol., 1985, 9, 2, 49-54, https://doi.org/10.1093/jat/9.2.49
. [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]
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]
University Centre for Pharmacy, 2003
University Centre for Pharmacy, University of Groninger,
Systematic toxicological analysis, 2003, retrieved from http://www.farm.rug.nl/InterACT/wijopnet.html. [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]
Yashiki, Kojima, et al., 1995
Yashiki, M.; Kojima, T.; Miyazaki, T.; Nagasawa, N.; Iwasaki, Y.; Hara, K.,
Detection of amphetamines in urine using head space-solid phase microextraction and chemical ionization selected ion monitoring,
Forensic Sci. Int., 1995, 76, 3, 169-177, https://doi.org/10.1016/0379-0738(95)01819-0
. [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]
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]
Grigoriev and Savchuk, 2010
Grigoriev, A.M.; Savchuk, S.A.,
Correlation of the parameters of screening libraries of the gas-chromatographic retention data,
Rus. J. Anal. Chem. (Engl. Transl.), 2010, 65, 4, 388-397. [all data]
Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A.,
New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments,
Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [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, Gas phase ion energetics data, Gas Chromatography, References
- Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.