Acetaminophen
- Formula: C8H9NO2
- Molecular weight: 151.1626
- IUPAC Standard InChI: InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
- IUPAC Standard InChIKey: RZVAJINKPMORJF-UHFFFAOYSA-N
- CAS Registry Number: 103-90-2
- 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. - Other names: Acetamide, N-(4-hydroxyphenyl)-; Acetanilide, 4'-hydroxy-; p-(Acetylamino)phenol; p-Acetamidophenol; p-Hydroxyacetanilide; p-Hydroxyphenolacetamide; Abensanil; Acamol; Acetagesic; Acetalgin; Acetaminofen; Algotropyl; Alvedon; Amadil; Anaflon; Anelix; Apamid; Apamide; APAP; Ben-u-Ron; Bickie-mol; Calpol; Cetadol; Clixodyne; Dial-a-gesic; Dirox; Dymadon; Eneril; Febrilix; Febro-Gesic; Febrolin; Fendon; Finimal; Hedex; Homoolan; Lestemp; Liquagesic; Lonarid; Lyteca; Lyteca Syrup; Multin; N-(4-Hydroxyphenyl)acetamide; N-Acetyl-p-aminophenol; N-Acetyl-4-aminophenol; Napafen; Naprinol; Nobedon; NAPA; NAPAP; Pacemo; Panadol; Panets; Paracetamol; Paracetamole; Paracetanol; Parmol; Pedric; Phendon; Pyrinazine; Tabalgin; Temlo; Tempanal; Tempra; Tralgon; Tussapap; Tylenol; Valadol; Valgesic; 4-Acetamidophenol; 4-Acetaminophenol; 4-Hydroxyacetanilide; 4'-Hydroxyacetanilide; Accu-Tap; Acetamide, N-(p-hydroxyphenyl)-; Alpiny; Anapap; Anhiba; Apadon; Datril; Dimindol; Dularin; Dypap; Elixodyne; Febridol; Febrinol; G 1; Gelocatil; Injectapap; Janupap; Korum; Nealgyl; Nebs; Neotrend; NCI-C55801; Painex; Paracet; Paracetamol DC; Parapan; Phenol, p-acetamido-; Rivalgyl; Servigesic; St. Joseph Fever Reducer; SK-Apap; Tapar; Alpinyl; Doliprane; Enelfa; Exdol; 4-Hydroxyanilid kyseliny octove; Momentum; Panex; Panofen; Paracetamolo; Paraspen; Banesin; Phenaphen; Captin; Dafalgan; Disprol; Dolprone; Eu-Med; Ortensan; Paldesic; Panaleve; Panasorb; Parelan; Pasolind N; Salzone; 4-(Acetylamino)phenol; 4-(N-Acetylamino)phenol; Acenol; Biocetamol; Citramon P; Claratal; Cyclopam; Daga; Daphalgan; Minoset; N-Acetyl-4-hydroxyaniline; Pacemol; Panodil; Pinex; Pyral; Resfenol; Resprin; Vermidon; p-Acetoaminophen; N-(p-Hydroxyphenyl) acetamide; Actifed Plus (Salt/Mix); Anexsia (Salt/Mix); Aspirin-Free Anacin (Salt/Mix); Bayer Select Allergy-Sinus (Salt/Mix); Bayer Select Head Cold (Salt/Mix); Bayer Select Menstrual Multi-Symptom (Salt/Mix); Bayer Select Sinus Pain Relief (Salt/Mix); Contac Cough & Sore Throat Formula (Salt/Mix); Coricidin (Salt/Mix); Coricidin D (Salt/Mix); Coricidin Sinus (Salt/Mix); DHCplus (Salt/Mix); Darvocet-N (Salt/Mix); Demilets (Salt/Mix); Drixoral Cold & Flu (Salt/Mix); Drixoral Sinus (Salt/Mix); Empracet (Salt/Mix); Endecon (Salt/Mix); Hy-Phen (Salt/Mix); Hycomine Compound (Salt/Mix); Intensin (Salt/Mix); Liquiprin (Salt/Mix); Midol Maximum Strength (Salt/Mix); Midol PM Night Time Formula (Salt/Mix); Midol Regular Strength (Salt/Mix); Midol Teen Formula (Salt/Mix); Naldegesic (Salt/Mix); Ornex Severe Cold Formula (Salt/Mix); Percocet (Salt/Mix); Propacet (Salt/Mix); Quiet World (Salt/Mix); Rhinex D-Lay Tablets (Salt/Mix); Robitussin Night Relief (Salt/Mix); Sine-Aid, Maximum Strength (Salt/Mix); Sine-Off Sinus Medicine Caplets (Salt/Mix); Sinubid (Salt/Mix); St. Joseph Cold Tablets for Children (Salt/Mix); Sudafed Cold and Cough (Salt/Mix); Sudafed Severe Cold Formula (Salt/Mix); Sudafed Sinus (Salt/Mix); Supac (Salt/Mix); Talacen (Salt/Mix); TheraFlu (Salt/Mix); Triaminic Sore Throat Formula (Salt/Mix); Tylenol Allergy Sinus (Salt/Mix); Tylox (Salt/Mix); Vanquish (Salt/Mix); Vicodin (Salt/Mix); Zydone (Salt/Mix); Wygesic (Salt/Mix)
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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 by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
| IE (eV) | Method | Reference |
|---|---|---|
| 7.57 ± 0.02 | EI | Benezra and Bursey, 1972 |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C6H6NO+ | 13.52 ± 0.02 | CH3CO | EI | Benezra and Bursey, 1972 | |
| C6H7NO+ | 9.82 ± 0.02 | CH2=C=O | EI | Benezra and Bursey, 1972 |
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 | DB-5 | 220. | 1697. | Phillips, Logan, et al., 1990 | 15. m/0.25 mm/0.2 μm, He |
| Capillary | BP-1 | 200. | 1632. | Japp, Gill, et al., 1987 | 25. m/0.22 mm/0.25 μm, N2 |
| Capillary | BP-1 | 200. | 1643. | Japp, Gill, et al., 1987 | 25. m/0.53 mm/1. μm, N2 |
| Capillary | SPB-1 | 250. | 1650. | Lora-Tamayo, Rams, et al., 1986 | He; Column length: 25. m; Column diameter: 0.20 mm |
| Packed | OV-101 | 190. | 1664. | Möller, 1976 | N2, Chromosorb W; Column length: 2. m |
| Packed | OV-101 | 230. | 1678. | Möller, 1976 | N2, Chromosorb W; Column length: 2. m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SPB-1 | 1668. | 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 | 1631. | 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 | 5 % Phenyl methyl siloxane | 1694.0 | 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 | 1631. | Perrigo, Ballantyne, et al., 1984 | 15. m/0.25 mm/0.25 μm, He, 8. K/min, 280. C @ 5. min; Tstart: 120. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | BP-1 | 1636. | 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 |
|---|---|---|---|---|
| Capillary | BPX5 | 1703. | Boustie, Rapior, et al., 2005 | 25. m/0.20 mm/0.13 μm, He, 50. C @ 2. min, 3. K/min; Tend: 230. C |
| Capillary | BP-1 | 1631. | Stowell and Wilson, 1985 | 12. m/0.22 mm/0.25 μm, He, 8. K/min; Tstart: 120. C; Tend: 280. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | BP-1 | 1636. | 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) |
| Other | Methyl Silicone | 1687. | 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.
Benezra and Bursey, 1972
Benezra, S.A.; Bursey, M.M.,
Hydrogen bonding in mass spectral activated complexes. A correction,
J. Chem. Soc. Perkin Trans. 2, 1972, 11, 1537. [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]
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]
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]
Möller, 1976
Möller, M.R.,
Comparability of retention indices of polar substances at elevated temperatures,
Chromatographia, 1976, 9, 7, 311-314, https://doi.org/10.1007/BF02268832
. [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]
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]
Boustie, Rapior, et al., 2005
Boustie, J.; Rapior, S.; Fortin, H.; Tomas, S.; Bessiere, J.-M.,
Chemotaxonomic interest of volatile components in Lepista inversa and Lepista flaccida distinctions,
Cryptogamie, Mycologie, 2005, 26, 1, 1-4. [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]
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
- Symbols used in this document:
AE Appearance energy - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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