Fentanyl

• Formula: C₂₂H₂₈N₂O
• Molecular weight: 336.4705
• IUPAC Standard InChI: InChI=1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3 Copy

  
• IUPAC Standard InChIKey: PJMPHNIQZUBGLI-UHFFFAOYSA-N Copy
• CAS Registry Number: 437-38-7
• 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: Duragesic; Fentora; Sublimaze; Propanamide, N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]-; Propionanilide, N-(1-phenethyl-4-piperidyl)-; Fentanest; Fentanil; Phentanyl; R 4263; Sentonil; 1-Phenethyl-4-(N-Phenylpropionamido)piperidine; 1-Phenethyl-4-N-propionylanilinopiperidine; N-Phenethyl-4-(N-propionylanilino)piperidine; 1-(2-Phenylethyl)-4-(N-propananilido)piperidine; N-(1-Phenylethyl-4-piperidinyl)propionanilide; Matrifen; Sublimase; N-phenyl-N[1-(2-phenylethyl)-4-piperidinyl]propanamide (fentanyl)
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• Information on this page:
  • Phase change data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
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Phase change data

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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 vaporization

Enthalpy of fusion

Gas Chromatography

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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

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Gupta, Ganesan, et al., 2008
Gupta, Pradeep K.; Ganesan, Kumaran; Gutch, Pranav K.; Manral, Laxmi; Dubey, Devendra K., Vapor Pressure and Enthalpy of Vaporization of Fentanyl, J. Chem. Eng. Data, 2008, 53, 3, 841-845, https://doi.org/10.1021/je7005067 . [all data]

Roy and Flynn, 1988
Roy, Samir D.; Flynn, Gordon L., Pharmaceutical Research, 1988, 05, 9, 580-586, https://doi.org/10.1023/A:1015994030251 . [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]

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]

Manral, Gupta, et al., 2008
Manral, L.; Gupta, P.K.; Ganesan, K.; Malhotra, R.C., Gas chromatographic retention indices of fentanyl and its analogues, J. Chromatogr. Sci., 2008, 46, 7, 551-555, https://doi.org/10.1093/chromsci/46.6.551 . [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]

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

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• Symbols used in this document:
  

  ΔfusH	Enthalpy of fusion
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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