Norethindrone
- Formula: C20H26O
- Molecular weight: 282.4198
- IUPAC Standard InChIKey: VIKNJXKGJWUCNN-BROHZWGRSA-N
- CAS Registry Number: 68-22-4
- 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: 19-Norpregn-4-en-20-yn-3-one, 17-hydroxy-, (17α)-; 19-Nor-17α-pregn-4-en-20-yn-3-one, 17-hydroxy-; Anovule; Conludaf; Ethinylnortestosterone; Ethynylnortestosterone; Gestest; Micronett; Micronor; Micronovum; Mini-Pe; Noralutin; Norethisteron; Norethisterone; Norethynodrone; Norfor; Norgestin; Norluten; Norlutin; Norluton; Norpregneninolone; NSC-9564; Primolut N; Proluteasi; SC 4640; 17α-Ethinyl-19-Nortestosterone; 17α-Ethynyl-19-nortestosterone; 19-Nor-17α-ethynyltestosterone; 19-Nortestosterone, 17-ethynyl-; 4-Estren-17α-ethynyl-17β-ol-3-one; Anhydrohydroxynorprogesterone; Conludag; Estr-4-en-3-one, 17α-ethynyl-17-hydroxy-; Minovlar; Nor-Q.D.; Noresthisterone; Norethyndron; Norpregneninlone; Utovlar; 17α-Ethinyl-17β-hydroxy-δ(sup:4)-estren-3-one; 17α-Ethinylestra-4-en-17β-ol-3-one; 17α-Ethynyl-17β-hydroxy-19-norandrost-4-en-3-one; 17α-Ethynyl-17β-hydroxyestr-4-en-3-one; 17α-Ethynyl-17-hydroxy-4-estren-3-one; 17α-Ethynyl-19-nor-4-androsten-17β-ol-3-one; 17α-Ethynyl-19-norandrost-4-en-17β-ol-3-one; 17α-Ethynyl-4-estren-17-ol-3-one; 17β-Hydroxy-19-norpregn-4-en-20-yn-3-one; 17-Hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one; 19-nor-17α-Ethynyl-17β-hydroxy-4-androsten-3-one; 19-nor-17α-Ethynylandrosten-17β-ol-3-one; 19-Norethisterone; ENT; Ethinyl-19-nortestosterone; 17-α-Ethynyl-17-β-hydroxy-4-estren-3-one; (17-α)-17-Hydroxy-19-norpregn-4-en-20-yn-3-one; 17-Hydroxy-17-α-19-norpregn-4-en-20-yn-3-one; NET; 19-Nor-ethindrone; 19-Norethinyltestosterone; 19-Nor-17-ethinyltestosterone; 17-α-19-Norpregn-4-en-20-yn-3-one, 17-hydroxy-; Menzol; Mini-pill; Nor-QD; Norcolut; Utovlan; 17α-Ethynyl-17-hydroxyest-4-en-3-one; 19-Norandrost-4-en-3-one, 17α-ethynyl-17β-hydroxy-; Normapause; 17α-Ethynyl-3-oxo-4-estren-17β-ol; 17β-Hydroxy-17α-ethynylestr-4-en-3-one; 17-Ethinyl-19-nor-testosterone
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Phase change data
Go To: Top, IR Spectrum, 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DH - Eugene S. Domalski and Elizabeth D. Hearing
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 479. | K | N/A | Lewis and Enever, 1979 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 481. | K | N/A | Grady, Hays, et al., 1973 | Uncertainty assigned by TRC = 1. K; TRC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
39.600 | 479. | Lewis and Enever, 1979, 2 | DH |
39.6 | 479. | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
82.7 | 479. | Lewis and Enever, 1979, 2 | DH |
IR Spectrum
Go To: Top, Phase change data, 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: Coblentz Society, Inc.
Condensed Phase Spectrum
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | COBLENTZ SOC. Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Source reference | COBLENTZ NO. 05134 |
Date | 1962/07/27 |
Name(s) | 17-ethynyl-17-hydroxyestr-4-en-3-one |
State | SOLID (KBr DISC) VS KBr |
Instrument | PERKIN-ELMER 21 (GRATING) |
Instrument parameters | FILTER AT ABOUT 10 MICRONS |
Resolution | 2 |
Sampling procedure | TRANSMISSION |
Data processing | DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY |
Gas Chromatography
Go To: Top, Phase change data, IR Spectrum, 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
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Other | Methyl Silicone | 2625. | Ardrey and Moffat, 1981 | Program: not specified |
References
Go To: Top, Phase change data, IR Spectrum, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Lewis and Enever, 1979
Lewis, G.A.; Enever, R.P.,
Solution thermodynamics of some potentially long-acting norethindrone derivatives. I. Variation of enthalpies and entropies of fusion with temp.,
Int. J. Pharm., 1979, 22, 203. [all data]
Grady, Hays, et al., 1973
Grady, L.T.; Hays, S.E.; King, R.H.; Klein, H.R.; Mader, W.J.; Wyatt, D.K.; Zimmere, R.O.,
Drug purity profiles,
J. Pharm. Sci., 1973, 62, 459. [all data]
Lewis and Enever, 1979, 2
Lewis, G.A.; Enever, R.P.,
Solution thermodynamics of some potentially long-acting norethindrone derivatives. I. Variation of enthalpies and entropies of fusion with temperature,
Int. J. Pharm., 1979, 22, 203-214. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [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, IR Spectrum, Gas Chromatography, References
- Symbols used in this document:
Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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