Norethindrone
- Formula: C20H26O
- Molecular weight: 282.4198
- IUPAC Standard InChI: InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15?,16?,17?,18?,19?,20-/m0/s1
- 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
- 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.
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
View scan of original (hardcopy) spectrum.
View image of digitized spectrum (can be printed in landscape orientation).
View spectrum image in SVG format.
Download spectrum in JCAMP-DX format.
| 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
- 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.