Norethynodrel

Modify Date: 2025-08-21 10:45:18

Norethynodrel Structure
Norethynodrel structure
 Common Name Norethynodrel
CAS Number 68-23-5 Molecular Weight 298.41900
Density 1.15g/cm3 Boiling Point 441.6ºC at 760 mmHg
Molecular Formula C20H26O2 Melting Point 169-170ºC
MSDS N/A Flash Point 188.2ºC

 Use of Norethynodrel


Norethynodrel (Enidre) is a 19-nortestosterone derivative to be used as a progestagen. Norethynodrel can be used for researching inhibition of ovulation[1].

 Names

Name (8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Synonym More Synonyms

 Norethynodrel Biological Activity

Description Norethynodrel (Enidre) is a 19-nortestosterone derivative to be used as a progestagen. Norethynodrel can be used for researching inhibition of ovulation[1].
Related Catalog
References

[1]. D F HAWKINS, et al. 2 - The Clinical Pharmacology of Oestrogens and Progestagens. 1979,

 Chemical & Physical Properties

Density 1.15g/cm3
Boiling Point 441.6ºC at 760 mmHg
Melting Point 169-170ºC
Molecular Formula C20H26O2
Molecular Weight 298.41900
Flash Point 188.2ºC
Exact Mass 298.19300
PSA 37.30000
LogP 3.63660
Index of Refraction 1.577
InChIKey ICTXHFFSOAJUMG-SLHNCBLASA-N
SMILES C#CC1(O)CCC2C3CCC4=C(CCC(=O)C4)C3CCC21C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RC8980000
CHEMICAL NAME :
19-Nor-17-alpha-pregn-5(10)-en-20-yn-3-one, 17-hydroxy-
CAS REGISTRY NUMBER :
68-23-5
BEILSTEIN REFERENCE NO. :
2389771
LAST UPDATED :
199612
DATA ITEMS CITED :
48
MOLECULAR FORMULA :
C20-H26-O2
MOLECULAR WEIGHT :
298.46
WISWESSER LINE NOTATION :
L E5 B666 OV MUTJ E1 F1UU1 QQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
54900 mg/kg/17W-C
TOXIC EFFECTS :
Behavioral - alteration of operant conditioning
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
60 mg/kg/17W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
135 mg/kg/83W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Reproductive - Tumorigenic effects - ovarian tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
120 mg/kg/78W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Reproductive - Tumorigenic effects - ovarian tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
119 mg/kg/77W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Tumorigenic - increased incidence of tumors in susceptible strains
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
8 mg/kg
SEX/DURATION :
female 16 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
8 mg/kg
SEX/DURATION :
female 20 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
480 mg/kg
SEX/DURATION :
female 26 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1 mg/kg
SEX/DURATION :
female 20 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
4200 ug/kg
SEX/DURATION :
female 21 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
25 mg/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - oogenesis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
10 mg/kg
SEX/DURATION :
female 2-3 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
10 mg/kg
SEX/DURATION :
female 2-3 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
100 mg/kg
SEX/DURATION :
female 17-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
150 mg/kg
SEX/DURATION :
female 10-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Newborn - stillbirth Reproductive - Effects on Newborn - live birth index (measured after birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
12 mg/kg
SEX/DURATION :
male 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2100 ug/kg
SEX/DURATION :
female 14 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Administration onto the skin
DOSE :
240 mg/kg
SEX/DURATION :
male 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
1400 ug/kg
SEX/DURATION :
female 14 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
3 mg/kg
SEX/DURATION :
male 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
66400 ng/kg
SEX/DURATION :
female 10-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
500 ug/kg
SEX/DURATION :
female 3 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
500 ug/kg
SEX/DURATION :
female 3 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
12600 ug/kg
SEX/DURATION :
female 3 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
60 mg/kg
SEX/DURATION :
female 17-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - breasts, lactation (prior to or during pregnancy)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
9600 ug/kg
SEX/DURATION :
female 48 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Maternal Effects - menstrual cycle changes or disorders
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
25 mg/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
80 mg/kg
SEX/DURATION :
female 8-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
450 ug/kg
SEX/DURATION :
female 8-10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - eye/ear
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
900 ug/kg
SEX/DURATION :
female 11-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
12 mg/kg
SEX/DURATION :
female 2 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
240 mg/kg
SEX/DURATION :
female 8-10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
50 mg/kg
SEX/DURATION :
female 10 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands Reproductive - Maternal Effects - other effects
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
50 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
4600 ug/kg
SEX/DURATION :
female 1-2 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
5 mg/kg
SEX/DURATION :
female 5 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
50 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
2400 ug/kg
SEX/DURATION :
female 3 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles)
TYPE OF TEST :
Mutation test systems - not otherwise specified

MUTATION DATA

TYPE OF TEST :
Cytogenetic analysis
TEST SYSTEM :
Mammal - cattle Cells - not otherwise specified
DOSE/DURATION :
100 ug/L
REFERENCE :
AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 120,390,1974 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 21,461,1979 TOXICOLOGY REVIEW ACEDAB Acta Endocrinologica, Supplementum (Copenhagen). (Periodica, Skolegade 12 E, DK-2500 Valby, Denmark) No.1- 1948- Volume(issue)/page/year: 185,169,1974 TOXICOLOGY REVIEW COGYAK Clinical Obstetrics and Gynecology. (Lippincott/Harper, Journal Fulfillment Dept., 2350 Virginia Ave., Hagerstown, MD 21740) V.1- 1958- Volume(issue)/page/year: 16(4),37,1973

 Safety Information

Hazard Codes T
Risk Phrases 45-61
Safety Phrases 53-22-36/37/39-45
WGK Germany 3
RTECS RC8980000

 Synthetic Route

N/A structure

N/A

CAS#:19357-36-9

~%

Norethynodrel Structure

Norethynodrel

CAS#:68-23-5

Literature: US2691028 , ;

 Precursor & DownStream

Precursor  0

DownStream  2

 NorethynodrelBioassay

View more

Name: Luminescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: mu-type opioid receptor isoform MOR-1 [Homo sapiens]
External Id: OPRM1-OPRD1_AG_LUMI_1536_1X%ACT PRUN
Name: Fluorescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_AG_FLUO8_1536_1X%ACT PRUN
Name: Dicer-mediated maturation of pre-microRNA
Source: Center for Chemical Genomics, University of Michigan
Target: N/A
External Id: TargetID_659_CEMA
Name: Fluorescence-based cell-based primary high throughput screening assay to identify pos...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_PAM_FLUO8_1536_1X%ACT PRUN
Name: Fluorescence polarization-based biochemical high throughput primary assay to identify...
Source: The Scripps Research Institute Molecular Screening Center
Target: RecName: Full=Sialate O-acetylesterase; AltName: Full=H-Lse; AltName: Full=Sialic acid-specific 9-O-acetylesterase; Flags: Precursor [Homo sapiens]
External Id: SIAE_INH_FP_1536_1X%INH PRUN
Name: MITF Measured in Cell-Based System Using Plate Reader - 2084-01_Activator_SinglePoint...
Source: Broad Institute
Target: N/A
External Id: 2084-01_Activator_SinglePoint_HTS_Activity
Name: Counterscreen for inhibitors of the fructose-bisphosphate aldolase (FBA) of M. tuberc...
Source: The Scripps Research Institute Molecular Screening Center
Target: N/A
External Id: GDH-TPI_INH_ABS_1536_1X%INH CSRUN
Name: qHTS Assay for Small Molecule Inhibitors of the Human hERG Channel Activity
Source: NCGC
External Id: HERG01
Name: Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Cac...
Source: ChEMBL
Target: Severe acute respiratory syndrome coronavirus 2
External Id: CHEMBL4303805
Name: Inhibition of cell viability relative to arbidol control (inhibition index > 1 indica...
Source: ChEMBL
Target: Severe acute respiratory syndrome coronavirus 2
External Id: CHEMBL4303819
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 Synonyms

SC-4642
Enovid
Norethynodrel [Progestins]
norethynodrel
Noretynodrel
Noretinodrel [DCIT]
19-Norethynodrel
Norethinodrel
Lynestrol
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