Norethynodrel

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Names

[ CAS No. ]:
68-23-5

[ Name ]:
Norethynodrel

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

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

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

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Norethindrone
19-Norpregn-4-en-20-yn-3-one,10,17-dihydroxy-, (17a)- (9CI)

Related Compounds

(2-Benzyl-6-chloro-5-phenylpyrimidin-4-yl)hydrazine
(4-Fluoro-1-methylpiperidin-4-yl)methanamine
2-(Oxolan-3-yl)-1-(pyridin-3-yl)ethan-1-one
2-(3-Methoxyphenyl)propan-1-ol
1-(2,5-Dichlorophenyl)-2-(oxolan-3-yl)ethan-1-one
Cis-6-methyl-3,4,4a,5,7,7a-hexahydro-2H-pyrrolo[3,4-b][1,4]oxazine
2-methoxy-5-[[4-(trifluoromethyl)-2-pyridyl]oxy]aniline
1-(5-(Benzyloxy)pyrimidin-2-yl)ethan-1-ol
5-[[3-chloro-5-(trifluoromethyl)-2-pyridyl]oxy]-2-methoxy-aniline
(5-Bromopyrimidin-2-yl)methyl pivalate

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