(-)-N,N-DIMETHYLEPHEDRINIUMBROMIDE
Names
[ CAS No. ]:
797-64-8
[ Name ]:
(-)-N,N-DIMETHYLEPHEDRINIUMBROMIDE
[Synonym ]:
(8alpha,9beta,10alpha,13alpha,14beta)-17alpha-ethynyl-17beta-hydroxy-18a-homoestr-4-en-3-one
Dextronorgestrel
(8S,9R,10S,13R,14R,17S)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
(+)-Norgestrel
Norgestrel (+)-form
L-Norgestrel
Chemical & Physical Properties
[ Molecular Formula ]:
C21H28O2
[ Molecular Weight ]:
312.44600
[ Exact Mass ]:
312.20900
[ PSA ]:
37.30000
[ LogP ]:
3.88260
[ Index of Refraction ]:
1.571
Toxicological Information
CHEMICAL IDENTIFICATION
- RTECS NUMBER :
- JF8259000
- CHEMICAL NAME :
- 18,19-Dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, (8-alpha,9-beta,10-alpha,13-alpha, 14-beta)-
- CAS REGISTRY NUMBER :
- 797-64-8
- LAST UPDATED :
- 199606
- DATA ITEMS CITED :
- 28
- MOLECULAR FORMULA :
- C21-H28-O2
- MOLECULAR WEIGHT :
- 312.49
- WISWESSER LINE NOTATION :
- L E5 B666 OV MUTJ E2 FQ F1UU1
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >5 gm/kg
- TOXIC EFFECTS :
- Nutritional and Gross Metabolic - weight loss or decreased weight gain
- REFERENCE :
- OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 41,295,1991
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 1470 mg/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - altered sleep time (including change in righting reflex) Behavioral - ataxia
- REFERENCE :
- OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 41,295,1991
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >5 gm/kg
- TOXIC EFFECTS :
- Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - weight loss or decreased weight gain
- REFERENCE :
- OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 41,295,1991
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- >5 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 41,295,1991
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 2990 mg/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - lacrimation Behavioral - ataxia Skin and Appendages - hair
- REFERENCE :
- OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 41,295,1991
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- >5 gm/kg
- TOXIC EFFECTS :
- Skin and Appendages - dermatitis, other (after systemic exposure)
- REFERENCE :
- OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 41,295,1991 ** OTHER MULTIPLE DOSE TOXICITY DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 9100 mg/kg/52W-C
- TOXIC EFFECTS :
- Liver - changes in liver weight Endocrine - changes in adrenal weight Nutritional and Gross Metabolic - other changes
- REFERENCE :
- OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 42,291,1991
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Primate - monkey
- DOSE/DURATION :
- 910 mg/kg/1Y-C
- TOXIC EFFECTS :
- Nutritional and Gross Metabolic - other changes
- REFERENCE :
- OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 42,301,1991 ** REPRODUCTIVE DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 2607 ug/kg
- SEX/DURATION :
- male 52 week(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - other effects on male Endocrine - androgenic
- REFERENCE :
- CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 21,631,1980
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 219 ug/kg
- SEX/DURATION :
- female 52 week(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
- REFERENCE :
- CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 25,243,1982
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Implant
- DOSE :
- 875 ug/kg
- SEX/DURATION :
- female 35 week(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Fertility - other measures of fertility
- REFERENCE :
- CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 22,71,1980
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Implant
- DOSE :
- 3171 ug/kg
- SEX/DURATION :
- male 60 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - impotence
- REFERENCE :
- CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 25,591,1982
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Implant
- DOSE :
- 110 ug/kg
- SEX/DURATION :
- female 52 week(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Maternal Effects - menstrual cycle changes or disorders Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
- REFERENCE :
- CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 18,151,1978
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Implant
- DOSE :
- 4080 ug/kg
- SEX/DURATION :
- female 52 week(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
- REFERENCE :
- CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 27,473,1983
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravaginal
- DOSE :
- 102 ug/kg
- SEX/DURATION :
- female 17 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Maternal Effects - uterus, cervix, vagina
- REFERENCE :
- CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 22,71,1980
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intracervical
- DOSE :
- 12 ug/kg
- SEX/DURATION :
- female 30 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Maternal Effects - menstrual cycle changes or disorders
- REFERENCE :
- CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 23,473,1981
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intracervical
- DOSE :
- 36 ug/kg
- SEX/DURATION :
- female 90 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
- REFERENCE :
- CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 23,473,1981
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- DOSE :
- 250 mg/kg
- SEX/DURATION :
- female 1-4 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)
- REFERENCE :
- CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 21,537,1980
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- DOSE :
- 2800 ug/kg
- SEX/DURATION :
- male 14 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Paternal Effects - testes, epididymis, sperm duct
- REFERENCE :
- ENDKAC Endokrinologie. (Leipzig, Ger. Dem. Rep.) V.1-80, 1928-82. For publisher information, see EXCEDS. Volume(issue)/page/year: 76,13,1980
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 500 mg/kg
- SEX/DURATION :
- female 8-12 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death
- REFERENCE :
- EXCEDS Experimental and Clinical Edocrinology. (Johann Ambrosius Barth Verlag, Postfach 109, Leipzig DDR-7010, Ger. Dem. Rep.) V.81- 1983- Volume(issue)/page/year: 81,197,1983
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 50 mg/kg
- SEX/DURATION :
- female 3-7 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Maternal Effects - parturition Reproductive - Specific Developmental Abnormalities - musculoskeletal system
- REFERENCE :
- EXCEDS Experimental and Clinical Edocrinology. (Johann Ambrosius Barth Verlag, Postfach 109, Leipzig DDR-7010, Ger. Dem. Rep.) V.81- 1983- Volume(issue)/page/year: 81,197,1983
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 5 mg/kg
- SEX/DURATION :
- female 8-12 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - stillbirth
- REFERENCE :
- EXCEDS Experimental and Clinical Edocrinology. (Johann Ambrosius Barth Verlag, Postfach 109, Leipzig DDR-7010, Ger. Dem. Rep.) V.81- 1983- Volume(issue)/page/year: 81,197,1983
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 5 gm/kg
- SEX/DURATION :
- female 3-7 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
- REFERENCE :
- EXCEDS Experimental and Clinical Edocrinology. (Johann Ambrosius Barth Verlag, Postfach 109, Leipzig DDR-7010, Ger. Dem. Rep.) V.81- 1983- Volume(issue)/page/year: 81,197,1983
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- DOSE :
- 200 mg/kg
- SEX/DURATION :
- female 1-4 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)
- REFERENCE :
- CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 21,537,1980
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 80 ug/kg
- SEX/DURATION :
- female 1 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
- REFERENCE :
- CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 21,537,1980
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 80 mg/kg
- SEX/DURATION :
- male 56 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles)
- REFERENCE :
- CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 21,641,1980
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 500 ug/kg
- SEX/DURATION :
- female 1 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Fertility - other measures of fertility
- REFERENCE :
- ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 33,231,1983
Safety Information
[ Risk Phrases ]:
20/21/22-40
[ WGK Germany ]:
3
[ RTECS ]:
JF8259000