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Related CAS#:
72-33-3 51414-87-0
45019-19-0 10382-22-6
14009-70-2 65694-22-6
26011-40-5 8064-51-5

72-33-3

72-33-3 structure
72-33-3 structure
  • Name: mestranol
  • Chemical Name: mestranol
  • CAS Number: 72-33-3
  • Molecular Formula: C21H26O2
  • Molecular Weight: 310.430
  • Catalog: API Hormone and endocrine-regulating drugs Estrogen and progestogen drugs
  • Create Date: 2018-04-15 08:00:00
  • Modify Date: 2024-01-03 09:55:07
  • Mestranol is the 3-methyl ether of ethinylestradiol. It was the estrogen used in many of the first oral contraceptives.Target: Estrogen Receptor/ERRMestranol is absorbed very rapidly from the digestive tract and maximum plasma levels are attained in 1-4 hours, the majority at 1-2 hours. Detectable levels of mestranol are present 24 hours postingestion in 58% of subjects after a 50 μg dose and in 79% after a 100 μg dose. At all dose levels, highest plasma mestranol levels and area under the curve of plasma levels (AUC) occurred in Sri Lankan women, and lowest plasma levels in Nigerian women, even when corrected for body surface differences [1].
Name mestranol
Synonyms (17b)-17-ethynyl-3-methoxyestra-1,3,5(10)-trien-17-ol
SC 4725
d-MVE
EE3ME
8027 C. B.
Ovastol
Estra-1,3,5(10)-trien-17β-ol, 17-ethynyl-3-methoxy-
17a-Ethynylestradiol 3-Methyl Ether
19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-, (17α)-
EINECS 200-777-8
17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-methyl ether
Devocin
(17a)-3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17-ol
Estra-1(10),2,4-trien-17-ol, 17-ethynyl-3-methoxy-, (17β)-
RS 1044
δ-MVE
(17α)-3-Methoxy-19-norpregna-1(10),2,4-trien-20-yn-17-ol
(8R,9S,13S,14S,17R)-17-éthynyl-3-méthoxy-13-méthyl-7,8,9,11,12,13,14,15,16,17-décahydro-6H-cyclopenta[a]phénanthrén-17-ol
(8R,9S,13S,14S,17R)-17-Ethinyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol
mestranol
Norquen
17a-Ethynyl-3-methoxy-1,3,5(10)-estratrien-17b-ol
MFCD00003689
estra-1,3,5(10)-trien-17-ol, 17-ethynyl-3-methoxy-, (17b)-
17α-Ethynylestradiol 3-methyl ether
3-Methoxy-19-nor-17α-pregna-1,3,5(10)-trien-20-yn-17-ol
Description Mestranol is the 3-methyl ether of ethinylestradiol. It was the estrogen used in many of the first oral contraceptives.Target: Estrogen Receptor/ERRMestranol is absorbed very rapidly from the digestive tract and maximum plasma levels are attained in 1-4 hours, the majority at 1-2 hours. Detectable levels of mestranol are present 24 hours postingestion in 58% of subjects after a 50 μg dose and in 79% after a 100 μg dose. At all dose levels, highest plasma mestranol levels and area under the curve of plasma levels (AUC) occurred in Sri Lankan women, and lowest plasma levels in Nigerian women, even when corrected for body surface differences [1].
Related Catalog
References

[1]. Goldzieher, J.W., T.S. Dozier, and A. de la Pena, Plasma levels and pharmacokinetics of ethynyl estrogens in various populations: II. Mestranol. Contraception, 1980. 21(1): p. 17-27.
Density 1.2±0.1 g/cm3
Boiling Point 442.3±45.0 °C at 760 mmHg
Melting Point 153-155 °C(lit.)
Molecular Formula C21H26O2
Molecular Weight 310.430
Flash Point 190.8±23.0 °C
Exact Mass 310.193268
PSA 29.46000
LogP 5.17
Vapour Pressure 0.0±1.1 mmHg at 25°C
Index of Refraction 1.591
Storage condition -20°C Freezer

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RC8960000
CHEMICAL NAME :
17-alpha-19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-
CAS REGISTRY NUMBER :
72-33-3
BEILSTEIN REFERENCE NO. :
2625905
LAST UPDATED :
199612
DATA ITEMS CITED :
54
MOLECULAR FORMULA :
C21-H26-O2
MOLECULAR WEIGHT :
310.47
WISWESSER LINE NOTATION :
L E5 B666TTT&J E1 FQ F1UU1 OO1

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 :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>3 gm/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - changes in structure or function of salivary glands Skin and Appendages - hair
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - changes in structure or function of salivary glands Skin and Appendages - hair
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ptosis Behavioral - somnolence (general depressed activity) Skin and Appendages - hair
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>3200 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - lacrimation Behavioral - somnolence (general depressed activity) Skin and Appendages - hair
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2500 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - lacrimation Sense Organs and Special Senses (Eye) - ptosis Skin and Appendages - hair
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
300 mg/kg/30D-C
TOXIC EFFECTS :
Endocrine - changes in thymus weight Blood - normocytic anemia Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5490 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 :
2400 ug/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 :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
61 mg/kg/84W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Reproductive - Tumorigenic effects - ovarian tumors Reproductive - Tumorigenic effects - uterine tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
19 mg/kg/30W-C
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Skin and Appendages - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
20 mg/kg/28W-C
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Skin and Appendages - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
20 ug/kg
SEX/DURATION :
female 20 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 :
25600 ng/kg
SEX/DURATION :
female 16 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
160 ug/kg
SEX/DURATION :
female 57 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 :
2500 ug/kg
SEX/DURATION :
female 10 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
150 ug/kg
SEX/DURATION :
female 2-4 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
430 ug/kg
SEX/DURATION :
female 1-22 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - urogenital system Reproductive - Effects on Newborn - delayed effects
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
700 ug/kg
SEX/DURATION :
female 7 day(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 :
690 ng/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
336 ug/kg
SEX/DURATION :
male 14 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 :
1 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 :
Subcutaneous
DOSE :
1050 ug/kg
SEX/DURATION :
female 3-9 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 :
60 ug/kg
SEX/DURATION :
female 2-4 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
500 ng/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
400 ng/kg
SEX/DURATION :
male 1 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 :
35 ug/kg
SEX/DURATION :
female 35 day(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 :
Unreported
DOSE :
150 ug/kg
SEX/DURATION :
female 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
3 mg/kg
SEX/DURATION :
female 1 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
250 ug/kg
SEX/DURATION :
female 4-8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
132 ng/kg
SEX/DURATION :
female 3 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
2 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 :
5 mg/kg
SEX/DURATION :
female 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility Reproductive - Effects on Newborn - live birth index (measured after birth)
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 :
500 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
30 ug/kg
SEX/DURATION :
female 1-3 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 :
15 ug/kg
SEX/DURATION :
female 1-3 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
25 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 :
Unreported
DOSE :
95 ug/kg
SEX/DURATION :
female 1-19 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 - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
Unscheduled DNA synthesis
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Mutation test systems - not otherwise specified
TYPE OF TEST :
Cytogenetic analysis

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
100 ug/kg
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 322,173,1994 *** REVIEWS *** IARC Cancer Review:Animal Sufficient 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: 21,257,1979 IARC Cancer Review:Animal Sufficient 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: 6,87,1974 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 CRTXB2 CRC Critical Reviews in Toxicology. (CRC Press, Inc., 2000 Corporate Blvd., NW, Boca Raton, FL 33431) V.1- 1971- Volume(issue)/page/year: 1(1),93,1971 TOXICOLOGY REVIEW JTEHD6 Journal of Toxicology and Environmental Health. (Hemisphere Pub., 1025 Vermont Ave., NW, Washington, DC 20005) V.1- 1975/76- Volume(issue)/page/year: 3,197,1977 TOXICOLOGY REVIEW CMROCX Current Medical Research and Opinion. (Clayton-Wray Pub. Ltd., 1a High St., Alton, Hants., UK) V.1- 1972- Volume(issue)/page/year: 4,309,1976
Symbol GHS07 GHS08
GHS07, GHS08
Signal Word Warning
Hazard Statements H315-H319-H351
Precautionary Statements P280-P305 + P351 + P338
Personal Protective Equipment Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes Xn: Harmful;
Risk Phrases R36/37/38;R40;R48
Safety Phrases S22-S26-S36/37/39-S45-S36/37
RIDADR 2811.0
WGK Germany 3
RTECS RC8960000
1624-62-0 structure

1624-62-0
1066-54-2 structure

1066-54-2

~92%

72-33-3 structure

72-33-3
Literature: Wong, Fung Fuh; Chuang, Shih Hsien; Yang, Sheng-chuan; Lin, Yu-Hsiang; Tseng, Wen-Che; Lin, Shao-Kai; Huang, Jiann-Jyh Tetrahedron, 2010 , vol. 66, # 23 p. 4068 - 4072
57-63-6 structure

57-63-6
74-88-4 structure

74-88-4

~82%

72-33-3 structure

72-33-3
Literature: Choudhary, Muhammad Iqbal; Musharraf, Syed Ghulam; Siddiqui, Zafar Ali; Khan, Naik Tameen; Ali, Rahat Azhar; Atta-ur-Rahman Chemical and Pharmaceutical Bulletin, 2005 , vol. 53, # 8 p. 1011 - 1013
1624-62-0 structure

1624-62-0
74-86-2 structure

74-86-2

~%

72-33-3 structure

72-33-3
Literature: Journal of the American Chemical Society, , vol. 79, p. 1123,1126

Chemsrc provides CAS#:72-33-3 MSDS, density, melting point, boiling point, structure, formula, molecular weight, synthetic route, etc.
title: CAS No. 72-33-3 | Chemsrc address: https://www.chemsrc.com/en/baike/1150788.html

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