mestranol

Modify Date: 2024-01-03 09:55:07

mestranol structure	Common Name	mestranol
	CAS Number	72-33-3	Molecular Weight	310.430
	Density	1.2±0.1 g/cm3	Boiling Point	442.3±45.0 °C at 760 mmHg
	Molecular Formula	C₂₁H₂₆O₂	Melting Point	153-155 °C(lit.)
	MSDS	Chinese USA	Flash Point	190.8±23.0 °C
	Symbol	GHS07, GHS08	Signal Word	Warning

Use of mestranol

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
Synonym	More Synonyms

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	Signaling Pathways >> Others >> Estrogen Receptor/ERR Research Areas >> Endocrinology
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

mestranol MSDS(Chinese)

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
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

Estrone 3-methy...

CAS#:1624-62-0

TMS-acetylene

CAS#:1066-54-2

~92%

mestranol

CAS#: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

Ethynyl estradiol

CAS#:57-63-6

methyl iodide

CAS#:74-88-4

~82%

mestranol

CAS#: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

Estrone 3-methy...

CAS#:1624-62-0

Acetylene

CAS#:74-86-2

mestranol

CAS#:72-33-3

Literature: Journal of the American Chemical Society, , vol. 79, p. 1123,1126

Precursor 5
CAS#:1624-62-0 Estrone 3-methy... CAS#:1066-54-2 TMS-acetylene CAS#:57-63-6 Ethynyl estradiol CAS#:74-88-4 methyl iodide
CAS#:74-86-2 Acetylene
DownStream 9
CAS#:57-63-6 Ethynyl estradiol CAS#:26011-40-5 (8S,9S,13S,14S)... CAS#:22415-44-7 2-Methoxy-Ethyn... CAS#:60134-76-1 Ethynylestradio...
CAS#:75803-39-3 17 alpha-ethyny... CAS#:75812-41-8 17-ethynyl-1,2,... CAS#:1624-62-0 Estrone 3-methy... CAS#:10382-22-6 [(8R,9S,13S,14S...
CAS#:17550-03-7 19-Norpregna-1,...

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(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

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China
Product Name: Mestranol
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mestranol

Use of mestranol

Names

mestranol Biological Activity

Chemical & Physical Properties

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

Safety Information

Synthetic Route

Precursor & DownStream

Articles33

Synonyms