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Home > Encyclopedia > β-Ethyl-6-methoxy-α,α-dimethyl-2-naphthalenepropanoic acid

β-Ethyl-6-methoxy-α,α-dimethyl-2-naphthalenepropanoic acid

β-Ethyl-6-methoxy-α,α-dimethyl-2-naphthalenepropanoic acid structure

β-Ethyl-6-methoxy-α,α-dimethyl-2-naphthalenepropanoic acid 

structure
  • CAS No:

    517-18-0

  • Formula:

    C18H22O3

  • Chemical Name:

    β-Ethyl-6-methoxy-α,α-dimethyl-2-naphthalenepropanoic acid

  • Synonyms:

    2-Naphthalenepropanoic acid,β-ethyl-6-methoxy-α,α-dimethyl-;2-Naphthalenepropionic acid,β-ethyl-6-methoxy-α,α-dimethyl-;β-Ethyl-6-methoxy-α,α-dimethyl-2-naphthalenepropanoic acid;β-Ethyl-6-methoxy-α,α-dimethyl-2-naphthalenepropionic acid;3-(6-Methoxy-2-naphthyl)-2,2-dimethylpentanoic acid;β-(6-Methoxy-2-naphthyl)-α,α-dimethylvaleric acid;Vallestril;Methallenestril;Methallenestrol;Novestrine;(±)-Methallenestril;NSC 74235;15372-35-7

  • Categories:

    Active Pharmaceutical Ingredients  >  Hormones and the Endocrine System

Description

Crystals.Soluble in ether, vegetable oils.


Methallenestril is a member of naphthalenes.

β-Ethyl-6-methoxy-α,α-dimethyl-2-naphthalenepropanoic acid Basic Attributes

286.369

286.37

208-232-6

81399|81398|74235

DTXSID7023275

CRYSTALS FROM DIL METHANOL

G - Genito urinary system and sex hormones

Characteristics

46.5

4.45280

1.108g/cm3

139-140 °C

437ºC at 760mmHg

154.7ºC

1.572

SOL IN ETHER & VEGETABLE OILS; INSOL IN WATER; FREELY SOL IN CHLOROFORM

Drug Information

Estrogens, Non-Steroidal|MENOPAUSAL & POSTMENOPAUSAL ...; TO PREVENT POSTPARTUM BREAST ENGORGEMENT ...; FOR PROSTATIC CARCINOMA ...|ESTROGENS ARE USED IN YOUNG WOMEN IN WHOM THERE IS FAILURE OF STEROIDOGENESIS... /ESTROGENS/|A NUMBER OF MENSTRUAL IRREGULARITIES MAY BE TREATED WITH ESTROGENS. ...SUCH AS AMENORRHEA... USED CYCLICALLY MAY REGULARIZE...SECONDARY AMENORRHEA... IN ENDOMETRIOSIS, ESTROGENS ARE EFFECTIVE FOR ONLY SHORT TIME... /ESTROGENS/|For more Therapeutic Uses (Complete) data for METHALLENESTRIL (6 total), please visit the HSDB record page.

...DISADVANTAGE OF SOME SYNTHETIC ESTROGENIC COMPD IS THAT NAUSEA FOLLOWS USE OF...MINIMUM EFFECTIVE DOSE IN SOME WOMEN, BUT...NOT OVER 20% OF THOSE WHO USE MATERIALS CAREFULLY. IN SUCH WOMEN SYNTHETIC MATERIALS MUST BE REPLACED BY NATURAL PRODUCTS. /SYNTHETIC ESTROGEN/|CHANGES IN SECONDARY SEXUAL CHARACTERISTICS ARE FULLY REVERSIBLE ON CESSATION OF EXPOSURE. /ESTROGENS/

3(?). 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) IS 0.5-5 G/KG, BETWEEN 1 OZ & 1 PINT FOR 70 KG PERSON (150 LB). ... ALTHOUGH LITTLE INFORMATION APPEARS TO BE AVAILABLE, THESE COMPD MUST HAVE A VERY LOW SINGLE DOSE TOXICITY. /ESTROGENS/

ESTROGENS USED IN THERAPY ARE...READILY ABSORBED THROUGH SKIN & MUCOUS MEMBRANES. WHEN THEY ARE APPLIED FOR LOCAL ACTION, ABSORPTION IS OFTEN SUFFICIENT TO CAUSE SYSTEMIC EFFECTS, & IN FACTORY WORKERS GYNECOMASTIA HAS FOLLOWED HANDLING OF DIETHYLSTILBESTROL WITHOUT GLOVES. /ESTROGENS/|URINARY EXCRETION RATE OF ESTROGENS IS QUITE SIMILAR WHETHER AGENTS ARE GIVEN ORALLY OR INTRAVENOUSLY, WHICH SUGGESTS THAT ABSORPTION OF MOST ESTROGENS FROM GI TRACT IS PROMPT & QUITE COMPLETE. /ESTROGENS/|NATURAL ESTROGENS ARE SOL IN WATER, &, WHEN INJECTED DISSOLVED IN OIL, ARE RAPIDLY ABSORBED & QUICKLY METABOLIZED. ... INACTIVATION OF ESTROGEN IN BODY IS CARRIED OUT MAINLY IN THE LIVER. /ESTROGENS/|CERTAIN PROPORTION OF ESTROGEN REACHING.../THE LIVER/ IS EXCRETED INTO THE BILE, ONLY TO BE REABSORBED FROM THE INTESTINE & CARRIED BACK AGAIN TO THE LIVER BY THE PORTAL VEIN. /ESTROGENS/

CONSIDERABLE PROGRESS HAS BEEN MADE IN ELUCIDATION OF MECHANISM OF ACTION OF ESTROGENS... PUTATIVE RECEPTOR PROTEINS FOR HORMONE HAVE BEEN DETECTED IN QUANTITY ONLY IN ESTROGEN-RESPONSIVE TISSUES... /ESTROGENS/|ESTROGENS ARE FIRST BOUND WITH VERY HIGH AFFINITY TO A CYTOPLASMIC 8 S RECEPTOR PROTEIN, WHICH THEN DISSOCIATES INTO A 4 S WITH ESTROGEN ATTACHED. ... THE ESTROGEN COMPLEX IS CONVERTED TO A 5 S SPECIES THAT IS TRANSPORTED TO THE NUCLEUS, WHERE ULTIMATE BINDING OF ESTROGEN-CONTAINING COMPLEX OCCURS. /ESTROGENS/|THE ACTIVITY OF...SYNTHETIC...ESTROGENS DEPENDS ON PRESENCE OF HYDROXYL GROUPS @ EXTREMITIES OF THEIR MOLECULES... HYDROXYLS...INVOLVED IN BINDING WITH SPECIFIC RECEPTOR PROTEINS, PRESENT IN CYTOSOL OF CELLS IN TARGET ORGANS. /ESTROGENS/

BREAST ENLARGEMENT & NODULARITY OCCURRED IN BOTH MALE & FEMALE CHILDREN AFTER CONSUMPTION OF VITAMIN CAPSULES CONTAMINATED WITH ESTROGENS. /ESTROGEN/|MALAISE, IRRITABILITY, & DEPRESSION...OCCUR WITH SMALL DOSES &...WITH LARGE DOSES. EFFECT ON LIBIDO IS ERRATIC, BEING INCR IN SOME & DECR IN OTHERS. ... CHANGES IN CONCN OF SOME OF CLOTTING FACTORS IN BLOOD...INCR INCIDENCE OF THROMBOPHLEBITIS & THROMBOEMBOLISM IN...SUPERFICIAL & DEEP VEINS. /ESTROGENS/|PULMONARY EMBOLISM, CEREBRAL EMBOLISM WITH STROKE & MESENTERIC VASCULAR OCCULSION OCCUR. CORONARY THROMBOSIS...INCR... ALTER HEPATIC FUNCTION, WHICH... ALTER...TESTS OF LIVER FUNCTION AS WELL AS VARIOUS SYNTHETIC & BIOTRANSFORMATION PROCESSES. ...DECR IN GLUCOSE TOLERANCE, & DIABETES MELLITUS MAY BE EXACERBATED. /ESTROGENS/|SERUM TRIGLYCERIDES RISE, &...HYPERLIPIDEMIA MAY OCCUR... COMPOSITION IS ALTERED...INCR OF GALL STONES... PORPHYRIA MAY BE PROVOKED. CHANGES IN CONCN OF BLOOD PROTEINS MAY OCCUR; THYROXINE- & GLUCOCORTICOID-BINDING PROTEINS ARE INCR, WHICH MAY ALTER ENDOCRINE RELATIONSHIPS. /ESTROGENS/|For more Human Toxicity Excerpts (Complete) data for METHALLENESTRIL (10 total), please visit the HSDB record page.

methallenestril

β-Ethyl-6-methoxy-α,α-dimethyl-2-naphthalenepropanoic acid Use and Manufacturing

Methods of Manufacturing

HOREAU, JACQUES, COMPT REND 224, 862 (1947); BULL SOC CHIM FRANCE 1948, 711; GAY, HOREAU, BULL SOC CHIM FRANCE 1955, 955.

Uses

Medicine (estrogen).

DETERMINATION OF TOTAL ESTROGENS BY SPECTROPHOTOMETRY.

Computed Properties

Molecular Weight:286.4
XLogP3:4.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:286.15689456
Monoisotopic Mass:286.15689456
Topological Polar Surface Area:46.5
Heavy Atom Count:21
Complexity:364
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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