7α-Methylestradiol

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7α-Methylestradiol.svg

Synthetic estrogen

7α-Methylestradiol




Synonyms 7α-Methyl-17β-estradiol; 7α-Methyl-E2; 7α-Methylestra-1,3,5(10)-triene-3,17β-diol
Chemical nomenclature
IUPAC name (8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol










Identifiers
CAS Number 13110-72-4
PubChem 66435


ChemSpider 59808



ChEMBL 303926
Chemical data


Chemical formula C19H26O2


SMILES CC12CCC3C(C1CCC2O)CCC4=C3C=CC(=C4)O




7α-Methylestradiol is a synthetic estrogen and a derivative of estradiol. It is characterized by the presence of a methyl group at the 7α position of the estradiol molecule. This modification alters its pharmacokinetics and pharmacodynamics compared to estradiol.

Chemical Structure[edit]

7α-Methylestradiol is a steroid with the IUPAC name (8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol. Its molecular formula is C19H26O2, and it has a molecular weight of 286.41 g/mol.

Pharmacology[edit]

As an estrogen, 7α-Methylestradiol binds to and activates the estrogen receptors (ERs), which are involved in the regulation of various physiological processes. The addition of the 7α-methyl group is intended to enhance its bioavailability and metabolic stability.

Uses[edit]

7α-Methylestradiol is primarily used in research settings to study the effects of estrogens and their receptors. It is not commonly used in clinical practice.

Synthesis[edit]

The synthesis of 7α-Methylestradiol involves the chemical modification of estradiol through the introduction of a methyl group at the 7α position. This process typically requires several steps, including protection and deprotection of functional groups, as well as oxidation and reduction reactions.

Related Compounds[edit]

See Also[edit]

References[edit]


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