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CAS 391901-45-4 Mirabegron Intermediate / Impurity Mirabegron Intermediate / Impurity High Purity GMP Grade

(R)-2-((4-Aminophenethyl)amino)-1-phenylethan-1-ol

IUPAC: (R)-2-((4-Aminophenethyl)amino)-1-phenylethan-1-ol View on PubChem
CAS NUMBER
391901-45-4
MOL. FORMULA
C16H20N2O
MOL. WEIGHT
256.35 g/mol
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Scientific Overview

This compound represents the key des-thiazolylacetamide fragment of mirabegron --- it contains the chiral (R)-phenylethanolamine core bonded to a 4-aminophenethyl group via a secondary amine linkage, structurally corresponding to mirabegron with the 2-aminothiazole-acetamide side chain removed. Notably, it also arises as a genuine circulating human metabolite of mirabegron (designated M16), making it relevant both as a synthetic building block and as an analytical reference standard for pharmacokinetic and drug metabolism studies.

(R)-2-((4-Aminophenethyl)amino)-1-phenylethan-1-ol, also known as Mirabegron Impurity 6 or Mirabegron M16, is a chiral aminoalcohol intermediate central to the synthesis and metabolism of mirabegron, a selective ß3-adrenergic receptor agonist used to treat overactive bladder syndrome.

Full Technical Data
Chemical Name (R)-2-((4-Aminophenethyl)amino)-1-phenylethan-1-ol
CAS Number 391901-45-4
IUPAC Name (R)-2-((4-Aminophenethyl)amino)-1-phenylethan-1-ol
Molecular Formula C16H20N2O
Molecular Weight 256.35 g/mol g/mol
Reaction Scheme
(R)-2-((4-Nitrophenethyl)amino)-1-phenylethanol Hydrochloride
NA
NA
(R)-2-((4-Aminophenethyl)amino)-1-phenylethan-1-ol
NA
Commercial Applications

Mirabegron API Synthesis

Direct synthetic intermediate in the manufacturing route to mirabegron, used to construct the drug's core aminoalcohol-arylethylamine scaffold.

Pharmacopeial Impurity Reference Standard

Designated Mirabegron EP Impurity B / Impurity 6 for drug substance quality control testing.

Metabolite Reference Standard

Used as an authentic reference for identifying and quantifying the M16 human metabolite in pharmacokinetic studies.

Chiral Building Block Applications

Applied in asymmetric synthesis research requiring enantiopure phenylethanolamine-arylethylamine scaffolds.

Market Therapeutic Focus
MIRABEGRON INTERMEDIATE / IMPURITY PHARMACEUTICAL MANUFACTURING UROLOGY / OVERACTIVE BLADDER THERAPEUTICS ANALYTICAL REFERENCE STANDARDS DRUG METABOLISM & PHARMACOKINETICS CRO/CDMO
Scientific Literature

Mirabegron: A Review of its Use in Overactive Bladder Syndrome

Authors: Cui, Y. et al.

Drugs

DOI: 10.1007/s40265-014-0287-9

Metabolism and Disposition of the ß3-Adrenoceptor Agonist Mirabegron in Humans

Authors: Krauwinkel, W. et al.

Drug Metab. Dispos.

DOI: 10.1124/dmd.111.043828

Synthesis and Structure-Activity Relationships of ß3-Adrenergic Receptor Agonists

Authors: Ohtake, Y. et al.

J. Med. Chem.

DOI: 10.1021/jm300148g
Peer Queries & FAQs
How does this compound relate to mirabegron?
It corresponds to mirabegron's core structure with the 2-aminothiazole-acetamide side chain removed, serving as both a synthetic precursor and a genuine circulating metabolite (M16) of the drug.
Why is chirality important for this compound?
The (R)-configuration at the phenylethanolamine stereocenter is essential for correct downstream coupling and consistency with mirabegron's defined stereochemistry, which underlies its ß3-adrenergic receptor selectivity.
Is this compound pharmacologically active on its own?
As the M16 metabolite, it represents a biotransformation product studied for pharmacokinetic characterization; it is not the primary pharmacologically active species compared to the parent drug.
What is the recommended storage condition?
Store in a tightly sealed container at 2--8°C, protected from light and moisture.

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