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Merck
CN

00881

(±)-4-Hydroxypropranolol hydrochloride

analytical standard

Synonym(s):

1-[(4-Hydroxy-1-naphthyl)oxy]-3-(isopropylamino)- 2-propanol hydrochloride, 4′-Hydroxypropranolol hydrochloride, 4-{2-Hydroxy-3-[(1-methylethyl)amino]propoxy}-1-naphthalenol hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C16H21NO3·HCl
CAS Number:
14133-90-5
Molecular Weight:
311.80
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329747156
MDL number:
MFCD06656370
Beilstein/REAXYS Number:
4036845

Key Documents

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Product Name

(±)-4-Hydroxypropranolol hydrochloride, analytical standard

InChI

1S/C16H21NO3.ClH/c1-11(2)17-9-12(18)10-20-16-8-7-15(19)13-5-3-4-6-14(13)16;/h3-8,11-12,17-19H,9-10H2,1-2H3;1H

SMILES string

CC(C)NCC(O)COC1=CC=C(O)C2=CC=CC=C21.Cl

InChI key

ROUJENUXWIFONU-UHFFFAOYSA-N

grade

analytical standard

assay

≥98.5% (AT)
≥98.5% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

forensics and toxicology
pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

Quality Level

100

Related Categories

Other Notes

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL5746
BCCH1537
BCCC6246
BCBV6968

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Takeshi Shimizudani et al.
Chemico-biological interactions, 183(1), 67-78 (2009-10-27)
Oxidative metabolism of propranolol (PL) enantiomers (R-PL and S-PL) to 4-hydroxypropranolol (4-OH-PL), 5-OH-PL and N-deisopropylpropranolol (NDP) was examined in hepatic microsomes from cynomolgus and marmoset monkeys and in small intestinal microsomes from monkeys and humans. In hepatic microsomes, levels of
Keyller Bastos Borges et al.
Electrophoresis, 30(22), 3910-3917 (2009-10-31)
A CE method is described for the enantioselective analysis of propranolol (Prop) and 4-hydroxypropranolol (4-OH-Prop) in liquid Czapek medium with application in the study of the enantioselective biotransformation of Prop by endophytic fungi. The electrophoretic conditions previously optimized were as
Propranolol 4- and 5-hydroxylation and N-desisopropylation by cloned human cytochrome P4501A1 and P4501A2.
M S Ching et al.
Drug metabolism and disposition: the biological fate of chemicals, 24(6), 692-694 (1996-06-01)
S Narimatsu et al.
Chemical research in toxicology, 8(5), 721-728 (1995-07-01)
We have characterized a chemically reactive propranolol (PL) metabolite which binds to proteins in rat liver microsomes. During incubation with rat liver microsomes (1 mg of protein) fortified with an NADPH-generating system, 4-hydroxypropranolol (4-OH-PL) quickly disappeared from the reaction medium
V L Herring et al.
Journal of chromatography, 612(2), 215-221 (1993-02-26)
A method is described for quantitation of underivatized enantiomers of propranolol and its major basic metabolite, 4-hydroxypropranolol, in urine samples by high-performance liquid chromatography with fluorescence detection, using a cellulose tris(3,5-dimethylphenylcarbamate) chiral stationary phase. This method was found to be
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