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Merck
CN

U101

5-Methylurapidil

solid

Synonym(s):

5-Methyl-6[[3-[4-(2-methoxyphenyl)-1-piperazinyl]­propyl]­amino]-1,3-dimethyluracil

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About This Item

Empirical Formula (Hill Notation):
C21H31N5O3
CAS Number:
Molecular Weight:
401.50
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
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InChI

1S/C21H31N5O3.ClH/c1-16-19(23(2)21(28)24(3)20(16)27)22-10-7-11-25-12-14-26(15-13-25)17-8-5-6-9-18(17)29-4;/h5-6,8-9,22H,7,10-15H2,1-4H3;1H

SMILES string

Cl[H].COc1ccccc1N2CCN(CCCNC3=C(C)C(=O)N(C)C(=O)N3C)CC2

InChI key

WAZDYFHTLYHMKO-UHFFFAOYSA-N

form

solid

color

white

solubility

H2O: 0.4 mg/mL, 0.1 M HCl: 3.8 mg/mL

Quality Level

Gene Information

Application

5-Methylurapidil has been used for competitive binding in radioligand binding assays.

Biochem/physiol Actions

Selective α1A-adrenoceptor antagonist; antihypertensive.

Features and Benefits

This compound is featured on the α1-Adrenoceptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

5-Methylurapidil is soluble in water at 0.4 mg/ml and is also soluble in 0.1 M HCl at 3.8 mg/ml.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Wesley B Asher et al.
Journal of chemical information and modeling, 47(5), 1906-1912 (2007-08-25)
In this study, we have developed a two model system to mimic the active and inactive states of a G-protein coupled receptor specifically the alpha1A adrenergic receptor. We have docked two agonists, epinephrine (phenylamine type) and oxymetazoline (imidazoline type), as
Kim Davenport et al.
BJU international, 98(3), 651-655 (2006-08-24)
To compare the in vitro human ureteric muscle response to calcium-channel and alpha-adrenoceptor antagonists, to determine the promoting factor for stone passage. Clinical trials suggest that stone passage in renal colic can be promoted by ureteric relaxation using these agents
Rocío Alcántara-Hernández et al.
Biochimica et biophysica acta, 1864(12), 2378-2388 (2017-09-11)
In LNCaP cells that stably express α
Caroline Putzke et al.
Cardiovascular research, 75(1), 59-68 (2007-03-29)
The outward current flowing through the two-pore domain acid-sensitive potassium channel TASK-1 (I(TASK)) and its inhibition via alpha1-adrenergic receptors was studied in rat ventricular cardiomyocytes. Quantitative RT-PCR experiments were carried out with mRNA from rat heart. Patch-clamp recordings were performed
D W Gil et al.
British journal of pharmacology, 153(4), 769-774 (2007-08-19)
The most common preclinical models of neuropathic pain involve surgical ligation of sensory nerves, which is especially difficult in mice. Transient models of chemically sensitized allodynia are potentially useful for rapidly characterizing the analgesic profile of compounds and conducting mechanistic

Articles

Review alpha 1 adrenoceptors as well as their agonists, antagonists, and tissue expression patterns. We suggest several modulators and alternatives for working with a-1 adrenoreceptors.

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