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U101

Sigma-Aldrich

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:
34661-85-3
Molecular Weight:
401.50
MDL number:
MFCD00078602
UNSPSC Code:
12352200
PubChem Substance ID:
24277800
NACRES:
NA.77

form

solid

Quality Level

100

color

white

solubility

H2O: 0.4 mg/mL
0.1 M HCl: 3.8 mg/mL

SMILES string

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

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

InChI key

WAZDYFHTLYHMKO-UHFFFAOYSA-N

Gene Information

human ... ADRA1A(148) , ADRA1B(147) , ADRA1D(146)

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A Armenia et al.
Acta pharmacologica Sinica, 29(5), 564-572 (2008-04-24)
This study investigates the subtypes of the alpha1-adrenoceptor mediating the adrenergically-induced renal vasoconstrictor responses in streptozotocin-induced diabetic and non-diabetic 2-kidney one clip (2K1C) Goldblatt hypertensive rats. The renal blood flow responses to renal nerve stimulation, noradrenaline, phenylephrine, and methoxamine were
Enio S A Pacini et al.
The Journal of pharmacology and experimental therapeutics, 366(1), 21-28 (2018-04-25)
The cauda epididymis (CE), the site of sperm storage until the ejaculation, is densely innervated by the sympathetic nervous system. Contraction of CE smooth muscle via α1-adrenoceptors (α1-ARs) plays a key role during the seminal emission phase of ejaculation and
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
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
Z Huang et al.
Journal of dental research, 85(3), 251-256 (2006-02-25)
alpha(1)-Adrenoceptor has been discovered to exist in many human tissues and mediates important physiological functions. The purpose of this study was to detect the expression, distribution, and function of alpha(1)-adrenoceptor subtypes in human submandibular glands. alpha(1A)- and alpha(1B)-Adrenoceptor mRNAs were
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