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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

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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G Gross et al.
European journal of pharmacology, 169(2-3), 325-328 (1989-10-10)
Radioligand binding studies suggest that alpha 1-adrenoceptor recognition sites are heterogeneous. Several adrenergic agents discriminate between two adrenoceptor binding sites designated alpha 1A and alpha 1B. In the present study we demonstrate for the first time that these two subtypes
M Endoh et al.
Naunyn-Schmiedeberg's archives of pharmacology, 345(5), 578-585 (1992-05-01)
In order to elucidate the contribution of alpha 1A subtype to the positive inotropic effect mediated by myocardial alpha 1 adrenoceptors, the influence of the alpha 1A selective antagonists WB 4101 and 5-methylurapidil on the alpha 1-mediated positive inotropic effect
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
G Gross et al.
European journal of pharmacology, 151(2), 333-335 (1988-07-07)
The affinity of 5-methyl-urapidil for alpha 1-adrenoceptors was determined from the inhibition of [3H]prazosin binding on membrane of different rat tissues. In hippocampus, vas deferens and heart 5-methyl-urapidil displaced [3H]prazosin in a biphasic manner with mean pKI values between 9.1
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