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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

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Certificates of Analysis (COA)

Lot/Batch Number
101K4608

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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
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
Abdul H Khan et al.
European journal of pharmacology, 569(1-2), 110-118 (2007-06-15)
This study investigated whether the alpha(1)-adrenoceptor subtype(s) mediating the vasoconstrictor actions of the renal sympathetic nerves were altered in rats with cisplatin-induced renal failure. Male Wistar Kyoto rats were used and half received cisplatin (5 mg/kg i.p.) to induce renal
Rocío Alcántara-Hernández et al.
Biochimica et biophysica acta, 1864(12), 2378-2388 (2017-09-11)
In LNCaP cells that stably express α
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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