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U104

Sigma-Aldrich

UK 14,304

Synonym(s):

5-Bromo-N-(2-imidazolin-2-yl)-6-quinoxalinamine, 5-Bromo-N-(4,5-dihydro-1H-imidazol-2-yl)-6-quinoxalinamine, Brimonidine

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About This Item

Empirical Formula (Hill Notation):
C11H10BrN5
CAS Number:
59803-98-4
Molecular Weight:
292.13
MDL number:
MFCD00153878
UNSPSC Code:
12352200
PubChem Substance ID:
24277812
NACRES:
NA.77

Quality Level

100

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: <0.8 mg/mL
DMSO: >6.5 mg/mL
ethanol: <8 mg/mL (warm)
H2O: insoluble

SMILES string

Brc1c(NC2=NCCN2)ccc3nccnc13

InChI

1S/C11H10BrN5/c12-9-7(17-11-15-5-6-16-11)1-2-8-10(9)14-4-3-13-8/h1-4H,5-6H2,(H2,15,16,17)

InChI key

XYLJNLCSTIOKRM-UHFFFAOYSA-N

Gene Information

human ... ADRA1A(148) , ADRA2A(150) , ADRA2B(151) , ADRA2C(152)

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Application

UK 14,304 has been used for the activation of extracellular signal-regulated kinase (ERK) in epicardial coronary artery culture
UK 14,304 has been used in myenteric neurons to study the inhibition of R-type calcium currents. UK 14,304 has also been used for immunofluorescence microscopy assays.

Biochem/physiol Actions

UK 14,304 is an α2-adrenoceptor agonist. UK 14,304 inhibits hormone-sensitive lipase (HSL) activity and suppresses lipogenesis in adipose tissue.

Features and Benefits

This compound is featured on the α2-Adrenoceptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

UK 14,304 is soluble in 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin (<0.8 mg/mL), DMSO (>6.5 mg/ml) and ethanol (<8 mg/mL). However, it is insoluble in water.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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X Bian et al.
Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society, 19(10), 845-855 (2007-09-22)
Alpha2-adrenoceptors inhibit Ca2+ influx through voltage-gated Ca2+ channels throughout the nervous system and Ca2+ channel function is modulated following activation of some G-protein coupled receptors. We studied the specific Ca2+ channel inhibited following alpha2-adrenoceptor activation in guinea-pig small intestinal myenteric
J T Turner et al.
Molecular pharmacology, 28(5), 422-430 (1985-11-01)
We have characterized the alpha 2-adrenergic receptor in membranes from the human colonic adenocarcinoma cell line, HT29, using the recently introduced alpha 2-agonist 5-bromo-6-[2-imidazolin-2-yl-amino]quinoxaline [( 3H]UK-14,304), two other radioligands, and a series of adrenergic agonists and antagonists. We also investigated
Hung-Yu Lin et al.
Medicine, 96(47), e8868-e8868 (2018-02-01)
To evaluate the safety and efficiency in macular edema patients who concurrently received a single injection of a dexamethasone intravitreal implant (DEX, 0.7 mg) and ranibizumab (2.3 mg).A retrospective cohort study was conducted, and medical records from 2012 to 2016 were reviewed.
The alpha2-adrenergic receptor agonist UK 14,304 inhibits secretin-stimulated ductal secretion by downregulation of the cAMP system in bile duct-ligated rats.
Francis H, et al.
American Journal of Physiology. Cell Physiology, 293(4), C1252-C1262 (2007)
Kenric Rui-Pin Fan et al.
Acta ophthalmologica, 97(6), e827-e832 (2019-03-28)
To investigate the neuroprotective effect of Copolymer-1 (Cop-1) in patients with acute primary angle closure (APAC) in a randomized double-masked controlled trial. After initial medical management, APAC patients were randomized to receive either subcutaneous Cop-1 or placebo within 24 hr and
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