187173-05-3

Basic information

• Product Name: 2-(4,5-DIHYDROIMIDAZOL-2-YL)QUINOLINE HYDROCHLORIDE
• Synonyms: BU 224 HYDROCHLORIDE;2-(4,5-DIHYDROIMIDAZOL-2-YL)QUINOLINE HYDROCHLORIDE
• CAS NO: 187173-05-3
• Molecular Formula: C12H12ClN3
• Molecular Weight: 233.7
• Mol File: 187173-05-3.mol

Chemical Properties

• Boiling Point: 372.9°Cat760mmHg
• Flash Point: 179.3°C
• Appearance: white/solid
• Density: g/cm³
• Vapor Pressure: 9.33E-06mmHg at 25°C
• Storage Temp.: Desiccate at RT
• Solubility: ethanol: 1.2 mg/mL
• PKA: 9.87±0.40(Predicted)
• CAS DataBase Reference: 2-(4,5-DIHYDROIMIDAZOL-2-YL)QUINOLINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4,5-DIHYDROIMIDAZOL-2-YL)QUINOLINE HYDROCHLORIDE(187173-05-3)
• EPA Substance Registry System: 2-(4,5-DIHYDROIMIDAZOL-2-YL)QUINOLINE HYDROCHLORIDE(187173-05-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 187173-05-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(4,5-Dihydroimidaazol-2-y)quinoline hydrochloride is used as a receptor ligand for the I2 receptors, which are involved in various physiological processes. Its interaction with these receptors has been found to have potential therapeutic applications.
Used in Pain Management:
In the field of pain management, BU224 is used as an antinociceptive agent for the treatment of pain. Its action on the I2 receptors helps in reducing pain perception and providing relief to patients suffering from various types of pain.
Used in Psychiatry:
2-(4,5-Dihydroimidaazol-2-yl)quinoline hydrochloride is also used as an antidepressant-like agent in rodents. Its interaction with the I2 receptors may contribute to the modulation of mood and the alleviation of depressive symptoms, making it a potential candidate for the development of new antidepressant medications.

Biological Activity

High affinity ligand for the imidazoline I 2 binding site (K i = 2.1 nM). Putative I 2 antagonist; antagonizes the effects of imidazoline ligands on morphine antinociception. Produces ipsiversive rotational behavior in rats with a full 6-OHDA lesion of the nigrostriatal tract.

InChI:InChI=1/C12H11N3.ClH/c1-2-4-10-9(3-1)5-6-11(15-10)12-13-7-8-14-12;/h1-6H,7-8H2,(H,13,14);1H

Upstream product

• 1436-43-7 quinoline-2-carbonitrile 
• 107-15-3 ethylenediamine 
• 5470-96-2 quinoline 2-carbaldehyde 

Relevant articles and documents

Iridium-catalyzed chemoselective transfer hydrogenation of α, β-unsaturated ketones to saturated ketones in water

A chemoselective iridium-catalyzed transfer hydrogenation of α, β-unsaturated ketones was realized in water. The C[dbnd]C double bonds of 2-benzylidene indanones and analogues were hydrogenated exclusively catalyzed by an iridium complex (0.1 mol%) bearin

Iridium-catalyzed highly chemoselective and efficient reduction of nitroalkenes to nitroalkanes in water

An iridium-catalyzed highly chemoselective and efficient transfer hydrogenation reduction of structurally diverse nitroalkenes was realized at very low catalyst loading (S/C = up to 10000 or 20?000), using formic acid or sodium formate as a traceless hydride donor in water. Excellent functionality tolerance is also observed. The turnover number and turnover frequency of the catalyst reach as high as 18?600 and 19?200 h-1, respectively. An inert atmosphere protection is not required. The reactivities of nitroalkenes are dependent on their substitution pattern, and the pH value is a key factor to accomplish the complete conversion and excellent chemoselectivity. Purification of products is achieved by simple extraction without column chromatography. The reduction procedure is facilely amplified to 10 g scale at 10?000 S/C ratio. The potential of this green reduction in enantioselective hydrogenation has been demonstrated.

Ultrasound promoted synthesis of 2-imidazolines in water: A greener approach toward monoamine oxidase inhibitors

A series of sixteen 2-substituted-2-imidazolines (where the substituent R = Ph, Me-4-Ph; MeO-4-Ph; (MeO)2-3,4-Ph; (MeO)3-3,4,5-Ph; Ph-4-O-C(O)-Ph; Cl-4-Ph; Cl-2-Ph; Cl2-2,4-Ph; NO2-4-Ph; NO2-3-Ph; Naphth-2-yl; Fur-2-yl; Benzofur-2-yl; Pyridin-2-yl; Quinolin-2-yl) has been synthesized from the reaction of the substituted-aldehydes and ethylenediamine by ultrasound irradiation with NBS in an aqueous medium in high yields (80-99%). The 2-imidazoline ability to inhibit the activity of the A and B isoforms of monoamine oxidase (MAO) was investigated and some of them showed potent and selective MAO inhibitory activity especially for the MAO-B isoform and could become promising candidates for future development.

Synthesis and pharmacological evaluation of imidazoline sites I1 and I2 selective ligands

Several series of 2-aryl or heterocyclic-imidazoline compounds have been prepared and evaluated in vitro as imidazoline sites (I1 and I2) and α-adrenergic (α1 and α2) receptor ligands. Their pKi values indicate that linkage of the imidazoline moiety at the 2-position with an aromatic substituent dramatically decreases α-adrenergic affinity. I1 sites are more accessible by phenyl imidazolines substituted by a methyl or a methoxy group at the ortho or meta position. Indeed, 2-(2′-methoxyphenyl)-imidazoline (17) is one of the best I1 ligands ever reported (pKi=8.53 and I1/I2>3388). On the other hand, I2 selectivity increases in the presence of a methyl group in the para position. The original compound, 2-(3′-fluoro-4′-tolyl)-imidazoline (31) is a new potent ligand for the I2 sites with high selectivity (pKi=8.53 and I2/I1>3388). Copyright