119520-06-8

Basic information

• Product Name: Zilpaterol hydrochloride
• Synonyms: Zilpaterol Hcl;(+/1)-trans-4,5,6,7-Tetrahydro-7-hydroxy-6-(isopropylamino)imidazo[4,5,1-jk]-[1]benzazepin-2(1H)-one hydrochloride;Zilpaterol hydrochloride;paterol hydrochloride;IMidazo[4,5,1-jk][1]benzazepin-2(1H)-one,4,5,6,7-tetrahydro-7-hydroxy-6-[(1-Methylethyl)aMino]-, hydrochloride (1:1),(6R,7R)-rel-;(6RS,7RS)-4,5,6, 7-Tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[ 4,5,1-jk][1]benzazepin-2(1H)-one hydrochloride;Zilpaterol hydrochloride (relstereo);GIEFXLLRTJNFGT-JZKFLRDJSA-N
• CAS NO: 119520-06-8
• Molecular Formula: C14H19N3O2.HCl
• Molecular Weight: 297.78
• EINECS: 601-619-4
• Mol File: 119520-06-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Zilpaterol hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Zilpaterol hydrochloride(119520-06-8)
• EPA Substance Registry System: Zilpaterol hydrochloride(119520-06-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 119520-06-8(Hazardous Substances Data)

Usage

Description

Zilpaterol is a β-adrenergic receptor agonist that putatively through activation of protein kinase A increases protein synthesis in skeletal muscle fibers, as well as reduces lipogenesis and increases lipolysis in adipose tissues. It was approved by the FDA in 2006 as a veterinary food additive for the purpose of increasing lean body weight and improving feed efficiency in commercial beef cattle.

Definition

Zilpaterol hydrochloride, (±)-trans-4,5,6,7-tetrahydro-7-hydroxy-6-(isopropylamino) imidazo[4,5,1-jk]-[1]benzazepin-2(1H)-one hydrochloride; (zilpaterol HCl; CAS No. 119520- 06-8), is a β2-adrenoreceptor agonist repartitioning agent (FAO, 2013). It is used to increase rate of body weight gain, improve feed efficiency and increase carcass muscle ratio in cattle fed in confinement before slaughter . There are four enantiomers of zilpaterol HCl. The product in use is racemic trans-zilpaterol HCl, a mixture of the (6R,7R) and (6S,7S) enantiomers.

Materials Uses

Zilpaterol hydrochloride is marketed as a compound that will increase rate of BW gain, improve feed efficiency, and increase carcass leanness in cattle fed in confinement systems. Zilpaterol hydrochloride has also been shown to increase weight of gross primal and boneless closely trimmed primals, and boneless closely trimmed retail cuts as a percentage of carcass weight, when carcass weights were held constant (Plascencia et al., 1999). Additionally, slaughtering a lot of cattle on the same date can be problematic and may require longer than expected withdrawal periods and may result in withdrawal periods in excess of 3 d.

Solubility in organics

Zilpaterol hydrochloride is very soluble in water and in other aqueous media (about 50% of product dissolved) at different pH values (1–10). It is only slightly soluble in methanol (about 3%) and practically insoluble in most organic solvents (<0.1%) such as ethanol, acetone, ethyl-acetate, isopropyl ether, hexane, toluene, chloroform, dichloromethane or n-octanol.

InChI:InChI=1/C14H19N3O2.ClH/c1-8(2)15-11-6-7-17-12-9(13(11)18)4-3-5-10(12)16-14(17)19;/h3-5,8,11,13,15,18H,6-7H2,1-2H3,(H,16,19);1H/t11-,13-;/m1./s1

Upstream product

• 1021987-10-9 6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]-benzazepin-2[1H]-one 
• 67-64-1 acetone 
• 3273-68-5 4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid 
• 1021910-67-7 chloro 2,3-dihydro-2-oxo-1H-benzimidazol-1-butanoate 
• 92260-82-7 4,5,6,7-tetrahydro-6-hydroxyimino-imidazo[4,5,1-jk]-[1]-benzazepine-2,7(1H,6H)-dione 
• 92260-81-6 5,6-dihydroimidazo[4,5,1-jk][1]benzazepin-2,7-[1H,4H]-dione 
• 1001395-75-0 (6S,7S)-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[4,5,1-jk][1]benzazepin-2(1H)-one 
• 1019837-22-9 (6R,7R)-6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]-benzazepin-2[1H]-one 

Relevant articles and documents

A method for synthesizing uneven handkerchief Trow hydrochloric acid

An embodiment of the invention provides a method for synthesizing zilpaterol Hydrochloride, belonging to a medical synthesizing technology field. The method comprises: resolving 4,5,6,7-tetrahydro-6- hydroximino-imidazo[4,5,1-jk]-[1] benzoaza-2,7(1H,6H)-dione into a mixed solvent of methanol and DMF, adding the mixed solvent and a first catalyst together into a reactor, displacing air in the reactor through nitrogen and hydrogen, filling hydrogen into the reactor, stirring and raising temperature until the temperature is 30-50 DEG C and hydrogen pressure is 1-10 MPa, reacting for 4-24h, filtrating and recovering the catalyst after the reaction; and processing the filtrate through enamine forming, hydrogenation reduction, salt forming, crystallization and hydrochloride forming to obtain the zilpaterol Hydrochloride. The synthetic method of the zilpaterol Hydrochloride utilizes methanol and DMF as reaction solvents to raise a reaction rate, and the method provided by the invention can reduce hydrogenation reaction time below 12h.

PROCESS FOR MAKING A CRYSTALLINE ZILPATEROL SALT

This invention generally relates to processes for making a crystalline zilpaterol salt, particularly zilpaterol hydrochloride. This invention also relates to methods of treatment using a crystalline zilpaterol salt prepared in accordance with this invention to increase the rate of weight gain, improve feed efficiency, and/or increase carcass leanness in livestock, poultry, and fish.

Synthesis and pharmacological characterization of β2- adrenergic agonist enantiomers: Zilpaterol

The β-adrenergic agonist 1 (zilpaterol) is used as production enhancer in cattle. Binding experiments of separated enantiomers on recombinant human β2-adrenergic and μ-opioid receptors and functional studies showed that the (-)-1 enantiomer acc