614726-85-1

Basic information

• Product Name: 1H-Pyrazole-3-carboxamide, 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-
• Synonyms: 5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid amide;5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide;AM4113;5-(4-chlorophenyl)-1-(2,4-dichloroohenyl)-4-methyl-1H-pyrazole-3-carboxylic acid amide
• CAS NO: 614726-85-1
• Molecular Formula: C17H12Cl3N3O
• Molecular Weight: 380.661
• Mol File: 614726-85-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 185 - 186 °C
• CAS DataBase Reference: 1H-Pyrazole-3-carboxamide, 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazole-3-carboxamide, 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-(614726-85-1)
• EPA Substance Registry System: 1H-Pyrazole-3-carboxamide, 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-(614726-85-1)

Safety Data

• Hazardous Substances Data: 614726-85-1(Hazardous Substances Data)

Usage

Uses

AM4113 is a novel cannabinoid CB1 receptor neutral antagonist and reverses the effects of the CB1 agonist AM411. CB1 antagonists like AM4113 are used in the development of treatment for diseases associated with neuronal dendritic abnormalities

Biological Activity

am4113, a pyrazole analog structurally related to sr141716 and am251, is a novel cannabinoid cb1 neutral antagonist. am4113 suppressed food intake and food-reinforced behavior in rats.

in vitro

am4113 was able to bind with high affinity to cb1 receptors, exhibiting 100-fold selectivity for cb1 against cb2 receptors. the ki value for cb1 was 0.897 ± 0.44 nm, while the ki value for hcb2 was 92 ± 6.9 nm [1].

in vivo

in rats, treatment with am4113 (2.0 and 4.0 mg/kg) attenuated the am411-induced locomotor suppression and analgesia. in addition, 4.0 mg/kg am4113 alone significantly suppressed locomotor activity when compared with vehicle. am4113 dose-dependently decreased lever pressing on an fr1 schedule. am4113 produced conditioned taste avoidance and suppression of ingestive (hedonic) taste reactivity scores in a dose-dependent manner [1]. am4113 didn’t induce signs of nausea [1].

references

[1] sink k s, mclaughlin p j, wood j a t, et al. the novel cannabinoid cb1 receptor neutral antagonist am4113 suppresses food intake and food-reinforced behavior but does not induce signs of nausea in rats[j]. neuropsychopharmacology, 2008, 33(4): 946-955.

Upstream product

• 162758-35-2 rimonabant acid 
• 6285-05-8 4'-chloropropiophenone 
• 158941-22-1 ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylate 
• 169544-41-6 4-(4-chlorophenyl)-3-methyl-2,4-dioxobutyric acid ethyl ester 
• 168273-05-0 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl chloride 
• 168272-78-4 5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid methyl ester 
• 124-41-4 sodium methylate 

Downstream Products

• 1072113-14-4 N-(tert-butylcarbamoyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1072113-13-3 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(isopropylcarbamoyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1072113-00-8 5-(4-chlorophenyl)-N-(cyclobutanecarbonyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1072113-08-6 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(2-ethylhexanoyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1072113-12-2 5-(4-chlorophenyl)-N-(cyclohexylmethylcarbamoyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1072113-16-6 N-(benzylcarbamoyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1072113-18-8 butyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl carbamate 
• 1072113-03-1 N-butyryl-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1072113-04-2 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-isobutyryl-4-methyl-1H-pyrazole-3-carboxamide 
• 1072113-02-0 N-acetyl-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1072113-10-0 5-(4-chlorophenyl)-N-(cyclohexylcarbamoyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1072113-20-2 neopentyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonylcarbamate 
• 1072113-19-9 tert-butyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonylcarbamate 
• 1072113-15-5 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(phenylcarbamoyl)-1H-pyrazole-3-carboxamide 

Relevant articles and documents

"Photo-Rimonabant": Synthesis and Biological Evaluation of Novel Photoswitchable Molecules Derived from Rimonabant Lead to a Highly Selective and Nanomolar " Cis-On" CB1R Antagonist

Human cannabinoid receptor type 1 (hCB1R) plays important roles in the regulation of appetite and development of addictive behaviors. Herein, we describe the design, synthesis, photocharacterization, molecular docking, and in vitro characterization of "photo-rimonabant", i.e., azo-derivatives of the selective hCB1R antagonist SR1411716A (rimonabant). By applying azo-extension strategies, we yielded compound 16a, which shows marked affinity for CB1R (Ki (cis form) = 29 nM), whose potency increases by illumination with ultraviolet light (CB1R Kitrans/cis ratio = 15.3). Through radioligand binding, calcium mobilization, and cell luminescence assays, we established that 16a is highly selective for hCB1R over hCB2R. These selective antagonists can be valuable molecular tools for optical modulation of CBRs and better understanding of disorders associated with the endocannabinoid system.

Synthesis and structure-activity relationship of novel diarylpyrazole imide analogues as CB1 cannabinoid receptor ligands

A myriad of research groups have been engaged in searching for novel CB1 receptor antagonists, since SR141716A (rimonabant), a CB1 receptor antagonist, was discovered for an obesity treatment. In this research, extended series, based on the 1,5-diarylpyra

Tetrazole-biarylpyrazole derivatives as cannabinoid CB1 receptor antagonists

Cannabinoid CB1 receptors have been the focus of extensive studies since the first clinical results of rimonabant (SR141716) for the treatment of obesity and related metabolic disorders were reported in 2001. To further evaluate the properties of CB recep