183232-66-8 Usage
Description
AM251 is a cannabinoid 1 (CB1) receptor antagonist, belonging to the biarylpyrazole class of compounds. It selectively binds to CB1 receptors with high affinity and has been widely studied for its potential applications in various fields. AM251 exhibits a range of biological activities, including effects on spatial memory, food intake, body weight, and cell cycle regulation.
Uses
Used in Neuroscience Research:
AM251 is used as a research tool for studying the role of CB1 receptors in the central nervous system. It helps researchers understand the interactions between hippocampal neurons and spatial memory in mice, providing insights into the potential therapeutic applications for cognitive disorders.
Used in Drug Development:
As an inhibitor of CB1 receptors, AM251 is used in the development of drugs targeting the endocannabinoid system. Its antagonistic properties make it a valuable compound for investigating the potential therapeutic effects of modulating CB1 receptor activity in various conditions.
Used in Obesity and Eating Disorder Research:
AM251 is used as a research compound to study its effects on fasting-induced food intake and body weight gain in mice. This helps researchers understand the role of CB1 receptors in appetite regulation and the potential for developing treatments for obesity and eating disorders.
Used in Cancer Research:
AM251 is used as a research tool to investigate its effects on cell cycle arrest and apoptosis in cancer cells, such as A375 human melanoma cells. This contributes to the understanding of the potential role of CB1 receptor antagonists in cancer therapy.
Used in Cell Signaling and Epithelial-to-Mesenchymal Transition (EMT) Research:
AM251 is used to study its effects on TGF-β1-induced EMT, SMAD2/3 and p38 MAPK activation, and the expression of EMT-related transcription factors in HK-2 renal tubule epithelial cells. This research helps to elucidate the role of CB1 receptors in cellular processes and the potential for targeting these receptors in disease treatment.
Chemical Properties:
AM251 is a white to off-white solid, which is an important characteristic for its formulation and stability in various applications.
Biological Activity
Potent CB 1 receptor antagonist (IC 50 = 8 nM, K i = 7.49 nM) that displays 306-fold selectivity over CB 2 receptors. Also potent GPR55 agonist (EC 50 = 39 nM). Also available as part of the Cannabinoid CB 1 Receptor Tocriset? .
Biochem/physiol Actions
AM251 is a CB1 cannabinoid receptor antagonist.
References
1) Gatley et al. (1996), 123I-labeled AM251: a radioiodinated ligand which binds in vivo to mouse brain cannabinoid CB1 receptors; Eur. J. Pharmacol., 307 331
2) Gatley et al. (1997), Binding of the non-classical cannabinoid CP 55,940 and the diarylpyrazole AM251 to rodent brain cannabinoid receptors; Life Sci., 61 191
3) Pertwee et al. (2005), Inverse agonism and neutral antagonism at cannabinoid CB1 receptors; Life Sci., 76 1307
4) Shearman et al. (2003), Antidepressant-like and anorectic effects of the cannabinoid CB1 receptor inverse agonist AM251 in mice; behave. Pharmacol., 14 573
5) Ryberg et al. (2007), The orphan receptor GPR55 is a novel cannabinoid receptor; Br. J. Pharmacol., 152 1092
Check Digit Verification of cas no
The CAS Registry Mumber 183232-66-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,8,3,2,3 and 2 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 183232-66:
(8*1)+(7*8)+(6*3)+(5*2)+(4*3)+(3*2)+(2*6)+(1*6)=128
128 % 10 = 8
So 183232-66-8 is a valid CAS Registry Number.
InChI:InChI=1/C22H21Cl2IN4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-7-16(23)13-18(19)24)21(14)15-5-8-17(25)9-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)
183232-66-8Relevant articles and documents
A method for parallel solid-phase synthesis of Lodinated analogues of the CB1 receptor inverse agonist rimonabant
Spivey, Alan C.,Tseng, Chih-Chung,Jones, Teyrnon C.,Kohler, Andrew D.,Ellames, George J.
supporting information; experimental part, p. 4760 - 4763 (2009/12/27)
A method for the parallel solid-phase synthesis (SPS) of iodinated analogues of Sanofi-Aventis' type 1 cannabinoid (CB1) receptor Inverse agonist rimonabant (acomplia) has been developed. The method allows the synthesis of a range of C3 amide/hydrazide derivatives from a resin-bound C3 ester precursor. The C-Ge linkage to the Hypogel-200 resin Is stable to the diversification conditions but allows ipsoiododegermylative cleavage using Nal/NCS even for the products containing the oxidatively labile hydrazide moiety.
Preparation of iodine-123 labeled AM251: A potential spect radioligand for the brain cannabinoid CB1 receptor
Lan, Ruoxi,Gatley, S. John,Makriyannis, Alexandros
, p. 875 - 881 (2007/10/03)
We report the synthesis and labeling with iodine-123 of N-(piperidin-1-yl)-5-(4-iodophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole -3-carboxamide (AM251). This compound is an anlog of the recently described cannabinoid receptor antagonist, R141716A,
