AM 251

ChemicalBook > CAS DataBase List > AM 251

Product Name: AM 251
CAS No.: 183232-66-8
Chemical Name: AM 251
Synonyms: AM AM;AM 251;CS-985;AM 251 NEW;AM-251 ,99%;AM251;AM-251;AM 251 (pharmaceutical);Inhibitor,AM251,AM 251,inhibit,Cannabinoid Receptor,AM-251;1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide;1-(2,4-DICHLOROPHENYL)-5-(4-IODOPHENYL)-4-METHYL-N-1-PIPERIDINYL-1 H-PYRAZOLE-3-CARBOXAMIDE
CBNumber: CB2169367
Molecular Formula: C22H21Cl2IN4O
Formula Weight: 555.24
MOL File: 183232-66-8.mol

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AM 251 Property

Melting point:: 195-196℃
Density: 1.65±0.1 g/cm3(Predicted)
storage temp.: Store at RT
solubility: DMSO: >10 mg/mL, soluble
form: solid
pka: 11.31±0.20(Predicted)
color: white
Stability:: Stable for 1 year as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
CAS DataBase Reference: 183232-66-8

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36
WGK Germany: 3
HS Code: 2933.39.6190

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: A6226
Product name: AM 251
Purity: >98% (HPLC), solid
Packaging: 10mg
Price: $279
Updated: 2024/03/01

Sigma-Aldrich

Product number: A6226
Product name: AM 251
Purity: >98% (HPLC), solid
Packaging: 50mg
Price: $951
Updated: 2024/03/01

Sigma-Aldrich

Product number: 5.04275
Product name: CB1 antagonist AM251 - CAS 183232-66-8 - Calbiochem
Packaging: 5MG
Price: $228
Updated: 2022/05/15

TCI Chemical

Product number: A3151
Product name: AM 251
Purity: >97.0%(HPLC)
Packaging: 10mg
Price: $190
Updated: 2024/03/01

TCI Chemical

Product number: A3151
Product name: AM 251
Purity: >97.0%(HPLC)
Packaging: 50mg
Price: $572
Updated: 2024/03/01

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AM 251 Chemical Properties,Usage,Production

Description

AM251 is a cannabinoid 1 (CB₁) receptor 1 antagonist. It binds to CB₁ receptors in rat forebrain membrane preparations (K_i = 7.5 nM) and is selective over CB₂ receptors in mouse spleen preparations (K_i = 2,290 nM) in radioligand binding assays. AM251 inhibits GTPγS binding induced by the CB receptor agonist CP 55,940 in HEK293 cells expressing human CB₁ receptors (EC₅₀ = 8 nM). AM251 (10 mg/kg) decreases immobility time in the forced swim test in wild-type but not CB₁ receptor-deficient mice. It reduces fasting-induced food intake and body weight gain in mice when administered at a dose of 30 mg/kg. AM251 also induces GTPγS binding in HEK293 cells expressing the orphan receptor GPR55 (EC₅₀ = 39 nM) and potentiates GABA-induced GABA_A receptor currents (EC₅₀ = 0.4 μM). It prevents TGF-β1-induced epithelial-to-mesenchymal transition (EMT), inhibits SMAD2/3 and p38 MAPK activation, and reduces the expression of EMT-related transcription factors in HK-2 renal tubule epithelial cells. AM251 induces cell cycle arrest at the G₂/M phase and apoptosis in A375 human melanoma cells.

Chemical Properties

White to Off-White Solid

Uses

Inhibitor of CB1 receptors. AM 251is a biarylpyrazole compound which has been considered for many years as the prototypical cannabinoid (CB) receptor antagonist

Uses

AM251, a CB₁ cannabinoid receptor antagonist, has been used in a study to determine its interaction with hippocampal neurons to enhance spatial memory in mice.

Definition

ChEBI: AM-251 is a carbohydrazide obtained by formal condensation of the carboxy group of 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid with the amino group of 1-aminopiperidine. An antagonist at the CB1 cannabinoid receptor. It has a role as a CB1 receptor antagonist, an apoptosis inducer, an antidepressant and an antineoplastic agent. It is a member of pyrazoles, a dichlorobenzene, an organoiodine compound, an amidopiperidine and a carbohydrazide.

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.

storage

Room temperature

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

AM 251 Preparation Products And Raw materials

Raw materials

Preparation Products

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AM 251 Suppliers

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183232-66-8, AM 251Related Search:

Olaparib 5-(1,1-DIMETHYLHEPTYL)-2-[5-HYDROXY-2-(3-HYDROXYPROPYL)CYCLOHEXYL]PHENOL ACEA AM 630 2-AG BML-190 ACPA NOLADIN ETHER MEAD ACID ETHANOLAMIDE R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE ARACHIDONIC ACID-(2-AMINOETHYL)-ESTER HYDROCHLORIDE ARACHIDONAMIDE Arachidonyl-2′-chloroethylamide hydrate Pyrazole-3-carboxamide N-Aminopiperidine hydrochloride AM 251 AM 251 TRIFLUOROACETATE AM 251 TRIFLUOROACETATE SALT

AM 251

1-(2,4-DICHLOROPHENYL)-5-(4-IODOPHENYL)-4-METHYL-N-1-PIPERIDINYL-1 H-PYRAZOLE-3-CARBOXAMIDE

N-(PIPERIDIN-1-YL)-5-(4-IODOPHENYL)-1-(2,4-DICHLOROPHENYL)-4-METHYL-1H-PYRAZOLE-3-CARBOXAMIDE

AM-251 ,99%

CS-985

AM 251 NEW

AM 251 (pharmaceutical)

1H-Pyrazole-3-carboxamide, 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-1-piperidinyl-

1-(2,4-Dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-1-piperidinyl-1H-pyrazole-3-carboxamide AM251

AM251;AM-251

AM AM

1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide

Inhibitor,AM251,AM 251,inhibit,Cannabinoid Receptor,AM-251

183232-66-8

C22H21Cl2IN4O

C22H21N4OCl2I

Inhibitors

Cannabinoid receptor

Cannabinoid

Aromatics

Heterocycles

Cannabinoids