ChemicalBook > CAS DataBase List > AM 251

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;AM251, 10 mM in DMSO;CB1 antagonist AM251;AM 251 (pharmaceutical);Inhibitor,AM251,AM 251,inhibit,Cannabinoid Receptor,AM-251
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.
InChI
1S/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)
InChIKey
BUZAJRPLUGXRAB-UHFFFAOYSA-N
SMILES
Cc1c(nn(-c2ccc(Cl)cc2Cl)c1-c3ccc(I)cc3)C(=O)NN4CCCCC4
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
Storage Class
11 - Combustible Solids
Hazard Classifications
Aquatic Chronic 4
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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
$287
Updated
2025/07/31
Sigma-Aldrich
Product number
A6226
Product name
AM 251
Purity
>98% (HPLC), solid
Packaging
50mg
Price
$978
Updated
2025/07/31
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
$171
Updated
2025/07/31
TCI Chemical
Product number
A3151
Product name
AM 251
Purity
>97.0%(HPLC)
Packaging
50mg
Price
$515
Updated
2025/07/31
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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 (Ki = 7.5 nM) and is selective over CB2 receptors in mouse spleen preparations (Ki = 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 GABAA 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] S.JOHN GATLEY . 123I-labeled AM251: a radioiodinated ligand which binds in vivo to mouse brain cannabinoid CB1 receptors[J]. European journal of pharmacology, 1996, 307 3: Pages 331-338. DOI:10.1016/0014-2999(96)00279-8
[2] S JOHN GATLEY . Binding of the non-classical cannabinoid CP 55,940, and the diarylpyrazole AM251 to rodent brain cannabinoid receptors[J]. Life sciences, 1997, 61 14: Pages PL191-PL197. DOI:10.1016/s0024-3205(97)00690-5
[3] PERTWEE R G. Inverse agonism and neutral antagonism at cannabinoid CB1 receptors[J]. Life sciences, 2005, 76 12: Pages 1307-1324. DOI:10.1016/j.lfs.2004.10.025
[4] L P SHEARMAN. Antidepressant-like and anorectic effects of the cannabinoid CB1 receptor inverse agonist AM251 in mice.[J]. Behavioural Pharmacology, 2003, 14 8: 573-582. DOI:10.1097/00008877-200312000-00001
[5] E RYBERG. The orphan receptor GPR55 is a novel cannabinoid receptor[J]. British Journal of Pharmacology, 2009, 152 7: 1092-1101. DOI:10.1038/sj.bjp.0707460

AM 251 Preparation Products And Raw materials

Raw materials

Preparation Products

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AM 251 Suppliers

Americas 1 Canada 1 China 103 Europe 2 Germany 3 India 2 Japan 1 Switzerland 2 The Netherlands 1 United Kingdom 5 United States 23 Global 144
J & K SCIENTIFIC LTD.
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18210857532; 18210857532
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86-10-82849933
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jkinfo@jkchemical.com
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China
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3B Pharmachem (Wuhan) International Co.,Ltd.
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821-50328103-801 18930552037
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86-21-50328109
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3bsc@sina.com
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China
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Ascent Scientific
Tel
4401179829988
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4402030 700 369
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customerservice@ascentscientific.co.uk
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United Kingdom
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VDM Biochemicals
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0330-2528181
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0330-2528171
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sales@vdmbio.com
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United States
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Chemsky（shanghai）International Co.,Ltd.
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021-50135380
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shchemsky@sina.com
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China
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BOC Sciences
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1-631-485-4226; 16314854226
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info@bocsci.com
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United States
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Dalian Meilun Biotech Co., Ltd.
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0411-62910999 13889544652
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sales@meilune.com
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Haoyuan Chemexpress Co., Ltd.
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021-58950125
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(86) 21-58955996
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TOKYO CHEMICAL INDUSTRY CO., LTD.
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03-36680489
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03-3668-0520
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Sales-JP@TCIchemicals.com
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TCI Europe
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320-37350700
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+32 (0)37350701
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sales@tcieurope.eu
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Europe
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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
  • AM251, 10 mM in DMSO
  • CB1 antagonist AM251
  • 183232-66-8
  • C22H21Cl2IN4O
  • C22H21N4OCl2I
  • Inhibitors
  • Cannabinoid receptor
  • Cannabinoid
  • Aromatics
  • Heterocycles
  • Cannabinoids