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;WIZ degrader 9;AM251, 10 mM in DMSO;CB1 antagonist AM251;AM 251 (pharmaceutical)
- CBNumber:
- CB2169367
- Molecular Formula:
- C22H21Cl2IN4O
- Molecular Weight:
- 555.24
- MDL Number:
- MFCD01861181
- MOL File:
- 183232-66-8.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| 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 |
| EWG's Food Scores | 1 |
| FDA UNII | 3I4FA44MAI |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H319-H335 | |||||||||
| Precautionary statements | P261-P305+P351+P338 | |||||||||
| PPE | dust mask type N95 (US), Eyeshields, Gloves | |||||||||
| 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 | |||||||||
| NFPA 704 |
|
AM 251 price More Price(65)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | A6226 | AM 251 >98% (HPLC), solid | 183232-66-8 | 10mg | $308 | 2026-04-30 | Buy |
| Sigma-Aldrich | A6226 | AM 251 >98% (HPLC), solid | 183232-66-8 | 50mg | $1050 | 2026-04-30 | Buy |
| Sigma-Aldrich | 5.04275 | CB1 antagonist AM251 - CAS 183232-66-8 - Calbiochem | 183232-66-8 | 5MG | $228 | 2022-05-15 | Buy |
| TCI Chemical | A3151 | AM 251 >97.0%(HPLC) | 183232-66-8 | 10mg | $120 | 2026-04-30 | Buy |
| TCI Chemical | A3151 | AM 251 >97.0%(HPLC) | 183232-66-8 | 50mg | $419 | 2026-04-30 | Buy |
AM 251 Chemical Properties, Uses, 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
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| 3B Pharmachem (Wuhan) International Co.,Ltd. | 18930552037 | 3bsc@sina.com | China | 15813 | 69 |
| Ascent Scientific | 4401179829988 | customerservice@ascentscientific.co.uk | United Kingdom | 279 | 60 |
| VDM Biochemicals | 0330-2528181 | sales@vdmbio.com | United States | 510 | 64 |
| Chemsky（shanghai）International Co.,Ltd. | 021-50135380 | shchemsky@sina.com | China | 32273 | 50 |
| Dalian Meilun Biotech Co., Ltd. | 0411-62910999 13889544652 | sales@meilune.com | China | 4765 | 58 |
| Haoyuan Chemexpress Co., Ltd. | 021-58950125 | info@chemexpress.com | China | 7545 | 61 |
| TOKYO CHEMICAL INDUSTRY CO., LTD. | 03-36680489 | Sales-JP@TCIchemicals.com | Japan | 28364 | 80 |
| TCI Europe | 320-37350700 | sales@tcieurope.eu | Europe | 23654 | 75 |
| TCI AMERICA | 800-4238616 | sales@tciamerica.com | Americas | 23636 | 75 |
