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A6226

Sigma-Aldrich

AM251

>98% (HPLC), solid, cannabinoid receptor (CB1) antagonist

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C22H21N4OCl2I
CAS Number:
183232-66-8
Molecular Weight:
555.24
MDL number:
MFCD01861181
UNSPSC Code:
12352200
PubChem Substance ID:
24891069
NACRES:
NA.77

product name

AM251, >98% (HPLC), solid

Quality Level

100

Assay

>98% (HPLC)

form

solid

color

white

solubility

DMSO: >10 mg/mL
H2O: insoluble

originator

Sanofi Aventis

SMILES string

Cc1c(nn(-c2ccc(Cl)cc2Cl)c1-c3ccc(I)cc3)C(=O)NN4CCCCC4

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)

InChI key

BUZAJRPLUGXRAB-UHFFFAOYSA-N

Gene Information

mouse ... Cnr1(12801) , Cnr2(12802)
rat ... Cnr1(25248)

Application

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.

Biochem/physiol Actions

AM251 is a CB1 cannabinoid receptor antagonist.

Features and Benefits

This compound is featured on the Cannabinoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Sanofi Aventis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Other Notes

Salt content may vary.

Hazard Statements

H413

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nozomi Asaoka et al.
The Journal of toxicological sciences, 41(6), 813-816 (2016-11-18)
N-[[1-(5-fluoropentyl)-1H-indazol-3-yl]carbonyl]-3-methyl-D-valine methyl ester (5F-ADB) is one of the most potent synthetic cannabinoids and elicits severe psychotic symptoms in humans, sometimes causing death. To investigate the neuronal mechanisms underlying its toxicity, we examined the effects of 5F-ADB on midbrain dopaminergic and
Mahsa Shahidi et al.
The Journal of general virology, 95(Pt 11), 2468-2479 (2014-07-24)
Direct-acting antivirals have significantly improved treatment outcomes in chronic hepatitis C (CHC), but side effects, drug resistance and cost mean that better treatments are still needed. Lipid metabolism is closely linked with hepatitis C virus (HCV) replication, and endocannabinoids are
Elahe Mohammadi Vosough et al.
Life sciences, 232, 116670-116670 (2019-07-23)
Migraine is a neurological debilitating disorder. Previous studies have shown that cannabinoid receptor agonists have analgesic effects in various models of pain. In this study, therefore, we investigated anti-nociceptive effects of WIN 55,212-2, and the role of either CB1 or
Christine Gebhardt et al.
Neurobiology of learning and memory, 136, 1-12 (2016-11-05)
Recently we have shown that capsaicin attenuates the strength of LTP in the lateral amygdala (LA) and demonstrated that this effect is mediated by the transient receptor potential (TRP) channel TRPV1. Here we further show that capsaicin, which is thought
Ramy Khella et al.
Psychopharmacology, 231(16), 3071-3087 (2014-04-08)
Whilst cannabinoid CB2 receptors were thought to exist predominantly in immune cells in the periphery, the recent discovery of CB2 receptors in the brain has led to an increased interest in the role of these central CB2 receptors. Several studies
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