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A0980

Sigma-Aldrich

AM281

≥98% (HPLC)

Sinónimos:

1-(2,4-Dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-4-morpholinyl-1H-pyrazole-3-carboxamide, AM 281

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About This Item

Fórmula empírica (notación de Hill):
C21H19Cl2IN4O2
Número de CAS:
202463-68-1
Peso molecular:
557.21
MDL number:
MFCD01861180
UNSPSC Code:
12352200
PubChem Substance ID:
24724384
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white

solubility

DMSO: >6 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

Cc1c(nn(-c2ccc(Cl)cc2Cl)c1-c3ccc(I)cc3)C(=O)NN4CCOCC4

InChI

1S/C21H19Cl2IN4O2/c1-13-19(21(29)26-27-8-10-30-11-9-27)25-28(18-7-4-15(22)12-17(18)23)20(13)14-2-5-16(24)6-3-14/h2-7,12H,8-11H2,1H3,(H,26,29)

InChI key

AJFFBPZYXRNAIC-UHFFFAOYSA-N

Gene Information

rat ... Cnr1(25248)

Application

AM281 has been used as a cannabinoid 1 receptor antagonist:
  • to study its effects on memory deficit following naloxone-precipitated morphine withdrawal in mice
  • to study the role of CB1 receptor system in modulating acetaldehyde-induced effects in rats during the extinction-, relapse-, and conflict-experiments
  • to study its effect on scopolamine-induced memory deficit using object recognition paradigm
  • to block synthetic cannabinoid (HU210)-induced analgesia in the ventrolateral orbital cortex (VLO) to evaluate the effect of CB1 receptors on the VLO modulation of pain

Biochem/physiol Actions

AM281 is less lipophilic compared to its analog SR 141716A, a cannabinoid receptor antagonist. AM281 may prevent memory deficit post morphine withdrawal by inhibiting cannabinoid receptors in mice.
Potent and selective CB1 cannabinoid receptor antagonist/inverse agonist

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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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GW405833 hydrochloride ≥98% (HPLC), solid

Sigma-Aldrich

G1421

GW405833 hydrochloride

Arachidonylethanolamide ≥97.0% (TLC), oil

Sigma-Aldrich

A0580

Arachidonylethanolamide

2-Arachidonyl glycerol ~10 mg/mL, ≥98% (HPLC)

Sigma-Aldrich

A8973

2-Arachidonyl glycerol

Francisco Molina-Holgado et al.
Molecular and cellular neurosciences, 28(1), 189-194 (2004-12-21)
Cannabinoids (CBs) are neuroprotective in vivo and in vitro, but the mechanisms of their actions are unknown. The aim of this study was to elucidate the signaling pathways that mediate the protective effect of CBs on primary cultured neurons. The
A N Gifford et al.
Neuroscience letters, 238(1-2), 84-86 (1998-02-17)
The SPECT ligand AM 281, a less lipophilic analog of the cannabinoid receptor antagonist SR 141716A, robustly potentiated electrically-evoked release of acetylcholine from superfused hippocampal slices and prevented the inhibition of acetylcholine release by the cannabimimetic drug WIN 55212-2. These
Yuwei Wu et al.
Neuroscience letters, 736, 135286-135286 (2020-08-04)
The prefrontal ventrolateral orbital cortex (VLO) is involved in antinociception. It has been found that dopamine receptors, adrenoceptors, serotonin receptors and μ-opioid receptors are involved in this effect through direct/indirect activation of the VLO output neurons. However, the effect of
Golnaz Vaseghi et al.
Basic & clinical pharmacology & toxicology, 111(3), 161-165 (2012-03-21)
Morphine withdrawal leads to the activation of endocannabinoid system and cognitive deficits. The aim of this study was to evaluate the effects of AM281, a cannabinoid antagonist/inverse agonist, on memory deficit following naloxone-precipitated morphine withdrawal in mice. Male mice were
Angel Arevalo-Martin et al.
PloS one, 7(11), e49057-e49057 (2012-11-16)
Spinal cord injury (SCI) induces a cascade of processes that may further expand the damage (secondary injury) or, alternatively, may be part of a safeguard response. Here we show that after a moderate-severe contusive SCI in rats there is a
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