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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
Número MDL:
MFCD01861180
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
24724384
NACRES:
NA.77

Nivel de calidad

100

Ensayo

≥98% (HPLC)

Formulario

powder

condiciones de almacenamiento

desiccated

color

white

solubilidad

DMSO: >6 mg/mL
H2O: insoluble

temp. de almacenamiento

2-8°C

cadena SMILES

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)

Clave InChI

AJFFBPZYXRNAIC-UHFFFAOYSA-N

Información sobre el gen

rat ... Cnr1(25248)

Aplicación

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

Acciones bioquímicas o fisiológicas

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

Características y beneficios

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.

Pictogramas

Skull and crossbones
GHS06

Palabra de señalización

Danger

Frases de peligro

H300,H315,H319,H335

Clasificaciones de peligro

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

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

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

Elija entre una de las versiones más recientes:

Certificados de análisis (COA)

Lot/Batch Number
0000383609
0000383609
0000162107
0000108647

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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

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
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
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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