| Identification | Back Directory | [Name]
ACEA | [CAS]
220556-69-4 | [Synonyms]
ACEA
2'-CHLORO-AEA
ACEA (ethanol solution)
ARACHIDONYL-2-CHLOROETHYLAMIDE
ARACHIDONYL-2'-CHLOROETHYLAMIDE
ARACHIDONOYL 2'-CHLOROETHYLAMIDE
ARACHIDONYL-2'-CHLOROETHYLAMIDE HYDRATE
N-(2-CHLOROETHYL)-5Z,8Z,11Z,14Z-EICOSATETRAENAMIDE
(5Z,8Z,11Z,14Z)-N-(2-Chloroethyl)-5,8,11,14-eicosatetraenaMide
5,8,11,14-Eicosatetraenamide, N-(2-chloroethyl)-, (5Z,8Z,11Z,14Z)- | [Molecular Formula]
C22H36ClNO | [MDL Number]
MFCD02683581 | [MOL File]
220556-69-4.mol | [Molecular Weight]
365.98 |
| Hazard Information | Back Directory | [Description]
Arachidonoyl 2-chloroethylamide (ACEA) is a potent and selective cannabinoid (CB) receptor 1 agonist with Ki values of 1.4 and >2,000 nM for CB1 and CB2 receptors, respectively.1 In whole animal experiments, ACEA induces hypothermia in mice with the same efficacy as arachidonoyl ethanolamide (AEA; Item No. 90050), in spite of its higher affinity for the CB1 receptor. These data have been interpreted to indicate that ACEA may be a substrate for fatty acid amide hydrolase (FAAH), and thus only transiently available in whole animal experiments.2 | [Uses]
A synthetic agonist of the cannabinoid receptor 1 (CB1R). ACEA is considered to be a selective cannabinoid agonist as it binds primarily to the CB1R and has low affinity to the cannabinoid receptor 2
(CB2R). | [Definition]
ChEBI: Arachidonyl-2'-chloroethylamide is a fatty amide obtained by the formal condensation of arachidonic acid with 2-chloroethanamine. It is a potent agonist of the CB1 receptor (Ki = 1.4 nM) and also has a low affinity for the CB2 receptor (Ki = 3100 nM). It has a role as a CB1 receptor agonist, a neuroprotective agent and a CB2 receptor agonist. It is an organochlorine compound, a secondary carboxamide, a fatty amide and a synthetic cannabinoid. It is functionally related to an arachidonic acid. | [Biological Activity]
Potent and highly selective CB 1 receptor agonist (K i = 1.4 nM). Displays > 1400-fold selectivity over CB 2 receptors. Active in vivo . Also available as part of the Cannabinoid CB 1 Receptor Tocriset™ . | [Biochem/physiol Actions]
Potent and selective neuronal CB1 cannabinoid receptor agonist. | [Enzyme inhibitor]
This synthetic CB1 receptor agonist and anandamide (N- arachidonylethanolamide) analogue (FW = 365.99 g/mol; CAS 220556-69-4; Symbol: ACEA) is a selective agonist of cannabinoid receptor-1 (Ki = 1.4 nM) but has low affinity to the cannabinoid receptor 2 (Ki = 3.1 μM). ACEA inhibits forskolin-induced cAMP accumulation in Chinese hamster ovary cells expressing the human CB1 receptor. It also increases the binding of [ 35 S]GTPgS to cerebellar membranes and inhibits electrically evoked contractions of the mouse vas deferens. ACEA produces hypothermia in mice, an effect that is inhibited by co-administration of the CB1 receptor antagonist SR141716A. | [storage]
Store at -20°C |
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Sigma-Aldrich
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