Basic information
- CAS
220556-69-4- Standard SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCCl- InChIKey
SCJNCDSAIRBRIA-DOFZRALJSA-N- Molecular formula
- C22H36ClNO
- Average molar mass
- 366 g/mol
- Monoisotopic mass
- 365.24854245
Overview
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 CB2 receptor agonist, a CB1 receptor agonist and a neuroprotective agent. It is a secondary carboxamide, a fatty amide, an organochlorine compound and a synthetic cannabinoid. It is functionally related to an arachidonic acid.
Names & identifiers
- Preferred name
- Arachidonyl-2-chloroethylamide
- IUPAC
- (5Z,8Z,11Z,14Z)-N-(2-chloroethyl)icosa-5,8,11,14-tetraenamide
- English name
- ACEA
- Molecular formula
- C22H36ClNO
- Molecular weight
- 365.98
Names & synonyms
arachidonyl-2-chloroethylamideArachidonyl-2'-chloroethylamide(5Z,8Z,11Z,14Z)-N-(2-chloroethyl)icosa-5,8,11,14-tetraenamideACEA cpdCHEBI:191854N-(2-chloroethyl)-5,8,11,14-eicosatetraenamideRefChem:113680acea220556-69-4CHEMBL151167MFCD02683581ACEA; 2'-chloro-AEA
Show more names
2'-CHLORO-AEAACEA (ethanol solution)Terfenadine Impurity 23Arachidonoyl 2'-ChloroethylamideACEA, 5mg/ml solution in ethanolEicosapentaenoic Acid Impurity 51ARACHIDONYL-2'-CHLOROETHYLAMIDE HYDRATE
N-(2-chloroethyl)icosa-5,8,11,14-tetraenamideC22H36ClNOArachidonoyl-2-chloroethylamideN-(2-Chloroethyl)-5Z,8Z,11Z,14Z-eicosatetraenamideGTPL738orb1692278SCHEMBL1517676DTXSID60274346
Database identifiers
- CAS
220556-69-4- PubChem CID
- 5311006
Properties
Computed structural properties
- XLogP
- 6.6
- Topological polar surface area
- 29.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 16
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 410
Physicochemical properties
- RTECS
- 3840800 · JX3840800
- storage temp.
- 20 °C · −20°C
- solubility
- DMSO: soluble
- form
- oil
- color
- pale yellow
- Sensitive
- Air Sensitive
- InChIKey
- SCJNCDSAIRBRIA-DOFZRALJSA-N
- SMILES
- C(NCCCl)(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC
- UNSPSC Code
- 51111800 · 51111800
- NACRES
- 77 · NA.77
- WGK Germany
- 3 · 3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
Chemistry & industry
Applications
DescriptionArachidonoyl 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. In whole animal experiments, ACEA induces hypothermia in mice with the same efficacy as arachidonoyl ethanolamide (AEA; ), 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.
UsesA 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).
Suppliers31 total
陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
江苏南创化学与生命健康研究院有限公司15720605021
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
星基医药（上海）有限公司15705593425
United Life Science020-82099279 18988941402 · [email protected]
Ascent Scientific4401179829988 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
金瓯生物医药（南京）有限公司13000000000 · [email protected]
上海毕得医药科技股份有限公司400-164-7117 18317119277 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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