Arachidonyl-2'-chloroethylamide

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid =

| ImageFile= Arachidonyl-2-chloroethylamide.svg

| ImageSize=200px

| PIN=(5Z,8Z,11Z,14Z)-N-(2-Chloroethyl)icosa-5,8,11,14-tetraenamide

| OtherNames= Arachidonyl-2'-chloroethylamide; ACEA

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 738

| CASNo=220556-69-4

| CASNo_Ref = {{cascite|changed|??}}

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 151167

| PubChem = 5311006

| ChEBI = 191854

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4470547

| SMILES = ClCCNC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC

| InChI = 1/C22H36ClNO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)24-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,24,25)/b7-6-,10-9-,13-12-,16-15-

| InChIKey = SCJNCDSAIRBRIA-DOFZRALJBU

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C22H36ClNO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)24-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,24,25)/b7-6-,10-9-,13-12-,16-15-

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = SCJNCDSAIRBRIA-DOFZRALJSA-N

}}

|Section2={{Chembox Properties

| C=22 | H=36 | Cl=1 | N=1 | O=1

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| SolubleOther = soluble in ethanol, chloroform, THF and DMSO

| Solvent = other solvents

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

Arachidonyl-2'-chloroethylamide (ACEA) is a synthetic agonist of the CB1 (CB1R). ACEA is considered to be a selective cannabinoid agonist as it binds primarily to the CB1R and has low affinity to the CB2 (CB2R) (Ki = 1.4 nM for CB1R; Ki = 3100 nM for CB2R). {{cite journal | pmid = 10336536 | year = 1999 | last1 = Hillard | first1 = CJ | last2 = Manna | first2 = S | last3 = Greenberg | first3 = MJ | last4 = Dicamelli | first4 = R | last5 = Ross | first5 = RA | last6 = Stevenson | first6 = LA | last7 = Murphy | first7 = V | last8 = Pertwee | first8 = RG | last9 = Campbell | first9 = WB | title = Synthesis and characterization of potent and selective agonists of the neuronal cannabinoid receptor (CB1) | volume = 289 | issue = 3 | pages = 1427–33 | journal = The Journal of Pharmacology and Experimental Therapeutics}}

References