Enadoline

{{Short description|Chemical compound}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 443319625

| IUPAC_name = 2-(1-Benzofuran-4-yl)-N-methyl-N-[(5R,7S,8S)-7-pyrrolidin-1-yl-1-oxaspiro[4.5]decan-8-yl]acetamide

| image = Enadoline2d.png

| width = 200px

| image2 = Enadoline 3D BS.png

| width2 = 200px

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 124378-77-4

| ATC_prefix = none

| ATC_suffix =

| PubChem = 60768

| IUPHAR_ligand = 1646

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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

| ChemSpiderID = 54765

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = KJL283326C

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

| ChEMBL = 318859

| C=24 | H=32 | N=2 | O=3

| smiles = O=C(Cc1cccc2occc12)N(C)C1CCC2(CCCO2)CC1N1CCCC1

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

| StdInChI = 1S/C24H32N2O3/c1-25(23(27)16-18-6-4-7-22-19(18)9-15-28-22)20-8-11-24(10-5-14-29-24)17-21(20)26-12-2-3-13-26/h4,6-7,9,15,20-21H,2-3,5,8,10-14,16-17H2,1H3/t20-,21-,24-/m0/s1

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

| StdInChIKey = JMBYBVLCYODBJQ-HFMPRLQTSA-N

}}

Enadoline is a drug which acts as a highly selective κ-opioid agonist.

In human studies, it produced visual distortions and feelings of dissociation, reminiscent of the effects of salvinorin A.{{cite journal | vauthors = Walsh SL, Strain EC, Abreu ME, Bigelow GE | title = Enadoline, a selective kappa opioid agonist: comparison with butorphanol and hydromorphone in humans | journal = Psychopharmacology | volume = 157 | issue = 2 | pages = 151–162 | date = September 2001 | pmid = 11594439 | doi = 10.1007/s002130100788 | s2cid = 10507758 }}

It was studied as a potential analgesic, but abandoned because of the dose-limiting effects of dysphoria, which could be expected from a κ-opioid agonist. There was mention of its potential in treating comatose head injury or stroke victims, where that type of side effect would be immaterial.{{cite journal | vauthors = Barber A, Gottschlich R | title = Novel developments with selective, non-peptidic kappa-opioid receptor agonists | journal = Expert Opinion on Investigational Drugs | volume = 6 | issue = 10 | pages = 1351–1368 | date = October 1997 | pmid = 15989506 | doi = 10.1517/13543784.6.10.1351 }}