Enadoline

Enadoline

Systematic (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
Identifiers
CAS Number	124378-77-4 Y
ATC code	none
PubChem	CID: 60768
IUPHAR/BPS	1646
ChemSpider	54765 Y
UNII	KJL283326C Y
ChEMBL	CHEMBL318859 Y
Chemical data
Formula	C24H32N2O3
Molecular mass	396.52 g/mol
SMILES O=C(Cc1cccc2occc12)N(C)C1CCC2(CCCO2)CC1N1CCCC1
InChI InChI=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 Y Key:JMBYBVLCYODBJQ-HFMPRLQTSA-N Y
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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.

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.

Potency

When enadoline was first reported in 1990, it was "the most potent κ-selective analgesic ever reported ... 25 times more potent than morphine and 17 times more potent than U-62066".

See also

• Salvinorin A
• Spiradoline