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Enadoline

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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
Clinical data
Legal status
?
Identifiers
CAS number  YesY
ATC code None
PubChem
IUPHAR ligand
ChemSpider  YesY
UNII  YesY
ChEMBL  YesY
Chemical data
Formula C24H32N2O3 
Mol. mass 396.52 g/mol
 YesY   

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.[1]

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.[2]

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".[3]

See also

References

  1. ^ Walsh SL, Strain EC, Abreu ME, Bigelow GE (2001). "Enadoline, a selective kappa opioid agonist: comparison with butorphanol and hydromorphone in humans". Psychopharmacology (Berl.) 157 (2): 151–62.  
  2. ^ Barber A, Gottschlich R (1997). "Novel developments with selective, non-peptidic kappa-opioid receptor agonists". Expert Opin Investig Drugs 6 (10): 1351–68.  
  3. ^ Halfpenny, Paul R. (1990). "Highly selective .kappa.-opioid analgesics. 3. Synthesis and structure-activity relationships of novel N-[2-(1-pyrrolidinyl)-4- or -5-substituted cyclohexyl]arylacetamide derivatives". Journal of Medicinal Chemistry 33 (1): 286–291.  


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