Enadoline

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Enadoline
Enadoline2d.png
Systematic (IUPAC) name
2-(benzofuran-4-yl)-N-methyl-N-((5R,7S,8S)-7-
Clinical data
Legal status
?
Identifiers
CAS number 124378-77-4 YesY
ATC code None
PubChem CID 60768
IUPHAR ligand 1646
ChemSpider 54765 YesY
UNII KJL283326C YesY
ChEMBL CHEMBL318859 YesY
Chemical data
Formula C24H32N2O3 
Mol. mass 396.52 g/mol
 YesY (what is this?)  (verify)

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 looked at 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]

Synthesis[edit]

Enadoline synthesis:[3]

The chemical synthesis of enadoline is similar to that of the related compound spiradoline, since both compounds share the same intermediate and only differ from one another with respect to the final step.

The NCS is N-chlorosuccinimide not to be confused with isothiocyanate.

Potency[edit]

According to the abstract,[3] Enadoline "is the most potent K-selective analgesic ever reported. Compound 21 is 25 times more potent than morphine and 17 times more potent than U-62066" (c.f. JDTic antagonist).

See also[edit]

References[edit]

  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. doi:10.1007/s002130100788. PMID 11594439. 
  2. ^ Barber A, Gottschlich R (1997). "Novel developments with selective, non-peptidic kappa-opioid receptor agonists". Expert Opin Investig Drugs 6 (10): 1351–68. doi:10.1517/13543784.6.10.1351. PMID 15989506. 
  3. ^ a b c 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. doi:10.1021/jm00163a047.  edit