Enadoline

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Enadoline
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Systematic (IUPAC) name
2-(benzofuran-4-yl)-N-methyl-N-((5R,7S,8S)-7- (pyrrolidin-1-yl)-1-oxaspiro[4.5] decan-8-yl)ethanamide
Identifiers
CAS Number 124378-77-4
ATC code none
PubChem CID 60768
IUPHAR/BPS 1646
Chemical data
Formula C24H32N2O3
Molar mass 396.52 g/mol[[Script error: No such module "String".]]
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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.[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

See the related spiradoline since both compounds share the same intermediate and only differ from one another with respect to the final step.

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Halfpenny, Paul R.; Horwell, David C.; Hughes, John; Hunter, John C.; Rees, David C. (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. doi:10.1021/jm00163a047. PMID 2153208. 

See also

References

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Butane • Chloroform • Diethyl Ether (Ether) • Enflurane • Freon • Gasoline (Petrol) • Kerosene (Paraffin) • Propane
Others
  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. 
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