Enadoline
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|---|---|
| Systematic (IUPAC) name | |
| 2-(benzofuran-4-yl)-N-methyl-N-((5R,7S,8S)-7- | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 124378-77-4  |
| ATC code | None |
| PubChem | CID 60768 |
| IUPHAR ligand | 1646 |
| ChemSpider | 54765 |
| UNII | KJL283326C |
| ChEMBL | CHEMBL318859 |
| Chemical data | |
| Formula | C24H32N2O3 |
| Mol. mass | 396.52 g/mol |
| SMILES | eMolecules & PubChem |
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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]
[edit] Synthesis
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.[3]
[edit] See also
[edit] References
- ^ 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.
- ^ 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.
- ^ 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): 286–91. doi:10.1021/jm00163a047. PMID 2153208.
