Spiradoline
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|---|---|
| Systematic (IUPAC) name | |
| 2-(3,4-dichlorophenyl)- N-methyl- N-[(5R,7S,8S)- 7-pyrrolidin-1-yl- 1-oxaspiro[4.5]decan-8-yl] acetamide | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Routes | N/A |
| Identifiers | |
| CAS number | 87151-85-7 |
| ATC code | None |
| PubChem | CID 55652 |
| IUPHAR ligand | 1653 |
| UNII | N18ZH0M4NP  |
| Chemical data | |
| Formula | C22H30Cl2N2O2 |
| Mol. mass | 425.392 g/mol |
| SMILES | eMolecules & PubChem |
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Spiradoline (U-62066) is a drug which acts as a highly selective κ-opioid agonist.[1] It has analgesic,[2] diuretic[3] and antitussive effects,[4] and produces subjective effects in animals similar to those of ketocyclazocine and allylnormetazocine.[5] The main effect in humans is sedation, along with analgesic and diuretic effects, but significant side effects such as dysphoria and hallucinations have stopped it from being used clinically.[6] Kappa-agonists have been shown to react negatively with the Mu-receptor, instead of having an assumed synergy since they are both opiate receptors, such as with the Mu and Delta receptors(which both mediate pain-relief, euphoria(mainly Mu) and overall potency of Opiate/Opioid effects).
[edit] Chemistry
Kaplan, L. J.; 1984, U.S. Patent 4,588,591.
[edit] References
- ^ Vonvoigtlander PF, Lewis RA. Analgesic and mechanistic evaluation of spiradoline, a potent kappa opioid. Journal of Pharmacology and Experimental Therapeutics. 1988 Jul;246(1):259-62. PMID 2839665
- ^ Kunihara M, Ohyama M, Nakano M, Hayashi S. Analgesic activity of spiradoline mesylate (U-62,066E), a kappa opioid agonist in mice. Life Sciences. 1989;45(13):1191-8. PMID 2796604
- ^ Yamada K, Imai M, Yoshida S. Mechanism of diuretic action of U-62,066E, a kappa opioid receptor agonist. European Journal of Pharmacology. 1989 Jan 31;160(2):229-37. doi:10.1016/0014-2999(89)90495-0 PMID 2547626
- ^ Kamei J, Tanihara H, Kasuya Y. Antitussive effects of two specific kappa-opioid agonists, U-50,488H and U-62,066E, in rats. European Journal of Pharmacology. 1990 Oct 9;187(2):281-6. PMID 2272363
- ^ Holtzman SG. Further characterization of the discriminative stimulus effects of spiradoline. Pharmacology, Biochemistry and Behaviour. 2000 Jul;66(3):517-22. PMID 10899364
- ^ Wadenberg ML. A review of the properties of spiradoline: a potent and selective kappa-opioid receptor agonist. CNS Drug Reviews. 2003 Summer;9(2):187-98. PMID 12847558
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