Spiradoline

Spiradoline
Clinical data
Routes of; administration	N/A
ATC code	none;
Identifiers
	IUPAC name 2-(3,4-dichlorophenyl)- N-methyl- N-[(5R,7S,8S)- 7-pyrrolidin-1-yl- 1-oxaspiro[4.5]decan-8-yl] acetamide;
CAS Number	87151-85-7 ;
PubChem CID	55652;
IUPHAR/BPS	1653;
ChemSpider	50257;
UNII	N18ZH0M4NP;
ChEMBL	ChEMBL118865 ;
CompTox Dashboard (EPA)	DTXSID1048679 ;
Chemical and physical data
Formula	C22H30Cl2N2O2
Molar mass	425.392 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN([C@H]1CC[C@@]2(CCCO2)C[C@@H]1N3CCCC3)C(=O)CC4=CC(=C(C=C4)Cl)Cl;
	InChI InChI=1S/C22H30Cl2N2O2/c1-25(21(27)14-16-5-6-17(23)18(24)13-16)19-7-9-22(8-4-12-28-22)15-20(19)26-10-2-3-11-26/h5-6,13,19-20H,2-4,7-12,14-15H2,1H3/t19-,20-,22-/m0/s1; Key:NYKCGQQJNVPOLU-ONTIZHBOSA-N;
	(what is this?) (verify)

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 ketazocine and alazocine.^[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^{[citation needed]}, instead of having an assumed synergy since they are both opioid receptors, such as with the mu (μ) receptors and delta (δ) receptors (which both mediate pain-relief, euphoria and overall potency of opioid effects).

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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