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Spiradoline

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From Wikipedia, the free encyclopedia

Selective κ-opioid agonist drug

Pharmaceutical compound

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^Y
PubChemCID	55652
IUPHAR/BPS	1653
ChemSpider	50257^N
UNII	N18ZH0M4NP
ChEMBL	ChEMBL118865^N
CompTox Dashboard(EPA)	DTXSID1048679
Chemical and physical data
Formula	C₂₂H₃₀Cl₂N₂O₂
Molar mass	425.39 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^N Key:NYKCGQQJNVPOLU-ONTIZHBOSA-N^N
^NY (what is this?) (verify)

Spiradoline (U-62066) is a drug which acts as a highly selectiveκ-opioid agonist.^[1] It hasanalgesic,^[2]diuretic,^[3] andantitussive effects,^[4] and produces subjective effects in animals similar to those ofketazocine andalazocine.^[5] The main effect in humans issedation, along with analgesic and diuretic effects, but significant side effects such asdysphoria andhallucinations have stopped it from being used clinically.^[6]

References

[edit]

^Vonvoigtlander PF, Lewis RA (July 1988). "Analgesic and mechanistic evaluation of spiradoline, a potent kappa opioid".The Journal of Pharmacology and Experimental Therapeutics.246 (1):259–62.PMID 2839665.
^Kunihara M, Ohyama M, Nakano M, Hayashi S (1989). "Analgesic activity of spiradoline mesylate (U-62,066E), a kappa opioid agonist in mice".Life Sciences.45 (13):1191–8.doi:10.1016/0024-3205(89)90508-0.PMID 2796604.
^Yamada K, Imai M, Yoshida S (January 1989). "Mechanism of diuretic action of U-62,066E, a kappa opioid receptor agonist".European Journal of Pharmacology.160 (2):229–37.doi:10.1016/0014-2999(89)90495-0.PMID 2547626.
^Kamei J, Tanihara H, Kasuya Y (October 1990). "Antitussive effects of two specific kappa-opioid agonists, U-50,488H and U-62,066E, in rats".European Journal of Pharmacology.187 (2):281–6.doi:10.1016/0014-2999(90)90014-w.PMID 2272363.
^Holtzman SG (July 2000). "Further characterization of the discriminative stimulus effects of spiradoline".Pharmacology, Biochemistry, and Behavior.66 (3):517–22.doi:10.1016/s0091-3057(00)00172-6.PMID 10899364.S2CID 27712517.
^Wadenberg ML (2003)."A review of the properties of spiradoline: a potent and selective kappa-opioid receptor agonist".CNS Drug Reviews.9 (2):187–98.doi:10.1111/j.1527-3458.2003.tb00248.x.PMC 6741666.PMID 12847558.

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KOR agonists	Salvinoids (terpenoids):2-EMSB 2-MMSB RB-64 (22-thiocyanatosalvinorin A) Salvinorin A Benzomorphans:Alazocine Bremazocine Cyclazocine Ketazocine Metazocine MR-2034 Pentazocine Phenazocine Morphinans:Butorphanol Cyclorphan Cyprenorphine Diprenorphine Heroin Levallorphan Levomethorphan Levorphanol Morphine Nalbuphine Nalmefene Nalorphine Oxilorphan Proxorphan Racemethorphan Racemorphan Xorphanol Arylacetamides:Enadoline LPK-26 Niravoline Spiradoline U-50488 U-69593 Others:HZ-2 Tifluadom
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See also:Psychedelics Dissociatives Entactogens Stimulants Depressants List of hallucinogens