Spiradoline

• CAT Number: I036545
• CAS Number: 87151-85-7
• Molecular Formula: C22H30Cl2N2O2
• Molecular Weight: 425.39
• Purity: 98%
• Synonyms: Spiradoline; Espiradolina; Spiradolinum; U-62066; U62066; U 62066
• Solubility: To be determined
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: Benzeneacetamide, 3,4-dichloro-N-methyl-N-(7-(1-pyrrolidinyl)-1-oxaspiro(4,5)dec-8-yl)-, (5alpha,7alpha,8beta)-(+-)-
• 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-/m1/s1
• InChIKey: NYKCGQQJNVPOLU-KCZVDYSFSA-N
• SMILES: O=C(N(C)[C@H](CC1)[C@H](N2CCCC2)C[C@]31CCCO3)CC4=CC=C(Cl)C(Cl)=C4

Spiradoline (Cat.No:I036545) is a drug which acts as a highly selective κ-opioid agonist. It has analgesic, diuretic, and antitussive effects, and produces subjective effects in animals similar to those of ketazocine and alazocine.

Reference

1: Wadenberg ML. A review of the properties of spiradoline: a potent and selective kappa-opioid receptor agonist. CNS Drug Rev. 2003 Summer;9(2):187-98. doi: 10.1111/j.1527-3458.2003.tb00248.x. PMID: 12847558; PMCID: PMC6741666.
2: Vonvoigtlander PF, Lewis RA. Analgesic and mechanistic evaluation of spiradoline, a potent kappa opioid. J Pharmacol Exp Ther. 1988 Jul;246(1):259-62. PMID: 2839665.
3: Holtzman SG, Steinfels GF, Schmidt WK. Assessing spiradoline-like discriminative effects of DuP 747: influence of route of administration. Pharmacol Biochem Behav. 1994 Mar;47(3):487-91. doi: 10.1016/0091-3057(94)90148-1. PMID: 8208766.
4: Kunihara M, Ohyama M, Nakano M, Hayashi S. Analgesic activity of spiradoline mesylate (U-62,066E), a kappa opioid agonist in mice. Life Sci. 1989;45(13):1191-8. doi: 10.1016/0024-3205(89)90508-0. PMID: 2796604.
5: Holtzman SG, Steinfels GF. Monoamine systems in the discriminative effects of spiradoline, a kappa-opioid agonist. Pharmacol Biochem Behav. 1994 Mar;47(3):575-8. doi: 10.1016/0091-3057(94)90161-9. PMID: 8208776.
6: Holtzman SG. Further characterization of the discriminative stimulus effects of spiradoline. Pharmacol Biochem Behav. 2000 Jul;66(3):517-22. doi: 10.1016/s0091-3057(00)00172-6. PMID: 10899364.
7: Minervini V, Dahal S, France CP. Behavioral Characterization of κ Opioid Receptor Agonist Spiradoline and Cannabinoid Receptor Agonist CP55940 Mixtures in Rats. J Pharmacol Exp Ther. 2017 Feb;360(2):280-287. doi: 10.1124/jpet.116.235630. Epub 2016 Nov 30. PMID: 27903642; PMCID: PMC5267513.
8: Chappell PB, Leckman JF, Scahill LD, Hardin MT, Anderson G, Cohen DJ. Neuroendocrine and behavioral effects of the selective kappa agonist spiradoline in Tourette’s syndrome: a pilot study. Psychiatry Res. 1993 Jun;47(3):267-80. doi: 10.1016/0165-1781(93)90084-t. PMID: 8396784.
9: Pugsley MK, Saint DA, Hayes ES, Kramer D, Walker MJ. Sodium channel-blocking properties of spiradoline, a kappa receptor agonist, are responsible for its antiarrhythmic action in the rat. J Cardiovasc Pharmacol. 1998 Dec;32(6):863-74. doi: 10.1097/00005344-199812000-00002. PMID: 9869491.
10: Briggs SL, Rech RH, Sawyer DC. Kappa antinociceptive activity of spiradoline in the cold-water tail-flick assay in rats. Pharmacol Biochem Behav. 1998 Jun;60(2):467-72. doi: 10.1016/s0091-3057(98)00017-3. PMID: 9632230.