MedKoo Cat#: 414092 | Name: Spiradoline free base
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Spiradoline 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.

Chemical Structure

Spiradoline free base
Spiradoline free base
CAS#87151-85-7 (free base)

Theoretical Analysis

MedKoo Cat#: 414092

Name: Spiradoline free base

CAS#: 87151-85-7 (free base)

Chemical Formula: C22H30Cl2N2O2

Exact Mass: 424.1684

Molecular Weight: 425.39

Elemental Analysis: C, 62.12; H, 7.11; Cl, 16.67; N, 6.59; O, 7.52

Price and Availability

Size Price Availability Quantity
25mg USD 350.00 2 Weeks
100mg USD 650.00 2 Weeks
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Synonym
Spiradoline; Espiradolina; Spiradolinum; U-62066; U62066; U 62066
IUPAC/Chemical Name
Benzeneacetamide, 3,4-dichloro-N-methyl-N-(7-(1-pyrrolidinyl)-1-oxaspiro(4,5)dec-8-yl)-, (5alpha,7alpha,8beta)-(+-)-
InChi Key
NYKCGQQJNVPOLU-KCZVDYSFSA-N
InChi Code
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
SMILES Code
O=C(N(C)[C@H](CC1)[C@H](N2CCCC2)C[C@]31CCCO3)CC4=CC=C(Cl)C(Cl)=C4
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 425.39 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Peters GR, Ward NJ, Antal EG, Lai PY, deMaar EW. Diuretic actions in man of a selective kappa opioid agonist: U-62,066E. J Pharmacol Exp Ther. 1987 Jan;240(1):128-31. PMID: 3027300. 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: Hall ED, Pazara KE. Quantitative analysis of effects of kappa-opioid agonists on postischemic hippocampal CA1 neuronal necrosis in gerbils. Stroke. 1988 Aug;19(8):1008-12. doi: 10.1161/01.str.19.8.1008. PMID: 2840759. 4: Althaus JS, DiFazio CA, Moscicki JC, VonVoigtlander PF. Enhancement of anesthetic effect of halothane by spiradoline, a selective kappa-agonist. Anesth Analg. 1988 Sep;67(9):823-7. PMID: 3414991. 5: Hall ED, Wolf DL, McCall RB. Cardiovascular depressant effects of the kappa opioid receptor agonists U50488H and spiradoline mesylate. Circ Shock. 1988 Dec;26(4):409-17. PMID: 2850873. 6: 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. 7: Yamada K, Imai M, Yoshida S. Mechanism of diuretic action of U-62,066E, a kappa opioid receptor agonist. Eur J Pharmacol. 1989 Jan 31;160(2):229-37. doi: 10.1016/0014-2999(89)90495-0. PMID: 2547626. 8: Piercey MF, Einspahr FJ. Spinal analgesic actions of kappa receptor agonists, U-50488H and spiradoline (U-62066). J Pharmacol Exp Ther. 1989 Oct;251(1):267-71. PMID: 2552077. 9: Meecham KG, Boyle SJ, Hunter JC, Hughes J. An in vitro profile of activity for the (+) and (-) enantiomers of spiradoline and PD117302. Eur J Pharmacol. 1989 Dec 7;173(2-3):151-7. doi: 10.1016/0014-2999(89)90512-8. PMID: 2560430. 10: Hamon G, Jouquey S. Kappa agonists and vasopressin secretion. Horm Res. 1990;34(3-4):129-32. doi: 10.1159/000181811. PMID: 1966562. 11: Halfpenny PR, Horwell DC, Hughes J, Hunter JC, Rees DC. Highly selective kappa-opioid analgesics. 3. Synthesis and structure-activity relationships of novel N-[2-(1-pyrrolidinyl)-4- or -5-substituted-cyclohexyl]arylacetamide derivatives. J Med Chem. 1990 Jan;33(1):286-91. doi: 10.1021/jm00163a047. PMID: 2153208. 12: Yamada K, Nakano M, Yoshida S. Inhibition of elevated arginine vasopressin secretion in response to osmotic stimulation and acute haemorrhage by U-62066E, a kappa-opioid receptor agonist. Br J Pharmacol. 1990 Feb;99(2):384-8. doi: 10.1111/j.1476-5381.1990.tb14713.x. PMID: 2158377; PMCID: PMC1917399. 13: Gulat-Marnay C, Lafitte A, Arrang JM, Schwartz JC. Modulation of histamine release in the rat brain by kappa-opioid receptors. J Neurochem. 1990 Jul;55(1):47-53. doi: 10.1111/j.1471-4159.1990.tb08819.x. PMID: 1693948. 14: Kamei J, Tanihara H, Kasuya Y. Antitussive effects of two specific kappa- opioid agonists, U-50,488H and U-62,066E, in rats. Eur J Pharmacol. 1990 Oct 9;187(2):281-6. doi: 10.1016/0014-2999(90)90014-w. PMID: 2272363. 15: Holtzman SG, Cook L, Steinfels GF. Discriminative stimulus effects of spiradoline, a kappa-opioid agonist. Psychopharmacology (Berl). 1991;105(4):447-52. doi: 10.1007/BF02244362. PMID: 1663252. 16: Engber TM, Boldry RC, Chase TN. The kappa-opioid receptor agonist spiradoline differentially alters the rotational response to dopamine D1 and D2 agonists. Eur J Pharmacol. 1991 Jul 23;200(1):171-3. doi: 10.1016/0014-2999(91)90682-g. PMID: 1663039. 17: Kamei J, Tanihara H, Kasuya Y. The abilities of specific kappa-opioid agonists, U-50,488H and U-62,066E, to cause antitussive tolerance were lower than that of morphine. Jpn J Pharmacol. 1991 Aug;56(4):557-61. doi: 10.1254/jjp.56.557. PMID: 1744997. 18: Yamada K, Yoshida S, Shimada Y. Atrial natriuretic polypeptide secretion via selective activation of kappa-opioid receptor: role of dynorphin. Am J Physiol. 1991 Sep;261(3 Pt 1):E293-7. doi: 10.1152/ajpendo.1991.261.3.E293. PMID: 1716056. 19: Harasawa Y, Kimura M, Hayashi S. Inhibitory effect of spiradoline, a kappa opioid receptor agonist, on Ca2+ induced contraction and the intracellular Ca2+ concentration in porcine coronary artery. Cardiovasc Res. 1991 Oct;25(10):802-6. doi: 10.1093/cvr/25.10.802. PMID: 1660789. 20: Rimoy GH, Bhaskar NK, Wright DM, Rubin PC. Mechanism of diuretic action of spiradoline (U-62066E)--a kappa opioid receptor agonist in the human. Br J Clin Pharmacol. 1991 Nov;32(5):611-5. doi: 10.1111/j.1365-2125.1991.tb03960.x. PMID: 1659438; PMCID: PMC1368639.