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MedKoo Cat#: 412255 | Name: Enadoline free base

Description:

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

Enadoline (Free Base) is a kappa-opioid receptor agonist; PD 129290 (CAM 570; CI 977) is the S,S(-)-enantiomer; PD 129289 (CAM 569) is the corresponding R,R (+)-enantiomer. In human studies, it produced visual distortions and feelings of dissociation, reminiscent of the effects of salvinorin A. It was studied as a potential analgesic, but abandoned because of the dose-limiting effects of dysphoria, which could be expected from a κ-opioid agonist. There was mention of its potential in treating comatose head injury or stroke victims, where that type of side effect would be immaterial.

Chemical Structure

Enadoline free base
Enadoline free base
CAS#107431-28-7 (free base)

Theoretical Analysis

MedKoo Cat#: 412255

Name: Enadoline free base

CAS#: 107431-28-7 (free base)

Chemical Formula: C24H32N2O3

Exact Mass: 396.2413

Molecular Weight: 396.53

Elemental Analysis: C, 72.70; H, 8.13; N, 7.06; O, 12.10

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
124378-77-4 (free base) 124439-07-2 (HCl)
Synonym
Enadoline; PD129289; PD-129289; PD 129289; CAM 570; CAM570; CAM-570; NIH 10672; NIH-10672; NIH10672; PD 129290; PD-129290; PD129290;
IUPAC/Chemical Name
2-(benzofuran-4-yl)-N-methyl-N-((5R,7S,8S)-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]decan-8-yl)acetamide
InChi Key
JMBYBVLCYODBJQ-HFMPRLQTSA-N
InChi Code
InChI=1S/C24H32N2O3/c1-25(23(27)16-18-6-4-7-22-19(18)9-15-28-22)20-8-11-24(10-5-14-29-24)17-21(20)26-12-2-3-13-26/h4,6-7,9,15,20-21H,2-3,5,8,10-14,16-17H2,1H3/t20-,21-,24-/m0/s1
SMILES Code
O=C(N(C)[C@@H](CC1)[C@@H](N2CCCC2)C[C@@]31CCCO3)CC4=C5C=COC5=CC=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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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 396.53 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: Walsh SL, Strain EC, Abreu ME, Bigelow GE. Enadoline, a selective kappa opioid agonist: comparison with butorphanol and hydromorphone in humans. Psychopharmacology (Berl). 2001 Sep;157(2):151-62. PubMed PMID: 11594439. 2: Walsh SL, Geter-Douglas B, Strain EC, Bigelow GE. Enadoline and butorphanol: evaluation of kappa-agonists on cocaine pharmacodynamics and cocaine self-administration in humans. J Pharmacol Exp Ther. 2001 Oct;299(1):147-58. PubMed PMID: 11561074. 3: Carey GJ, Bergman J. Enadoline discrimination in squirrel monkeys: effects of opioid agonists and antagonists. J Pharmacol Exp Ther. 2001 Apr;297(1):215-23. PubMed PMID: 11259547. 4: Hinton JP, Hudson G. Unbound plasma concentrations may predict neuroprotective brain concentrations: a brain microdialysis and pharmacokinetic study of enadoline in rats. Acta Neurochir Suppl. 1999;75:7-9. PubMed PMID: 10635368. 5: Hill MP, Brotchie JM. The adrenergic receptor agonist, clonidine, potentiates the anti-parkinsonian action of the selective kappa-opioid receptor agonist, enadoline, in the monoamine-depleted rat. Br J Pharmacol. 1999 Dec;128(7):1577-85. PubMed PMID: 10602339; PubMed Central PMCID: PMC1571785. 6: Field MJ, Carnell AJ, Gonzalez MI, McCleary S, Oles RJ, Smith R, Hughes J, Singh L. Enadoline, a selective kappa-opioid receptor agonist shows potent antihyperalgesic and antiallodynic actions in a rat model of surgical pain. Pain. 1999 Mar;80(1-2):383-9. PubMed PMID: 10204752. 7: Becker A, Braun H, Schröder H, Grecksch G, Höllt V. Effects of enadoline on the development of pentylenetetrazol kindling, learning performance, and hippocampal morphology. Brain Res. 1999 Mar 27;823(1-2):191-7. PubMed PMID: 10095026. 8: Faber ES, Chambers JP, Evans RH. Selective depression of dorsal root-evoked high threshold synaptic excitation by the selective kappa opioid receptor agonist enadoline in the neonatal rat hemisected spinal cord in vitro. Neuropharmacology. 1998 Jun;37(6):745-50. PubMed PMID: 9707288. 9: Tortella FC, Rose J, Robles L, Moreton JE, Hughes J, Hunter JC. EEG spectral analysis of the neuroprotective kappa opioids enadoline and PD117302. J Pharmacol Exp Ther. 1997 Jul;282(1):286-93. PubMed PMID: 9223566. 10: Panegyres PK, Hughes J. Activation of c-fos mRNA in the brain by the kappa-opioid receptor agonist enadoline and the NMDA receptor antagonist dizocilpine. Eur J Pharmacol. 1997 Jun 5;328(1):31-6. PubMed PMID: 9203564. 11: Pande AC, Pyke RE, Greiner M, Wideman GL, Benjamin R, Pierce MW. Analgesic efficacy of enadoline versus placebo or morphine in postsurgical pain. Clin Neuropharmacol. 1996 Oct;19(5):451-6. PubMed PMID: 8889289. 12: Brandt MR, France CP. Discriminative stimulus effects on enadoline in pigeons. J Pharmacol Exp Ther. 1996 May;277(2):960-7. PubMed PMID: 8627579. 13: MacKay KB, Patel TR, Galbraith SL, Woodruff GN, McCulloch J. The relationship between glutamate release and cerebral blood flow after focal cerebral ischaemia in the cat: effect of pretreatment with enadoline (a kappa receptor agonist). Brain Res. 1996 Mar 18;712(2):329-34. PubMed PMID: 8814909. 14: Pande AC, Pyke RE, Greiner M, Cooper SA, Benjamin R, Pierce MW. Analgesic efficacy of the kappa-receptor agonist, enadoline, in dental surgery pain. Clin Neuropharmacol. 1996 Feb;19(1):92-7. PubMed PMID: 8867523. 15: Millan MH, Chapman AG, Meldrum BS. Dual inhibitory action of enadoline (CI977) on release of amino acids in the rat hippocampus. Eur J Pharmacol. 1995 Jun 6;279(1):75-81. PubMed PMID: 7556386. 16: McLaughlin CR, Tao Q, Abood ME. Analysis of the antinociceptive actions of the kappa-opioid agonist enadoline (CI-977) in neonatal and adult rats: comparison to kappa-opioid receptor mRNA ontogeny. Drug Alcohol Depend. 1995 Jun;38(3):261-9. PubMed PMID: 7555627. 17: Pitts RC, Dykstra LA. Antinociceptive and response rate-altering effects of kappa opioid agonists, spiradoline, enadoline and U69,593, alone and in combination with opioid antagonists in squirrel monkeys. J Pharmacol Exp Ther. 1994 Dec;271(3):1501-8. PubMed PMID: 7996463. 18: Woodburn VL, Hayward NJ, Poat JA, Woodruff GN, Hughes J. The effect of dizocilpine and enadoline on immediate early gene expression in the gerbil global ischaemia model. Neuropharmacology. 1993 Oct;32(10):1047-59. PubMed PMID: 8295713. 19: Woodburn VL, Oles R, Poat J, Woodruff GN, Hughes J. Anticonvulsant agents, dizocilpine maleate, enadoline and HA 966 have different effects on N-methyl-DL-aspartate-induced immediate early gene induction in mice. Neuroscience. 1993 Oct;56(3):703-9. PubMed PMID: 8255428. 20: Hayward NJ, McKnight AT, Woodruff GN. Neuroprotective effect of the kappa-agonist enadoline (CI-977) in rat models of focal cerebral ischaemia. Eur J Neurosci. 1993 Jul 1;5(7):961-7. PubMed PMID: 8281306.