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MedKoo Cat#: 510298 | Name: Encenicline HCl salt
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Description:

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

Encenicline, also known as EVP-6124 and MT-4666, is a novel α7 nicotinic acetylcholine receptor agonist that enhances dopamine, acetylcholine, and glutamate efflux in rat cortex and nucleus accumbens. EVP-6124 improves memory performance by potentiating the acetylcholine response of α7 nicotinic acetylcholine receptors.

Chemical Structure

Encenicline HCl salt
Encenicline HCl salt
CAS#550999-74-1 (HCl)

Theoretical Analysis

MedKoo Cat#: 510298

Name: Encenicline HCl salt

CAS#: 550999-74-1 (HCl)

Chemical Formula: C16H18Cl2N2OS

Exact Mass: 356.0517

Molecular Weight: 357.30

Elemental Analysis: C, 53.79; H, 5.08; Cl, 19.84; N, 7.84; O, 4.48; S, 8.97

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 650.00 2 Weeks
50mg USD 950.00 2 Weeks
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Related CAS #
550999-75-2 (free base) 550999-74-1 (HCl)
Synonym
EVP-6124; EVP 6124; EVP6124; MT-4666; MT4666; MT 4666; Encenicline HCl.
IUPAC/Chemical Name
(R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride.
InChi Key
OIJYTJGIDVTCFF-ZOWNYOTGSA-N
InChi Code
InChI=1S/C16H17ClN2OS.ClH/c17-12-3-1-2-11-8-14(21-15(11)12)16(20)18-13-9-19-6-4-10(13)5-7-19;/h1-3,8,10,13H,4-7,9H2,(H,18,20);1H/t13-;/m0./s1
SMILES Code
O=C(C1=CC2=CC=CC(Cl)=C2S1)N[C@H]3CN4CCC3CC4.[H]Cl
Appearance
white to off-white solid powder
Purity
>95% (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, not in water
Shelf Life
>2 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
      
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Encenicline hydrochloride (EVP-6124 hydrochloride) is a partial agonist of α7 neuronal nicotinic acetylcholine receptors (nAChRs).
In vitro activity:
EVP-6124, (R)-7-chloro-N-quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide, is a novel partial agonist of α7 neuronal nicotinic acetylcholine receptors (nAChRs) that was evaluated here in vitro and in vivo. In binding and functional experiments, EVP-6124 showed selectivity for α7 nAChRs and did not activate or inhibit heteromeric α4β2 nAChRs. Reference: Neuropharmacology. 2012 Feb;62(2):1099-110. https://pubmed.ncbi.nlm.nih.gov/22085888/
In vivo activity:
Treatment with encenicline significantly reduced the infiltration of macrophages, neutrophils, and B cells in the colon of TNBS-treated animals, as indicated by IHC. In the TNBS model encenicline reduced the frequency of FoxP3(+) IL-17A(+) T cells in the colon. In the DSS-model treatment encenicline increased the frequency of FoxP3(+) T cells and reduced IL-17A(+) T cells. Stimulation of α7 nAChR with partial agonist encenicline alleviates colitis via alteration of the number and/or activation status of the immune cells in the gut, emphasizing a potential role of α7 nAChRs as a target for anticolitic drugs. Reference: J Pharmacol Exp Ther. 2016 Jan;356(1):157-69. https://pubmed.ncbi.nlm.nih.gov/26462538/
Solvent mg/mL mM
Solubility
DMSO 40.0 111.95
DMSO:PBS (pH 7.2) (1:5) 0.2 0.45
DMF 30.0 83.96
Ethanol 20.0 55.98
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 357.30 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
Formulation protocol:
1. Prickaerts J, van Goethem NP, Chesworth R, Shapiro G, Boess FG, Methfessel C, Reneerkens OA, Flood DG, Hilt D, Gawryl M, Bertrand S, Bertrand D, König G. EVP-6124, a novel and selective α7 nicotinic acetylcholine receptor partial agonist, improves memory performance by potentiating the acetylcholine response of α7 nicotinic acetylcholine receptors. Neuropharmacology. 2012 Feb;62(2):1099-110. doi: 10.1016/j.neuropharm.2011.10.024. Epub 2011 Nov 10. PMID: 22085888. 2. Salaga M, Blomster LV, Piechota-Polańczyk A, Zielińska M, Jacenik D, Cygankiewicz AI, Krajewska WM, Mikkelsen JD, Fichna J. Encenicline, an α7 Nicotinic Acetylcholine Receptor Partial Agonist, Reduces Immune Cell Infiltration in the Colon and Improves Experimental Colitis in Mice. J Pharmacol Exp Ther. 2016 Jan;356(1):157-69. doi: 10.1124/jpet.115.228205. Epub 2015 Oct 13. PMID: 26462538. 3. Hayward A, Adamson L, Neill JC. Partial agonism at the α7 nicotinic acetylcholine receptor improves attention, impulsive action and vigilance in low attentive rats. Eur Neuropsychopharmacol. 2017 Apr;27(4):325-335. doi: 10.1016/j.euroneuro.2017.01.013. Epub 2017 Feb 1. PMID: 28161246.
In vitro protocol:
1. Prickaerts J, van Goethem NP, Chesworth R, Shapiro G, Boess FG, Methfessel C, Reneerkens OA, Flood DG, Hilt D, Gawryl M, Bertrand S, Bertrand D, König G. EVP-6124, a novel and selective α7 nicotinic acetylcholine receptor partial agonist, improves memory performance by potentiating the acetylcholine response of α7 nicotinic acetylcholine receptors. Neuropharmacology. 2012 Feb;62(2):1099-110. doi: 10.1016/j.neuropharm.2011.10.024. Epub 2011 Nov 10. PMID: 22085888.
In vivo protocol:
1. Salaga M, Blomster LV, Piechota-Polańczyk A, Zielińska M, Jacenik D, Cygankiewicz AI, Krajewska WM, Mikkelsen JD, Fichna J. Encenicline, an α7 Nicotinic Acetylcholine Receptor Partial Agonist, Reduces Immune Cell Infiltration in the Colon and Improves Experimental Colitis in Mice. J Pharmacol Exp Ther. 2016 Jan;356(1):157-69. doi: 10.1124/jpet.115.228205. Epub 2015 Oct 13. PMID: 26462538. 2. Hayward A, Adamson L, Neill JC. Partial agonism at the α7 nicotinic acetylcholine receptor improves attention, impulsive action and vigilance in low attentive rats. Eur Neuropsychopharmacol. 2017 Apr;27(4):325-335. doi: 10.1016/j.euroneuro.2017.01.013. Epub 2017 Feb 1. PMID: 28161246.
1: Salaga M, Blomster LV, Piechota-Polańczyk A, Zielińska M, Jacenik D, Cygankiewicz AI, Krajewska WM, Mikkelsen JD, Fichna J. Encenicline, an α7 Nicotinic Acetylcholine Receptor Partial Agonist, Reduces Immune Cell Infiltration in the Colon and Improves Experimental Colitis in Mice. J Pharmacol Exp Ther. 2016 Jan;356(1):157-69. doi: 10.1124/jpet.115.228205. Epub 2015 Oct 13. PMID: 26462538. 2: Barbier AJ, Hilhorst M, Van Vliet A, Snyder P, Palfreyman MG, Gawryl M, Dgetluck N, Massaro M, Tiessen R, Timmerman W, Hilt DC. Pharmacodynamics, pharmacokinetics, safety, and tolerability of encenicline, a selective α7 nicotinic receptor partial agonist, in single ascending-dose and bioavailability studies. Clin Ther. 2015 Feb 1;37(2):311-24. doi: 10.1016/j.clinthera.2014.09.013. Epub 2014 Oct 14. PMID: 25438724. 3: Keefe RS, Meltzer HA, Dgetluck N, Gawryl M, Koenig G, Moebius HJ, Lombardo I, Hilt DC. Randomized, Double-Blind, Placebo-Controlled Study of Encenicline, an α7 Nicotinic Acetylcholine Receptor Agonist, as a Treatment for Cognitive Impairment in Schizophrenia. Neuropsychopharmacology. 2015 Dec;40(13):3053-60. doi: 10.1038/npp.2015.176. Epub 2015 Jun 19. PMID: 26089183; PMCID: PMC4864641. 4: Godyń J, Jończyk J, Panek D, Malawska B. Therapeutic strategies for Alzheimer's disease in clinical trials. Pharmacol Rep. 2016 Feb;68(1):127-38. doi: 10.1016/j.pharep.2015.07.006. Epub 2015 Aug 5. PMID: 26721364. 5: Schuster RM, Pachas GN, Stoeckel L, Cather C, Nadal M, Mischoulon D, Schoenfeld DA, Zhang H, Ulysse C, Dodds EB, Sobolewski S, Hudziak V, Hanly A, Fava M, Evins AE. Phase IIb Trial of an α7 Nicotinic Receptor Partial Agonist With and Without Nicotine Patch for Withdrawal-Associated Cognitive Deficits and Tobacco Abstinence. J Clin Psychopharmacol. 2018 Aug;38(4):307-316. doi: 10.1097/JCP.0000000000000919. PMID: 29912798; PMCID: PMC6019566. 6: Citrome L. Unmet needs in the treatment of schizophrenia: new targets to help different symptom domains. J Clin Psychiatry. 2014;75 Suppl 1:21-6. doi: 10.4088/JCP.13049su1c.04. PMID: 24581451. 7: Werner FM, Coveñas R. The Novel Antipsychotic Drug Cariprazine and Cognition Enhancing Drugs: Indications for their Use as the Add-on Therapy in Schizophrenia. Curr Pharm Des. 2021;27(39):4033-4038. doi: 10.2174/1381612826666201210123229. PMID: 33302854. 8: Hashimoto K. Tropisetron and its targets in Alzheimer's disease. Expert Opin Ther Targets. 2015 Jan;19(1):1-5. doi: 10.1517/14728222.2014.983901. Epub 2014 Nov 15. PMID: 25399811. 9: Hashimoto K. Targeting of α7 Nicotinic Acetylcholine Receptors in the Treatment of Schizophrenia and the Use of Auditory Sensory Gating as a Translational Biomarker. Curr Pharm Des. 2015;21(26):3797-806. doi: 10.2174/1381612821666150605111345. PMID: 26044974; PMCID: PMC5024727. 10: Keefe RS, Davis VG, Spagnola NB, Hilt D, Dgetluck N, Ruse S, Patterson TD, Narasimhan M, Harvey PD. Reliability, validity and treatment sensitivity of the Schizophrenia Cognition Rating Scale. Eur Neuropsychopharmacol. 2015 Feb;25(2):176-84. doi: 10.1016/j.euroneuro.2014.06.009. Epub 2014 Jun 28. PMID: 25028065; PMCID: PMC4277931. 11: Hayward A, Adamson L, Neill JC. Partial agonism at the α7 nicotinic acetylcholine receptor improves attention, impulsive action and vigilance in low attentive rats. Eur Neuropsychopharmacol. 2017 Apr;27(4):325-335. doi: 10.1016/j.euroneuro.2017.01.013. Epub 2017 Feb 1. PMID: 28161246. 12: Koola MM. Attenuated Mismatch Negativity in Attenuated Psychosis Syndrome Predicts Psychosis: Can Galantamine-Memantine Combination Prevent Psychosis? Mol Neuropsychiatry. 2018 Oct;4(2):71-74. doi: 10.1159/000488797. Epub 2018 Jun 7. PMID: 30397594; PMCID: PMC6206967. 13: Deardorff WJ, Shobassy A, Grossberg GT. Safety and clinical effects of EVP-6124 in subjects with Alzheimer's disease currently or previously receiving an acetylcholinesterase inhibitor medication. Expert Rev Neurother. 2015 Jan;15(1):7-17. doi: 10.1586/14737175.2015.995639. Epub 2014 Dec 15. PMID: 25495510. 14: Garay RP, Citrome L, Samalin L, Liu CC, Thomsen MS, Correll CU, Hameg A, Llorca PM. Therapeutic improvements expected in the near future for schizophrenia and schizoaffective disorder: an appraisal of phase III clinical trials of schizophrenia-targeted therapies as found in US and EU clinical trial registries. Expert Opin Pharmacother. 2016;17(7):921-36. doi: 10.1517/14656566.2016.1149164. Epub 2016 Feb 19. PMID: 26831200. 15: Plagenhoef MR, Callahan PM, Beck WD, Blake DT, Terry AV Jr. Aged rhesus monkeys: Cognitive performance categorizations and preclinical drug testing. Neuropharmacology. 2021 Apr 1;187:108489. doi: 10.1016/j.neuropharm.2021.108489. Epub 2021 Feb 6. PMID: 33561449; PMCID: PMC8286428. 16: Stoiljkovic M, Kelley C, Hajós GP, Nagy D, Koenig G, Leventhal L, Hajós M. Hippocampal network dynamics in response to α7 nACh receptors activation in amyloid-β overproducing transgenic mice. Neurobiol Aging. 2016 Sep;45:161-168. doi: 10.1016/j.neurobiolaging.2016.05.021. Epub 2016 Jun 6. PMID: 27459936. 17: Lin MW, Chen YH, Yang HB, Lin CC, Hung SY. Galantamine Inhibits Aβ1-42-Induced Neurotoxicity by Enhancing α7nAChR Expression as a Cargo Carrier for LC3 Binding and Aβ1-42 Engulfment During Autophagic Degradation. Neurotherapeutics. 2020 Apr;17(2):676-689. doi: 10.1007/s13311-019-00803-7. PMID: 31823156; PMCID: PMC7283419. 18: Stoiljkovic M, Leventhal L, Chen A, Chen T, Driscoll R, Flood D, Hodgdon H, Hurst R, Nagy D, Piser T, Tang C, Townsend M, Tu Z, Bertrand D, Koenig G, Hajós M. Concentration-response relationship of the α7 nicotinic acetylcholine receptor agonist FRM-17874 across multiple in vitro and in vivo assays. Biochem Pharmacol. 2015 Oct 15;97(4):576-589. doi: 10.1016/j.bcp.2015.07.006. Epub 2015 Jul 20. PMID: 26206187.