WAY 100635

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

MedKoo CAT#: 526564

CAS#: 162760-96-5

Description: WAY 100635 is a piperazine drug and research chemical widely used in scientific studies. It was originally believed to act as a selective 5-HT1A receptor antagonist, but subsequent research showed that it also acts as potent full agonist at the D4 receptor. It is sometimes referred to as a silent antagonist at the former receptor. It is closely related to WAY-100,135.


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WAY 100635 is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote..


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526564
Name: WAY 100635
CAS#: 162760-96-5
Chemical Formula: C25H34N4O2
Exact Mass: 422.2682
Molecular Weight: 422.573
Elemental Analysis: C, 71.06; H, 8.11; N, 13.26; O, 7.57


Synonym: WAY-100635; WAY100635; WAY 100635

IUPAC/Chemical Name: N-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyl)-N-(pyridin-2-yl)cyclohexanecarboxamide

InChi Key: SBPRIAGPYFYCRT-UHFFFAOYSA-N

InChi Code: InChI=1S/C25H34N4O2/c1-31-23-12-6-5-11-22(23)28-18-15-27(16-19-28)17-20-29(24-13-7-8-14-26-24)25(30)21-9-3-2-4-10-21/h5-8,11-14,21H,2-4,9-10,15-20H2,1H3

SMILES Code: O=C(C1CCCCC1)N(CCN2CCN(C3=CC=CC=C3OC)CC2)C4=NC=CC=C4


Technical Data

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, 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).

Harmonized System Code:
293490


Additional Information

Related CAS#
162760-96-5 ( WAY 100635 free)
634908-75-1 ( WAY 100635 maleate)


References

1: Penttilä J, Hirvonen J, Tuominen L, Lumme V, Ilonen T, Någren K, Hietala J. Verbal memory and 5-HT1A receptors in healthy volunteers - A PET study with [carbonyl-(11)C]WAY-100635. Eur Neuropsychopharmacol. 2016 Mar;26(3):570-7. doi: 10.1016/j.euroneuro.2015.12.028. Epub 2015 Dec 21. PubMed PMID: 26775837.

2: Zheng Z, Im SH, Lee BH, Seo H, Bae MA, Ahn SH. In vitro permeability, pharmacokinetics and brain uptake of WAY-100635 and FCWAY in rats using liquid chromatography electrospray ionization tandem mass spectrometry. Arch Pharm Res. 2015 Jun;38(6):1072-9. doi: 10.1007/s12272-014-0369-6. Epub 2014 May 17. PubMed PMID: 24838378.

3: Kranz GS, Rami-Mark C, Kaufmann U, Baldinger P, Hahn A, Höflich A, Savli M, Stein P, Wadsak W, Mitterhauser M, Winkler D, Lanzenberger R, Kasper S. Effects of hormone replacement therapy on cerebral serotonin-1A receptor binding in postmenopausal women examined with [carbonyl-¹¹C]WAY-100635. Psychoneuroendocrinology. 2014 Jul;45:1-10. doi: 10.1016/j.psyneuen.2014.03.004. Epub 2014 Mar 20. PubMed PMID: 24845171.

4: Rami-Mark C, Ungersboeck J, Haeusler D, Nics L, Philippe C, Mitterhauser M, Willeit M, Lanzenberger R, Karanikas G, Wadsak W. Reliable set-up for in-loop ¹¹C-carboxylations using Grignard reactions for the preparation of [carbonyl-¹¹C]WAY-100635 and [¹¹C]-(+)-PHNO. Appl Radiat Isot. 2013 Dec;82:75-80. doi: 10.1016/j.apradiso.2013.07.023. Epub 2013 Aug 3. PubMed PMID: 23974301; PubMed Central PMCID: PMC3842501.

5: Schwen Z, Matsuta Y, Shen B, Wang J, Roppolo JR, de Groat WC, Tai C. Inhibition of bladder overactivity by duloxetine in combination with foot stimulation or WAY-100635 treatment in cats. Am J Physiol Renal Physiol. 2013 Dec 15;305(12):F1663-8. doi: 10.1152/ajprenal.00523.2013. Epub 2013 Oct 23. PubMed PMID: 24154699; PubMed Central PMCID: PMC3882444.

6: Maximino C, Puty B, Benzecry R, Araújo J, Lima MG, de Jesus Oliveira Batista E, Renata de Matos Oliveira K, Crespo-Lopez ME, Herculano AM. Role of serotonin in zebrafish (Danio rerio) anxiety: relationship with serotonin levels and effect of buspirone, WAY 100635, SB 224289, fluoxetine and para-chlorophenylalanine (pCPA) in two behavioral models. Neuropharmacology. 2013 Aug;71:83-97. doi: 10.1016/j.neuropharm.2013.03.006. Epub 2013 Mar 28. PubMed PMID: 23541719.

7: Hahn A, Nics L, Baldinger P, Wadsak W, Savli M, Kraus C, Birkfellner W, Ungersboeck J, Haeusler D, Mitterhauser M, Karanikas G, Kasper S, Frey R, Lanzenberger R. Application of image-derived and venous input functions in major depression using [carbonyl-(11)C]WAY-100635. Nucl Med Biol. 2013 Apr;40(3):371-7. doi: 10.1016/j.nucmedbio.2012.12.011. Epub 2013 Jan 30. PubMed PMID: 23375480.

8: Sullivan GM, Ogden RT, Huang YY, Oquendo MA, Mann JJ, Parsey RV. Higher in vivo serotonin-1a binding in posttraumatic stress disorder: a PET study with [11C]WAY-100635. Depress Anxiety. 2013 Mar;30(3):197-206. doi: 10.1002/da.22019. Epub 2013 Feb 13. PubMed PMID: 23408467; PubMed Central PMCID: PMC3785097.

9: Nics L, Hahn A, Zeilinger M, Vraka C, Ungersboeck J, Haeusler D, Hartmann S, Wagner KH, Lanzenberger R, Wadsak W, Mitterhauser M. Quantification of the radio-metabolites of the serotonin-1A receptor radioligand [carbonyl-11C]WAY-100635 in human plasma: an HPLC-assay which enables measurement of two patients in parallel. Appl Radiat Isot. 2012 Dec;70(12):2730-6. doi: 10.1016/j.apradiso.2012.08.016. Epub 2012 Sep 13. PubMed PMID: 23041392.

10: Al Hussainy R, Verbeek J, van der Born D, Molthoff C, Booij J, Herscheid JK. Synthesis, biodistribution and PET studies in rats of (18)F-Labeled bridgehead fluoromethyl analogues of WAY-100635. Nucl Med Biol. 2012 Oct;39(7):1068-76. doi: 10.1016/j.nucmedbio.2012.04.002. Epub 2012 May 17. PubMed PMID: 22609028.

11: Hahn A, Nics L, Baldinger P, Ungersböck J, Dolliner P, Frey R, Birkfellner W, Mitterhauser M, Wadsak W, Karanikas G, Kasper S, Lanzenberger R. Combining image-derived and venous input functions enables quantification of serotonin-1A receptors with [carbonyl-11C]WAY-100635 independent of arterial sampling. Neuroimage. 2012 Aug 1;62(1):199-206. doi: 10.1016/j.neuroimage.2012.04.047. Epub 2012 May 2. PubMed PMID: 22579604.

12: Mangin F, Dilly S, Joly B, Scuvée-Moreau J, Evans J, Setola V, Roth BL, Liégeois JF. Moderate chemical modifications of WAY-100635 improve the selectivity for 5-HT1A versus D4 receptors. Bioorg Med Chem Lett. 2012 Jul 15;22(14):4550-4. doi: 10.1016/j.bmcl.2012.05.119. Epub 2012 Jun 7. PubMed PMID: 22738628.

13: Al Hussainy R, Verbeek J, van der Born D, Booij J, Herscheid JK. Design, synthesis and in vitro evaluation of bridgehead fluoromethyl analogs of N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl}-N-(pyridin-2-yl)cyclohexanecarboxa mide (WAY-100635) for the 5-HT(1A) receptor. Eur J Med Chem. 2011 Dec;46(12):5728-35. doi: 10.1016/j.ejmech.2011.06.023. Epub 2011 Jun 29. PubMed PMID: 22000209.

14: Hunt GE, McGregor IS, Cornish JL, Callaghan PD. MDMA-induced c-Fos expression in oxytocin-containing neurons is blocked by pretreatment with the 5-HT-1A receptor antagonist WAY 100635. Brain Res Bull. 2011 Aug 10;86(1-2):65-73. doi: 10.1016/j.brainresbull.2011.06.011. Epub 2011 Jul 1. PubMed PMID: 21745546.

15: Al Hussainy R, Verbeek J, van der Born D, Braker AH, Leysen JE, Knol RJ, Booij J, Herscheid JK. Design, synthesis, radiolabeling, and in vitro and in vivo evaluation of bridgehead iodinated analogues of N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl}-N-(pyridin-2-yl)cyclohexanecarboxa mide (WAY-100635) as potential SPECT ligands for the 5-HT1A receptor. J Med Chem. 2011 May 26;54(10):3480-91. doi: 10.1021/jm1009956. Epub 2011 Apr 26. PubMed PMID: 21520940.

16: Assem-Hilger E, Lanzenberger R, Savli M, Wadsak W, Mitterhauser M, Mien LK, Stögmann E, Baumgartner C, Kletter K, Asenbaum S. Central serotonin 1A receptor binding in temporal lobe epilepsy: a [carbonyl-(11)C]WAY-100635 PET study. Epilepsy Behav. 2010 Nov;19(3):467-73. doi: 10.1016/j.yebeh.2010.07.030. Epub 2010 Sep 17. PubMed PMID: 20850389.

17: Saijo T, Takano A, Suhara T, Arakawa R, Okumura M, Ichimiya T, Ito H, Okubo Y. Effect of electroconvulsive therapy on 5-HT1A receptor binding in patients with depression: a PET study with [11C]WAY 100635. Int J Neuropsychopharmacol. 2010 Jul;13(6):785-91. doi: 10.1017/S1461145709991209. Epub 2010 Jan 13. PubMed PMID: 20067660.

18: Zanderigo F, Ogden RT, Chang C, Choy S, Wong A, Parsey RV. Robust fitting of [11C]-WAY-100635 PET data. J Cereb Blood Flow Metab. 2010 Jul;30(7):1366-72. doi: 10.1038/jcbfm.2010.20. Epub 2010 Feb 24. PubMed PMID: 20179725; PubMed Central PMCID: PMC2949218.

19: Sargent PA, Rabiner EA, Bhagwagar Z, Clark L, Cowen P, Goodwin GM, Grasby PM. 5-HT(1A) receptor binding in euthymic bipolar patients using positron emission tomography with [carbonyl-(11)C]WAY-100635. J Affect Disord. 2010 Jun;123(1-3):77-80. doi: 10.1016/j.jad.2009.07.015. Epub 2009 Sep 2. PubMed PMID: 19726088.

20: Paquette MA, Foley K, Brudney EG, Meshul CK, Johnson SW, Berger SP. The sigma-1 antagonist BMY-14802 inhibits L-DOPA-induced abnormal involuntary movements by a WAY-100635-sensitive mechanism. Psychopharmacology (Berl). 2009 Jul;204(4):743-54. doi: 10.1007/s00213-009-1505-8. Epub 2009 Mar 13. Erratum in: Psychopharmacology (Berl). 2009 May;204(1):185-7. PubMed PMID: 19283364; PubMed Central PMCID: PMC2845289.