WAY-163909

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

MedKoo CAT#: 532959

CAS#: 428868-32-0

Description: WAY-163909 is a 5-HT2C agonist which enhances the preclinical potency of current antipsychotics.


Price and Availability

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WAY-163909 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#: 532959
Name: WAY-163909
CAS#: 428868-32-0
Chemical Formula: C14H18N2
Exact Mass: 214.147
Molecular Weight: 214.31
Elemental Analysis: C, 78.46; H, 8.47; N, 13.07


Synonym: WAY-163909 ; WAY 163909 ; WAY163909

IUPAC/Chemical Name: (11R,15R)-7,10-diazatetracyclo[8.5.1.0^{5,16}.0^{11,15}]hexadeca-1,3,5(16)-triene

InChi Key: XOSKJKGKWRIMGV-DGCLKSJQSA-N

InChi Code: InChI=1S/C14H18N2/c1-3-10-9-15-7-8-16-13-6-2-4-11(13)12(5-1)14(10)16/h1,3,5,11,13,15H,2,4,6-9H2/t11-,13-/m1/s1

SMILES Code: [H][C@]1(CCC[C@]21[H])N3CCNCC4=C3C2=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

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


References

1: Kim J, Moon BS, Lee BC, Lee HY, Kim HJ, Choo H, Pae AN, Cho YS, Min SJ. A Potential PET Radiotracer for the 5-HT(2C) Receptor: Synthesis and in Vivo Evaluation of 4-(3-[(18)F]fluorophenethoxy)pyrimidine. ACS Chem Neurosci. 2017 May 17;8(5):996-1003. doi: 10.1021/acschemneuro.6b00445. Epub 2017 Feb 27. PubMed PMID: 28194935.

2: Swinford-Jackson SE, Anastasio NC, Fox RG, Stutz SJ, Cunningham KA. Incubation of cocaine cue reactivity associates with neuroadaptations in the cortical serotonin (5-HT) 5-HT2C receptor (5-HT2CR) system. Neuroscience. 2016 Jun 2;324:50-61. doi: 10.1016/j.neuroscience.2016.02.052. Epub 2016 Feb 27. PubMed PMID: 26926963; PubMed Central PMCID: PMC4838519.

3: Anastasio NC, Liu S, Maili L, Swinford SE, Lane SD, Fox RG, Hamon SC, Nielsen DA, Cunningham KA, Moeller FG. Variation within the serotonin (5-HT) 5-HT₂C receptor system aligns with vulnerability to cocaine cue reactivity. Transl Psychiatry. 2014 Mar 11;4:e369. doi: 10.1038/tp.2013.131. PubMed PMID: 24618688; PubMed Central PMCID: PMC3966037.

4: Neelamegam R, Hellenbrand T, Schroeder FA, Wang C, Hooker JM. Imaging evaluation of 5HT2C agonists, [(11)C]WAY-163909 and [(11)C]vabicaserin, formed by Pictet-Spengler cyclization. J Med Chem. 2014 Feb 27;57(4):1488-94. doi: 10.1021/jm401802f. Epub 2014 Feb 12. PubMed PMID: 24491146; PubMed Central PMCID: PMC3983360.

5: Cunningham KA, Anastasio NC, Fox RG, Stutz SJ, Bubar MJ, Swinford SE, Watson CS, Gilbertson SR, Rice KC, Rosenzweig-Lipson S, Moeller FG. Synergism between a serotonin 5-HT2A receptor (5-HT2AR) antagonist and 5-HT2CR agonist suggests new pharmacotherapeutics for cocaine addiction. ACS Chem Neurosci. 2013 Jan 16;4(1):110-21. doi: 10.1021/cn300072u. Epub 2012 Aug 11. PubMed PMID: 23336050; PubMed Central PMCID: PMC3547488.

6: Cunningham KA, Fox RG, Anastasio NC, Bubar MJ, Stutz SJ, Moeller FG, Gilbertson SR, Rosenzweig-Lipson S. Selective serotonin 5-HT(2C) receptor activation suppresses the reinforcing efficacy of cocaine and sucrose but differentially affects the incentive-salience value of cocaine- vs. sucrose-associated cues. Neuropharmacology. 2011 Sep;61(3):513-23. doi: 10.1016/j.neuropharm.2011.04.034. Epub 2011 May 11. PubMed PMID: 21575646; PubMed Central PMCID: PMC3115535.

7: Zaniewska M, McCreary AC, Wydra K, Filip M. Differential effects of serotonin (5-HT)2 receptor-targeting ligands on locomotor responses to nicotine-repeated treatment. Synapse. 2010 Jul;64(7):511-9. doi: 10.1002/syn.20756. PubMed PMID: 20196140.

8: Grauer SM, Graf R, Navarra R, Sung A, Logue SF, Stack G, Huselton C, Liu Z, Comery TA, Marquis KL, Rosenzweig-Lipson S. WAY-163909, a 5-HT2C agonist, enhances the preclinical potency of current antipsychotics. Psychopharmacology (Berl). 2009 May;204(1):37-48. doi: 10.1007/s00213-008-1433-z. Epub 2008 Dec 20. PubMed PMID: 19107466.

9: Navarra R, Comery TA, Graf R, Rosenzweig-Lipson S, Day M. The 5-HT(2C) receptor agonist WAY-163909 decreases impulsivity in the 5-choice serial reaction time test. Behav Brain Res. 2008 Apr 9;188(2):412-5. doi: 10.1016/j.bbr.2007.11.016. Epub 2007 Nov 29. PubMed PMID: 18191235.

10: Zaniewska M, McCreary AC, Przegaliński E, Filip M. Effects of the serotonin 5-HT2A and 5-HT2C receptor ligands on the discriminative stimulus effects of nicotine in rats. Eur J Pharmacol. 2007 Oct 1;571(2-3):156-65. Epub 2007 Jun 13. PubMed PMID: 17617403.

11: Rosenzweig-Lipson S, Sabb A, Stack G, Mitchell P, Lucki I, Malberg JE, Grauer S, Brennan J, Cryan JF, Sukoff Rizzo SJ, Dunlop J, Barrett JE, Marquis KL. Antidepressant-like effects of the novel, selective, 5-HT2C receptor agonist WAY-163909 in rodents. Psychopharmacology (Berl). 2007 Jun;192(2):159-70. Epub 2007 Feb 13. PubMed PMID: 17297636.

12: Dunlop J, Marquis KL, Lim HK, Leung L, Kao J, Cheesman C, Rosenzweig-Lipson S. Pharmacological profile of the 5-HT(2C) receptor agonist WAY-163909; therapeutic potential in multiple indications. CNS Drug Rev. 2006 Fall-Winter;12(3-4):167-77. Review. PubMed PMID: 17227285.

13: Marquis KL, Sabb AL, Logue SF, Brennan JA, Piesla MJ, Comery TA, Grauer SM, Ashby CR Jr, Nguyen HQ, Dawson LA, Barrett JE, Stack G, Meltzer HY, Harrison BL, Rosenzweig-Lipson S. WAY-163909 [(7bR,10aR)-1,2,3,4,8,9,10,10a-octahydro-7bH-cyclopenta-[b][1,4]diazepino[6,7,1hi ]indole]: A novel 5-hydroxytryptamine 2C receptor-selective agonist with preclinical antipsychotic-like activity. J Pharmacol Exp Ther. 2007 Jan;320(1):486-96. Epub 2006 Oct 12. PubMed PMID: 17038512.

14: Dunlop J, Sabb AL, Mazandarani H, Zhang J, Kalgaonker S, Shukhina E, Sukoff S, Vogel RL, Stack G, Schechter L, Harrison BL, Rosenzweig-Lipson S. WAY-163909 [(7bR, 10aR)-1,2,3,4,8,9,10,10a-octahydro-7bH-cyclopenta-[b][1,4]diazepino[6,7,1hi]indol e], a novel 5-hydroxytryptamine 2C receptor-selective agonist with anorectic activity. J Pharmacol Exp Ther. 2005 May;313(2):862-9. Epub 2005 Feb 10. PubMed PMID: 15705738.