Vabicaserin HCl

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

MedKoo CAT#: 529113

CAS#: 887258-94-8

Description: Vabicaserin HCl is an 5-HT2C agonist potentially for the treatment of schizophrenia.


Price and Availability

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Vabicaserin HCl 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#: 529113
Name: Vabicaserin HCl
CAS#: 887258-94-8
Chemical Formula: C15H21ClN2
Exact Mass: 264.1393
Molecular Weight: 264.79
Elemental Analysis: C, 68.04; H, 7.99; Cl, 13.39; N, 10.58


Related CAS #: 887258-95-9 (free)   887258-94-8 (HCl)  

Synonym: SCA-136; PF-05208769; PF-5208769; SCA136; PF05208769; PF5208769; SCA 136; PF 05208769; PF 5208769

IUPAC/Chemical Name: (9aR,12aS)-4,5,6,7,9,9a,10,11,12,12a-decahydrocyclopenta[c][1,4]diazepino[6,7,1-ij]quinoline hydrochloride

InChi Key: PYPPENBDXAWXJC-QNTKWALQSA-N

InChi Code: InChI=1S/C15H20N2.ClH/c1-3-11-9-16-7-8-17-10-12-4-2-5-13(12)14(6-1)15(11)17;/h1,3,6,12-13,16H,2,4-5,7-10H2;1H/t12-,13-;/m0./s1

SMILES Code: [H][C@]12CN3C4=C(C=CC=C4CNCC3)[C@@]1([H])CCC2.[H]Cl


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: Shen JH, Zhao Y, Rosenzweig-Lipson S, Popp D, Williams JB, Giller E, Detke MJ, Kane JM. A 6-week randomized, double-blind, placebo-controlled, comparator referenced trial of vabicaserin in acute schizophrenia. J Psychiatr Res. 2014 Jun;53:14-22. doi: 10.1016/j.jpsychires.2014.02.012. PubMed PMID: 24613032.

2: Tong Z, Chandrasekaran A, DeMaio W, Jordan R, Li H, Moore R, Poola N, Burghart P, Hultin T, Scatina J. Species differences in the formation of vabicaserin carbamoyl glucuronide. Drug Metab Dispos. 2010 Apr;38(4):581-90. doi: 10.1124/dmd.109.028639. PubMed PMID: 20032194.

3: Tong Z, Chandrasekaran A, DeMaio W, Espina R, Lu W, Jordan R, Scatina J. Metabolism of vabicaserin in mice, rats, dogs, monkeys, and humans. Drug Metab Dispos. 2010 Dec;38(12):2266-77. doi: 10.1124/dmd.110.033670. PubMed PMID: 20739639.

4: Dunlop J, Watts SW, Barrett JE, Coupet J, Harrison B, Mazandarani H, Nawoschik S, Pangalos MN, Ramamoorthy S, Schechter L, Smith D, Stack G, Zhang J, Zhang G, Rosenzweig-Lipson S. Characterization of vabicaserin (SCA-136), a selective 5-hydroxytryptamine 2C receptor agonist. J Pharmacol Exp Ther. 2011 Jun;337(3):673-80. doi: 10.1124/jpet.111.179572. PubMed PMID: 21402690.

5: Liu J, Ogden A, Comery TA, Spiros A, Roberts P, Geerts H. Prediction of Efficacy of Vabicaserin, a 5-HT2C Agonist, for the Treatment of Schizophrenia Using a Quantitative Systems Pharmacology Model. CPT Pharmacometrics Syst Pharmacol. 2014 Apr 23;3:e111. doi: 10.1038/psp.2014.7. PubMed PMID: 24759548; PubMed Central PMCID: PMC4011163.

6: Dziechciejewski WJ, Weber R, Sowada O, Boysen MM. Cycloalkene Carbonitriles in Rhodium-Catalyzed 1,4-Addition and Formal Synthesis of Vabicaserin. Org Lett. 2015 Sep 4;17(17):4132-5. doi: 10.1021/acs.orglett.5b01849. PubMed PMID: 26274890.

7: 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. PubMed PMID: 24491146; PubMed Central PMCID: PMC3983360.

8: Dragan V, McWilliams JC, Miller R, Sutherland K, Dillon JL, O'Brien MK. Asymmetric synthesis of vabicaserin via oxidative multicomponent annulation and asymmetric hydrogenation of a 3,4-substituted quinolinium salt. Org Lett. 2013 Jun 21;15(12):2942-5. doi: 10.1021/ol401029k. PubMed PMID: 23751116.

9: Rosenzweig-Lipson S, Comery TA, Marquis KL, Gross J, Dunlop J. 5-HT(2C) agonists as therapeutics for the treatment of schizophrenia. Handb Exp Pharmacol. 2012;(213):147-65. doi: 10.1007/978-3-642-25758-2_6. Review. PubMed PMID: 23027415.

10: Ogino S, Nagakura Y, Tsukamoto M, Watabiki T, Ozawa T, Oe T, Shimizu Y, Ito H. Systemic administration of 5-HT(2C) receptor agonists attenuates muscular hyperalgesia in reserpine-induced myalgia model. Pharmacol Biochem Behav. 2013 Jul;108:8-15. doi: 10.1016/j.pbb.2013.04.007. PubMed PMID: 23603031.

11: Garay RP, Bourin M, de Paillette E, Samalin L, Hameg A, Llorca PM. Potential serotonergic agents for the treatment of schizophrenia. Expert Opin Investig Drugs. 2016;25(2):159-70. doi: 10.1517/13543784.2016.1121995. Review. PubMed PMID: 26576669.

12: Hovelsø N, Sager TN, Mørk A. Combination of escitalopram and a 5-HT(₁A) receptor antagonist selectively decreases the extracellular levels of dopamine in the nucleus accumbens relative to striatum through 5-HT(₂C) receptor stimulation; suggestive of antipsychotic potential. Pharmacol Biochem Behav. 2011 Jan;97(3):479-85. doi: 10.1016/j.pbb.2010.10.003. PubMed PMID: 20937301.