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MedKoo Cat#: 341364 | Name: Vabicaserin free base

Description:

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

Vabicaserin is a selective 5-HT2C receptor agonist investigated for its potential antipsychotic and antidepressant effects. It exhibits high affinity for the 5-HT2C receptor (Ki = 3.7 nM) with over 100-fold selectivity against 5-HT2A and 5-HT2B receptors. Functional assays indicate potent activation of 5-HT2C-mediated intracellular signaling (EC50 = 18 nM). In preclinical models, Vabicaserin demonstrated dose-dependent efficacy in reducing dopamine-related behaviors and enhancing serotoninergic neurotransmission.

Chemical Structure

Vabicaserin free base
Vabicaserin free base
CAS#887258-95-9 (free base)

Theoretical Analysis

MedKoo Cat#: 341364

Name: Vabicaserin free base

CAS#: 887258-95-9 (free base)

Chemical Formula: C15H20N2

Exact Mass: 228.1626

Molecular Weight: 228.34

Elemental Analysis: C, 78.90; H, 8.83; N, 12.27

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 #
887258-95-9 (free base) 887258-94-8 (HCl)
Synonym
Vabicaserin free base; SCA-136; SCA 136; SCA136; PF-05208769; PF 05208769; PF05208769; PF-5208769; PF 5208769; PF5208769;
IUPAC/Chemical Name
Cyclopenta(4,5)pyrido(3,2,1-jk)(1,4)benzodiazepine, 4,5,6,7,9,9a,10,11,12,12a-decahydro-, (9aR,12aS)-rel-(-)-
InChi Key
NPTIPEQJIDTVKR-CHWSQXEVSA-N
InChi Code
InChI=1S/C15H20N2/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/t12-,13-/m1/s1
SMILES Code
[H][C@]1(C2)[C@](C3=C(N2CCNC4)C4=CC=C3)([H])CCC1
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 228.34 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: Palacios JM, Pazos A, Hoyer D. A short history of the 5-HT(2C) receptor: from the choroid plexus to depression, obesity and addiction treatment. Psychopharmacology (Berl). 2017 May;234(9-10):1395-1418. doi: 10.1007/s00213-017-4545-5. Epub 2017 Mar 7. Review. PubMed PMID: 28265714. 2: 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. Epub 2015 Dec 15. Review. PubMed PMID: 26576669. 3: 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. Epub 2015 Aug 14. PubMed PMID: 26274890. 4: 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. 5: 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. Epub 2014 Feb 24. PubMed PMID: 24613032. 6: 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. 7: 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. Epub 2013 Jun 10. PubMed PMID: 23751116. 8: 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. Epub 2013 Apr 18. PubMed PMID: 23603031. 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: 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. Epub 2011 Mar 14. PubMed PMID: 21402690. 11: 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. Epub 2010 Oct 16. PubMed PMID: 20937301. 12: 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. Epub 2010 Aug 25. PubMed PMID: 20739639. 13: 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. Epub 2009 Dec 23. PubMed PMID: 20032194.

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