SB-242084 HCl | 1049747-87-6 | 181632-25-7 | 5HT2C Receptor

MedKoo Cat#: 522509 | Name: SB-242084 HCl

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Description:

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

SB-242084 is a psychoactive drug and research chemical which acts as a selective antagonist for the 5HT2C receptor. It has anxiolytic effects, and enhances dopamine signaling in the limbic system, as well as having complex effects on the dopamine release produced by cocaine, increasing it in some brain regions but reducing it in others. It has been shown to increase the effectiveness of the selective serotonin reuptake inhibitor (SSRI) class of antidepressants, and may also reduce their side effects. In animal studies, SB-242084 produced stimulant-type activity and reinforcing effects, somewhat similar to but much weaker than cocaine or amphetamines.

Chemical Structure

SB-242084 HCl

CAS#1049747-87-6 (HCl)

Theoretical Analysis

MedKoo Cat#: 522509

Name: SB-242084 HCl

CAS#: 1049747-87-6 (HCl)

Chemical Formula: C21H21Cl3N4O2

Exact Mass:

Molecular Weight: 467.78

Elemental Analysis: C, 53.92; H, 4.53; Cl, 22.74; N, 11.98; O, 6.84

Price and Availability

Size	Price	Availability
5mg	USD 120.00	Ready to ship
10mg	USD 190.00	Ready to ship
25mg	USD 425.00	Ready to ship
50mg	USD 750.00	Ready to ship
100mg	USD 1,250.00	Ready to ship
200mg	USD 2,250.00	Ready to ship

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Related CAS #

1049747-87-6 (HCl) 181632-25-7 (free base)

Synonym

SB-242084; SB 242084; SB242084; SB-242084 HCl

IUPAC/Chemical Name

6-chloro-2,3-dihydro-5-methyl-N-[6-[(2-methyl-3-pyridinyl)oxy]-3-pyridinyl]-1H-indole-1-carboxamide, dihydrochloride

InChi Key

GCMNSEILNIPNSX-UHFFFAOYSA-N

InChi Code

InChI=1S/C21H19ClN4O2.2ClH/c1-13-10-15-7-9-26(18(15)11-17(13)22)21(27)25-16-5-6-20(24-12-16)28-19-4-3-8-23-14(19)2;;/h3-6,8,10-12H,7,9H2,1-2H3,(H,25,27);2*1H

SMILES Code

O=C(N1CCC2=C1C=C(Cl)C(C)=C2)NC3=CC=C(OC4=CC=CN=C4C)N=C3.[H]Cl.[H]Cl

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).

HS Tariff Code

2934.99.9001

More Info

Related CAS# 1049747-87-6 (HCl salt); 181632-25-7 (free base)

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A8T11K27

View CoA: current batch, Lot#A8T08K24

QC Data

View QC data: current batch, Lot#A8T11K27

View QC data: current batch, Lot#A8T08K24

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

SB 242084 hydrochloride is a 5-HT2C receptor antagonist (pKi=9.0) that displays 158- and 100-fold selectivity over 5-HT2A and 5-HT2B receptors respectively.

In vitro activity:

This study added SB242084 (10−8–10−5 mol/L) to U251 cells after 30 min incubation of RO-60-0175 10−6 mol/L. U251 cells were conducted with RO-60-0175 and SB242084 at 37 °C for 2 h. Changes in mRNA expression were detected by real-time PCR and calculated by 2-ΔΔCt method. Overexpression of NEP mRNA induced by RO-60-0175 is almost inhibited completely at concentration 10−5 mol/L of SB242084 (Fig. 2a). The dose–response curve was plotted by Origin 6.0 (OriginLab, Northampton, USA), and the inhibitory concentration 50 % (IC50) of SB242084 was calculated to be 2.9 × 10−6 mol/L (Fig. 2b). Reference: Cell Mol Neurobiol. 2015 Apr;35(3):425-432. https://pubmed.ncbi.nlm.nih.gov/25452160/

In vivo activity:

One of the more remarkable findings from this study is that LR (low-responder) animals were overall more susceptible to the effects induced by the selective 5-HT2C receptor antagonist SB242084 than HR (high-responder) rats. Indeed, repeated co-administration of SB242084+cocaine, during the conditioning phase produced a significant increase in the CPP (conditioned place preference) response in LR rats only. Moreover, a negative correlation between locomotion and CPP in animals pretreated with SB242084+cocaine was observed. These effects were present only when SB242084 was co-administered with cocaine. In fact, injection of SB242084 followed by saline did not to induce CPP in LR animals. These finding suggests that in this study the 5-HT2C receptor blockade facilitated the acquisition of cocaine-induced place preference in LR animals by either increasing the efficacy of the cocaine rewarding actions or improving the learning conditions. Reference: Psychopharmacology (Berl). 2012 Apr; 220(4): 731–740. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3314106/

	Solvent	mg/mL	mM
Solubility
	Ethanol	1.0	2.14
	PBS (pH 7.2)	10.0	21.38
	DMSO	59.6	127.47
	DMF	30.0	64.13

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 467.78 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.

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. Papp N, Koncz S, Kostyalik D, Kitka T, Petschner P, Vas S, Bagdy G. Acute 5-HT2C Receptor Antagonist SB-242084 Treatment Affects EEG Gamma Band Activity Similarly to Chronic Escitalopram. Front Pharmacol. 2020 Jan 29;10:1636. doi: 10.3389/fphar.2019.01636. PMID: 32063851; PMCID: PMC7000428. 2. Capriles N, Watson S Jr, Akil H. Individual differences in the improvement of cocaine-induced place preference response by the 5-HT2C receptor antagonist SB242084 in rats. Psychopharmacology (Berl). 2012 Apr;220(4):731-40. doi: 10.1007/s00213-011-2524-9. Epub 2011 Oct 12. PMID: 21989806; PMCID: PMC3314106. 3. Watanabe Y, Tsujimura A, Aoki M, Taguchi K, Tanaka M. Development of the 5-HT2CR-Tango System Combined with an EGFP Reporter Gene. J Mol Neurosci. 2016 Feb;58(2):162-9. doi: 10.1007/s12031-015-0650-2. Epub 2015 Sep 15. PMID: 26374432. 4. Tian XL, Yu LH, Li WQ, Hu Y, Yin M, Wang ZJ. Activation of 5-HT(2C) receptor promotes the expression of neprilysin in U251 human glioma cells. Cell Mol Neurobiol. 2015 Apr;35(3):425-432. doi: 10.1007/s10571-014-0138-6. Epub 2014 Dec 2. PMID: 25452160.

In vitro protocol:

1. Watanabe Y, Tsujimura A, Aoki M, Taguchi K, Tanaka M. Development of the 5-HT2CR-Tango System Combined with an EGFP Reporter Gene. J Mol Neurosci. 2016 Feb;58(2):162-9. doi: 10.1007/s12031-015-0650-2. Epub 2015 Sep 15. PMID: 26374432. 2. Tian XL, Yu LH, Li WQ, Hu Y, Yin M, Wang ZJ. Activation of 5-HT(2C) receptor promotes the expression of neprilysin in U251 human glioma cells. Cell Mol Neurobiol. 2015 Apr;35(3):425-432. doi: 10.1007/s10571-014-0138-6. Epub 2014 Dec 2. PMID: 25452160.

In vivo protocol:

1: Manvich DF, Kimmel HL, Cooper DA, Howell LL. The serotonin 2C receptor antagonist SB 242084 exhibits abuse-related effects typical of stimulants in squirrel monkeys. J Pharmacol Exp Ther. 2012 Sep;342(3):761-9. doi: 10.1124/jpet.112.195156. Epub 2012 Jun 8. PubMed PMID: 22685342; PubMed Central PMCID: PMC3422522. 2: Andrade AL, Abrahao KP, Goeldner FO, Souza-Formigoni ML. Administration of the 5-HT2C receptor antagonist SB-242084 into the nucleus accumbens blocks the expression of ethanol-induced behavioral sensitization in Albino Swiss mice. Neuroscience. 2011 Aug 25;189:178-86. doi: 10.1016/j.neuroscience.2011.05.028. Epub 2011 May 27. PubMed PMID: 21658435. 3: Strong PV, Greenwood BN, Fleshner M. The effects of the selective 5-HT(2C) receptor antagonist SB 242084 on learned helplessness in male Fischer 344 rats. Psychopharmacology (Berl). 2009 May;203(4):665-75. doi: 10.1007/s00213-008-1413-3. Epub 2008 Nov 27. PubMed PMID: 19037632. 4: Kantor S, Jakus R, Molnar E, Gyongyosi N, Toth A, Detari L, Bagdy G. Despite similar anxiolytic potential, the 5-hydroxytryptamine 2C receptor antagonist SB-242084 [6-chloro-5-methyl-1-[2-(2-methylpyrid-3-yloxy)-pyrid-5-yl carbamoyl] indoline] and chlordiazepoxide produced differential effects on electroencephalogram power spectra. J Pharmacol Exp Ther. 2005 Nov;315(2):921-30. Epub 2005 Aug 5. PubMed PMID: 16085759. 5: Martin JR, Ballard TM, Higgins GA. Influence of the 5-HT2C receptor antagonist, SB-242084, in tests of anxiety. Pharmacol Biochem Behav. 2002 Apr;71(4):615-25. PubMed PMID: 11888553. 6: Bagdy G, Graf M, Anheuer ZE, Modos EA, Kantor S. Anxiety-like effects induced by acute fluoxetine, sertraline or m-CPP treatment are reversed by pretreatment with the 5-HT2C receptor antagonist SB-242084 but not the 5-HT1A receptor antagonist WAY-100635. Int J Neuropsychopharmacol. 2001 Dec;4(4):399-408. PubMed PMID: 11806866. 7: Hemrick-Luecke SK, Evans DC. Comparison of the potency of MDL 100,907 and SB 242084 in blocking the serotonin (5-HT)(2) receptor agonist-induced increases in rat serum corticosterone concentrations: evidence for 5-HT(2A) receptor mediation of the HPA axis. Neuropharmacology. 2002 Feb;42(2):162-9. PubMed PMID: 11804612. 8: Di Matteo V, Di Giovanni G, Di Mascio M, Esposito E. SB 242084, a selective serotonin2C receptor antagonist, increases dopaminergic transmission in the mesolimbic system. Neuropharmacology. 1999 Aug;38(8):1195-205. PubMed PMID: 10462132. 9: Bromidge SM, Duckworth M, Forbes IT, Ham P, King FD, Thewlis KM, Blaney FE, Naylor CB, Blackburn TP, Kennett GA, Wood MD, Clarke SE. 6-Chloro-5-methyl-1-[[2-[(2-methyl-3-pyridyl)oxy]-5-pyridyl]carbamoyl]- indoline (SB-242084): the first selective and brain penetrant 5-HT2C receptor antagonist. J Med Chem. 1997 Oct 24;40(22):3494-6. PubMed PMID: 9357513. 10: Kennett GA, Wood MD, Bright F, Trail B, Riley G, Holland V, Avenell KY, Stean T, Upton N, Bromidge S, Forbes IT, Brown AM, Middlemiss DN, Blackburn TP. SB 242084, a selective and brain penetrant 5-HT2C receptor antagonist. Neuropharmacology. 1997 Apr-May;36(4-5):609-20. PubMed PMID: 9225286.