(S)-SNAP 5114 | CAS#157604-55-2 |GABA transport inhibitor

MedKoo Cat#: 532760 | Name: (S)-SNAP 5114

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Description:

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

(S)-SNAP 5114 is a GABA transport inhibitor. It shows selectivity for GAT-3 and GAT-2. (S)-SNAP 5114 increases thalamic GABA levels and is an anticonvulsant following systemic administration in vivo.

Chemical Structure

(S)-SNAP 5114

CAS#157604-55-2

Theoretical Analysis

MedKoo Cat#: 532760

Name: (S)-SNAP 5114

CAS#: 157604-55-2

Chemical Formula: C30H35NO6

Exact Mass: 505.2464

Molecular Weight: 505.61

Elemental Analysis: C, 71.27; H, 6.98; N, 2.77; O, 18.99

Price and Availability

Size	Price	Availability
5mg	USD 400.00	2 weeks
10mg	USD 650.00	2 weeks
25mg	USD 1,100.00	2 Weeks

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Synonym

SNAP-5114; SNAP 5114; SNAP5114; (S)-SNAP 5114; (S)-SNAP5114; (S)-SNAP-5114

IUPAC/Chemical Name

(3S)-1-{2-[tris(4-methoxyphenyl)methoxy]ethyl}piperidine-3-carboxylic acid

InChi Key

VDLDUZLDZBVOAS-QFIPXVFZSA-N

InChi Code

InChI=1S/C30H35NO6/c1-34-26-12-6-23(7-13-26)30(24-8-14-27(35-2)15-9-24,25-10-16-28(36-3)17-11-25)37-20-19-31-18-4-5-22(21-31)29(32)33/h6-17,22H,4-5,18-21H2,1-3H3,(H,32,33)/t22-/m0/s1

SMILES Code

O=C([C@@H]1CN(CCOC(C2=CC=C(OC)C=C2)(C3=CC=C(OC)C=C3)C4=CC=C(OC)C=C4)CCC1)O

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).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

(S)-SNAP5114 is a selective GABA transport inhibitor, with IC50 values of 5 μM and 21 μM for hGAT-3 and rGAT-2, respectively. (S)-SNAP5114 is an anticonvulsant agent.

In vitro activity:

To be determined

In vivo activity:

In the study, the GAT2/3 inhibitor, (S)-SNAP-5114, was administered to mice following induced brain ischemia. The results revealed that (S)-SNAP-5114, along with the GAT1/BGT1 inhibitor EF-1502, had no effect on motor performance or infarct volume. Additionally, treatment with (S)-SNAP-5114 led to increased mortality, highlighting potential risks associated with using GABA transporter inhibitors in the context of brain ischemia. Reference: J Cereb Blood Flow Metab. 2018 Jan;38(1):166-173. https://pubmed.ncbi.nlm.nih.gov/29148909/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	197.78

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 505.61 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. Lie ME, Gowing EK, Clausen RP, Wellendorph P, Clarkson AN. Inhibition of GABA transporters fails to afford significant protection following focal cerebral ischemia. J Cereb Blood Flow Metab. 2018 Jan;38(1):166-173. doi: 10.1177/0271678X17743669. Epub 2017 Nov 17. PMID: 29148909; PMCID: PMC5757447.

In vitro protocol:

To be determined

In vivo protocol:

1: Borden LA, Dhar TG, Smith KE, Branchek TA, Gluchowski C, Weinshank RL. Cloning of the human homologue of the GABA transporter GAT-3 and identification of a novel inhibitor with selectivity for this site. Recept Channels. 1994;2(3):207-13. PMID: 7874447. 2: Fülep GH, Hoesl CE, Höfner G, Wanner KT. New highly potent GABA uptake inhibitors selective for GAT-1 and GAT-3 derived from (R)- and (S)-proline and homologous pyrrolidine-2-alkanoic acids. Eur J Med Chem. 2006 Jul;41(7):809-24. doi: 10.1016/j.ejmech.2006.01.019. PMID: 16766089. 3: Christiansen B, Meinild AK, Jensen AA, Braüner-Osborne H. Cloning and characterization of a functional human gamma-aminobutyric acid (GABA) transporter, human GAT-2. J Biol Chem. 2007 Jul 6;282(27):19331-41. doi: 10.1074/jbc.M702111200. Epub 2007 May 14. PMID: 17502375. 4: Galvan A, Hu X, Smith Y, Wichmann T. Localization and function of GABA transporters in the globus pallidus of parkinsonian monkeys. Exp Neurol. 2010 Jun;223(2):505-15. doi: 10.1016/j.expneurol.2010.01.018. Epub 2010 Feb 4. PMID: 20138865; PMCID: PMC2864357. 5: Novak B, Schulten R, Lübbert H. δ-Aminolevulinic acid and its methyl ester induce the formation of Protoporphyrin IX in cultured sensory neurones. Naunyn Schmiedebergs Arch Pharmacol. 2011 Dec;384(6):583-602. doi: 10.1007/s00210-011-0683-1. Epub 2011 Sep 25. PMID: 21947250. 6: Pabel J, Faust M, Prehn C, Wörlein B, Allmendinger L, Höfner G, Wanner KT. Development of an (S)-1-{2-[tris(4-methoxyphenyl)methoxy]ethyl}piperidine-3-carboxylic acid [(S)-SNAP-5114] carba analogue inhibitor for murine γ-aminobutyric acid transporter type 4. ChemMedChem. 2012 Jul;7(7):1245-55. doi: 10.1002/cmdc.201200126. Epub 2012 Apr 27. PMID: 22544452. 7: Schulten R, Novak B, Schmitz B, Lübbert H. Comparison of the uptake of 5-aminolevulinic acid and its methyl ester in keratinocytes and skin. Naunyn Schmiedebergs Arch Pharmacol. 2012 Oct;385(10):969-79. doi: 10.1007/s00210-012-0777-4. Epub 2012 Jul 17. PMID: 22801976. 8: Steffan T, Renukappa-Gutke T, Höfner G, Wanner KT. Design, synthesis and SAR studies of GABA uptake inhibitors derived from 2-substituted pyrrolidine-2-yl- acetic acids. Bioorg Med Chem. 2015 Mar 15;23(6):1284-306. doi: 10.1016/j.bmc.2015.01.035. Epub 2015 Feb 3. PMID: 25698617. 9: Damgaard M, Al-Khawaja A, Vogensen SB, Jurik A, Sijm M, Lie ME, Bæk MI, Rosenthal E, Jensen AA, Ecker GF, Frølund B, Wellendorph P, Clausen RP. Identification of the First Highly Subtype-Selective Inhibitor of Human GABA Transporter GAT3. ACS Chem Neurosci. 2015 Sep 16;6(9):1591-9. doi: 10.1021/acschemneuro.5b00150. Epub 2015 Jul 23. PMID: 26154082. 10: Lie ME, Gowing EK, Clausen RP, Wellendorph P, Clarkson AN. Inhibition of GABA transporters fails to afford significant protection following focal cerebral ischemia. J Cereb Blood Flow Metab. 2018 Jan;38(1):166-173. doi: 10.1177/0271678X17743669. Epub 2017 Nov 17. PMID: 29148909; PMCID: PMC5757447. 11: Tóth K, Höfner G, Wanner KT. Synthesis and biological evaluation of novel N-substituted nipecotic acid derivatives with an alkyne spacer as GABA uptake inhibitors. Bioorg Med Chem. 2018 Jul 23;26(12):3668-3687. doi: 10.1016/j.bmc.2018.05.049. Epub 2018 Jun 1. PMID: 29886082. 12: Tóth K, Höfner G, Wanner KT. Synthesis and biological evaluation of novel N-substituted nipecotic acid derivatives with a trans-alkene spacer as potent GABA uptake inhibitors. Bioorg Med Chem. 2018 Dec 1;26(22):5944-5961. doi: 10.1016/j.bmc.2018.11.002. Epub 2018 Nov 3. PMID: 30442505. 13: Hauke TJ, Höfner G, Wanner KT. Generation and screening of pseudostatic hydrazone libraries derived from 5-substituted nipecotic acid derivatives at the GABA transporter mGAT4. Bioorg Med Chem. 2019 Jan 1;27(1):144-152. doi: 10.1016/j.bmc.2018.11.028. Epub 2018 Nov 22. PMID: 30503411. 14: Böck MC, Höfner G, Wanner KT. N-Substituted Nipecotic Acids as (S)-SNAP-5114 Analogues with Modified Lipophilic Domains. ChemMedChem. 2020 May 6;15(9):756-771. doi: 10.1002/cmdc.201900719. Epub 2020 Apr 7. PMID: 32187815; PMCID: PMC7317212. 15: Andersen JV, Jakobsen E, Westi EW, Lie MEK, Voss CM, Aldana BI, Schousboe A, Wellendorph P, Bak LK, Pinborg LH, Waagepetersen HS. Extensive astrocyte metabolism of γ-aminobutyric acid (GABA) sustains glutamine synthesis in the mammalian cerebral cortex. Glia. 2020 Dec;68(12):2601-2612. doi: 10.1002/glia.23872. Epub 2020 Jun 25. PMID: 32584476.