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MedKoo Cat#: 530964 | Name: EF1502 free base

Description:

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

EF1502 is a potent and selective GABA transporter inhibitor. EF1502 exhibit mechanistic differences in their ability to modulate the ataxia and anticonvulsant action of the extrasynaptic GABA(A) receptor agonist gaboxadol.

Chemical Structure

EF1502 free base
EF1502 free base
CAS#684645-54-3 (free base)

Theoretical Analysis

MedKoo Cat#: 530964

Name: EF1502 free base

CAS#: 684645-54-3 (free base)

Chemical Formula: C22H26N2O2S2

Exact Mass: 414.1436

Molecular Weight: 414.58

Elemental Analysis: C, 63.74; H, 6.32; N, 6.76; O, 7.72; S, 15.47

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 #
684645-54-3 (free base) 182316-85-4 (HCl) 847354-37-4 (R-isomer) 847233-24-3 (R-isomer HCl) 847354-38-5 (S-isomer) 847233-25-4 (S-isomer HCl)
Synonym
EF1502; EF-1502; EF 1502; (R,S)-EF 1502; Rac-EF 1502; EF 1502 racemic.
IUPAC/Chemical Name
(RS)-4-[N-[1,1-bis(3-methyl-2-thienyl)but-1-en-4-yl]-N-methylamino]-4,5,6,7-tetrahydrobenzo[d]isoxazol-3-ol
InChi Key
CUESOMOCKVRNIW-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H26N2O2S2/c1-14-9-12-27-20(14)16(21-15(2)10-13-28-21)6-5-11-24(3)17-7-4-8-18-19(17)22(25)23-26-18/h6,9-10,12-13,17H,4-5,7-8,11H2,1-3H3,(H,23,25)
SMILES Code
OC1=NOC2=C1C(N(CC/C=C(C3=C(C)C=CS3)\C4=C(C)C=CS4)C)CCC2
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

Preparing Stock Solutions

The following data is based on the product molecular weight 414.58 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: Madsen KK, Ebert B, Clausen RP, Krogsgaard-Larsen P, Schousboe A, White HS. Selective GABA transporter inhibitors tiagabine and EF1502 exhibit mechanistic differences in their ability to modulate the ataxia and anticonvulsant action of the extrasynaptic GABA(A) receptor agonist gaboxadol. J Pharmacol Exp Ther. 2011 Jul;338(1):214-9. doi: 10.1124/jpet.111.179671. Epub 2011 Mar 30. PubMed PMID: 21450931; PubMed Central PMCID: PMC3126646. 2: Madsen KK, Hansen GH, Danielsen EM, Schousboe A. The subcellular localization of GABA transporters and its implication for seizure management. Neurochem Res. 2015 Feb;40(2):410-9. doi: 10.1007/s11064-014-1494-9. Epub 2014 Dec 18. PubMed PMID: 25519681. 3: Madsen KK, Clausen RP, Larsson OM, Krogsgaard-Larsen P, Schousboe A, White HS. Synaptic and extrasynaptic GABA transporters as targets for anti-epileptic drugs. J Neurochem. 2009 May;109 Suppl 1:139-44. doi: 10.1111/j.1471-4159.2009.05982.x. PubMed PMID: 19393020. 4: White HS, Watson WP, Hansen SL, Slough S, Perregaard J, Sarup A, Bolvig T, Petersen G, Larsson OM, Clausen RP, Frølund B, Falch E, Krogsgaard-Larsen P, Schousboe A. First demonstration of a functional role for central nervous system betaine/{gamma}-aminobutyric acid transporter (mGAT2) based on synergistic anticonvulsant action among inhibitors of mGAT1 and mGAT2. J Pharmacol Exp Ther. 2005 Feb;312(2):866-74. Epub 2004 Nov 18. PubMed PMID: 15550575. 5: Hiramatsu M. [Functional role for GABA transporters in the CNS]. Nihon Yakurigaku Zasshi. 2014 Apr;143(4):187-92. Review. Japanese. PubMed PMID: 24717607. 6: Schousboe A, Larsson OM, Sarup A, White HS. Role of the betaine/GABA transporter (BGT-1/GAT2) for the control of epilepsy. Eur J Pharmacol. 2004 Oct 1;500(1-3):281-7. Review. PubMed PMID: 15464040. 7: Lehre AC, Rowley NM, Zhou Y, Holmseth S, Guo C, Holen T, Hua R, Laake P, Olofsson AM, Poblete-Naredo I, Rusakov DA, Madsen KK, Clausen RP, Schousboe A, White HS, Danbolt NC. Deletion of the betaine-GABA transporter (BGT1; slc6a12) gene does not affect seizure thresholds of adult mice. Epilepsy Res. 2011 Jun;95(1-2):70-81. doi: 10.1016/j.eplepsyres.2011.02.014. Epub 2011 Apr 3. PubMed PMID: 21459558; PubMed Central PMCID: PMC3376448. 8: Clausen RP, Frølund B, Larsson OM, Schousboe A, Krogsgaard-Larsen P, White HS. A novel selective gamma-aminobutyric acid transport inhibitor demonstrates a functional role for GABA transporter subtype GAT2/BGT-1 in the CNS. Neurochem Int. 2006 May-Jun;48(6-7):637-42. Epub 2006 Mar 3. Review. PubMed PMID: 16517017. 9: Vogensen SB, Jørgensen L, Madsen KK, Borkar N, Wellendorph P, Skovgaard-Petersen J, Schousboe A, White HS, Krogsgaard-Larsen P, Clausen RP. Selective mGAT2 (BGT-1) GABA uptake inhibitors: design, synthesis, and pharmacological characterization. J Med Chem. 2013 Mar 14;56(5):2160-4. doi: 10.1021/jm301872x. Epub 2013 Feb 27. PubMed PMID: 23398473. 10: Smith MD, Saunders GW, Clausen RP, Frølund B, Krogsgaard-Larsen P, Larsson OM, Schousboe A, Wilcox KS, White HS. Inhibition of the betaine-GABA transporter (mGAT2/BGT-1) modulates spontaneous electrographic bursting in the medial entorhinal cortex (mEC). Epilepsy Res. 2008 Mar;79(1):6-13. doi: 10.1016/j.eplepsyres.2007.12.009. Epub 2008 Feb 8. PubMed PMID: 18262393; PubMed Central PMCID: PMC4314296. 11: Schousboe A, Sarup A, Larsson OM, White HS. GABA transporters as drug targets for modulation of GABAergic activity. Biochem Pharmacol. 2004 Oct 15;68(8):1557-63. PubMed PMID: 15451399. 12: Kragholm B, Kvist T, Madsen KK, Jørgensen L, Vogensen SB, Schousboe A, Clausen RP, Jensen AA, Bräuner-Osborne H. Discovery of a subtype selective inhibitor of the human betaine/GABA transporter 1 (BGT-1) with a non-competitive pharmacological profile. Biochem Pharmacol. 2013 Aug 15;86(4):521-8. doi: 10.1016/j.bcp.2013.06.007. Epub 2013 Jun 19. PubMed PMID: 23792119. 13: Schousboe A, Madsen KK. Delineation of the Role of Astroglial GABA Transporters in Seizure Control. Neurochem Res. 2017 Jul;42(7):2019-2023. doi: 10.1007/s11064-017-2188-x. Epub 2017 Feb 11. PubMed PMID: 28190226.