EF1502 free base

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MedKoo CAT#: 530964

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

Description: 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

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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: 414.582
Elemental Analysis: C, 63.74; H, 6.32; N, 6.76; O, 7.72; S, 15.47

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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

Preparing Stock Solutions

The following data is based on the product molecular weight 414.582 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

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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.