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MedKoo Cat#: 540114 | Name: Efaroxan HCl
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Description:

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

Efaroxan HCl is an inhibitor of α2-adrenergic receptors, imidazoline-1 receptors, and ATP-sensitive K channels. It improves glucose tolerance, alters opiod-mediated tolerance and antinociception signaling pathways, and decreases symptoms of Parkinson's Disease.

Chemical Structure

Efaroxan HCl
Efaroxan HCl
CAS#89197-00-2

Theoretical Analysis

MedKoo Cat#: 540114

Name: Efaroxan HCl

CAS#: 89197-00-2

Chemical Formula: C13H17ClN2O

Exact Mass: 252.1029

Molecular Weight: 252.74

Elemental Analysis: C, 61.78; H, 6.78; Cl, 14.03; N, 11.08; O, 6.33

Price and Availability

Size Price Availability Quantity
10mg USD 250.00 2 Weeks
25mg USD 450.00 2 Weeks
50mg USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
Efaroxan HCl; Efaroxan hydrochloride; (±)-Efaroxan HCl; RX 821037A; RX821037A; RX-821037A;
IUPAC/Chemical Name
2-(2-ethyl-2,3-dihydrobenzofuran-2-yl)-4,5-dihydro-1H-imidazole hydrochloride
InChi Key
DWOIUCRHVWIHAH-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H16N2O.ClH/c1-2-13(12-14-7-8-15-12)9-10-5-3-4-6-11(10)16-13;/h3-6H,2,7-9H2,1H3,(H,14,15);1H
SMILES Code
CCC1(C2=NCCN2)OC3=C(C=CC=C3)C1.[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
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 252.74 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: Rusu-Zota G, Burlui A, Rezus E, Paduraru L, Sorodoc V. Idazoxan and Efaroxan Potentiate the Endurance Performances and the Antioxidant Activity of Ephedrine in Rats. Medicina (Kaunas). 2021 Feb 25;57(3):194. doi: 10.3390/medicina57030194. PMID: 33668888; PMCID: PMC7996498. 2: Carlisle MA, Smyth DD, Glavin GB. Efaroxan acts peripherally to block the antisecretory and gastroprotective effects of moxonidine in rats. J Pharmacol Exp Ther. 1995 Aug;274(2):598-601. PMID: 7636718. 3: Couture K, Gouverneur V, Mioskowski C. A new approach to the synthesis of efaroxan. Bioorg Med Chem Lett. 1999 Oct 18;9(20):3023-6. doi: 10.1016/s0960-894x(99)00530-2. PMID: 10571168. 4: Rascol O, Sieradzan K, Peyro-Saint-Paul H, Thalamas C, Brefel-Courbon C, Senard JM, Ladure P, Montastruc JL, Lees A. Efaroxan, an alpha-2 antagonist, in the treatment of progressive supranuclear palsy. Mov Disord. 1998 Jul;13(4):673-6. doi: 10.1002/mds.870130411. PMID: 9686773. 5: de Vos H, de Backer JP, Vauquelin G. Efaroxan (RX 821037) is a potent and selective ?(2)-adrenoceptor antagonist in human frontal cortex membranes. Neurochem Int. 1991;18(1):137-40. doi: 10.1016/0197-0186(91)90047-h. PMID: 20504687. 6: Lehner Z, Stadlbauer K, Adorjan I, Rustenbeck I, Belz M, Fenzl A, de Cillia VA, Gruber D, Bauer L, Frobel K, Brunmair B, Luger A, Fürnsinn C. Mechanisms of antihyperglycaemic action of efaroxan in mice: time for reappraisal of α2A-adrenergic antagonism in the treatment of type 2 diabetes? Diabetologia. 2012 Nov;55(11):3071-82. doi: 10.1007/s00125-012-2679-x. Epub 2012 Aug 18. PMID: 22898767. 7: Chan SL, Dunne MJ, Stillings MR, Morgan NG. The alpha 2-adrenoceptor antagonist efaroxan modulates K+ATP channels in insulin-secreting cells. Eur J Pharmacol. 1991 Oct 29;204(1):41-8. doi: 10.1016/0014-2999(91)90833-c. PMID: 1687123. 8: Milne B, Jhamandas K, Sutak M, Grenier P, Cahill CM. Stereo-selective inhibition of spinal morphine tolerance and hyperalgesia by an ultra-low dose of the alpha-2-adrenoceptor antagonist efaroxan. Eur J Pharmacol. 2013 Feb 28;702(1-3):227-34. doi: 10.1016/j.ejphar.2013.01.022. Epub 2013 Jan 29. PMID: 23376415. 9: Berridge TL, Doxey JC, Roach AG. Comparison of the effects of efaroxan and glibenclamide on plasma glucose and insulin levels in rats. Eur J Pharmacol. 1992 Mar 24;213(2):213-8. doi: 10.1016/0014-2999(92)90684-v. PMID: 1355734. 10: Rusu G, Mititelu-Tartau L, Lupusoru CE, Lupusoru RV, Grigoraş I, Popa G, Nechifor M. Imidazoline receptor antagonists idazoxan and efaroxan enhance locomotor functions in rats. Rev Med Chir Soc Med Nat Iasi. 2015 Jan- Mar;119(1):193-200. PMID: 25970966. 11: Bleck C, Wienbergen A, Rustenbeck I. Essential role of the imidazoline moiety in the insulinotropic effect but not the KATP channel-blocking effect of imidazolines; a comparison of the effects of efaroxan and its imidazole analogue, KU14R. Diabetologia. 2005 Dec;48(12):2567-75. doi: 10.1007/s00125-005-0031-4. Epub 2005 Nov 11. PMID: 16283242. 12: Chan SL, Morgan NG. Stimulation of insulin secretion by efaroxan may involve interaction with potassium channels. Eur J Pharmacol. 1990 Jan 25;176(1):97-101. doi: 10.1016/0014-2999(90)90137-u. PMID: 2178947. 13: Berridge TL, Doxey JC, Roach AG, Smith CF. Selectivity profile of the alpha 2-adrenoceptor antagonist efaroxan in relation to plasma glucose and insulin levels in the rat. Eur J Pharmacol. 1992 Mar 24;213(2):205-12. doi: 10.1016/0014-2999(92)90683-u. PMID: 1355733. 14: Chan SL, Monks LK, Gao H, Deaville P, Morgan NG. Identification of the monomeric G-protein, Rhes, as an efaroxan-regulated protein in the pancreatic beta-cell. Br J Pharmacol. 2002 May;136(1):31-6. doi: 10.1038/sj.bjp.0704680. PMID: 11976265; PMCID: PMC1762110. 15: Mayer P, Brunel P, Imbert T. A new efficient synthesis of efaroxan. Bioorg Med Chem Lett. 1999 Oct 18;9(20):3021-2. doi: 10.1016/s0960-894x(99)00531-4. PMID: 10571167. 16: Mayer G, Taberner PV. Effects of the imidazoline ligands efaroxan and KU14R on blood glucose homeostasis in the mouse. Eur J Pharmacol. 2002 Nov 1;454(1):95-102. doi: 10.1016/s0014-2999(02)02473-1. PMID: 12409010. 17: Tellez S, Colpaert F, Marien M. The alpha 2-adrenoceptor antagonist, (+)-efaroxan, enhances acetylcholine release in the rat cortex in vivo. Eur J Pharmacol. 1995 Apr 13;277(1):113-6. doi: 10.1016/0014-2999(95)00110-7. PMID: 7635166. 18: Papaccio G, Graziano A, Valiante S, D'Aquino R, Travali S, Nicoletti F. Interleukin (IL)-1beta toxicity to islet beta cells: Efaroxan exerts a complete protection. J Cell Physiol. 2005 Apr;203(1):94-102. doi: 10.1002/jcp.20198. PMID: 15389634. 19: Chan SL, Mourtada M, Morgan NG. Characterization of a KATP channel- independent pathway involved in potentiation of insulin secretion by efaroxan. Diabetes. 2001 Feb;50(2):340-7. doi: 10.2337/diabetes.50.2.340. PMID: 11272145. 20: Taylor JP, Jackson DA, Morgan NG, Chan SL. Rhes expression in pancreatic beta-cells is regulated by efaroxan in a calcium-dependent process. Biochem Biophys Res Commun. 2006 Oct 20;349(2):809-15. doi: 10.1016/j.bbrc.2006.08.102. Epub 2006 Aug 24. PMID: 16945334.

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