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MedKoo Cat#: 326965 | Name: Amibegron HCl
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Description:

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

Amibegron, also known as SR-58611; SR-58611A, is a selective agonist for the β3 adrenergic receptor. It is the first orally active β3 agonist developed that is capable of entering the central nervous system, and has antidepressant and anxiolytic effects.

Chemical Structure

Amibegron HCl
Amibegron HCl
CAS#121524-09-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 326965

Name: Amibegron HCl

CAS#: 121524-09-2 (HCl)

Chemical Formula: C22H27Cl2NO4

Exact Mass: 439.1417

Molecular Weight: 440.36

Elemental Analysis: C, 60.01; H, 6.18; Cl, 16.10; N, 3.18; O, 14.53

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 650.00 2 Weeks
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Related CAS #
121524-08-1 (free) 121524-09-2 (HCl)
Synonym
Amibegron hydrochloride; SR-58611; SR58611; SR 58611; SR58611A; SR-58611A; SR 58611A;
IUPAC/Chemical Name
ethyl 2-(((S)-7-(((R)-2-(3-chlorophenyl)-2-hydroxyethyl)amino)-5,6,7,8-tetrahydronaphthalen-2-yl)oxy)acetate hydrochloride
InChi Key
NQIZCDQCNYCVAS-RQBPZYBGSA-N
InChi Code
InChI=1S/C22H26ClNO4.ClH/c1-2-27-22(26)14-28-20-9-7-15-6-8-19(11-17(15)12-20)24-13-21(25)16-4-3-5-18(23)10-16;/h3-5,7,9-10,12,19,21,24-25H,2,6,8,11,13-14H2,1H3;1H/t19-,21-;/m0./s1
SMILES Code
O=C(OCC)COC1=CC=C2CC[C@H](NC[C@@H](C3=CC=CC(Cl)=C3)O)CC2=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 440.36 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: Tamburella A, Micale V, Leggio GM, Drago F. The beta3 adrenoceptor agonist, amibegron (SR58611A) counteracts stress-induced behavioral and neurochemical changes. Eur Neuropsychopharmacol. 2010 Oct;20(10):704-13. doi: 10.1016/j.euroneuro.2010.04.006. Epub 2010 May 26. PMID: 20537869. 2: Wang Z, Liu X, Liu M, Jiang K, Kajimura S, Kim H, Feeley BT. β3-Adrenergic receptor agonist treats rotator cuff fatty infiltration by activating beige fat in mice. J Shoulder Elbow Surg. 2021 Feb;30(2):373-386. doi: 10.1016/j.jse.2020.06.006. Epub 2020 Jun 27. PMID: 32599287; PMCID: PMC7765745. 3: Tanyeri P, Buyukokuroglu ME, Mutlu O, Ulak G, Akar FY, Celikyurt IK, Erden BF. Evidence that the anxiolytic-like effects of the beta3 receptor agonist amibegron involve serotoninergic receptor activity. Pharmacol Biochem Behav. 2013 Sep;110:27-32. doi: 10.1016/j.pbb.2013.05.017. Epub 2013 Jun 10. PMID: 23756183. 4: Zhang H, Liu M, Kim HT, Feeley BT, Liu X. Preconditioning improves muscle regeneration after ischemia-reperfusion injury. J Orthop Res. 2021 Sep;39(9):1889-1897. doi: 10.1002/jor.24909. Epub 2020 Nov 24. PMID: 33232533; PMCID: PMC9257970. 5: Overstreet DH, Stemmelin J, Griebel G. Confirmation of antidepressant potential of the selective beta3 adrenoceptor agonist amibegron in an animal model of depression. Pharmacol Biochem Behav. 2008 Jun;89(4):623-6. doi: 10.1016/j.pbb.2008.02.020. Epub 2008 Feb 26. PMID: 18358519. 6: Stemmelin J, Cohen C, Yalcin I, Keane P, Griebel G. Implication of beta3-adrenoceptors in the antidepressant-like effects of amibegron using Adrb3 knockout mice in the chronic mild stress. Behav Brain Res. 2010 Jan 20;206(2):310-2. doi: 10.1016/j.bbr.2009.09.003. Epub 2009 Sep 8. PMID: 19744528. 7: Tanyeri P, Buyukokuroglu ME, Mutlu O, Ulak G, Yıldız Akar F, Komsuoglu Celikyurt I, Erden BF. Involvement of serotonin receptor subtypes in the antidepressant-like effect of beta receptor agonist Amibegron (SR 58611A): an experimental study. Pharmacol Biochem Behav. 2013 Apr;105:12-6. doi: 10.1016/j.pbb.2013.01.010. Epub 2013 Feb 1. PMID: 23380524. 8: Wang Z, Liu X, Jiang K, Kim H, Kajimura S, Feeley BT. Intramuscular Brown Fat Activation Decreases Muscle Atrophy and Fatty Infiltration and Improves Gait After Delayed Rotator Cuff Repair in Mice. Am J Sports Med. 2020 Jun;48(7):1590-1600. doi: 10.1177/0363546520910421. Epub 2020 Apr 13. PMID: 32282238. 9: Davies MR, Chi H, Kaur G, Liu M, Ma CB, Kim HT, Liu X, Feeley BT. Rotator Cuff Tear Size Regulates Fibroadipogenic Progenitor Number and Gene Expression Profile in the Supraspinatus Independent of Patient Age. Am J Sports Med. 2022 Jan;50(1):208-215. doi: 10.1177/03635465211054512. Epub 2021 Nov 15. PMID: 34779676; PMCID: PMC9280916. 10: Claustre Y, Leonetti M, Santucci V, Bougault I, Desvignes C, Rouquier L, Aubin N, Keane P, Busch S, Chen Y, Palejwala V, Tocci M, Yamdagni P, Didier M, Avenet P, Le Fur G, Oury-Donat F, Scatton B, Steinberg R. Effects of the beta3-adrenoceptor (Adrb3) agonist SR58611A (amibegron) on serotonergic and noradrenergic transmission in the rodent: relevance to its antidepressant/anxiolytic-like profile. Neuroscience. 2008 Oct 2;156(2):353-64. doi: 10.1016/j.neuroscience.2008.07.011. Epub 2008 Jul 11. PMID: 18691638. 11: SR 58611A: SR 58611. Drugs R D. 2003;4(6):380-2. doi: 10.2165/00126839-200304060-00012. PMID: 14584972. 12: Feeley BT, Liu M, Ma CB, Agha O, Aung M, Lee C, Liu X. Human Rotator Cuff Tears Have an Endogenous, Inducible Stem Cell Source Capable of Improving Muscle Quality and Function After Rotator Cuff Repair. Am J Sports Med. 2020 Sep;48(11):2660-2668. doi: 10.1177/0363546520935855. Epub 2020 Jul 30. PMID: 32730704; PMCID: PMC9262007. 13: Stemmelin J, Cohen C, Terranova JP, Lopez-Grancha M, Pichat P, Bergis O, Decobert M, Santucci V, Françon D, Alonso R, Stahl SM, Keane P, Avenet P, Scatton B, le Fur G, Griebel G. Stimulation of the beta3-Adrenoceptor as a novel treatment strategy for anxiety and depressive disorders. Neuropsychopharmacology. 2008 Feb;33(3):574-87. doi: 10.1038/sj.npp.1301424. Epub 2007 Apr 25. PMID: 17460614. 14: Church TW, Brown JT, Marrion NV. β3-Adrenergic receptor-dependent modulation of the medium afterhyperpolarization in rat hippocampal CA1 pyramidal neurons. J Neurophysiol. 2019 Mar 1;121(3):773-784. doi: 10.1152/jn.00334.2018. Epub 2019 Jan 9. PMID: 30625002; PMCID: PMC6520626. 15: Sun X, Wang X, Zhou HC, Zheng J, Su YX, Luo F. β3-adrenoceptor activation exhibits a dual effect on behaviors and glutamate receptor function in the prefrontal cortex. Behav Brain Res. 2021 Aug 27;412:113417. doi: 10.1016/j.bbr.2021.113417. Epub 2021 Jun 19. PMID: 34157371. 16: Nisoli E, Tonello C, Carruba MO. SR 58611A: a novel thermogenic beta- adrenoceptor agonist. Eur J Pharmacol. 1994 Jul 1;259(2):181-6. doi: 10.1016/0014-2999(94)90508-8. PMID: 7957612. 17: Vasina V, Abu-Gharbieh E, Barbara G, de Giorgio R, Colucci R, Blandizzi C, Bernardini N, Croci T, Del Tacca M, de Ponti F. The beta3-adrenoceptor agonist SR58611A ameliorates experimental colitis in rats. Neurogastroenterol Motil. 2008 Sep;20(9):1030-41. doi: 10.1111/j.1365-2982.2008.01138.x. Epub 2008 May 15. PMID: 18492028. 18: Wu S, Ootawa T, Sekio R, Smith H, Islam MZ, Uno Y, Shiraishi M, Miyamoto A. Involvement of beta3-adrenergic receptors in relaxation mediated by nitric oxide in chicken basilar artery. Poult Sci. 2023 Jun;102(6):102633. doi: 10.1016/j.psj.2023.102633. Epub 2023 Mar 8. PMID: 37001317; PMCID: PMC10070147. 19: Mallem Y, Holopherne D, Reculeau O, Le Coz O, Desfontis JC, Gogny M. Beta- adrenoceptor-mediated vascular relaxation in spontaneously hypertensive rats. Auton Neurosci. 2005 Mar 31;118(1-2):61-7. doi: 10.1016/j.autneu.2005.01.003. PMID: 15795178. 20: Audigane L, Kerfant BG, El Harchi A, Lorenzen-Schmidt I, Toumaniantz G, Cantereau A, Potreau D, Charpentier F, Noireaud J, Gauthier C. Rabbit, a relevant model for the study of cardiac beta 3-adrenoceptors. Exp Physiol. 2009 Apr;94(4):400-11. doi: 10.1113/expphysiol.2008.045179. Epub 2009 Jan 16. PMID: 19151075.