SR 59230A HCl | CAS#1135278-41-9 | β3 Adrenoceptor Antagonist

SR-59230A HCl
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 532789

CAS#: 1135278-41-9 (HCl)

Description: SR-59230A is a potent and selective β3 adrenoceptor antagonist (IC50 values are 40, 408 and 648 nM for β3, β1 and β2 receptors respectively). SR-59230A was subsequently shown to also act at α1 adrenoceptors at high doses. It has been shown to block the hyperthermia produced by MDMA in animal studies. SR 59230A blocks MDMA-induced hyperthermia, while at high concentrations it blocks hyperthermia but also increases heat loss through an α1-AR antagonistic mechanism.

Chemical Structure

SR-59230A HCl

CAS# 1135278-41-9 (HCl)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 532789
Name: SR-59230A HCl
CAS#: 1135278-41-9 (HCl)
Chemical Formula: C21H28ClNO2
Exact Mass: 0.00
Molecular Weight: 361.910
Elemental Analysis: C, 69.69; H, 7.80; Cl, 9.80; N, 3.87; O, 8.84

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 355
25mg	USD 750
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 1135278-41-9 (HCl) 174689-39-5 (oxalate) 174689-38-4 (free base)

Synonym: SR 59230A HCl; SR59230A HCl; SR 59230A; SR59230A; SR-59230A.

IUPAC/Chemical Name: 1-(2-Ethylphenoxy)-3-[[(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]amino]-(2S)-2-propanol hydrochloride

InChi Key: SHUCXUIOEAAJJL-MKSBGGEFSA-N

InChi Code: InChI=1S/C21H27NO2.ClH/c1-2-16-8-4-6-13-21(16)24-15-18(23)14-22-20-12-7-10-17-9-3-5-11-19(17)20;/h3-6,8-9,11,13,18,20,22-23H,2,7,10,12,14-15H2,1H3;1H/t18-,20-;/m0./s1

SMILES Code: O[C@@H](CN[C@H]1CCCC2=C1C=CC=C2)COC3=CC=CC=C3CC.[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 and water

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:

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Biological target:	SR-59230A HCl is a β3-adrenergic receptor (β3-AR) antagonist (pA2s = 8.76, 7.31, and 6.63 in rat proximal colon, guinea pig atrium, and guinea pig trachea, respectively). It is less selective for β3-AR in cells transfected with the human β-AR subtypes (Kis = 16.4, 61.9, and 122 nM for β1-, β2-, and β3-AR, respectively).
In vitro activity:	SR-59230A displayed partial agonist properties in some cells and acted as a full agonist in others. It antagonized cAMP increases in adipocytes but showed agonist effects in a microphysiometer. In mouse ileum, it relaxed smooth muscle independently of cAMP levels. These results suggest SR-59230A exhibits dual agonist and antagonist actions at mouse beta(3)-adrenoceptors, possibly through cAMP-independent pathways. Reference: J Pharmacol Exp Ther. 2005 Mar;312(3):1064-74. https://pubmed.ncbi.nlm.nih.gov/15574684/
In vivo activity:	SR-59230A exerts beneficial effects on right ventricular performance in rats with monocrotaline (MCT)-induced pulmonary arterial hypertension (PAH). Blocking β3-AR with SR-59230A may alleviate the structural changes and inflammatory infiltration to the lung as a result of reduced oxidative stress. SR-59230A suppressed the elevated expression of endothelial nitric oxide and alleviated inflammatory infiltration to the lung under PAH conditions. Reference: Exp Ther Med. 2020 Jan;19(1):489-498. https://pubmed.ncbi.nlm.nih.gov/31853320/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	100.0	276.31
	Water	10.0	27.63

Preparing Stock Solutions

The following data is based on the product molecular weight 361.91 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. Pettersson US, Sandberg M, Jansson L. Two-week treatment with the β₃-adrenoceptor antagonist SR59230A normalizes the increased pancreatic islet blood flow in type 2 diabetic GK rats. Diabetes Obes Metab. 2012 Oct;14(10):960-2. doi: 10.1111/j.1463-1326.2012.01616.x. Epub 2012 May 28. PMID: 22564532. 2. Hutchinson DS, Sato M, Evans BA, Christopoulos A, Summers RJ. Evidence for pleiotropic signaling at the mouse beta3-adrenoceptor revealed by SR59230A [3-(2-Ethylphenoxy)-1-[(1,S)-1,2,3,4-tetrahydronapth-1-ylamino]-2S-2-propanol oxalate]. J Pharmacol Exp Ther. 2005 Mar;312(3):1064-74. doi: 10.1124/jpet.104.076901. Epub 2004 Dec 1. PMID: 15574684. 3. Sun J, Cheng J, Ding X, Chi J, Yang J, Li W. β3 adrenergic receptor antagonist SR59230A exerts beneficial effects on right ventricular performance in monocrotaline-induced pulmonary arterial hypertension. Exp Ther Med. 2020 Jan;19(1):489-498. doi: 10.3892/etm.2019.8236. Epub 2019 Nov 22. PMID: 31853320; PMCID: PMC6909721. 4. Zhao QQ, Jing JN, Li HQ, Liu R, Li XP, Cui XL. [Effect of β3-AR antagonist SR59230A on the tension and microRNA expression of rat thoracic aorta]. Zhongguo Ying Yong Sheng Li Xue Za Zhi. 2017 Jan 8;33(1):6-10. Chinese. doi: 10.12047/j.cjap.5448.2017.002. PMID: 29926599.
In vitro protocol:	1. Pettersson US, Sandberg M, Jansson L. Two-week treatment with the β₃-adrenoceptor antagonist SR59230A normalizes the increased pancreatic islet blood flow in type 2 diabetic GK rats. Diabetes Obes Metab. 2012 Oct;14(10):960-2. doi: 10.1111/j.1463-1326.2012.01616.x. Epub 2012 May 28. PMID: 22564532. 2. Hutchinson DS, Sato M, Evans BA, Christopoulos A, Summers RJ. Evidence for pleiotropic signaling at the mouse beta3-adrenoceptor revealed by SR59230A [3-(2-Ethylphenoxy)-1-[(1,S)-1,2,3,4-tetrahydronapth-1-ylamino]-2S-2-propanol oxalate]. J Pharmacol Exp Ther. 2005 Mar;312(3):1064-74. doi: 10.1124/jpet.104.076901. Epub 2004 Dec 1. PMID: 15574684.
In vivo protocol:	1. Sun J, Cheng J, Ding X, Chi J, Yang J, Li W. β3 adrenergic receptor antagonist SR59230A exerts beneficial effects on right ventricular performance in monocrotaline-induced pulmonary arterial hypertension. Exp Ther Med. 2020 Jan;19(1):489-498. doi: 10.3892/etm.2019.8236. Epub 2019 Nov 22. PMID: 31853320; PMCID: PMC6909721. 2. Zhao QQ, Jing JN, Li HQ, Liu R, Li XP, Cui XL. [Effect of β3-AR antagonist SR59230A on the tension and microRNA expression of rat thoracic aorta]. Zhongguo Ying Yong Sheng Li Xue Za Zhi. 2017 Jan 8;33(1):6-10. Chinese. doi: 10.12047/j.cjap.5448.2017.002. PMID: 29926599.

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1: Jing JN, Li FL, Wang X, Wan X, Zhao QQ, Cui XL. [SR 59230A on the expression of MicroRNAs in myocardium of heart failure rats]. Zhongguo Ying Yong Sheng Li Xue Za Zhi. 2017 May 8;33(5):456-460. Chinese. doi: 10.12047/j.cjap.5561.2017.109. PMID: 29926593.

2: Kulzer M, Seyler C, Welke F, Scherer D, Xynogalos P, Scholz EP, Thomas D, Becker R, Karle CA, Katus HA, Zitron E. Inhibition of cardiac Kir2.1-2.3 channels by beta3 adrenoreceptor antagonist SR 59230A. Biochem Biophys Res Commun. 2012 Jul 27;424(2):315-20. doi: 10.1016/j.bbrc.2012.06.114. Epub 2012 Jun 27. PMID: 22749993.

3: Pettersson US, Henriksnäs J, Jansson L. Reversal of high pancreatic islet and white adipose tissue blood flow in type 2 diabetic GK rats by administration of the beta3-adrenoceptor inhibitor SR-59230A. Am J Physiol Endocrinol Metab. 2009 Aug;297(2):E490-4. doi: 10.1152/ajpendo.00140.2009. Epub 2009 Jun 2. PMID: 19491297.

4: Leblais V, Pourageaud F, Ivorra MD, Guibert C, Marthan R, Muller B. Role of alpha-adrenergic receptors in the effect of the beta-adrenergic receptor ligands, CGP 12177, bupranolol, and SR 59230A, on the contraction of rat intrapulmonary artery. J Pharmacol Exp Ther. 2004 Apr;309(1):137-45. doi: 10.1124/jpet.103.061192. Epub 2004 Jan 12. PMID: 14718590.

5: MacDonald A, Watt K. Characterisation of the atypical beta-adrenoceptor in rabbit isolated jejunum using BRL 37344, cyanopindolol and SR 59230A. J Auton Pharmacol. 1999 Apr;19(2):91-5. doi: 10.1046/j.1365-2680.1999.00121.x. PMID: 10466941.

6: Dumas M, Dumas JP, Bardou M, Rochette L, Advenier C, Giudicelli JF. Influence of beta-adrenoceptor agonists on the pulmonary circulation. Effects of a beta3-adrenoceptor antagonist, SR 59230A. Eur J Pharmacol. 1998 May 8;348(2-3):223-8. doi: 10.1016/s0014-2999(98)00146-0. PMID: 9652337.

7: De Ponti F, Gibelli G, Croci T, Arcidiaco M, Crema F, Manara L. Functional evidence of atypical beta 3-adrenoceptors in the human colon using the beta 3-selective adrenoceptor antagonist, SR 59230A. Br J Pharmacol. 1996 Apr;117(7):1374-6. doi: 10.1111/j.1476-5381.1996.tb15294.x. PMID: 8730727; PMCID: PMC1909449.

8: Nisoli E, Tonello C, Landi M, Carruba MO. Functional studies of the first selective beta 3-adrenergic receptor antagonist SR 59230A in rat brown adipocytes. Mol Pharmacol. 1996 Jan;49(1):7-14. PMID: 8569714.

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