For research use only. Not for therapeutic Use.
Orciprenaline is a bronchodilator used in the treatment of asthma. Orciprenaline is a moderately selective β2 adrenergic receptor agonist that stimulates receptors of the smooth muscle in the lungs, uterus, and vasculature supplying skeletal muscle, with minimal or no effect on α adrenergic receptors. The pharmacologic effects of β adrenergic agonist drugs, such as orciprenaline, are at least in part attributable to stimulation through β adrenergic receptors of intracellular adenylyl cyclase, the enzyme which catalyzes the conversion of ATP to cAMP. Increased cAMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from many cells, especially from mast cells.
| Catalog Number | I008480 |
| CAS Number | 586-06-1 |
| Synonyms | Orciprenaline, Metaproterenol, Alotec, Alupent, Astmopent, Metaprel;5-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,3-diol |
| Molecular Formula | C11H17NO3 |
| Purity | ≥95% |
| Target | Neuronal Signaling |
| Solubility | Soluble in DMSO, not in water |
| Storage | 0 - 4 °C for short term, or -20 °C for long term |
| IUPAC Name | 5-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,3-diol |
| InChI | InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-9(13)5-10(14)4-8/h3-5,7,11-15H,6H2,1-2H3 |
| InChIKey | LMOINURANNBYCM-UHFFFAOYSA-N |
| SMILES | CC(C)NCC(C1=CC(=CC(=C1)O)O)O |
| Reference | </br>1:[Why isn/’t orciprenaline approved as antiarrhythmic agent?]. Janssens U.Dtsch Med Wochenschr. 2013 Oct;138(41):2114. doi: 10.1055/s-0033-1349546. Epub 2013 Oct 1. German. No abstract available. PMID: 24085370 </br>2:Successful acute and long-term management of electrical storm in Brugada syndrome using orciprenaline and quinine/quinidine. Schweizer PA, Becker R, Katus HA, Thomas D.Clin Res Cardiol. 2010 Jul;99(7):467-70. doi: 10.1007/s00392-010-0145-7. Epub 2010 Mar 11. No abstract available. PMID: 20221832 </br>3:Electrical storm in Brugada syndrome successfully treated with orciprenaline; effect of low-dose quinidine on the electrocardiogram. Kyriazis K, Bahlmann E, van der Schalk H, Kuck KH.Europace. 2009 May;11(5):665-6. doi: 10.1093/europace/eup070. Epub 2009 Apr 3. PMID: 19346290 </br>4:A novel chemiluminescence method for the determination of orciprenaline based on ferricyanide-rhodamine 6G. Lv Y, Zhao R, Zhu Z, Xu X, Zhang X.Luminescence. 2005 Jul-Oct;20(4-5):298-302. PMID: 16134198 </br>5:No major effect of orciprenaline and propranolol upon ACTH-induced cortisol secretion. Nonell A, Kerk S, Lederbogen F, Kopf D, Hamann B, Lewicka S, Deuschle M.Exp Clin Endocrinol Diabetes. 2004 Jan;112(1):59-61. PMID: 14758573 </br>6:Screening of beta-2 agonists and confirmation of fenoterol, orciprenaline, reproterol and terbutaline with gas chromatography-mass spectrometry as tetrahydroisoquinoline derivatives. Henze MK, Opfermann G, Spahn-Langguth H, Schänzer W.J Chromatogr B Biomed Sci Appl. 2001 Feb 10;751(1):93-105. PMID: 11232861 </br>7:Reproterol–A monomolecular combination of orciprenaline and theophylline: novel aspects of its mode of action in asthma. Juergens UR, Stöber M, Vetter H.Respiration. 1999;66(3):220-4. PMID: 10364737 </br>8:Determination of association constants between enantiomers of orciprenaline and methyl-beta-cyclodextrin as chiral selector by capillary zone electrophoresis using a partial filling technique. Amini A, Merclin N, Bastami S, Westerlund D.Electrophoresis. 1999 Jan;20(1):180-8. PMID: 10065975 </br>9:Comparison of cardiac Troponin T and cardiac Troponin I concentrations in peripheral blood during orciprenaline induced tachycardia in rats. Bertsch T, Bleuel H, Aufenanger J, Rebel W.Exp Toxicol Pathol. 1997 Dec;49(6):467-8. PMID: 9495647 </br>10:Supraventricular bradycardia after heart transplantation–orciprenaline or pacemaker implantation? Schmid C, Wahlers T, Schäfers HJ, Haverich A.Thorac Cardiovasc Surg. 1993 Apr;41(2):101-3. PMID: 8372387 |
