WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 318389
CAS#: 586-06-1
Description: 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.
MedKoo Cat#: 318389
Name: Orciprenaline
CAS#: 586-06-1
Chemical Formula: C11H17NO3
Exact Mass: 211.1208
Molecular Weight: 211.2576
Elemental Analysis: C, 62.54; H, 8.11; N, 6.63; O, 22.72
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).
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Synonym: Orciprenaline, Metaproterenol, Alotec, Alupent, Astmopent, Metaprel
IUPAC/Chemical Name: 5-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,3-diol
InChi Key: LMOINURANNBYCM-UHFFFAOYSA-N
InChi Code: 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
SMILES Code: OC1=CC(C(O)CNC(C)C)=CC(O)=C1
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, not in 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
The following data is based on the product molecular weight 211.2576 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 |
1: Janssens U. [Why isn't orciprenaline approved as antiarrhythmic agent?]. Dtsch Med Wochenschr. 2013 Oct;138(41):2114. doi: 10.1055/s-0033-1349546. Epub 2013 Oct 1. German. PubMed PMID: 24085370.
2: Schweizer PA, Becker R, Katus HA, Thomas D. Successful acute and long-term management of electrical storm in Brugada syndrome using orciprenaline and quinine/quinidine. Clin Res Cardiol. 2010 Jul;99(7):467-70. doi: 10.1007/s00392-010-0145-7. Epub 2010 Mar 11. PubMed PMID: 20221832.
3: Kyriazis K, Bahlmann E, van der Schalk H, Kuck KH. Electrical storm in Brugada syndrome successfully treated with orciprenaline; effect of low-dose quinidine on the electrocardiogram. Europace. 2009 May;11(5):665-6. doi: 10.1093/europace/eup070. Epub 2009 Apr 3. PubMed PMID: 19346290.
4: Henze MK, Opfermann G, Spahn-Langguth H, Schänzer W. Screening of beta-2 agonists and confirmation of fenoterol, orciprenaline, reproterol and terbutaline with gas chromatography-mass spectrometry as tetrahydroisoquinoline derivatives. J Chromatogr B Biomed Sci Appl. 2001 Feb 10;751(1):93-105. PubMed PMID: 11232861.
5: Juergens UR, Stöber M, Vetter H. Reproterol--A monomolecular combination of orciprenaline and theophylline: novel aspects of its mode of action in asthma. Respiration. 1999;66(3):220-4. PubMed PMID: 10364737.
6: Bertsch T, Bleuel H, Aufenanger J, Rebel W. Comparison of cardiac Troponin T and cardiac Troponin I concentrations in peripheral blood during orciprenaline induced tachycardia in rats. Exp Toxicol Pathol. 1997 Dec;49(6):467-8. PubMed PMID: 9495647.
7: el Sadek M, Abdel Latef H, Aboul Khier A. Spectrophotometric determination of terbutaline and orciprenaline sulphate through diazo coupling with o-nitroaniline and p-aminobenzoic acid. J Pharm Biomed Anal. 1991;9(1):83-6. PubMed PMID: 2043726.
8: Leis HJ, Gleispach H, Nitsche V, Malle E. Quantitative determination of terbutaline and orciprenaline in human plasma by gas chromatography/negative ion chemical ionization/mass spectrometry. Biomed Environ Mass Spectrom. 1990 Jun;19(6):382-6. PubMed PMID: 2357489.
9: Yeates DB, Spektor DM, Pitt BR. Effect of orally administered orciprenaline on tracheobronchial mucociliary clearance. Eur J Respir Dis. 1986 Aug;69(2):100-8. PubMed PMID: 3758238.
10: Paegelow I, Werner H. [Lymphocyte migration induced by orciprenaline using the Boyden technic]. Allerg Immunol (Leipz). 1986;32(4):233-41. German. PubMed PMID: 2951988.
11: el-Yazbi FA, Abdel-Hay MH, Korany MA. Spectrophotometric, fluorometric and colorimetric determination of terbutaline sulphate and orciprenaline sulphate. Farmaco Prat. 1985 Feb;40(2):50-7. PubMed PMID: 3979528.
12: Chapman RW, Kreutner W. Comparison of the protective effect of orciprenaline with an orciprenaline-oxymetazoline combination on experimental bronchospasm in guinea pigs. Arzneimittelforschung. 1985;35(9):1410-2. PubMed PMID: 4084341.
13: Meuret GH, Lenders HG, Schindler HF, Scholler KL. [Orciprenaline (Alupent) in resuscitation for circulatory arrest? Experimental comparison between orciprenaline and adrenaline in dogs]. Anaesthesist. 1983 Jul;32(7):352-8. German. PubMed PMID: 6614423.
14: Beumer HM. Pirbuterol versus orciprenaline aerosols in the treatment of bronchial asthma. Int J Clin Pharmacol Ther Toxicol. 1983 Mar;21(3):147-66. PubMed PMID: 6343262.
15: Mariotta S, Pasqua F, Montanari S, Ferrara G, Gammelli G, Gramiccioni E. [Hexoproline in broncho-obstructive syndromes: a double-blind method for comparison with orciprenaline]. Clin Ter. 1982 Aug 31;102(4):361-7. Italian. PubMed PMID: 7140186.
16: Drexel H, Regele M, Langle U. Successful treatment of terbutaline-induced bronchospasm with orciprenaline sulfate. Lancet. 1982 Aug 21;2(8295):446. PubMed PMID: 6124839.
17: [Effect of the beta-receptor blockers propranolol and tilinolol on glucose- orciprenaline-induced insulin secretion, glucose tolerance and the behavior of non-esterified free fatty acids in metabolically healthy subjects]. Z Gesamte Inn Med. 1982 Mar 15;37(6):186-90. German. PubMed PMID: 6124065.
18: Giec L, Kargul W, Gasior Z, Zajac T. [Effect of orciprenaline, strophanthin and propranolol on left-ventricular hemodynamics in patients with endocavitary pacemakers]. Kardiol Pol. 1982;25(12):1027-34. Polish. PubMed PMID: 7169731.
19: Traunecker W. Bronchospasmolytic effects of orciprenaline and fenoterol powder inhalation in anaesthetised dogs. Respiration. 1982;43(4):299-303. PubMed PMID: 7111876.
20: Matsuo A, Kast A, Tsunenari Y. Teratology study with orciprenaline sulfate in rabbits. Arzneimittelforschung. 1982;32(8):808-10. PubMed PMID: 6890356.
