Levisoprenaline
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Hodoodo CAT#: H596446

CAS#: 51-31-0 (free base)

Description: Levisoprenaline, also known as (R)-Isoprenaline, or isoproterenol, is a synthetic catechol compound and potent beta adrenergic agonist with peripheral vasodilator, bronchodilator, and cardiac stimulating properties. Isoproterenol can be used for the treatment of bradycardia (slow heart rate), heart block, and rarely for asthma. It is a non-selective β adrenoceptor agonist that is the isopropylamine analog of epinephrine (adrenaline).


Chemical Structure

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Levisoprenaline
CAS# 51-31-0 (free base)

Theoretical Analysis

Hodoodo Cat#: H596446
Name: Levisoprenaline
CAS#: 51-31-0 (free base)
Chemical Formula: C11H17NO3
Exact Mass: 211.12
Molecular Weight: 211.261
Elemental Analysis: C, 62.54; H, 8.11; N, 6.63; O, 22.72

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100mg USD 250 2 Weeks
500mg USD 550 2 Weeks
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Related CAS #: 5984-95-2 (HCl)   51-31-0 (free base)    

Synonym: Levisoprenaline; (R)-Isoprenaline, or isoproterenol; Brand name: Isoprenaline Macure.

IUPAC/Chemical Name: (R)-4-(1-hydroxy-2-(isopropylamino)ethyl)benzene-1,2-diol

InChi Key: JWZZKOKVBUJMES-NSHDSACASA-N

InChi Code: InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8/h3-5,7,11-15H,6H2,1-2H3/t11-/m0/s1

SMILES Code: OC1=CC=C([C@@H](O)CNC(C)C)C=C1O

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: It was first approved in the US in 1947. Between 1963 and 1968 in England, Wales, Scotland, Ireland, Australia, and New Zealand there was an increase in deaths among people using isoprenaline to treat asthma. This was attributed to overdose: the inhalers produced in that area were dispensing five times the dosage dispensed by inhalers produced in the US and Canada, where the deaths were not observed.

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 211.26 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Szymanski MW, Singh DP. Isoproterenol. 2021 May 1. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2021 Jan–. PMID: 30252298.


2: Allawadhi P, Khurana A, Sayed N, Kumari P, Godugu C. Isoproterenol-induced cardiac ischemia and fibrosis: Plant-based approaches for intervention. Phytother Res. 2018 Oct;32(10):1908-1932. doi: 10.1002/ptr.6152. Epub 2018 Jul 15. PMID: 30009418.


3: Wong ZW, Thanikachalam PV, Ramamurthy S. Molecular understanding of the protective role of natural products on isoproterenol-induced myocardial infarction: A review. Biomed Pharmacother. 2017 Oct;94:1145-1166. doi: 10.1016/j.biopha.2017.08.009. Epub 2017 Aug 17. PMID: 28826162.


4: Garg M, Khanna D. Exploration of pharmacological interventions to prevent isoproterenol-induced myocardial infarction in experimental models. Ther Adv Cardiovasc Dis. 2014 Aug;8(4):155-169. doi: 10.1177/1753944714531638. Epub 2014 May 9. PMID: 24817146.


5: Nichtova Z, Novotova M, Kralova E, Stankovicova T. Morphological and functional characteristics of models of experimental myocardial injury induced by isoproterenol. Gen Physiol Biophys. 2012 Jun;31(2):141-51. doi: 10.4149/gpb_2012_015. PMID: 22781817.


6: Matthews R. Isoproterenol-induced elevated bispectral indexes while undergoing radiofrequency ablation: a case report. AANA J. 2006 Jun;74(3):193-5. PMID: 16786912.


7: Calkins H. Isoproterenol-provoked versus nitroglycerin-provoked tilt tests: do they differ? J Cardiovasc Electrophysiol. 2001 Jul;12(7):797-9. doi: 10.1046/j.1540-8167.2001.00797.x. PMID: 11469430.


8: Shubnikova EA, Pogodina LS. Kompensatornaia funktsiia sliunnykh podcheliustnykh zhelez pri dibete i vozmozhnost' ee stimuliatsii izoproterenolom [Compensatory function of submandibular salivary glands in diabetes and prospects for stimulating them with isoproterenol]. Ontogenez. 2000 Nov- Dec;31(6):476-80. Russian. PMID: 11153445.


9: Huang CC, Wang SJ, Gean PW. Selective enhancement of P-type calcium currents by isoproterenol in the rat amygdala. J Neurosci. 1998 Mar 15;18(6):2276-82. doi: 10.1523/JNEUROSCI.18-06-02276.1998. PMID: 9482812; PMCID: PMC6792919.


10: Raybaud F, Camous JP, Jung M, Dadoun M, Baudouy M, Morand P. Données comparatives du test d'inclinaison avec ou sans isoprotérénol dans l'exploration des syncopes et lipothymies inexpliquées [Comparative data of tilt test with or without isoproterenol in investigation of unexplained unconsciousness and syncope]. Arch Mal Coeur Vaiss. 1996 Sep;89(9):1145-51. French. PMID: 8952838.


11: Kataoka H. Right precordial coved ST-T segment elevation in a healthy subject evaluated by isoproterenol infusion test. A case report. Angiology. 1994 May;45(5):409-11. doi: 10.1177/000331979404500512. PMID: 8172390.


12: Morrison Y, Thompson DF. Isoproterenol treatment of torsades de pointes. Ann Pharmacother. 1993 Feb;27(2):189-90. doi: 10.1177/106002809302700213. PMID: 8439698.


13: Howard PA. Isoproterenol in the diagnosis of vasodepressor syncope. Ann Pharmacother. 1992 Sep;26(9):1097-8. PMID: 1421676.


14: Victoria MS, Tayaba RG, Nangia BS. Isoproterenol infusion in the management of respiratory failure in children with status asthmaticus: experience in a small community hospital and review of the literature. J Asthma. 1991;28(2):103-8. doi: 10.3109/02770909109082734. PMID: 2013558.


15: Gallagher KP. Transmural steal with isoproterenol and exercise in poststenotic myocardium. Basic Res Cardiol. 1990;85 Suppl 1:145-55. doi: 10.1007/978-3-662-11038-6_12. PMID: 2091604.


16: Brownstein SL, Hopson RC, Martins JB, Aschoff AM, Olshansky B, Constantin L, Kienzle MG. Usefulness of isoproterenol in facilitating atrioventricular nodal reentry tachycardia during electrophysiologic testing. Am J Cardiol. 1988 May 1;61(13):1037-41. doi: 10.1016/0002-9149(88)90121-x. PMID: 2896452.


17: Dimsdale J, Ziegler M, Graham R. The effect of hypertension, sodium, and race on isoproterenol sensitivity. Clin Exp Hypertens A. 1988;10(5):747-56. doi: 10.1080/07300077.1988.11878781. PMID: 2846213.


18: Mokhtari A, Do Khac L, Tanfin Z, Harbon S. Forskolin modulates cyclic AMP generation in the rat myometrium. Interactions with isoproterenol and prostaglandins E2 and I2. J Cyclic Nucleotide Protein Phosphor Res. 1985;10(3):213-27. PMID: 2991348.


19: Saetersdal T, Jodalen H, Lie R, Rotevatn S, Engedal H, Myklebust R. Effects of isoproterenol on the dense core and perigranular membrane of atrial specific granules. Cell Tissue Res. 1979 Jun 27;199(2):213-24. doi: 10.1007/BF00236133. PMID: 383301.


20: Meerson FZ, Gomazkov OA. Rol' simpaticheskogo faktora v patogeneze infarkta i izoproterenolovye nekrozy miokarda [Role of the sympathetic factor in the pathogenesis of myocardial infarct and isoproterenol necrosis]. Kardiologiia. 1971 Sep;11(9):140-53. Russian. PMID: 4332677.