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MedKoo Cat#: 525209 | Name: Denopamine
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Description:

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

Denopamine is a ß1-Adrenoceptor agonist.

Chemical Structure

Denopamine
Denopamine
CAS#71771-90-9

Theoretical Analysis

MedKoo Cat#: 525209

Name: Denopamine

CAS#: 71771-90-9

Chemical Formula: C18H23NO4

Exact Mass: 317.1627

Molecular Weight: 317.39

Elemental Analysis: C, 68.12; H, 7.30; N, 4.41; O, 20.16

Price and Availability

Size Price Availability Quantity
5mg USD 650.00 2 Weeks
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Synonym
Denopamine; Kalgut; R(-)-Denopamine; (R)-(-)-Denopamine; TA-064; TA 064; TA064; (-)-Denopamine; Carguto
IUPAC/Chemical Name
4-[(1R)-2-[2-(3,4-Dimethoxyphenyl)ethylamino]-1-hydroxyethyl]phenol
InChi Key
VHSBBVZJABQOSG-INIZCTEOSA-N
InChi Code
InChI=1S/C18H23NO4/c1-22-17-8-3-13(11-18(17)23-2)9-10-19-12-16(21)14-4-6-15(20)7-5-14/h3-8,11,16,19-21H,9-10,12H2,1-2H3/t16-/m0/s1
SMILES Code
OC1=CC=C([C@@H](O)CNCCC2=CC=C(OC)C(OC)=C2)C=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
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
View handling instruction
Biological target:
Denopamine has been used as an β-adrenergic agonist to study its effects on contractility in isolated lymphatic vessels (LVs).
In vitro activity:
The mechanism of vascular relaxation by denopamine (Deno), an oral positive inotropic agent that has selective beta 1-adrenergic action, was investigated. Deno relaxed, dose-dependently (0.1-30 microM), ring segments of rabbit aorta, which were partially precontracted with 1 microM phenylephrine (Phe) or norepinephrine (NE). Deno produced parallel shifts in concentration-response curves to Phe. The specific binding of [3H]prazosin to a rabbit aorta membrane preparation was displaced in a concentrationdependent manner by the simultaneous addition of Deno. The pK1 value for Deno calculated from the displacement curve was 5.29 +/- 0.17, which was not significantly different from the pA2 value of Deno. In conclusion, vascular smooth muscle relaxation by Deno was mediated by the blocking effect of alpha 1-adrenoceptors. Thus, these findings suggest that Deno may be effective in the treatment of congestive heart failure because it elicits a positive inotropic effect by beta 1-adrenergic action and vasodilation by alpha 1-adrenergic blocking action. Reference: J Cardiovasc Pharmacol. 1991 Mar;17(3):440-4. https://pubmed.ncbi.nlm.nih.gov/1711606/
In vivo activity:
This study was designed to examine the effects of denopamine, a selective beta1-adrenergic agonist, in a murine model of congestive heart failure (CHF) due to viral myocarditis. Treatment with denopamine significantly improved the survival of the animals (14 of 25 (56%) treated, vs 5 of 25 (20%) control mice), attenuated myocardial lesions, and suppressed TNF-alpha production (66.5+/-7.5 pg/mg of heart in treated mice vs 113.5+/-15.1 pg/mg of heart in control mice, mean+/-SE). There was a strong linear relationship between mortality and TNF-alpha levels (r=0.98, n=4, p < 0.05). These results suggest that denopamine may exert its beneficial effects, in part, by suppressing the production of TNF-alpha via beta1-adrenoceptors. Reference: J Am Coll Cardiol. 1998 Sep;32(3):808-15. https://pubmed.ncbi.nlm.nih.gov/9741531/
Solvent mg/mL mM
Solubility
DMSO 20.0 63.01
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 317.39 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:
1. Suzuki T, Hashimura Y, Takeyama S. In vitro metabolism of the new cardiotonic agent denopamine (TA-064) by rat and rabbit liver preparations. Oxidation, methylation, and glucuronidation. Drug Metab Dispos. 1985 Mar-Apr;13(2):246-54. PMID: 2859176. 2. Aikawa J, Koike K, Takayanagi I. Vascular smooth muscle relaxation by alpha 1-adrenoceptor blocking action of denopamine in isolated rabbit aorta. J Cardiovasc Pharmacol. 1991 Mar;17(3):440-4. doi: 10.1097/00005344-199103000-00013. PMID: 1711606. 3. Nishio R, Matsumori A, Shioi T, Wang W, Yamada T, Ono K, Sasayama S. Denopamine, a beta1-adrenergic agonist, prolongs survival in a murine model of congestive heart failure induced by viral myocarditis: suppression of tumor necrosis factor-alpha production in the heart. J Am Coll Cardiol. 1998 Sep;32(3):808-15. doi: 10.1016/s0735-1097(98)00314-3. PMID: 9741531. 4. Yabana H, Naito K, Nagao T. Effect of chronic administration of denopamine (TA-064), a new positive inotropic agent, on cardiac response of rats to denopamine. Jpn J Pharmacol. 1986 Sep;42(1):87-97. doi: 10.1254/jjp.42.87. PMID: 3795620.
In vitro protocol:
1. Suzuki T, Hashimura Y, Takeyama S. In vitro metabolism of the new cardiotonic agent denopamine (TA-064) by rat and rabbit liver preparations. Oxidation, methylation, and glucuronidation. Drug Metab Dispos. 1985 Mar-Apr;13(2):246-54. PMID: 2859176. 2. Aikawa J, Koike K, Takayanagi I. Vascular smooth muscle relaxation by alpha 1-adrenoceptor blocking action of denopamine in isolated rabbit aorta. J Cardiovasc Pharmacol. 1991 Mar;17(3):440-4. doi: 10.1097/00005344-199103000-00013. PMID: 1711606.
In vivo protocol:
1. Nishio R, Matsumori A, Shioi T, Wang W, Yamada T, Ono K, Sasayama S. Denopamine, a beta1-adrenergic agonist, prolongs survival in a murine model of congestive heart failure induced by viral myocarditis: suppression of tumor necrosis factor-alpha production in the heart. J Am Coll Cardiol. 1998 Sep;32(3):808-15. doi: 10.1016/s0735-1097(98)00314-3. PMID: 9741531. 2. Yabana H, Naito K, Nagao T. Effect of chronic administration of denopamine (TA-064), a new positive inotropic agent, on cardiac response of rats to denopamine. Jpn J Pharmacol. 1986 Sep;42(1):87-97. doi: 10.1254/jjp.42.87. PMID: 3795620.
1: Mori A, Sekito A, Sakamoto K, Ishii K, Nakahara T. Stimulation of β(1)- and β(2)-adrenoceptors dilates retinal blood vessels in rats. Naunyn Schmiedebergs Arch Pharmacol. 2017 May;390(5):527-533. doi: 10.1007/s00210-017-1349-4. Epub 2017 Feb 3. PubMed PMID: 28160015. 2: Birrell MA, Bonvini SJ, Wortley MA, Buckley J, Yew-Booth L, Maher SA, Dale N, Dubuis ED, Belvisi MG. The role of adenylyl cyclase isoform 6 in β-adrenoceptor signalling in murine airways. Br J Pharmacol. 2015 Jan;172(1):131-41. doi: 10.1111/bph.12905. Epub 2014 Nov 24. PubMed PMID: 25205328; PubMed Central PMCID: PMC4280973. 3: Barresi M, Grasso C, Licata F, Li Volsi G. Noradrenergic modulation of neuronal responses to n-methyl-d-aspartate in the vestibular nuclei: an electrophysiological and immunohistochemical study. Neuroscience. 2014 Apr 18;265:172-83. doi: 10.1016/j.neuroscience.2014.01.054. Epub 2014 Feb 7. PubMed PMID: 24508745. 4: Murai K, Seino Y, Kimata N, Inami T, Murakami D, Abe J, Yodogawa K, Maruyama M, Takano M, Ohba T, Ibuki C, Mizuno K. Efficacy and limitations of oral inotropic agents for the treatment of chronic heart failure. Int Heart J. 2013;54(2):75-81. PubMed PMID: 23676366. 5: Salie R, Moolman JA, Lochner A. The mechanism of beta-adrenergic preconditioning: roles for adenosine and ROS during triggering and mediation. Basic Res Cardiol. 2012 Sep;107(5):281. doi: 10.1007/s00395-012-0281-5. Epub 2012 Jul 15. PubMed PMID: 22797560. 6: Downs CA, Kriener LH, Yu L, Eaton DC, Jain L, Helms MN. β-Adrenergic agonists differentially regulate highly selective and nonselective epithelial sodium channels to promote alveolar fluid clearance in vivo. Am J Physiol Lung Cell Mol Physiol. 2012 Jun 1;302(11):L1167-78. doi: 10.1152/ajplung.00038.2012. Epub 2012 Apr 13. PubMed PMID: 22505670; PubMed Central PMCID: PMC3379040. 7: Salie R, Moolman JA, Lochner A. The role of β-adrenergic receptors in the cardioprotective effects of beta-preconditioning (βPC). Cardiovasc Drugs Ther. 2011 Feb;25(1):31-46. doi: 10.1007/s10557-010-6275-3. PubMed PMID: 21225332. 8: Baker JG. The selectivity of beta-adrenoceptor agonists at human beta1-, beta2- and beta3-adrenoceptors. Br J Pharmacol. 2010 Jul;160(5):1048-61. doi: 10.1111/j.1476-5381.2010.00754.x. PubMed PMID: 20590599; PubMed Central PMCID: PMC2936015. 9: Luchowska E, Kloc R, Olajossy B, Wnuk S, Wielosz M, Owe-Larsson B, Urbanska EM. beta-adrenergic enhancement of brain kynurenic acid production mediated via cAMP-related protein kinase A signaling. Prog Neuropsychopharmacol Biol Psychiatry. 2009 Apr 30;33(3):519-29. doi: 10.1016/j.pnpbp.2009.02.002. Epub 2009 Feb 12. PubMed PMID: 19439240. 10: Marcantoni A, Carabelli V, Vandael DH, Comunanza V, Carbone E. PDE type-4 inhibition increases L-type Ca(2+) currents, action potential firing, and quantal size of exocytosis in mouse chromaffin cells. Pflugers Arch. 2009 Mar;457(5):1093-110. doi: 10.1007/s00424-008-0584-4. Epub 2008 Sep 9. PubMed PMID: 18779976. 11: Shang G, Liu D, Allen SE, Yang Q, Zhang X. Asymmetric hydrogenation of alpha-primary and secondary amino ketones: efficient asymmetric syntheses of (-)-arbutamine and (-)-denopamine. Chemistry. 2007;13(27):7780-4. PubMed PMID: 17591728. 12: Ohgo T, Okamura H, Noda T, Satomi K, Suyama K, Kurita T, Aihara N, Kamakura S, Ohe T, Shimizu W. Acute and chronic management in patients with Brugada syndrome associated with electrical storm of ventricular fibrillation. Heart Rhythm. 2007 Jun;4(6):695-700. Epub 2007 Feb 20. PubMed PMID: 17556186. 13: Hayashi M, Ikomi F, Ohhashi T. Noradrenaline-induced smooth muscle relaxation in the specific region of canine facial vein: implications for facial and cranial circulation. J Physiol Sci. 2006 Oct;56(5):369-78. Epub 2006 Oct 12. Erratum in: J Physiol Sci. 2007 Apr;57(2):137. PubMed PMID: 17026784. 14: Gu X, Wang Z, Xu J, Maeda S, Sugita M, Sagawa M, Toga H, Sakuma T. Denopamine stimulates alveolar fluid clearance via cystic fibrosis transmembrane conductance regulator in rat lungs. Respirology. 2006 Sep;11(5):566-71. PubMed PMID: 16916328. 15: Gu X, Li SQ, Sakuma T. [Effects of beta-adrenergic agonists on alveolar fluid clearance in rat lungs]. Zhonghua Jie He He Hu Xi Za Zhi. 2005 Jun;28(6):390-3. Chinese. PubMed PMID: 16008976. 16: Nakajima D, Negoro N, Nakaboh A, Nakakoji T, Hoshiga M, Nariyama J, Ishihara T, Hanafusa T. Effectiveness of low dose denopamine, a beta1-adrenoceptor agonist, in a patient with vasospastic angina refractory to intensive medical treatment. Int J Cardiol. 2006 Apr 4;108(2):281-3. PubMed PMID: 15913812. 17: Shimizu W, Aiba T, Antzelevitch C. Specific therapy based on the genotype and cellular mechanism in inherited cardiac arrhythmias. Long QT syndrome and Brugada syndrome. Curr Pharm Des. 2005;11(12):1561-72. Review. PubMed PMID: 15892662; PubMed Central PMCID: PMC1475802. 18: Kaji H, Kume T. Regioselective glucuronidation of denopamine: marked species differences and identification of human udp-glucuronosyltransferase isoform. Drug Metab Dispos. 2005 Mar;33(3):403-12. Epub 2004 Dec 17. PubMed PMID: 15608137. 19: Ishide T. Denopamine, a selective beta1-receptor agonist and a new coronary vasodilator. Curr Med Res Opin. 2002;18(7):407-13. Review. PubMed PMID: 12487507. 20: Trost BM, Yeh VS, Ito H, Bremeyer N. Effect of ligand structure on the zinc-catalyzed Henry reaction. Asymmetric syntheses of (-)-denopamine and (-)-arbutamine. Org Lett. 2002 Aug 8;4(16):2621-3. PubMed PMID: 12153193.