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MedKoo Cat#: 461862 | Name: Pranolium

Description:

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

Pranolium is a quaternary dimethyl derivative of Propranolol, a well-known powerful betareceptor-blocking agent.

Chemical Structure

Pranolium
Pranolium
CAS#50643-33-9 (free base)

Theoretical Analysis

MedKoo Cat#: 461862

Name: Pranolium

CAS#: 50643-33-9 (free base)

Chemical Formula: C18H26NO2

Exact Mass: 288.1958

Molecular Weight: 288.41

Elemental Analysis: C, 74.96; H, 9.09; N, 4.86; O, 11.09

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
42879-47-0 (Cl) 50643-33-9 (free base)
Synonym
Pranolium; SC 27761; SC-27761; SC27761; UM 272; UM-272; UM272;
IUPAC/Chemical Name
2-hydroxy-N-isopropyl-N,N-dimethyl-3-(naphthalen-1-yloxy)propan-1-aminium
InChi Key
VOPWPUXOWBDNBN-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H26NO2/c1-14(2)19(3,4)12-16(20)13-21-18-11-7-9-15-8-5-6-10-17(15)18/h5-11,14,16,20H,12-13H2,1-4H3/q+1
SMILES Code
CC([N+](C)(C)CC(O)COC1=C2C=CC=CC2=CC=C1)C
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 288.41 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
1: Allan L, Barrow A, Haskins NJ, Rogers M, Rose DA, Palmer RF. Disposition of pranolium chloride in dogs, baboons and monkeys. Eur J Drug Metab Pharmacokinet. 1981;6(3):179-87. PubMed PMID: 7308238. 2: Barrow A, Brownsill RD, Spalton PN, Walls CM, Gunn Y, Haskins NJ, Rose DA, Palmer RF. Disposition of pranolium chloride in small mammals. Xenobiotica. 1980 Mar;10(3):219-28. PubMed PMID: 7467406. 3: Foken H, Gerbsch S, Schmauder HP, Heyde R, Lohmann D, Hagen A, Grünheid K, Flöther FU, Gröger D. [Synthesis and pharmacologic properties of pranolium and its optical isomers]. Pharmazie. 1990 Mar;45(3):180-3. German. PubMed PMID: 2381959. 4: Reele SB, Kornhauser D, Shand D, Carr K, Oates JA, Woosley RL. Antiarrhythmic effects of the quaternary propranolol analog that does not induce beta-adrenergic blockade. Clin Pharmacol Ther. 1982 Jul;32(1):33-40. PubMed PMID: 7083729. 5: Alkondon M, Ray A, Sen P. Autonomic regulation involved in the ocular hypotensive action of beta-adrenergic blocking agents. J Pharm Pharmacol. 1986 Apr;38(4):319-22. PubMed PMID: 2872303. 6: Gibson JK, Lucchesi BR. Electrophysiologic actions of UM-272 (Pranolium) on reentrant ventricular arrhythmias in postinfarction canine myocardium. J Pharmacol Exp Ther. 1980 Aug;214(2):347-53. PubMed PMID: 7391982. 7: Liu TF, Wei JH, Wang ZM, Chai Z, Liu XB, Gu XG. [Effects of pranolium on action potentials of myocardiac cells and on aconitine-induced arrhythmias]. Zhongguo Yao Li Xue Bao. 1985 Dec;6(4):258-60. Chinese. PubMed PMID: 2945366. 8: Eller BT, Patterson E, Lucchesi BR. Ventricular fibrillation in a conscious canine model--its prevention by UM-272. Eur J Pharmacol. 1983 Mar 4;87(4):407-13. PubMed PMID: 6852097. 9: Garnett ME, Godin DV, Tuchek JM. In vivo and in vitro studies of bacterial endotoxin-membrane interactions and the effects of membrane-active agents. Br J Pharmacol. 1984 Sep;83(1):15-21. PubMed PMID: 6386087; PubMed Central PMCID: PMC1987181. 10: Patterson E, Stetson P, Lucchesi BR. Sublingual absorption of the quaternary ammonium antiarrhythmic agent, UM-272. Pharmacology. 1983;27(4):192-6. PubMed PMID: 6634932. 11: Ray A, Alkondon M, Sen P. Involvement of brain transmitters in the modulation of shock-induced aggression in rats by propranolol and related drugs. Pharmacol Biochem Behav. 1987 Feb;26(2):229-34. PubMed PMID: 3575348. 12: Mak IT, Weglicki WB. Membrane antiperoxidative activities of D-propranolol, L-propranolol and dimethyl quaternary propranolol (UM-272). Pharmacol Res. 1992 Jan;25(1):25-30. PubMed PMID: 1738755. 13: Stowe N, Magnusson M, Novick A, Palleschi J, Pechan W, Khairallah P, Gifford R Jr, Straffon R. Pharmacologic protection against prolonged ischemia during harvesting and preservation of canine kidneys. Transplant Proc. 1981 Mar;13(1 Pt 2):699-701. PubMed PMID: 7022935. 14: Gupta M, Seth SD, Gupta MP, Manchanda SC. Mechanism of action of dimethyl quaternary propranolol (UM-272) in isoproterenol-induced cardiomyopathy in rats. Indian J Med Res. 1983 Jun;77:886-94. PubMed PMID: 6642587. 15: Alkondon M, Ray A, Sen P. Role of vagus in the antagonism of ouabain induced arrhythmias in dogs by beta-adrenoceptor antagonists and related drugs. J Pharm Pharmacol. 1984 Oct;36(10):702-4. PubMed PMID: 6150094. 16: Patterson E, Stetson P, Lucchesi BR. Plasma and myocardial tissue concentrations of UM-272 (N,N-dimethylpropranolol) after oral administration in dogs. J Pharmacol Exp Ther. 1980 Aug;214(2):449-53. PubMed PMID: 7391989. 17: Seth SD, Gupta M, Gupta MP, Manchanda SC, Srivastava LM. Alterations in isoproterenol-induced cardiac metabolic changes by a quaternary analog of propranolol, UM-272. Acta Cardiol. 1985;40(2):237-46. PubMed PMID: 3158144. 18: Daemmgen JW, Gross GJ. AQ-AH 208, a new bradycardic agent, increases coronary collateral blood flow to ischemic myocardium. J Cardiovasc Pharmacol. 1985 Nov-Dec;7(6):1048-54. PubMed PMID: 2418287. 19: Kodama I, Kondo N, Shibata S, Yamada K. Effects of dimethylpropranolol (UM-272) on the electrophysiological properties of guinea-pig ventricular muscles. J Pharmacol Exp Ther. 1985 Aug;234(2):507-14. PubMed PMID: 2410595. 20: Vogel WM, Romson JL, Bush LR, Shlafer M, Lucchesi BR. Protective effects of dimethyl-propranolol (UM-272) during global ischemia of isolated feline hearts. J Pharmacol Exp Ther. 1980 Mar;212(3):560-8. PubMed PMID: 7359356.