Bethanidine Sulfate

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

MedKoo CAT#: 317321

CAS#: 114-85-2 (sulfate)

Description: Bethanidine sulfate is a guanidinium antihypertensive agent that acts by blocking adrenergic transmission.

Chemical Structure

img
Bethanidine Sulfate
CAS# 114-85-2 (sulfate)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317321
Name: Bethanidine Sulfate
CAS#: 114-85-2 (sulfate)
Chemical Formula: C10H17N3O4S
Exact Mass: 0.00
Molecular Weight: 275.320
Elemental Analysis: C, 43.62; H, 6.22; N, 15.26; O, 23.24; S, 11.65

Price and Availability

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). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Related CAS #: 55-73-2 (free base)   114-85-2 (sulfate)    

Synonym: Bethanidine Sulfate; Bentanidol; Benzanidin; Benzanidine; Bendogen; Benzaidin; Benzoxine; Betaling; Eusmanid; Hypersin; Tenathan; Esbatal; Regulin; Batel; Bethanidine; hemisulfate, UNII-J4THI5N7O2, Bethanidine sulfate [USAN], 55-73-2 (Parent), EINECS 204-056-9, CID8248

IUPAC/Chemical Name: 1-benzyl-2,3-dimethylguanidine;sulfuric acid

InChi Key: WDLCALUKNKNIDF-UHFFFAOYSA-N

InChi Code: InChI=1S/C10H15N3.H2O4S/c1-11-10(12-2)13-8-9-6-4-3-5-7-9;1-5(2,3)4/h3-7H,8H2,1-2H3,(H2,11,12,13);(H2,1,2,3,4)

SMILES Code: CNC(=NC)NCC1=CC=CC=C1.OS(=O)(=O)O

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

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Bethanidine sulfate is a guanidinium antihypertensive agent that acts by blocking adrenergic transmission.
In vitro activity: The effects of bethanidine sulphate were studied on action potentials (APs) and K+, Na+, and Ca2+ currents of single cultured embryonic chick heart cells using the whole-cell current clamp and voltage clamp technique. Extracellular application of bethanidine (3 X 10(-4) M) increased the overshoot and the duration of the APs and greatly decreased the outward K+ current (IK) and potentiated the inward fast Na+ currents (INa) and the inward slow calcium current (ICa). However, intracellular introduction of bethanidine (10(-4) M) blocked Ina. These findings suggest that when applied extracellularly, bethanidine exerts a potentiating effect on the myocardial fast Na+ current and slow Ca2+ current and an inhibitory effect of IK. The positive inotropic effect of bethanidine could be due, at least in part, to an increase of Ca2+ influx via the slow Ca2+ channel and the Na-Ca exchange. It is suggested that the decrease of IK by bethanidine may account for its antifibrillatory action. Reference: Can J Physiol Pharmacol. 1988 Mar;66(3):190-6. https://cdnsciencepub.com/doi/10.1139/y88-033?url_ver=Z39.88-2003&rfr_id=ori:rid:crossref.org&rfr_dat=cr_pub%20%200pubmed
In vivo activity: TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 275.32 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. Dangman KH, Miura DS. Electrophysiological effects of bethanidine sulfate on canine cardiac Purkinje fibers and ventricular muscle cells. J Cardiovasc Pharmacol. 1985 Jan-Feb;7(1):50-8. doi: 10.1097/00005344-198501000-00009. PMID: 2580150. 2. Bkaily G, Payet MD, Benabderrazik M, Renaud JF, Sauvé R, Bacaner MB, Sperelakis N. Bethanidine increased Na+ and Ca2+ currents and caused a positive inotropic effect in heart cells. Can J Physiol Pharmacol. 1988 Mar;66(3):190-6. doi: 10.1139/y88-033. PMID: 3383015.
In vitro protocol: 1. Dangman KH, Miura DS. Electrophysiological effects of bethanidine sulfate on canine cardiac Purkinje fibers and ventricular muscle cells. J Cardiovasc Pharmacol. 1985 Jan-Feb;7(1):50-8. doi: 10.1097/00005344-198501000-00009. PMID: 2580150. 2. Bkaily G, Payet MD, Benabderrazik M, Renaud JF, Sauvé R, Bacaner MB, Sperelakis N. Bethanidine increased Na+ and Ca2+ currents and caused a positive inotropic effect in heart cells. Can J Physiol Pharmacol. 1988 Mar;66(3):190-6. doi: 10.1139/y88-033. PMID: 3383015.
In vivo protocol: TBD

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Bauman JL, Gallastegui J, Prechel D, Anderson JL. Bethanidine sulfate in paroxysmal ventricular tachycardia: toxicity and antifibrillatory actions. Pharmacotherapy. 1986 Jul-Aug;6(4):184-92. doi: 10.1002/j.1875-9114.1986.tb03474.x. PMID: 3774563.


2: Bethanidine. Br Med J. 1967 Feb 4;1(5535):285-6. PMID: 6017482; PMCID: PMC1840649.


3: Taghvaei S, Minuchehr Z, Sabouni F. Computational drug repurposing of bethanidine for SENP1 inhibition in cardiovascular diseases treatment. Life Sci. 2022 Mar 1;292:120122. doi: 10.1016/j.lfs.2021.120122. Epub 2021 Nov 6. PMID: 34748762.


4: Dangman KH, Miura DS. Electrophysiological effects of bethanidine sulfate on canine cardiac Purkinje fibers and ventricular muscle cells. J Cardiovasc Pharmacol. 1985 Jan-Feb;7(1):50-8. doi: 10.1097/00005344-198501000-00009. PMID: 2580150.


5: Benditt DG, Benson DW Jr, Dunnigan A, Kriett JM, Pritzker MR, Bacaner MB. Antiarrhythmic and electrophysiologic actions of bethanidine sulfate in primary ventricular fibrillation or life-threatening ventricular tachycardia. Am J Cardiol. 1984 May 1;53(9):1268-74. doi: 10.1016/0002-9149(84)90077-8. PMID: 6711426.


6: Teichman SL, Waspe LE, Matos JA, Kim SG, Fisher JD. Bethanidine sulfate: efficacy in prevention of ventricular tachyarrhythmias during programmed stimulation. Report of a multicenter study of 56 patients. J Am Coll Cardiol. 1985 Sep;6(3):510-7. doi: 10.1016/s0735-1097(85)80106-6. PMID: 3897340.


7: Kabell G. Ischemia-induced conduction delay and ventricular arrhythmias: comparative electropharmacology of bethanidine sulfate and bretylium tosylate. J Cardiovasc Pharmacol. 1989 Mar;13(3):471-82. doi: 10.1097/00005344-198903000-00017. PMID: 2471895.


8: Somberg JC, Butler B, Torres V, Flowers D, Tepper D, Wynn J, Keren G, Miura DS. Antiarrhythmic action of bethanidine. Am J Cardiol. 1984 Aug 1;54(3):343-6. doi: 10.1016/0002-9149(84)90194-2. PMID: 6465015.


9: GIFFORD RW Jr. BETHANIDINE SULFATE--A NEW ANTIHYPERTENSIVE AGENT. JAMA. 1965 Sep 13;193:901-5. doi: 10.1001/jama.1965.03090110039011. PMID: 14341134.


10: Villafane J, Xu H, McCormack J, Gelband H, Stolfi A, Pickoff AS. The non- catecholamine-mediated electrophysiological effects of intravenous bethanidine sulfate on the immature mammalian heart. J Cardiovasc Pharmacol. 1988 Oct;12(4):486-91. doi: 10.1097/00005344-198810000-00016. PMID: 2465451.


11: DiMarco JP, Sellers TD, Shipe JR, Savory J, Spyker DH. Acute electrophysiologic effects of bethanidine sulfate in patients with ventricular tachycardia or fibrillation. Am Heart J. 1984 Nov;108(5):1244-9. doi: 10.1016/0002-8703(84)90748-8. PMID: 6496282.


12: BEWLEY TH. TO-DAY'S DRUGS. BETHANIDINE SULPHATE. Br Med J. 1964 Oct 3;2(5413):865. PMID: 14185642; PMCID: PMC1816291.


13: Bacaner MB, Hoey MF, Macres MG. Suppression of ventricular fibrillation and positive inotropic action of bethanidine sulfate, a chemical analog of bretylium tosylate that is well absorbed orally. Am J Cardiol. 1982 Jan;49(1):45-55. doi: 10.1016/0002-9149(82)90276-4. PMID: 7053610.


14: Ramirez EA, Elson L, Gear AS, Oster JR, Talmers FN, Thomas JR. Multiclinic controlled trial of bethanidine and guanethidine in severe hypertension. Circulation. 1977 Mar;55(3):519-25. doi: 10.1161/01.cir.55.3.519. PMID: 319922.


15: Myers MG. New drugs in hypertension. Can Med Assoc J. 1977 Jan 22;116(2):173-6. PMID: 343894; PMCID: PMC1879000.


16: Corder CN, Klaniecki TS, McDonald RH Jr, Berlin C. Fluorometric assay of bethanidine in plasma. J Pharm Sci. 1975 May;64(5):785-92. doi: 10.1002/jps.2600640511. PMID: 239198.


17: Zimmerman JM, Patterson E, Pitt B, Lucchesi B. Antidysrhythmic actions of meobentine sulfate. Am Heart J. 1984 Jun;107(6):1117-24. doi: 10.1016/0002-8703(84)90266-7. PMID: 6720538.


18: Bacaner MB, Benditt DG. Antiarrhythmic, antifibrillatory, and hemodynamic actions of bethanidine sulfate: an orally effective analog of bretylium for suppression of ventricular tachyarrhythmias. Am J Cardiol. 1982 Oct;50(4):728-34. doi: 10.1016/0002-9149(82)91226-7. PMID: 6812406.


19: Green AF. The discovery of bretylium and bethanidine. Br J Clin Pharmacol. 1982 Jan;13(1):25-34. doi: 10.1111/j.1365-2125.1982.tb01333.x. PMID: 7066153; PMCID: PMC1401770.


20: Corder CN. Bethanidine dose, plasma levels, and antihypertensive effects. J Clin Pharmacol. 1978 May-Jun;18(5-6):249-58. doi: 10.1002/j.1552-4604.1978.tb02443.x. PMID: 641213.