Verapamil-d6 Hydrochloride

Cat. No.: B1140342

CAS No.: 1185032-80-7

M. Wt: 497.1

InChI Key:

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Overview

1. Description

6. Preparation methods

2. Scientific research applications

7. Chemical reactions analysis

3. Mechanism of action

8. Comparison with similar compounds

4. Safety and hazards

9. Properties

5. Future directions

10. Disclaimer

Description

Verapamil-d6 Hydrochloride is a deuterium-labeled version of Verapamil Hydrochloride, a well-known calcium channel blocker. The incorporation of deuterium, a stable isotope of hydrogen, into the molecule does not significantly alter its biochemical properties but allows for differentiation from non-labeled species in analytical techniques such as mass spectrometry . This compound is primarily used in scientific research to study chemical metabolism and kinetics.

Scientific Research Applications

Verapamil-d6 Hydrochloride is extensively used in scientific research, particularly in the following areas:

Chemistry: Used as an internal standard in mass spectrometry to accurately quantify the parent compound and its metabolites in biological matrices.

Biology: Studies involving the metabolic pathways and enzymatic processes involved in the biotransformation of Verapamil.

Medicine: Research on the pharmacokinetics and pharmacodynamics of Verapamil, including drug-drug interactions and metabolic profiling.

Industry: Utilized in the development of new analytical methods and quality control processes for pharmaceutical formulations.

Mechanism of Action

Verapamil is a calcium ion influx inhibitor (slow-channel blocker or calcium ion antagonist) that exerts its pharmacologic effects by modulating the influx of ionic calcium across the cell membrane of the arterial smooth muscle as well as in conductile and contractile myocardial cells.

Safety and Hazards

Verapamil is toxic if swallowed, in contact with skin, or if inhaled. It is advised to avoid dust formation, breathing vapors, mist, or gas, and to ensure adequate ventilation. It is also recommended to wear protective gloves, clothing, eye protection, and face protection.

Future Directions

Verapamil is used to prevent chest pain caused by angina as well as irregular heart rhythms (arrhythmias). It’s also used to treat high blood pressure (hypertension). If you have high blood pressure, taking verapamil helps to prevent future heart disease, heart attacks, and stroke. The future directions of Verapamil-d6 Hydrochloride would likely follow the same path as Verapamil, with ongoing research into its effects and potential uses.

Preparation Methods

Synthetic Routes and Reaction Conditions: The synthesis of Verapamil-d6 Hydrochloride involves the incorporation of deuterium into the Verapamil molecule. This process typically includes the use of deuterated reagents and solvents to replace hydrogen atoms with deuterium. The reaction conditions are carefully controlled to ensure the selective incorporation of deuterium without affecting the overall structure of the molecule .

Industrial Production Methods: Industrial production of this compound follows similar principles as its non-deuterated counterpart. The process involves multiple steps, including the synthesis of the Verapamil base, followed by deuteration and subsequent conversion to the hydrochloride salt. The final product is purified using techniques such as crystallization and chromatography to achieve high purity levels .

Chemical Reactions Analysis

Types of Reactions: Verapamil-d6 Hydrochloride undergoes various chemical reactions, including:

Oxidation: This reaction can be catalyzed by oxidizing agents such as potassium permanganate or hydrogen peroxide.

Reduction: Reduction reactions typically involve reagents like lithium aluminum hydride or sodium borohydride.

Substitution: Nucleophilic substitution reactions can occur with reagents such as sodium methoxide or potassium tert-butoxide.

Common Reagents and Conditions:

Oxidation: Potassium permanganate in acidic conditions.

Reduction: Sodium borohydride in methanol.

Substitution: Sodium methoxide in methanol.

Major Products: The major products formed from these reactions depend on the specific conditions and reagents used. For example, oxidation may yield carboxylic acids, while reduction can produce alcohols .

Comparison with Similar Compounds

Diltiazem Hydrochloride: Another calcium channel blocker with similar therapeutic uses but different chemical structure.

Nifedipine: A dihydropyridine calcium channel blocker used primarily for hypertension and angina.

Amlodipine: A long-acting dihydropyridine calcium channel blocker used for hypertension and angina.

Uniqueness: Verapamil-d6 Hydrochloride is unique due to its deuterium labeling, which allows for precise analytical studies without significantly altering its pharmacological properties. This makes it an invaluable tool in research settings, particularly for studying the metabolism and kinetics of Verapamil .

Properties

IUPAC Name	2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-(1,1,1,3,3,3-hexadeuteriopropan-2-yl)pentanenitrile;hydrochloride	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI	InChI=1S/C27H38N2O4.ClH/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6;/h9-12,17-18,20H,8,13-16H2,1-7H3;1H/i1D3,2D3;	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	DOQPXTMNIUCOSY-TXHXQZCNSA-N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	CC(C)C(CCCN(C)CCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C=C2)OC)OC.Cl	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Isomeric SMILES	[2H]C([2H])([2H])C(C([2H])([2H])[2H])C(CCCN(C)CCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C=C2)OC)OC.Cl	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C27H39ClN2O4	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Weight	497.1 g/mol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

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Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.

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