N-Demethyldiltiazem hydrochloride

Base Information

• Chemical Name: N-Demethyldiltiazem hydrochloride
• CAS No.: 130606-60-9
• Molecular Formula: C₂₁H₂₄N₂O₄S
• Molecular Weight: 400.499
• European Community (EC) Number: 641-708-5
• UNII: A825LGP73P
• DSSTox Substance ID: DTXSID601019739
• Wikidata: Q27273749
• Mol file: 130606-60-9.mol

Synonyms:130606-60-9;N-Demethyldiltiazem hydrochloride;N-Demethyl diltiazem hydrochloride;UNII-A825LGP73P;N-Desmethyl Diltiazem Hydrochloride;A825LGP73P;Diltiazem Impurity D (N-Desmethyl diltiazem HCl);Diltiazem N-desmethyl hydrochloride;1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-2,3-dihydro-2-(4-methoxyphenyl)-5-(2-(methylamino)ethyl)-, hydrochloride (1:1), (2S,3S)-;1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-2,3-dihydro-2-(4-methoxyphenyl)-5-(2-(methylamino)ethyl)-, monohydrochloride, (2S-cis)-;N-DESMETHYLDILTIAZEM HYDROCHLORIDE;[(2S,3S)-2-(4-methoxyphenyl)-5-[2-(methylamino)ethyl]-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl] acetate;hydrochloride;(2S,3S)-2-(4-Methoxyphenyl)-5-[2-(methylamino)ethyl]-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl Acetate Hydrochloride (N-Desmethyl-diltiazem Hydrochloride);N-desmethyl Diltiazem (hydrochloride);DESMETHYL DILTIAZEM HCL;DTXSID601019739;AKOS037645549;AS-6140;J-005838;Q27273749;Diltiazem N-desmethyl hydrochloride 100 microg/mL in Acetonitrile;N-Desmethyldiltiazem Hydrochloride 1.0 mg/ml in Acetonitrile (as free base)

Chemical Property of N-Demethyldiltiazem hydrochloride

Chemical Property:

• Melting Point: 156-158°C
• PSA: 93.17000
• LogP: 4.28420
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 436.1223562
• Heavy Atom Count: 29
• Complexity: 539

Purity/Quality:

99%, ^*data from raw suppliers

N-Desmethyl Diltiazem Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(SC2=CC=CC=C2N(C1=O)CCNC)C3=CC=C(C=C3)OC.Cl
• Isomeric SMILES: CC(=O)O[C@@H]1[C@@H](SC2=CC=CC=C2N(C1=O)CCNC)C3=CC=C(C=C3)OC.Cl
• Uses: A metabolite of diltiazem, an antianginal, antihypertensive pharmaceutical. Diltiazem regulates Calcium release from intracellular stores in neutrophils A metabolite of Diltiazem (D460620), an antianginal, antihypertensive pharmaceutical. Diltiazem regulates Calcium release from intracellular stores in neutrophils. N-Desmethyl Diltiazem Hydrochloride (Dilitiazem EP Impurity D) is a metabolite of Diltiazem (D460620), an antianginal and an antihypertensive pharmaceutical. Diltiazem regulates calcium release from intracellular stores in neutrophils.

Technology Process of N-Demethyldiltiazem hydrochloride

There total 2 articles about N-Demethyldiltiazem hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

diltiazem (42399-41-7) → N,N-Didesmethyldiltiazem + N-desmethyldiltiazem (85100-17-0,86408-41-5,86408-45-9,86408-46-0,130606-60-9)

Guidance literature:

With NADPH; In aq. buffer; at 30 ℃; pH=7.3; Enzymatic reaction;

DOI:10.1021/acs.joc.1c01407

Reference yield:

diltiazem (42399-41-7) → N-desmethyldiltiazem (85100-17-0,86408-41-5,86408-45-9,86408-46-0,130606-60-9)

Guidance literature:

With ethylenediaminetetraacetic acid; D-glucose 6-phosphate; human recombinant hepatic microsomal cytochrome P₄₅₀ A₄; NADP; magnesium chloride; glucose 6-phosphate dehydrogenase; at 37 ℃; for 0.25h; pH=7.4; Reagent/catalyst; Time; Kinetics; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1016/j.lfs.2011.02.017

Reference yield: 94.0%

N-desmethyldiltiazem (85100-17-0,86408-41-5,86408-45-9,86408-46-0,130606-60-9) + acrylonitrile (107-13-1,25014-41-9) → N-cyanoethyl-N-desmethyldiltiazem

Guidance literature:

In methanol; at 20 ℃;

DOI:10.1124/dmd.110.032391

upstream raw materials:

diltiazem