42399-40-6

Basic information

• Product Name: Deacetyldiltiazem
• Synonyms: (2S-cis)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one;(2S-cis)-5-[(Dimethylamino)ethyl]-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one;Deacetyl-d-diltiazem;Deacetyldiltiazem;Desacetyl Diltiazem;(3S,4S)-6-(2-dimethylaminoethyl)-4-hydroxy-3-(4-methoxyphenyl)-2-thia-6-azabicyclo[5.4.0]undeca-7,9,11-trien-5-one;(2S-cis)-5-(2-(Dimethylamino)ethyl)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one;(2S)-2-(4-Methoxyphenyl)-3β-hydroxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepine-4(5H)-one
• CAS NO: 42399-40-6
• Molecular Formula: C₂₀H₂₄N₂O₃S
• Molecular Weight: 372.49
• EINECS: 255-795-9
• Product Categories: Diltiazem;Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 42399-40-6.mol
• Article Data: 19

Chemical Properties

• Melting Point: 86-87 °C
• Boiling Point: 596.8 °C at 760mmHg
• Flash Point: 314.8°C
• Appearance: off-white to pale yellow solid
• Density: 1.225g/cm³
• Vapor Pressure: 4.3E-15mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 11.96±0.40(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Deacetyldiltiazem(CAS DataBase Reference)
• NIST Chemistry Reference: Deacetyldiltiazem(42399-40-6)
• EPA Substance Registry System: Deacetyldiltiazem(42399-40-6)

Safety Data

• Hazardous Substances Data: 42399-40-6(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Pale Yellow Solid

Uses

Desacetyl Diltiazem (Diltiazem EP Impurity F) is a metabolite of Diltiazem (D460620).

InChI:InChI=1/C20H24N2O3S/c1-21(2)12-13-22-16-6-4-5-7-17(16)26-19(18(23)20(22)24)14-8-10-15(25-3)11-9-14/h4-11,18-19,23H,12-13H2,1-3H3/t18-,19+/m1/s1

Upstream product

• 23515-44-8 5-(2-dimethylamino-ethyl)-3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 137-07-5 2-amino-benzenethiol 
• 42399-49-5 (2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one 
• 42399-41-7 diltiazem 
• 696-62-8 para-iodoanisole 
• 33286-22-5 diltiazem hydrochloride 
• 80344-17-8 3-[2-(2-dimethylamino-ethylamino)-phenylsulfanyl]-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid 
• 154076-93-4 ethyl (Z)-2-(2-methoxyethoxy)methoxy-3-(4-methoxyphenyl)-2-propenoate 
• 42245-42-1 methyl (2-RS,3-SR)-2,3-epoxy-3-(4-methoxyphenyl)propanoate 
• 30193-56-7 (+/-)-(R*,R*)-β-[(2-aminophenyl)thio]-α-hydroxy-4-methoxybenzenepropanoic acid, methyl ester 
• 123-11-5 4-methoxy-benzaldehyde 
• 96125-49-4 methyl trans-3-(4-methoxyphenyl)glycidate 
• 27068-88-8 3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 4584-46-7 (2-chloroethyl)dimethylamine hydrochloride 

Downstream Products

• 31953-21-6 3-methyl-butyric acid 5-(2-dimethylamino-ethyl)-2c-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3r-yl ester 
• 40602-20-8 5-(2-dimethylamino-ethyl)-2r-(4-methoxy-phenyl)-3c-pentanoyloxy-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 40602-19-5 3c-butyryloxy-5-(2-dimethylamino-ethyl)-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 42399-53-1 (2RS,3RS)-cis-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 
• 31964-29-1 {2-[3c-acetoxy-2r-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazepin-5-yl]-ethyl}-ethyl-dimethyl-ammonium; bromide 
• 31964-30-4 {2-[3c-acetoxy-2r-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazepin-5-yl]-ethyl}-dimethyl-propyl-ammonium; bromide 
• 31964-28-0 {2-[3c-acetoxy-2r-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazepin-5-yl]-ethyl}-trimethyl-ammonium; iodide 
• 42399-41-7 diltiazem 
• 33286-22-5 diltiazem hydrochloride 
• 139564-98-0 2-<(Z)-α-Chlor-4-methoxybenzyliden>-4-(2-dimethylaminoethyl)-2H-1,4-benzothiazin-3(4H)-on 
• 139564-97-9 2-<(E)-α-Chlor-4-methoxybenzyliden>-4-(2-dimethylaminoethyl)-2H-1,4-benzothiazin-3(4H)-on 
• 40602-22-0 5-(2-dimethylamino-ethyl)-3c-hexanoyloxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 129784-91-4 3c-benzoyloxy-5-(2-dimethylamino-ethyl)-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 68767-06-6 5-[2-(dimethyl-oxy-amino)-ethyl]-3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 

Related news

Improved Gas Chromatographic Determination of Diltiazem and Deacetyldiltiazem (cas 42399-40-6) in Human Plasma07/13/2019

This study describes an improved, simple, and specific gas chromatographic method for the determination of diltiazem (I) and deacetyldiltiazem (II) in human plasma using loxapine (III) as an internal standard. After extraction at pH 7.5 with anhydrous ether-ethyl acetate (1:1), II was silylated ...detailed

Assay of diltiazem and Deacetyldiltiazem (cas 42399-40-6) by capillary gas chromatography07/12/2019

A highly sensitive gas chromatographic method for the analysis of diltiazem and deacetyldiltiazem in plasma or serum is reported. After silylation with bis (trimethylsilyl) trifluoroacetamide, separation was obtained on a cross-linked fused-silica column and detection was by electron-capture. Th...detailed

Pharmacokinetics of diltiazem and Deacetyldiltiazem (cas 42399-40-6) in rats07/11/2019

Diltiazem (DTZ) was given intravenously (i.v.), orally (p.o.) and hepatoportally (p.v.) in solution form to rats in order to assess the pharmacokinetic behavior of DTZ and its major metabolite, deacetyldiltiazem (DAD). The plasma half-life at postdistributive phase (t12,β), total body (plasma) ...detailed

Relevant articles and documents

High-performance liquid chromatography method for assay of diltiazem hydrochloride and its related compounds in bulk drug and finished tablets

The method provides for the resolution of trans-diltiazem and seven known and several unknown related compounds from diltiazem HCl. Minimum detectable amounts were 0.1%, except for an intermediate which originates early in the synthetic process, for which the sensitivity is ~2%. The relative standard deviation of the assay procedure is 0.15%. Total related compounds in four bulk drugs and four tablet samples were 0.25%. The specific rotation of four samples of diltiazem HCl analyzed in duplicate was between +112 and +114°. The UV absorption spectra of all compounds exhibited two maxima, one between 203 and 213 nm and the other between 230 and 244 nm.

Synthesis of potential drug metabolites by a modified Udenfriend reaction

The scope and the limitations of a modified Udenfriend reaction for the one-step synthesis of potential drug metabolites were explored. Several drugs (clozapine, chlorpromazine, imipramine, buspirone, diltiazem, and propranolol) were subjected to modified Udenfriend conditions (Fe2+/Mn 2+/EDTA/ascorbic acid/O2). From each reaction, one to four oxidation products were obtained in 1-8% overall yield. Many of these products (9 out of 14) have been reported to be metabolites of the parent drugs in vivo. The products resulted mainly from aromatic hydroxylation, and are not readily accessible by conventional synthesis. Thus, the described reaction may be useful in drug discovery whenever a facile synthetic access is more important than high yields (e.g., for a fast derivatisation of compounds or the preparation of metabolites). Poorly water-soluble compounds cannot be converted, which is an important limitation of this method. 2010 American Chemical Society.

PROCESS FOR PREPARING DILTIAZEM USING A HETEROGENEOUS TRIFUNCTIONAL CATALYST

The present invention comprises a simplified synthesis of (+)-diltiazem through IE-PdOsW wherein IE is ion-exchanger, catalyzed three-component coupling reaction and Fe3+-exchanged clay catalyzed ring opening of sulfite with 2-aminothiophenol followed by cyclization as key steps.