38321-02-7

Basic information

• Product Name: (+)-3-(3,4-dimethoxyphenyl)-6-[(5,6-dimethoxyphenethyl)methylamino]hexane-3-carbonitrile
• Synonyms: Dexverapamil;(aR)-a-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-a-(1-methylethyl)-benzeneacetonitrile;Dexverapami;Benzeneacetonitrile, a-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-a-(1-methylethyl)-, (aR)- (9CI);Benzeneacetonitrile, a-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-a-(1-methylethyl)-, (R)-;d-Verapamil;(aR)-a-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-a-(1-methylethyl)-benzeneacetonitrile Hydrochloride;Dexverapamil Hydrochloride
• CAS NO: 38321-02-7
• Molecular Formula: C₂₇H₃₈N₂O₄
• Molecular Weight: 454.6
• EINECS: 253-878-4
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 38321-02-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 129-131°C
• Boiling Point: 586.1±50.0 °C(Predicted)
• Appearance: /
• Density: 1.058±0.06 g/cm3(Predicted)
• Refractive Index: 1.529
• PKA: 8.97±0.50(Predicted)
• CAS DataBase Reference: (+)-3-(3,4-dimethoxyphenyl)-6-[(5,6-dimethoxyphenethyl)methylamino]hexane-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-3-(3,4-dimethoxyphenyl)-6-[(5,6-dimethoxyphenethyl)methylamino]hexane-3-carbonitrile(38321-02-7)
• EPA Substance Registry System: (+)-3-(3,4-dimethoxyphenyl)-6-[(5,6-dimethoxyphenethyl)methylamino]hexane-3-carbonitrile(38321-02-7)

Safety Data

• Hazardous Substances Data: 38321-02-7(Hazardous Substances Data)

Usage

Description

(+)-3-(3,4-dimethoxyphenyl)-6-[(5,6-dimethoxyphenethyl)methylamino]hexane-3-carbonitrile, also known as Dexverapamil, is a chiral compound with the R configuration. It is an off-white solid that plays a crucial role in the pharmaceutical industry due to its ability to inhibit the multidrug resistance efflux pump P-glycoprotein (MDR-1, EC 3.6.3.44). This inhibition can potentially increase the effectiveness of a wide range of antineoplastic drugs that are inactivated by MDR-1 mechanisms. Dexverapamil also exhibits lower calcium antagonistic activity and toxicity compared to its racemic counterpart, verapamil.

Uses

Used in Pharmaceutical Industry:
Dexverapamil is used as a modulator in the pharmaceutical industry to enhance the effectiveness of various antineoplastic drugs. Its ability to inhibit the multidrug resistance efflux pump P-glycoprotein (MDR-1) allows for a potentially increased efficacy of these drugs, which are often inactivated by MDR-1 mechanisms. This application is particularly relevant for the treatment of cancer, as it can help overcome resistance and improve patient outcomes.
Used in Drug Delivery Systems:
In the field of drug delivery, Dexverapamil can be employed to improve the bioavailability and therapeutic outcomes of antineoplastic drugs. By inhibiting the MDR-1 pump, Dexverapamil can help reduce the resistance of cancer cells to these drugs, allowing for more effective treatment. This application can be particularly useful in the development of novel drug delivery systems, such as organic and metallic nanoparticles, which can serve as carriers for the compound and its associated antineoplastic drugs.
Used in Research and Development:
Dexverapamil is also utilized in research and development for the study of multidrug resistance and the development of new strategies to combat it. Its unique properties and ability to inhibit the MDR-1 pump make it a valuable tool for understanding the mechanisms behind drug resistance and for designing new drugs and therapies to overcome this challenge.

InChI:InChI=1/C26H36N2O4/c1-7-26(19-27,21-12-13-22(29-3)24(18-21)31-5)15-9-16-28(2)17-14-20-10-8-11-23(30-4)25(20)32-6/h8,10-13,18H,7,9,14-17H2,1-6H3

Upstream product

• 3490-06-0 N-methylhomoveratrylamine 
• 38176-01-1 (2R)-(+)-5-chloro-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile 
• 52-53-9 Verapamil 
• 54245-42-0 [11C]methyl iodide 
• 67018-85-3 (+)-Norverapamil 
• 145577-00-0 [11C]methyl triflate 
• 36770-70-4 (2R)-(+)-2-(3,4-dimethoxyphenyl)-5-hydroxy-2-isopropylpentanenitrile 
• 255721-21-2 (4S)-(-)-4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl acetate 
• 349078-89-3 (4E,3R)-(-)-3-(3,4-dimethoxyphenyl)-3-isopropylhex-4-enol 
• 349078-90-6 (4E,3S)-(+)-3-(3,4-dimethoxyphenyl)-3-isopropylhex-4-enol 
• 349078-83-7 Acetic acid (Z)-(S)-3-(3,4-dimethoxy-phenyl)-1,4-dimethyl-pent-2-enyl ester 
• 349078-78-0 Acetic acid (Z)-(R)-3-(3,4-dimethoxy-phenyl)-1,4-dimethyl-pent-2-enyl ester 
• 349078-84-8 (E,R)-(-)-3-(3,4-dimethoxyphenyl)-3-isopropylhex-4-enoic acid 
• 349078-85-9 (E,S)-(+)-3-(3,4-dimethoxyphenyl)-3-isopropylhex-4-enoic acid 

Downstream Products

• 152-11-4 (+)-Verapamil hydrochloride 

Relevant articles and documents

In-situ and one-step preparation of protein film in capillary column for open tubular capillary electrochromatography enantioseparation

In this work, the phase-transitioned BSA (PTB) film using the mild and fast fabrication process adhered to the capillary inner wall uniformly, and the fabricated PTB film-coated capillary column was applied to realize open tubular capillary electrochromatography (OT-CEC) enantioseparation. The enantioseparation ability of PTB film-coated capillary was evaluated with eight pairs of chiral analytes including drugs and neurotransmitters, all achieving good resolution and symmetrical peak shape. For three consecutive runs, the relative standard deviations (RSD) of migration time for intra-day, inter-day, and column-to-column repeatability were in the range of 0.3%–3.5%, 0.2%–4.9% and 2.1%–7.7%, respectively. Moreover, the PTB film-coated capillary column ran continuously over 300 times with high separation efficiency. Therefore, the coating method based on BSA self-assembly supramolecular film can be extended to the preparation of other proteinaceous capillary columns.

Quaternary Stereogenic Centers through Enantioselective Heck Arylation of Acyclic Olefins with Aryldiazonium Salts: Application in a Concise Synthesis of (R)-Verapamil

We describe herein a highly regio- and enantioselective Pd-catalyzed Heck arylation of unactivated trisubstituted acyclic olefins to provide all-carbon quaternary stereogenic centers. Chiral N,N ligands of the pyrimidine- and pyrazino-oxazoline class were developed for that purpose, providing the desired products in good to high yields with enantiomeric ratios up to >99:1. Both linear and branched substituents on the olefins were well-tolerated. The potential of this new method is demonstrated by the straightforward synthesis of several O-methyl lactols and lactones containing quaternary stereocenters, together with a concise enantioselective total synthesis of the calcium channel blocker verapamil.

Enzyme-mediated synthesis of (S)- And (R)-verapamil

A lipase-mediated synthesis of (S)- And (R)-verapamil is described. The key steps of the synthetic sequence are the enantioselective acetylation, mediated by Lipase PS, of allylic alcohol (Z)-(±)-2, affording the acetate derivative (Z,R)-(-)-3 (ee 92%) and the Ireland-Claisen rearrangement of this latter and of its enantiomer (Z,S)-(+)-3 (ee 92%) to afford acid derivatives (E,R)-(-)-4 (ee 94%) and (E,S)-(+)-4 (ee 93%), precursors of (S)- and (R)-verapamil, respectively.