Aprindine

Aprindine is a Class 1b antiarrhythmic agent.[1]

Aprindine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • {3-[2,3-dihydro-1H-inden-2-yl(phenyl)amino]propyl}diethylamine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H30N2
Molar mass322.496 g·mol−1
3D model (JSmol)
SMILES
  • c1cccc3c1CC(N(c2ccccc2)CCCN(CC)CC)C3
InChI
  • InChI=1S/C22H30N2/c1-3-23(4-2)15-10-16-24(21-13-6-5-7-14-21)22-17-19-11-8-9-12-20(19)18-22/h5-9,11-14,22H,3-4,10,15-18H2,1-2H3 Y
  • Key:NZLBHDRPUJLHCE-UHFFFAOYSA-N Y
  (verify)

It has been since discovered that the quat salts of Aprindine are also claimed to have an antiarrhythmic activity.[2][3]

Synthesis

The modern method uses Indene as the starting material since this is more stable than 2-indanone.

Thieme Patent:[4] Improved technology for the First step:[5]

The condensation between 2-Indanone [615-13-4] (1) and aniline gives an "anil" type Schiff's base[6] (2). The reduction with sodium borohydride forms the corresponding aminoindane [33237-72-8] (3). Sodium hydride catalyzed alkylation with 3-diethylaminopropyl chloride [104-77-8] (4) completed the synthesis of Aprindine (5).

See also
  • Moxaprindine [53076-26-9]
  • Pyrophendane [7009-69-0]
  • Indriline Fb: [7395-90-6].

References
  1. WHOCC. "WHOCC - ATC/DDD Index". www.whocc.no. Retrieved 2018-03-01.
  2. US 3917679, Molloy BB, Tuttle RR, issued 1975, assigned to Eli Lilly and Co
  3. US 4018897, Molloy BB, issued 1977, assigned to to Eli Lilly and Co
  4. US 3923813, Vanhoof PM, Clarebout PM, issued 1975, assigned to Christiaens Sa A.
  5. JPH 1045687, Sasaki T, et al., issued 1998, assigned to Nippon Steel Corp
  6. "N-(Indan-2-ylidene)aniline". PubChem. U.S. Library of Medicine.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.