Isolation of a major metabolite (i-OHAP) of aprindine and its identification as N-[3-(N,N-diethylamino)propyl]-N-phenyl-2-aminoindan-5-ol

Mikiko Shimizu, Kazuhiko Takatori, Masahiro Kajiwara, Hiroyasu Ogata

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

i-OHAP, a major metabolite of aprindine (AP), was isolated by TLC from rat feces and identified as N-13-(N,N-diethylamino)propyl]-N-phenyl-2- aminoindan-5-ol, based on 1H-NMR, the H-H correlation spectroscopy (COSY) spectrum, MS and LC-MS. Its structure was also confirmed by comparison with the synthesized compound. The hydroxy group of i-OHAP was located at the 5- position of the indan ring. AP is a prochiral compound, and the metabolism of AP to i-OHAP was stereoselective. The ratio of (+)/(-)-i-OHAP in rat feces and in human urine was about 5 and 15, respectively.

Original languageEnglish
Pages (from-to)530-534
Number of pages5
JournalBiological and Pharmaceutical Bulletin
Volume21
Issue number5
Publication statusPublished - 1998
Externally publishedYes

Fingerprint

Aprindine
Feces
Spectrum Analysis
Urine
N-(3-(N,N-diethylamino)propyl)-N-phenyl-2-aminoindan-5-ol

Keywords

  • Aprindine
  • I-OHAP
  • Isolation
  • Metabolite
  • Rat
  • Stereoselectivity

ASJC Scopus subject areas

  • Pharmacology
  • Pharmaceutical Science

Cite this

Isolation of a major metabolite (i-OHAP) of aprindine and its identification as N-[3-(N,N-diethylamino)propyl]-N-phenyl-2-aminoindan-5-ol. / Shimizu, Mikiko; Takatori, Kazuhiko; Kajiwara, Masahiro; Ogata, Hiroyasu.

In: Biological and Pharmaceutical Bulletin, Vol. 21, No. 5, 1998, p. 530-534.

Research output: Contribution to journalArticle

Shimizu, Mikiko ; Takatori, Kazuhiko ; Kajiwara, Masahiro ; Ogata, Hiroyasu. / Isolation of a major metabolite (i-OHAP) of aprindine and its identification as N-[3-(N,N-diethylamino)propyl]-N-phenyl-2-aminoindan-5-ol. In: Biological and Pharmaceutical Bulletin. 1998 ; Vol. 21, No. 5. pp. 530-534.
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