Etifelmine

Last updated
Etifelmine
Gilutensin-2d-skeletal.png
Clinical data
ATC code
  • none
Identifiers
  • 2-(Diphenylmethylidene)butan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C17H19N
Molar mass 237.346 g·mol−1
3D model (JSmol)
  • C(=C(/c1ccccc1)c2ccccc2)(\CN)CC
  • InChI=1S/C17H19N/c1-2-14(13-18)17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12H,2,13,18H2,1H3 Yes check.svgY
  • Key:WNKCJOWTKXGERE-UHFFFAOYSA-N Yes check.svgY
   (verify)

Etifelmine (INN; also known as gilutensin) is a stimulant drug. It was used for the treatment of hypotension (low blood pressure). [1]

Contents

Synthesis

The base-catalyzed reaction between benzophenone (1) and butyronitrile (2) gives 2-[hydroxy(diphenyl)methyl]butanenitrile (3). [2] [3] Catalytic hydrogenation reduces the nitrile group to a primary amine giving 1,1-diphenyl-2-ethyl-3-aminopropanol (4). The tertiary hydroxyl group is dehydrated by treatment with anhydrous hydrogen chloride gas, completing the synthesis of etifelmine (5).

Synthesis of etifelmine Etifelmine synthesis.svg
Synthesis of etifelmine

See also

References

  1. ↑ Poepelmann H (August 1964). "The treatment of hypotensive circulatory disorders with gilutensin". Therapie der Gegenwart (in German). 103: 1007–12. PMID   14254672.
  2. ↑ Etifelmine, Thieme
  3. ↑ Dr Werner Heinrich & Dr Walter Heigel, DE 1122514 (1962 to Giulini Gmbh Geb).
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