Zylofuramine

Chemical compound From Wikipedia, the free encyclopedia

Zylofuramine[1] is a stimulant drug. It was developed in 1961,[2][3] and was intended for use as an appetite suppressant and for the treatment of senile dementia in the elderly, but there is little information about it and it does not appear to have ever been marketed.[4]

ATC code
  • none
Quick facts Clinical data, ATC code ...
Zylofuramine
Clinical data
ATC code
  • none
Identifiers
  • (1R)-N-Ethyl-2-phenyl-1-[(2R)-tetrahydrofuran-2-yl]ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H21NO
Molar mass219.328 g·mol−1
3D model (JSmol)
  • O2[C@@H]([C@H](NCC)Cc1ccccc1)CCC2
  • InChI=1S/C14H21NO/c1-2-15-13(14-9-6-10-16-14)11-12-7-4-3-5-8-12/h3-5,7-8,13-15H,2,6,9-11H2,1H3/t13-,14-/m1/s1 checkY
  • Key:DOFCLOLKFGSRTG-ZIAGYGMSSA-N checkY
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Its chemical structure has a similarity to other N-ethyl substituted stimulant drugs such as ethylamphetamine and N-ethylhexedrone.

Synthesis

The Grignard reaction of benzylmagnesium bromide (1) and the imine of furfural and ethylamine, N-ethylfuran-2-methaneimine (2), gives the amine derivative (3). Hydrogenation using a Raney nickel catalyst yields zylofuramine.[1][2]

References

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