Zylofuramine

Last updated
Zylofuramine
Zylofuramine.svg
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
Formula C14H21NO
Molar mass 219.328 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 Yes check.svgY
  • Key:DOFCLOLKFGSRTG-ZIAGYGMSSA-N Yes check.svgY

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]

Its chemical structure has a similarity to other N-ethyl substituted stimulant drugs such as ethylamphetamine and N-Ethylhexedrone.

Synthesis

Zylofuramine synthesis.svg

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]

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References

  1. 1 2 USpatent 3091621,Clarke RL,"Alpha-Aryl or Aralkyl Tetrahydrofurfurylamines",issued 1963-05-28, assigned to Sterling Drugs
  2. 1 2 Clarke RL, Harris LS (January 1962). "α-Benzyltetrahydrofurfurylamines -- A New Series of Psychomotor Stimulants. I". Journal of Medicinal and Pharmaceutical Chemistry. 5 (1): 77–95. doi:10.1021/jm01236a010. PMID   14046619.
  3. Clarke RL, Tullar BF, Harris LS (March 1962). "α-Benzyltetrahydrofurfurylamines -- A New Series of Psychomotor Stimulants. II. Resolution of Isomers". Journal of Medicinal and Pharmaceutical Chemistry. 5 (2): 362–72. doi:10.1021/jm01237a014. PMID   14051912.
  4. Harris LS, Clarke RL, Dembinski JR (December 1963). "α-Benzyltetrahydrofurfurylamines -- A New Series of Psychomotor Stimulants. III. The Pharmacology of D-Threo α-Benzyl-N-Ethyltetrahydrofurfurylamine (Zylofuramine)". Archives Internationales de Pharmacodynamie et de Therapie. 146: 392–405. PMID   14099588.