Zylofuramine

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]

Zylofuramine
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • (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)
SMILES
  • O2[C@@H]([C@H](NCC)Cc1ccccc1)CCC2
InChI
  • 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 Y
  • Key:DOFCLOLKFGSRTG-ZIAGYGMSSA-N Y
  (verify)

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

References
  1. US patent 3091621, Clarke RL, "Alpha-Aryl or Aralkyl Tetrahydrofurfurylamines", issued 1963-05-28, assigned to Sterling Drugs
  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.
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