Zylofuramine

Zylofuramine

Clinical data
ATC code	none
Identifiers
IUPAC name (1R)-N-Ethyl-2-phenyl-1-[(2R)-tetrahydrofuran-2-yl]ethanamine
CAS Number	3563-92-6
PubChem CID	71129
ChemSpider	64277  Y
UNII	8N66VC535R
CompTox Dashboard (EPA)	DTXSID20912313
Chemical and physical data
Formula	C14H21NO
Molar mass	219.328 g·mol−1
3D model (JSmol)	Interactive image
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

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

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

1. USpatent 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.