Cyclazodone is a centrally acting stimulant drug developed by American Cyanamid Company in the 1960s.[1] The drug is related to other drugs such as pemoline and thozalinone. It displayed a favorable therapeutic index and margin of safety in comparison to pemoline and other N-lower-alkyl-substituted pemoline derivatives.[2] The patents concluded that cyclazodone possessed properties efficacious in reducing fatigue and as a potential anorectic.[3] Structural congeners of pemoline have been described as "excitants with unique properties distinguishing them from the sympathomimetic amines" whilst displaying less stimulatory activity and toxicity compared to amphetamine.[4]
Cyclazodone has not been evaluated by the United States Food and Drug Administration for use in humans as a nootropic, anorectic, or stimulant and thus safety information is lacking. However, in studies relating to the therapeutic uses of cyclazodone, it was noted that it exhibited less cardiotoxic and hepatotoxic effects than D-amphetamine in studies on mice.[2]
Synthesis
α-Chlorophenylacetyl chloride (1) and 1-cyclopropylurea (2) react to give the amide (3). The heterocycle cyclazodone is formed on threatment of this with sodium ethoxide.[2][6]
↑Howell Jr CF, Hardy RA, Quinones N, "5-Arylidene-2-Amino-2-Oxazolin-4-Ones", US patent 3321470, issued 23 May 1967, assigned to American Cyanamid
↑ 2.02.12.2De Marne V, Pierre D, Guidicelli RL, Najer H, "5-Phenyl-2-Cyclopropylamino-4-Oxazolinone", US patent 3609159, issued 28 September 1971, assigned to Les Laboratoires Dausse
↑De Marne V, Pierre D, Guidicelli RL, Najer H, "5-Phenyl-2-Cyclopropylamino-4-Oxazolinone", GB patent 1005738, issued 29 September 1965, assigned to Les Laboratoires Dausse
↑"Some pharmacologic properties of thozalinone, a new excitant". Toxicology and Applied Pharmacology7 (4): 566–78. July 1965. doi:10.1016/0041-008x(65)90042-6. PMID4378772.
