Cyclazodone is a centrally acting stimulant drug developed by American Cyanamid Company in the 1960s. 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. The patents concluded that cyclazodone possessed properties efficacious in reducing fatigue and as a potential anorectic. 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.
It is included under the World Anti-Doping Agency prohibited list.
Safety
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.6
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.78
See also
References
US 3321470, Howell Jr CF, Hardy RA, Quinones N, "5-Arylidene-2-Amino-2-Oxazolin-4-Ones", issued 23 May 1967, assigned to American Cyanamid https://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=US3321470 ↩
US 3609159, De Marne V, Pierre D, Guidicelli RL, Najer H, "5-Phenyl-2-Cyclopropylamino-4-Oxazolinone", issued 28 September 1971, assigned to Les Laboratoires Dausse https://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=US3609159 ↩
GB 1005738, De Marne V, Pierre D, Guidicelli RL, Najer H, "5-Phenyl-2-Cyclopropylamino-4-Oxazolinone", issued 29 September 1965, assigned to Les Laboratoires Dausse https://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=GB1005738 ↩
Greenblatt EN, Osterberg AC (July 1965). "Some pharmacologic properties of thozalinone, a new excitant". Toxicology and Applied Pharmacology. 7 (4): 566–78. doi:10.1016/0041-008x(65)90042-6. PMID 4378772. /wiki/Doi_(identifier) ↩
"World Anti-Doping Agency 2008 Prohibited List" (PDF). World Anti-Doping Agency. 22 September 2007. https://www.wada-ama.org/sites/default/files/resources/files/WADA_Prohibited_List_2008_EN.pdf ↩
US 3609159, De Marne V, Pierre D, Guidicelli RL, Najer H, "5-Phenyl-2-Cyclopropylamino-4-Oxazolinone", issued 28 September 1971, assigned to Les Laboratoires Dausse https://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=US3609159 ↩
US 3609159, De Marne V, Pierre D, Guidicelli RL, Najer H, "5-Phenyl-2-Cyclopropylamino-4-Oxazolinone", issued 28 September 1971, assigned to Les Laboratoires Dausse https://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=US3609159 ↩
Najer, H. et al, Bull. Soc. Chim. Fr., 1963, 1810. ↩