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Cyclazodone
Cyclazodone
Community hub for the Wikipedia article
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Cyclazodone
Cyclazodone
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Welcome to the community hub built on top of the Cyclazodone Wikipedia article. Here, you can discuss, collect, and organize anything related to Cyclazodone. The purpose of the hub is to connect people, f...
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Cyclazodone
Cyclazodone
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: legal
Identifiers
  • (RS)-2-(cyclopropylamino)-5-phenyl-1,3-oxazol-4-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H12N2O2
Molar mass216.240 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • C1CC1NC2=NC(=O)C(O2)C3=CC=CC=C3
  • InChI=1S/C12H12N2O2/c15-11-10(8-4-2-1-3-5-8)16-12(14-11)13-9-6-7-9/h1-5,9-10H,6-7H2,(H,13,14,15) checkY
  • Key:DNRKTAYPGADPGW-UHFFFAOYSA-N checkY

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]

It is included under the World Anti-Doping Agency prohibited list.[5]

Safety

[edit]

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

[edit]

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]

See also

[edit]

References

[edit]
  1. ^ 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 
  2. ^ a b c 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 
  3. ^ 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 
  4. ^ 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.
  5. ^ "World Anti-Doping Agency 2008 Prohibited List" (PDF). World Anti-Doping Agency. 22 September 2007.
  6. ^ Najer, H. et al, Bull. Soc. Chim. Fr., 1963, 1810.


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