Cyclazodone

Chemical compound From Wikipedia, the free encyclopedia

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 most other 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]

Routes of
administrationOral
ATC code
  • none
Legal status
  • In general: legal
CAS Number
Quick facts Clinical data, Routes ofadministration ...
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
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It is included under the World Anti-Doping Agency prohibited list.[5]

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 effects than dextroamphetamine in studies on mice.[2]

Synthesis

α-Chlorophenylacetyl chloride (1) and N-cyclopropylurea (2) react to give the diketone (3). Ring closure with sodium ethoxide in ethanol completes the synthesis.[2][6]

See also

References

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