Cyclazodone

Not to be confused with Cyclexanone.
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

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]

See also

References

  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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