Cyclazodone

Not to be confused with Cyclexanone.

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

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: legal
Identifiers
IUPAC name (RS)-2-(cyclopropylamino)-5-phenyl-1,3-oxazol-4-one
CAS Number	14461-91-7 Y
PubChem CID	26701
ChemSpider	24875 Y
UNII	O8U55ZRL9K
ChEMBL	ChEMBL2106536 Y
CompTox Dashboard (EPA)	DTXSID60864509
Chemical and physical data
Formula	C12H12N2O2
Molar mass	216.240 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES C1CC1NC2=NC(=O)C(O2)C3=CC=CC=C3
InChI 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) Y Key:DNRKTAYPGADPGW-UHFFFAOYSA-N Y

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

• Fenozolone
• Amiphenazole
• List of aminorex analogues