Thozalinone

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Thozalinone
Skeletal formula
Space-filling model
Clinical data
Other namesTozalinone, Thozalinon
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (RS)-2-(Dimethylamino)-5-phenyl-1,3-oxazol-4(5H)-one
JSmol)
ChiralityRacemic mixture
  • O=C2\N=C(/OC2c1ccccc1)N(C)C
  • InChI=1S/C11H12N2O2/c1-13(2)11-12-10(14)9(15-11)8-6-4-3-5-7-8/h3-7,9H,1-2H3 checkY
  • Key:JJSHYECKYLDYAR-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Thozalinone (

analogue pemoline, it is reportedly devoid of abuse potential unlike other dopaminergic psychostimulants.[2][7][8]

Synthesis

Synthesis: [9][10]

Sodium hydride is used as a strong base to abstract the alcohol proton in ethyl mandelate [774-40-3] (1); addition of the oxyanion to dimethylcyanamide [1467-79-4] gives the intermediate (2). Intramolecular cyclization then occurs giving Thozalinone (3).

Notes

  • In treatment of Parkinsonism: W. D. Gray, C. E. Edward, U.S. patent 3,665,075 (1972 to Am. Cyanamid).
  • Pharmacological studies:[11]

See also

References

  1. ISBN 978-1-4757-2085-3
    .
  2. ^
    PMID 4378772
    .
  3. ISBN 0-412-54090-8. Archived
    from the original on 2021-05-31. Retrieved 2021-05-31.
  4. ISBN 0-412-82910-X
    .
  5. PMID 4962734
    .
  6. PMID 5139648
    .
  7. ^
    PMID 6112126
    .
  8. PMID 2868876
    .
  9. doi:10.1021/jo01052a047
    .
  10. PMID 4386169
    .
  11. S2CID 31096140
    .
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