Thozalinone

Last updated
Thozalinone
Thozalinone.svg
Thozalinone molecule spacefill.png
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
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
Formula C11H12N2O2
Molar mass 204.229 g·mol−1
3D model (JSmol)
Chirality Racemic 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 Yes check.svgY
  • Key:JJSHYECKYLDYAR-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Thozalinone (USAN) (brand name Stimsen; former developmental code name CL-39808) is a psychostimulant that has been used as an antidepressant in Europe. [1] [2] [3] [4] [5] It has also been trialed as an anorectic. [6] Thozalinone is described as a "dopaminergic stimulant", [7] and likely acts via inducing the release of dopamine and to a minimal extent norepinephrine; similar to analogue pemoline, it is reportedly devoid of abuse potential unlike other dopaminergic psychostimulants. [2] [7] [8]

Contents

Synthesis

Synthesis: Thozalinone synthesis.svg
Synthesis:

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

See also

Related Research Articles

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References

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