Thozalinone

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Chemical compound

title: "Thozalinone" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["aminorexes", "antidepressants", "dimethylamino-compounds", "lactams", "norepinephrine-dopamine-releasing-agents", "stimulants"] description: "Chemical compound" topic_path: "general/aminorexes" source: "https://en.wikipedia.org/wiki/Thozalinone" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470609358 | IUPAC_name = (RS)-2-(Dimethylamino)-5-phenyl-1,3-oxazol-4(5H)-one | image = Thozalinone.svg | image_class = skin-invert-image | alt = Skeletal formula | image2 = Thozalinone molecule spacefill.png | image_class2 = bg-transparent | alt2 = Space-filling model | width2 = 155 | width = 200px | chirality = Racemic mixture | tradename = | pregnancy_category = | legal_status = Rx-only | routes_of_administration = Oral

| bioavailability = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 655-05-0 | ATC_prefix = none | ATC_suffix = | PubChem = 12602 | ChemSpiderID_Ref = | ChemSpiderID = 12082 | UNII_Ref = | UNII = 68X5932947 | KEGG_Ref = | KEGG = D06115 | ChEMBL = 2105457 | synonyms = Tozalinone, Thozalinon

| C=11 | H=12 | N=2 | O=2 | smiles = O=C2\N=C(/OC2c1ccccc1)N(C)C | StdInChI_Ref = | StdInChI = 1S/C11H12N2O2/c1-13(2)11-12-10(14)9(15-11)8-6-4-3-5-7-8/h3-7,9H,1-2H3 | StdInChIKey_Ref = | StdInChIKey = JJSHYECKYLDYAR-UHFFFAOYSA-N

Thozalinone (USAN) (brand name Stimsen; former developmental code name CL-39808) is a psychostimulant that has been used as an antidepressant in Europe. It has also been trialed as an anorectic. Thozalinone is described as a "dopaminergic stimulant", 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 most other dopaminergic psychostimulants.

Synthesis

::figure[src="https://upload.wikimedia.org/wikipedia/commons/8/84/Thozalinone_synthesis.svg" caption="url = }}"] ::

Sodium hydride is used as a strong base to abstract the alcohol proton in ethyl mandelate [774-40-3] (1); addition of this alkoxide 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, (1972 to Am. Cyanamid).
  • Pharmacological studies:

References

References

  1. (14 November 2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer.
  2. (July 1965). "Some pharmacologic properties of thozalinone, a new excitant". Toxicology and Applied Pharmacology.
  3. (1996). "Dictionary of organic compounds". Chapman & Hall.
  4. (1998). "Merck index on CD-ROM: Windows". Chapman & Hall EPD.
  5. (December 1966). "A double-blind study of thozalinone (C1 39,808) in depressed outpatients". Current Therapeutic Research, Clinical and Experimental.
  6. (September 1971). "[Clinical trial of Stimsem Thozalinone in the treatment of obese patients]". Revista Brasileira de Medicina.
  7. (1980). "Detection of dopaminergic supersensitivity induced by neuroleptic drugs in mice". Drug and Chemical Toxicology.
  8. (1985). "Inhibition of dopaminergic agonist-induced gnawing behavior by neuroleptic drugs in mice". Drug and Chemical Toxicology.
  9. (May 1962). "2-Amino-2-oxazolin-4-ones. I. Synthesis.". The Journal of Organic Chemistry.
  10. (February 1968). "Compounds related to pemoline. 2-amino-5-aryl-4-oxo-2-oxazolines". Acta Pharmaceutica Suecica.
  11. (1968). "Behavioral facilitation: The interaction of imipramine and desipramine with amphetamine, alpha-pipradrol, methylphenidate, and thozalinone". Psychopharmacologia.

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aminorexesantidepressantsdimethylamino-compoundslactamsnorepinephrine-dopamine-releasing-agentsstimulants