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Thozalinone

Chemical compound

Thozalinone

Chemical compound

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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

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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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aminorexes antidepressants dimethylamino-compounds lactams norepinephrine-dopamine-releasing-agents stimulants
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