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Thozalinone

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
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
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC11H12N2O2
Molar mass204.229 g·mol−1
3D model (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 (USAN) (brand nameStimsen; former developmental code nameCL-39808) is apsychostimulant that has been used as anantidepressant inEurope.[1][2][3][4][5] It has also beentrialed as ananorectic.[6] Thozalinone is described as a "dopaminergic stimulant",[7] and likely acts via inducing therelease ofdopamine and to a minimal extentnorepinephrine; similar toanaloguepemoline, it is reportedly devoid of abuse potential unlike other dopaminergic psychostimulants.[2][7][8]

Synthesis

[edit]
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

[edit]
  • 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

[edit]

References

[edit]
  1. ^Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 435–.ISBN 978-1-4757-2085-3.
  2. ^abGreenblatt EN, Osterberg AC (July 1965). "Some pharmacologic properties of thozalinone, a new excitant".Toxicology and Applied Pharmacology.7 (4):566–78.doi:10.1016/0041-008X(65)90042-6.PMID 4378772.
  3. ^Dictionary of organic compounds. London: Chapman & Hall. 1996.ISBN 0-412-54090-8.Archived from the original on 2021-05-31. Retrieved2021-05-31.
  4. ^Merck index on CD-ROM: Windows. London: Chapman & Hall EPD. 1998.ISBN 0-412-82910-X.
  5. ^Gallant DM, Bishop MP, Scrignar CB, Hornsby L, Moore B, Inturrisi BB (December 1966). "A double-blind study of thozalinone (C1 39,808) in depressed outpatients".Current Therapeutic Research, Clinical and Experimental.8 (12):621–2.PMID 4962734.
  6. ^Leite AC, Liepen LL, Costa VP (September 1971). "[Clinical trial of Stimsem Thozalinone in the treatment of obese patients]".Revista Brasileira de Medicina (in Portuguese).28 (9):475–8.PMID 5139648.
  7. ^abYen-Koo HC, Balazs T (1980). "Detection of dopaminergic supersensitivity induced by neuroleptic drugs in mice".Drug and Chemical Toxicology.3 (2):237–47.doi:10.3109/01480548009108286.PMID 6112126.
  8. ^Yen-Koo HC, Davis DA, Balazs T (1985). "Inhibition of dopaminergic agonist-induced gnawing behavior by neuroleptic drugs in mice".Drug and Chemical Toxicology.8 (6):495–502.doi:10.3109/01480548509041072.PMID 2868876.
  9. ^Howell CF, Quinones NQ, Hardy Jr RA (May 1962). "2-Amino-2-oxazolin-4-ones. I. Synthesis".The Journal of Organic Chemistry.27 (5):1679–1685.doi:10.1021/jo01052a047.
  10. ^Lindberg UH, Pedersen J (February 1968). "Compounds related to pemoline. 2-amino-5-aryl-4-oxo-2-oxazolines".Acta Pharmaceutica Suecica.5 (1):15–22.PMID 4386169.
  11. ^Bernstein BM, Latimer CN (1968). "Behavioral facilitation: The interaction of imipramine and desipramine with amphetamine, alpha-pipradrol, methylphenidate, and thozalinone".Psychopharmacologia.12 (4):338–345.doi:10.1007/BF00401412.PMID 4385109.S2CID 31096140.
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