Thozalinone

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]

Thozalinone

Clinical data
Other names	Tozalinone, Thozalinon
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (RS)-2-(Dimethylamino)-5-phenyl-1,3-oxazol-4(5H)-one
CAS Number	655-05-0 N
PubChem CID	12602
ChemSpider	12082 Y
UNII	68X5932947
KEGG	D06115 Y
ChEMBL	ChEMBL2105457
CompTox Dashboard (EPA)	DTXSID70862359
Chemical and physical data
Formula	C11H12N2O2
Molar mass	204.229 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES O=C2\N=C(/OC2c1ccccc1)N(C)C
InChI 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 Y Key:JJSHYECKYLDYAR-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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

• Fenozolone