U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C11H12N2O2
Molecular Weight 204.2252
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THOZALINONE

SMILES

CN(C)C1=NC(=O)C(O1)C2=CC=CC=C2

InChI

InChIKey=JJSHYECKYLDYAR-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Thozalinone (Stimsen) has been used as an antidepressant in Europe and has also been trialed as an anorectic. It acts via inducing the release of norepinephrine and dopamine as with its analogues pemoline and aminorex. Thozalinone has been shown to possess some pharmacologic actions similar to those of amphetamine and imipramine, but with important differences. It is less toxic than amphetamine, and its margin of safety in mice is greater. The stimulant action does not progress to tremors or convulsions as the dosage is increased. The anorexigenic activity of thozalinone is more pronounced and longer lasting than that of amphetamine. There is no evidence of the development of tolerance. The cardiovascular side effects of thozalinone are minimal, and analeptic actions are absent.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Stimsen

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Detection of dopaminergic supersensitivity induced by neuroleptic drugs in mice.
1980
Determination of the psychostimulants pemoline, fenozolone and thozalinone in human urine by gas chromatography/mass spectrometry and thin layer chromatography.
1982 Feb
Inhibition of dopaminergic agonist-induced gnawing behavior by neuroleptic drugs in mice.
1985
Patents

Sample Use Guides

Thozalinone (7.5-960 mg/kg orally) increased locomotor activity, preening, and searching movements in mice and rats, and increased the sensitivity to auditory and tactile stimuli (hyperesthesia) in mice. Rats treated with thozalinone (2-64 mg/kg orally) showed hyperesthesia, alertness, and increased exploratory behavior.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
THOZALINONE
MI   USAN  
USAN  
Official Name English
TOZALINONE
INN  
INN  
Official Name English
4(5H)-OXAZOLONE, 2-(DIMETHYLAMINO)-5-PHENYL-
Systematic Name English
CL-39808
Code English
THOZALINONE [MI]
Common Name English
NSC-170962
Code English
2-(Dimethylamino)-5-phenyl-2-oxazolin-4-one
Systematic Name English
CL 39808
Code English
THOZALINONE [USAN]
Common Name English
tozalinone [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47795
Created by admin on Fri Dec 15 18:55:11 GMT 2023 , Edited by admin on Fri Dec 15 18:55:11 GMT 2023
Code System Code Type Description
WIKIPEDIA
THOZALINONE
Created by admin on Fri Dec 15 18:55:11 GMT 2023 , Edited by admin on Fri Dec 15 18:55:11 GMT 2023
PRIMARY
EVMPD
SUB11204MIG
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PRIMARY
NSC
170962
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PRIMARY
MERCK INDEX
m10803
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PRIMARY Merck Index
INN
1188
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PRIMARY
SMS_ID
100000077195
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FDA UNII
68X5932947
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MESH
C034173
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EPA CompTox
DTXSID70862359
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PUBCHEM
12602
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PRIMARY
CAS
655-05-0
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NCI_THESAURUS
C152592
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PRIMARY
ChEMBL
CHEMBL2105457
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PRIMARY