Oxolamine

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Oxolamine

Systematic (IUPAC) name
N,N-diethyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethanamine
Clinical data
AHFS/Drugs.com	International Drug Names
Legal status	?
Identifiers
CAS number	959-14-8^Y
ATC code	R05DB07
PubChem	CID 13738
ChemSpider	13143^Y
UNII	90BEA145GY^Y
KEGG	D07387^Y
ChEMBL	CHEMBL1620875^N
Chemical data
Formula	C₁₄H₁₉N₃O
Mol. mass	245.32 g/mol
SMILES n1c(onc1c2ccccc2)CCN(CC)CC
InChI InChI=1S/C14H19N3O/c1-3-17(4-2)11-10-13-15-14(16-18-13)12-8-6-5-7-9-12/h5-9H,3-4,10-11H2,1-2H3^Y Key:IDCHQQSVJAAUQQ-UHFFFAOYSA-N^Y
N (what is this?) (verify)

Oxolamine is a cough suppressant.

Synthesis

The syntheses of 1,2,4-oxadiazole systems all rely on hydroxylamine for providing a preformed N-O linkage. The preparation of the respiratory anti-inflammatory and antitussive agent oxolamine starts by acylation of the alkoxide from the N-hydroxyamidine with 3-chloropropionyl chloride; the presence of the negative charge on oxygen results in the formation of the O-acylated product. Treatment of that intermediate with triethylamine leads to cyclization via imine formation to afford the 1,2,4-oxadiazole. Displacement of the terminal chlorine with diethylamine gives the corresponding amine oxolamine.

DE 1097998

Cough and cold preparations (R05)

Expectorants

Mucolytics

Cough suppressants

Opium alkaloids, opioids, and derivatives	Acetyldihydrocodeine Benzylmorphine Butorphanol Codeine Dextromethorphan Diacetylmorphine Dihydrocodeine Dimemorfan Droxypropine Ethylmorphine Hydrocodone Hydromorphone Isoaminile Laudanum Levomethadone Levopropoxyphene Methadone Nicocodeine Nicodicodeine Normethadone Noscapine Pholcodine Thebacon Tipepidine

Other	Benzonatate Benproperine Bibenzonium bromide Butamirate Clobutinol Clofedanol Cloperastine Diphenhydramine Dibunate Dimethoxanate Dropropizine Fedrilate Glaucine Levodropropizine Meprotixol Morclofone Nepinalone Oxolamine Oxeladin Pentoxyverine Pipazetate Prenoxdiazine Piperidione Zipeprol

M: RES

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proc, drug (R1/2/3/5/6/7)

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