Promazine

Promazine

Systematic (IUPAC) name
N,N-dimethyl-3-(10H-phenothiazin-10-yl)-propan-1-amine
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a600010
Pregnancy cat.	?
Legal status	?
Pharmacokinetic data
Protein binding	94%
Identifiers
CAS number	58-40-2 Y
ATC code	N05AA03
PubChem	CID 4926
DrugBank	APRD00358
ChemSpider	4757 Y
UNII	O9M39HTM5W Y
ChEBI	CHEBI:8459 Y
ChEMBL	CHEMBL564 Y
Chemical data
Formula	C17H20N2S
Mol. mass	284.42 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C17H20N2S/c1-18(2)12-7-13-19-14-8-3-5-10-16(14)20-17-11-6-4-9-15(17)19/h3-6,8-11H,7,12-13H2,1-2H3 Y Key:ZGUGWUXLJSTTMA-UHFFFAOYSA-N Y
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Promazine (Sparine) is a medication that belongs to the phenothiazine class of antipsychotics. An older medication used to treat schizophrenia, it is still prescribed, alongside newer agents such as olanzapine and quetiapine. It has predominantly anticholinergic side effects, though extrapyramidal side effects are not uncommon either.

Chemistry

Promazine, 10-(3-dimethylaminopropyl)phenothiazine, is prepared by the alkylation of phenothiazine with 3-dimethylaminopropylchloride in the presence of sodamide.

• P. Charpentier, U.S. Patent 2,519,886 (1950).
• P. Charpentier, DE 824944  (1950).
• W. Wirth, Arzneim.-Forsch., 8, 507 (1958).

Diethazine

A related drug, diethazine, is synthesized as follows: Charpentier, P.; Cmpt. Rend. 1947, 225, 306.

See also

• Chlorpromazine
• Triflupromazine
• Prochlorperazine
• Trifluoperazine
• Fluphenazine
• Thioridazine
• Mesoridazine