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 YesY
ATC code N05AA03
PubChem CID 4926
DrugBank APRD00358
ChemSpider 4757 YesY
UNII O9M39HTM5W YesY
ChEBI CHEBI:8459 N
ChEMBL CHEMBL564 YesY
Chemical data
Formula C17H20N2S 
Mol. mass 284.42 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

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. Promazine synthesis.png

Diethazine

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

See also