Profenamine (INN; also known as ethopropazine (BAN); solde under the trade name Parsidol and others) is a phenothiazine derivative used as an antiparkinsonian agent[1][2] that has anticholinergic, antihistamine, and antiadrenergic actions. It is also used in the alleviation of the extrapyramidal syndrome induced by drugs such as other phenothiazine compounds, but, like other compounds with antimuscarinic properties, is of no value against tardive dyskinesia.

Quick Facts Clinical data, Trade names ...
Profenamine
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Clinical data
Trade namesParsidol, Parsidan, Parkisol, Parkin
AHFS/Drugs.comInternational Drug Names
ATC code
Pharmacokinetic data
Protein binding93%
Elimination half-life1 to 2 hours
Identifiers
  • N,N-Diethyl-1-(10H-phenothiazin-10-yl)propan-2-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.566 Edit this at Wikidata
Chemical and physical data
FormulaC19H24N2S
Molar mass312.48 g·mol−1
3D model (JSmol)
  • S2c1ccccc1N(c3c2cccc3)CC(N(CC)CC)C
  • InChI=1S/C19H24N2S/c1-4-20(5-2)15(3)14-21-16-10-6-8-12-18(16)22-19-13-9-7-11-17(19)21/h6-13,15H,4-5,14H2,1-3H3 checkY
  • Key:CDOZDBSBBXSXLB-UHFFFAOYSA-N checkY
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Synthesis

For promoting bone growth:[3]

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Synthesis:[4] Patents:[5][6]

The alkylation between phenothiazine [92-84-2] (1) and 1-Diethylamino-2-chloropropane [761-21-7] (2) in the presence of Sodium amide gives ethopropazine (3).

  • The aziridinium salt helps to rationalize why a rearrangement product is observed (ala methadone). This was also observewd for Aceprometazine.

References

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