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Profenamine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Profenamine
Clinical data
Trade namesParsidol, Parsidan, Parkisol, Parkin[citation needed]
AHFS/Drugs.comInternational Drug Names
ATC code
Pharmacokinetic data
Protein binding93%
Eliminationhalf-life1 to 2 hours
Identifiers
  • N,N-Diethyl-1-(10H-phenothiazin-10-yl)propan-2-amine
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.007.566Edit 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
 ☒NcheckY (what is this?)  (verify)

Profenamine (INN; also known asethopropazine (BAN); sold under the trade nameParsidol and others) is aphenothiazinederivative used as anantiparkinsonian agent[1][2] that hasanticholinergic,antihistamine, andantiadrenergic actions. It is also used in the alleviation of theextrapyramidal syndrome induced by drugs such as other phenothiazine compounds, but, like other compounds with antimuscarinic properties, is of no value againsttardive dyskinesia.

Synthesis

[edit]

For promoting bone growth:[3]

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).

  • Theaziridinium salt helps to rationalize why a rearrangement product is observed (ala methadone). This was also observewd forAceprometazine.

References

[edit]
  1. ^"Prefenamine".drugs.com.
  2. ^Morton IK, Hall JM (1999)."Ethopropazine".Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Dordrecht: Springer Netherlands. p. 115.ISBN 9789401144391.
  3. ^Debra Ellies, William Rosenberg,WO 2010025135  (2010 to Osteogenex Inc.).
  4. ^Charpentier, P. et al, Compt. Rend., 1951, 232, 415.
  5. ^P. Carpentier,U.S. patent 2,526,118 (1950 to Societe desusines Chimiqiues).
  6. ^Julius Nicholson Ashley,U.S. patent 2,607,773 (1952 to Societe des Bsines Chhniques Rhone).
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