Profenamine

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Profenamine (INN; also known as ethopropazine (BAN); sold 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.

Synthesis

For promoting bone growth:[3]

File:Profenamine synthesis.svg
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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  2. Script error: No such module "citation/CS1".
  3. Debra Ellies, William Rosenberg, Template:Cite patent (2010 to Osteogenex Inc.).
  4. Charpentier, P. et al, Compt. Rend., 1951, 232, 415.
  5. P. Carpentier, U.S. patent 2526118 (1950 to Societe desusines Chimiqiues).
  6. Julius Nicholson Ashley, U.S. patent 2607773 (1952 to Societe des Bsines Chhniques Rhone).