Profenamine

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.

Profenamine

Clinical data
Trade names	Parsidol, Parsidan, Parkisol, Parkin
AHFS/Drugs.com	International Drug Names
ATC code	N04AA05 (WHO)
Pharmacokinetic data
Protein binding	93%
Elimination half-life	1 to 2 hours
Identifiers
IUPAC name N,N-Diethyl-1-(10H-phenothiazin-10-yl)propan-2-amine
CAS Number	522-00-9 N
PubChem CID	3290
IUPHAR/BPS	7181
DrugBank	DB00392 Y
ChemSpider	3174 Y
UNII	7WI4P02YN1
ChEBI	CHEBI:313639 Y
ChEMBL	ChEMBL1206 Y
CompTox Dashboard (EPA)	DTXSID2023018
ECHA InfoCard	100.007.566
Chemical and physical data
Formula	C19H24N2S
Molar mass	312.48 g·mol−1
3D model (JSmol)	Interactive image
SMILES S2c1ccccc1N(c3c2cccc3)CC(N(CC)CC)C
InChI 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 Y Key:CDOZDBSBBXSXLB-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Synthesis

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).

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

References

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).