View source for Profenamine

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 464215203
| IUPAC_name = ''N'',''N''-Diethyl-1-(10''H''-phenothiazin-10-yl)propan-2-amine
| image = Profenamine.svg
<!--Clinical data-->
| tradename =  Parsidol, Parsidan, Parkisol, Parkin{{fact|date=April 2025}}
| Drugs.com = {{drugs.com|international|profenamine}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = <!-- OTC / Rx-only -->
<!--Pharmacokinetic data-->
| protein_bound = 93%
| elimination_half-life = 1 to 2 hours
<!--Identifiers-->
| IUPHAR_ligand = 7181
| CAS_number_Ref = {{cascite|changed|CAS}}
| CAS_number = 522-00-9
| ATC_prefix = N04
| ATC_suffix = AA05
| PubChem = 3290
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00392
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3174
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 7WI4P02YN1
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 313639
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1206
<!--Chemical data-->
| C=19 | H=24 | N=2 | S=1
| smiles = S2c1ccccc1N(c3c2cccc3)CC(N(CC)CC)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CDOZDBSBBXSXLB-UHFFFAOYSA-N
}}

'''Profenamine''' ([[International Nonproprietary Name|INN]]; also known as '''ethopropazine''' ([[British Approved Name|BAN]]); sold under the trade name '''Parsidol''' and others) is a [[phenothiazine]] [[chemical derivative|derivative]] used as an [[Management of Parkinson's disease#Medication|antiparkinsonian]] agent<ref>{{Cite web | url = https://www.drugs.com/international/profenamine.html | title = Prefenamine | publisher = [[drugs.com]]}}</ref><ref>{{cite book | vauthors = Morton IK, Hall JM | chapter = Ethopropazine | chapter-url = https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA115 | page = 115 |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms |date=1999 |publisher=Springer Netherlands |location=Dordrecht |isbn=9789401144391}}</ref> 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:<ref>Debra Ellies, William Rosenberg, {{Cite patent|WO|2010025135}} (2010 to Osteogenex Inc.).</ref>
[[File:Profenamine synthesis.svg|thumb|center|500px|Synthesis:<ref>Charpentier, P. et al, Compt. Rend., 1951, 232, 415.</ref> Patents:<ref>P. Carpentier, {{US patent|2526118}} (1950 to Societe desusines Chimiqiues).</ref><ref>Julius Nicholson Ashley, {{US patent|2607773}} (1952 to Societe des Bsines Chhniques Rhone).</ref>]]

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 ==
{{Reflist}}

{{Antiparkinson}}
{{Navboxes
| title = [[Pharmacodynamics]]
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| list1 = 
{{Acetylcholine metabolism and transport modulators}}
{{Adrenergic receptor modulators}}
{{Histamine receptor modulators}}
{{Muscarinic acetylcholine receptor modulators}}
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{{Tricyclics}}

[[Category:Alpha-1 blockers]]
[[Category:Antihistamines]]
[[Category:H1 receptor antagonists]]
[[Category:Muscarinic antagonists]]
[[Category:Phenothiazines]]
[[Category:Diethylamino compounds]]

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