clocinizine
{{Short description|Chemical compound}}
{{Drugbox
| IUPAC_name = 1-[(4-chlorophenyl)-phenylmethyl]-4-[(E)-3-phenylprop-2-enyl]piperazine
| image = Clocinizine.png
| width = 250px
| tradename = Senioral (with {{abbrlink|PPA|phenylpropanolamine}})
| Drugs.com = {{drugs.com|international|clocinizine}}
| pregnancy_category =
| legal_status =
| routes_of_administration = By mouth
| bioavailability =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number = 298-55-5
| ATC_prefix = none
| ATC_suffix =
| PubChem = 5375618
| ChemSpiderID = 4525064
| ChEMBL = 2104069
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8HQJ711KH8
| C=26 | H=27 | Cl=1 | N=2
| SMILES = Clc1ccc(cc1)C(c2ccccc2)N3CCN(CC3)C\C=C\c4ccccc4
}}
Clocinizine is a first-generation antihistamine of the diphenylmethylpiperazine class. It is marketed in Spain in combination with phenylpropanolamine under the brand name Senioral.{{Cite web | vauthors = Fookes C | date = September 2022 | work = Drugs.com |url= https://www.drugs.com/international/clocinizine.html|title = List of Common Antihistamines + Uses & Side Effects}}
Synthesis
File:Clocinizine synthesis.svg
The reduction of 4-Chlorobenzophenone [134-85-0] (1) with NBH gives 4-Chlorobenzhydrol [119-56-2] (2). Halogenation of the alcohol in muriatic acid afforded 4-Chlorobenzhydryl chloride [134-83-8] (3). Alkylation with one equivalent of piperazine gives 1-(4-Chlorobenzhydryl)piperazine [303-26-4] (4). Alkylation of the remaining nitrogen with Cinnamyl Bromide [4392-24-9] (5) completed the synthesis of Clocinizine (6).
References
{{Reflist|2}}
{{Antihistamines}}
{{Histamine receptor modulators}}