Clocinizine
Chemical compound
- none
- 1-[(4-chlorophenyl)-phenylmethyl]-4-[(E)-3-phenylprop-2-enyl]piperazine
- 298-55-5
- 5375618
- 4525064
- 8HQJ711KH8
- ChEMBL2104069
- Interactive image
- 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.[1]
Synthesis
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
- ^ Fookes C (September 2022). "List of Common Antihistamines + Uses & Side Effects". Drugs.com.
- ^ Venkat Narsaiah A, Narsimha P (April 2012). "Efficient synthesis of antihistamines clocinizine and chlorcyclizine". Medicinal Chemistry Research. 21 (4): 538–541. doi:10.1007/s00044-011-9556-x. S2CID 253636495.
- ^ DE 2220242, Kato H, Kurata S, "Antiarrhythmic piperazine derivs prepn - from benzhydrylpiperazine cinnamaldehyde by leuckart reaction", issued 1972, assigned to Hokuriku Pharmaceutical
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Antihistamines (R06)
- Astemizole
- Azelastine
- Bilastine
- Emedastine
- Mizolastine
- Talastine
- Diarylmethoxyalkylamines: Bromazine (bromodiphenhydramine)
- Carbinoxamine
- Chlorphenoxamine
- Clemastine
- Diphenhydramine (+naproxen)
- Diphenylpyraline
- Doxylamine
- Ebastine
- Orphenadrine
- Diphenylmethylpiperazines: Buclizine
- Cetirizine
- Chlorcyclizine
- Cinnarizine
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- Hydroxyzine
- Meclizine
- Oxatomide
- Phenylpyridinylpropanamines: Brompheniramine
- Chlorphenamine
- Dexbrompheniramine (+pseudoephedrine)
- Dexchlorpheniramine (+betamethasone)
- Pheniramine
- Phenylpiperazines: Antidepressants (e.g., trazodone)
- Phenbenzamine
