Clocinizine

Clocinizine is a topic that has captured the interest of many people over time. Its relevance is manifested in different aspects of daily life, from popular culture to politics and economics. As we explore its implications, we discover a universe of possibilities that awaken our curiosity and invite us to reflect on human nature. In this article, we will delve into the depths of Clocinizine, exploring its origins, impact, and evolution throughout history. Through a detailed analysis, we will seek to better understand this phenomenon and its influence on the modern world.

Clocinizine
Clinical data
Trade namesSenioral (with PPATooltip phenylpropanolamine)
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth
ATC code
  • none
Identifiers
  • 1--4-piperazine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC26H27ClN2
Molar mass402.97 g·mol−1
3D model (JSmol)
  • 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

Synthesis:[2] Patent:[3]

The reduction of 4-Chlorobenzophenone (1) with NBH gives 4-Chlorobenzhydrol (2). Halogenation of the alcohol in muriatic acid afforded 4-Chlorobenzhydryl chloride (3). Alkylation with one equivalent of piperazine gives 1-(4-Chlorobenzhydryl)piperazine (4). Alkylation of the remaining nitrogen with Cinnamyl Bromide (5) completed the synthesis of Clocinizine (6).

References

  1. ^ Fookes C (September 2022). "List of Common Antihistamines + Uses & Side Effects". Drugs.com.
  2. ^ 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.
  3. ^ DE 2220242, Kato H, Kurata S, "Antiarrhythmic piperazine derivs prepn - from benzhydrylpiperazine cinnamaldehyde by leuckart reaction", issued 1972, assigned to Hokuriku Pharmaceutical