1-(Diphenylmethyl)-4-(3-phenylprop-2-enyl)piperazine
Basic information
- CAS
298-57-7- Standard SMILES
C(=Cc1ccccc1)CN1CCN(C(c2ccccc2)c2ccccc2)CC1- InChIKey
DERZBLKQOCDDDZ-UHFFFAOYSA-N- Molecular formula
- C26H28N2
- Average molar mass
- 368.5 g/mol
- Monoisotopic mass
- 368.2252489
Overview
First synthesized by Janssen Pharmaceuticals in 1955, cinnarizine is an anti-histaminic drug mainly used for the control of vestibular disorders and motion sickness. Cinnarizine is a specific calcium channel blocker that primarily works on the central vestibular system to interfere with the signal transmission between vestibular apparatus of the inner ear and the vomiting centre of the hypothalamus. Cinnarizine could be also viewed as a nootropic drug because of its vasorelaxating abilities (due to calcium channel blockage), which happen mostly in brain. Combination use of cinnarizine with other nootropics, such as [piracetam] resulted in enhanced effect of boosting brain oxygen supply.
Names & identifiers
- Preferred name
- 1-(Diphenylmethyl)-4-(3-phenylprop-2-enyl)piperazine
- IUPAC
- 1-benzhydryl-4-(3-phenylprop-2-enyl)piperazine
- English name
- Stugeron
- Molecular formula
- C26H28N2
- Molecular weight
- 368.51
Names & synonyms
1-(diphenylmethyl)-4-(3-phenylprop-2-enyl)piperazineMFCD00056037CinnaC26H28N2Prestwick0_000278Prestwick1_0002781-benzhydryl-4-(3-phenylprop-2-enyl)piperazineOprea1_696883SCHEMBL44958SPBio_002375HMS3372L161-benzhydryl-4-cinnamyl-piperazine
Show more names
CINNARIZINECinarizineCinnarizine, powderCinnarizine Hydrochlorider516516mdEglenR 516r1575Sepan
1-Cinnamyl-4-diphenylmethylpiperazineDB00568SY234515DB-047662C3459S47271-trans -Cinnamyl-4-diphenyl-methylpiperazineQ27224950
Database identifiers
- CAS
298-57-7- PubChem CID
- 2761
- DTXSID
DTXSID3022821
Properties
Computed structural properties
- XLogP
- 5.8
- Topological polar surface area
- 6.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 6
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 429
Experimental & physicochemical properties
DrugsPharmaceutical
LogP5.3
Solubility1.72e-03 g/L
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 117 · 117-120°C
- Boiling point
- 488.83 °C · 488.83°C (rough estimate)
- Density
- 1.1818 · 1.1818 (rough estimate)
- refractive index
- 1.762 · 1.7620 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- 50 mg/ml · Soluble in chloroform at 50mg/ml
- pka
- 7.47 · pKa 7.47(H2O t=25.0 ) (Uncertain)
- form
- powder
- color
- white
- Water Solubility
- 0.75 g/L · 0.75g/L(temperature not stated)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- rtecs
- TL3430000
- hs_code
- 2933.59.2100
- Toxicity
- LD50 oral in rat: > 6500mg/kg
- risk_code
- 20/22-36/37/38-42/43
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08,GHS09
- hazard_code
- Xn
- safety_code
- 22-24/25-36-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H360-H410
- Precautionary statements
- P273-P391-P501-P264-P280-P302+P352-P321-P332+P313-P362
Chemistry & industry
Pharmacology
Pharmacodynamics
Cinnarizine is an antihistamine and a calcium channel blocker. Histamines mediate a number of activities such as contraction of smooth muscle of the airways and gastrointestinal tract, vasodilatation, cardiac stimulation, secretion of gastric acid, promotion of interleukin release and chemotaxis of eosinophils and mast cells. Competitive antagonists at histamine H1 receptors may be divided into first (sedating) and second (non-sedating) generation agents. Some, such as Cinnarizine also block muscarinic acetylcholine receptors and are used as anti-emetic agents. Cinnarizine through its calcium channel blocking ability also inhibits stimulation of the vestibular system.
Mechanism of Action
Cinnarizine inhibits contractions of vascular smooth muscle cells by blocking L-type and T-type voltage gated calcium channels. Cinnarizine has also been implicated in binding to dopamine D2 receptors, histamine H1 receptors, and muscarinic acetylcholine receptors.
Cellular LocationsMembrane
Metabolite PathwaysCinnarizine H1-Antihistamine Action
Applications
UsesIt is long-efficacy, multifunction vasoconstriction antagonists. It can dilate blood vessels, improve blood circulation and prevent blood vessel embrittlement. It can be used in the treatment of cerebral vascular diseases as well as has efficacy in treating cervical vertigo caused headaches, dizziness, insomnia, memory loss, paralysis, numbness, weakness and slurred speech embolism.
UsesCalcium channel blocker with antiallergic and anti-vasoconstricting activity. Antihistaminic
Usesglucocorticoid, antiinflammatory
UsesHistamine H1 receptor antagonist; antihistamine.
UsesFor the treatment of vertigo/meniere's disease, nausea and vomiting, motion sickness and also useful for vestibular symptoms of other origins.
Related reactions
0 records
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Compound notes
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