Home > Compound List > Compound details
298-57-7 molecular structure
click picture or here to close

1-(diphenylmethyl)-4-(3-phenylprop-2-en-1-yl)piperazine

ChemBase ID: 450
Molecular Formular: C26H28N2
Molecular Mass: 368.51392
Monoisotopic Mass: 368.22524891
SMILES and InChIs

SMILES:
N1(CCN(CC1)CC=Cc1ccccc1)C(c1ccccc1)c1ccccc1
Canonical SMILES:
c1ccc(cc1)C=CCN1CCN(CC1)C(c1ccccc1)c1ccccc1
InChI:
InChI=1S/C26H28N2/c1-4-11-23(12-5-1)13-10-18-27-19-21-28(22-20-27)26(24-14-6-2-7-15-24)25-16-8-3-9-17-25/h1-17,26H,18-22H2
InChIKey:
DERZBLKQOCDDDZ-UHFFFAOYSA-N

Cite this record

CBID:450 http://www.chembase.cn/molecule-450.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-(diphenylmethyl)-4-(3-phenylprop-2-en-1-yl)piperazine
1-(diphenylmethyl)-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine
1-(diphenylmethyl)-4-[(2Z)-3-phenylprop-2-en-1-yl]piperazine
IUPAC Traditional name
cinnarizine
cinna
1-(diphenylmethyl)-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine
1-(diphenylmethyl)-4-[(2Z)-3-phenylprop-2-en-1-yl]piperazine
Brand Name
Abitrate
Aplactan
Aplexal
Apotomin
Artate
Carecin
Cerebolan
Cerepar
Cinaperazine
Cinazyn
Cinnacet
Cinnageron
Cinnarizine Stugeron
Corathiem
Denapol
Dimitron
Dimitronal
Eglen
Folcodal
Giganten
Glanil
Hilactan
Ixertol
Katoseran
Labyrin
Lazeta
Marisan
Midronal
Mitronal
Olamin
Processine
Sedatromin
Sepan
Siptazin
Spaderizine
Stugeron
Stutgeron
Stutgin
Toliman
Stugeron, Stunarone
Synonyms
Cinnarizine
1-trans-Cinnamyl-4-diphenylmethylpiperazine
Cinnarizine
1-trans-Cinnamyl-4-diphenyl-methylpiperazine
Stugeron
1-(Diphenylmethyl)-4-[(2Z)-3-phenyl-2-propen-1-yl]piperazine
(Z)-1-(Diphenylmethyl)-4-(3-phenyl-2-propenyl)piperazine
cis-Cinnarizine
(Z)-Cinnarizine
1-(Diphenylmethyl)-4-(3-phenyl-2-propenyl)piperazine
Aplactan
Aplexal
Cerepar
Cinaperazine
Midronal
Mitronal
Olamin
CAS Number
298-57-7
750512-44-8
EC Number
206-064-8
MDL Number
MFCD00056037
PubChem SID
46506769
24278320
160963913
PubChem CID
1547484
2761
CHEBI ID
31403
ATC CODE
N07CA02
CHEMBL
43064
Chemspider ID
1264793
DrugBank ID
DB00568
KEGG ID
D01295
Unique Ingredient Identifier
3DI2E1X18L
Wikipedia Title
Cinnarizine

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 3.0775893  LogD (pH = 7.4) 4.841679 
Log P 5.880391  Molar Refractivity 119.8648 cm3
Polarizability 46.581047 Å3 Polar Surface Area 6.48 Å2
Rotatable Bonds Lipinski's Rule of Five false 
Log P 5.19  LOG S -5.33 
Solubility (Water) 1.72e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
750 mg/L expand Show data source
Chloroform expand Show data source
Apperance
white powder expand Show data source
White Solid expand Show data source
Melting Point
117-120°C expand Show data source
Hydrophobicity(logP)
5.3 expand Show data source
Storage Condition
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
TL3430000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Admin Routes
Oral expand Show data source
Half Life
3–4 h expand Show data source
Pregnancy Category
C (US) expand Show data source
Gene Information
human ... CACNA1A(773), DRD2(1813), HRH1(3269) expand Show data source
Mechanism of Action
Calcium antagonist expand Show data source
Histamine H 1 receptor antagonist expand Show data source
Reported catecholamine depletor expand Show data source
Reported inhibitor of bioenergetics of chromaffin granule ghosts expand Show data source
Reported Mg-atpase inhibitor expand Show data source
Reported Proton pump uncoupler expand Show data source
Reported to inhibit cardiac liposomal lipid peroxidation mediated by the xanthine oxidase system expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Application(s)
Cerebral blood flow improver used for treatment of apoplexy and arteriosclerosis expand Show data source
Empirical Formula (Hill Notation)
C26H28N2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02154986 external link
(1-trans-Cinnamyl-4-diphenyl-methylpiperazine) Crystalline
DrugBank - DB00568 external link
Item Information
Drug Groups approved
Description Cinnarizine is an anti-histaminic drug which is mainly used for the control of vomiting due to motion sickness. Cinnarizine was first synthesized by Janssen Pharmaceutica in 1955.

It acts by interfering with the signal transmission between vestibular apparatus of the inner ear and the vomiting centre of the hypothalamus. The disparity of signal processing between inner ear motion receptors and the visual senses is abolished, so that the confusion of brain whether the individual is moving or standing is reduced. Vomiting in motion sickness is actually a physiological compensatory mechanism of the brain to keep the individual from moving so that it can adjust to the signal perception.

Cinnarizine could be also viewed as a nootropic drug because of its vasorelaxating abilities (due to calcium channel blockage), which happen mostly in brain. It is also effectively combined with other nootropics, primarily piracetam; in such combination each drug potentiate the other in boosting brain oxygen supply.
Indication For the treatment of vertigo/meniere's disease, nausea and vomiting, motion sickness and also useful for vestibular symptoms of other origins.
Pharmacology 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.
Affected Organisms
Humans and other mammals
External Links
Wikipedia
Sigma Aldrich - C5270 external link
Biochem/physiol Actions
Ca2+ channel blocker; central and peripheral vasodilator.
Toronto Research Chemicals - C465300 external link
Calcium channel blocker with antiallergic and anti-vasoconstricting activity. Antihistaminic.
Toronto Research Chemicals - C465290 external link
The Z-isomer of Cinnarizine (C465300).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Barber, J.H., et al.: Pharmatherapeutica, 2, 401 (1980)
  • • Spedding, M., et al.: Arch. Pharmacol., 318, 234 (1980)
  • • Morad, et al.: Pharmacol. Res., 35, 177 (1997)
  • • Barber, J.H., et al.: Pharmatherapeutica, 2, 401 (1980)
  • • Spedding, M., et al.: Arch. Pharmacol., 318, 234 (1980)
  • • Morad, et al.: Pharmacol. Res., 35, 177 (1997)
  • • Belg. Pat., 1960, 556 791; CA, 1960, 54, 590
  • • U.K. Pat., 1960, 809 760; CA, 1960, 54, 2379, (synth)
  • • Cotrait, M. et al., Acta Cryst. B, 1975, 31, 1495, (cryst struct)
  • • Towse, G., Int. Congr. Symp. Ser. R. Soc. Med., (Ed.), 1980, 33, (book)
  • • Gotfraind, T. et al., Drugs of Today (Barcelona), 1982, 18, 27, (rev, pharmacol)
  • • Spedding, M., Naunyn-Schmiedeberg's Arch. Pharmacol., 1982, 318, 234, (pharmacol)
  • • Yao, F. et al., CA, 1984, 101, 211103, (synth)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 7401, (synonyms)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 934
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CMR100; CMS125
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle