Cinnarizine (CED0006787)

Record Information

Version

1.0

Creation Date

2016-05-22 03:38:57 UTC

Update Date

2026-08-22 06:25:40 UTC

Accession Number

CHEM016632

Identification

Common Name

Cinnarizine

Class

Small Molecule

Description

Cinnarizine is an organic compound with the formula C26H28N2 and an average molecular weight of 368.52 g/mol. Cinnarizine belongs to the diphenylmethanes, a subclass of benzene and substituted derivatives within the organic compounds. The compound is found in or released from 13 recorded sources. These include various categories of electrical and electronic equipment, such as antennas, amplifiers, colour television systems, electric hearing aids, line transmission systems, and five additional sources. It is also associated with building and construction materials, specifically fencing, as well as household cleaning and consumer products, including non electric simulated smoking devices. Additionally, it is linked to food, food processing and cookware, specifically the processing of fish. Cinnarizine interacts with 16 recorded protein targets, acting as an antagonist, binder, inhibitor, or otherwise interacting with them. These targets include the histamine H1 receptor (HRH1), the D(2) dopamine receptor (DRD2), the voltage-dependent L-type calcium channel subunit alpha-1C (CACNA1C), and the voltage-dependent T-type calcium channel subunit alpha-1H (CACNA1H), along with 12 other proteins.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(Diphenylmethyl)-4-(3-phenyl-2-propenyl)piperazine	ChEBI
1-Benzhydryl-4-cinnamylpiperazin	ChEBI
1-Cinnamyl-4-(diphenylmethyl)piperazine	ChEBI
Cinarizina	ChEBI
Cinnarizinum	ChEBI
Cinnarizin siegfried	MeSH
Dihydrochloride cinnarizine	MeSH
Dimitronal	MeSH
Kendrick brand OF cinnarizine	MeSH
Cinnarizine, (e)-isomer	MeSH
Cinnarizine, dihydrochloride	MeSH
Cinnipirine	MeSH
Ratiopharm brand OF cinnarizine	MeSH
Cinarizina inkey	MeSH
Alpharma brand OF cinnarizine	MeSH
Ashbourne brand OF cinnarizine	MeSH
Cinarizina ratiopharm	MeSH
Cinarizine	MeSH
Cinnarizin al	MeSH
Cinnarizine	MeSH
Cinnarizin von CT	MeSH
Artu brand OF cinnarizine	MeSH
Cinna	MeSH
Cinnarizin-ratiopharm	MeSH
Cinnarizine L tartrate	MeSH
Cinnarizine L-tartrate	MeSH
L-Tartrate, cinnarizine	MeSH
Cisaken	MeSH
CT-Arzneimittel brand OF cinnarizine	MeSH
Aliud brand OF cinnarizine	MeSH
Cinnarizine L-tartrate (1:1)	MeSH
Esteve brand OF cinnarizine	MeSH
Janssen brand OF cinnarizine	MeSH
Stugeron	MeSH
Stugeron forte	MeSH
Cinazière	MeSH
Inkeysa brand OF cinnarizine	MeSH

Chemical Formula

C₂₆H₂₈N₂

Average Molecular Mass

368.524 g/mol

Monoisotopic Mass

368.225 g/mol

CAS Registry Number

298-57-7

IUPAC Name

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

Traditional Name

cinna

SMILES

[H]\C(CN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1)=C(\[H])C1=CC=CC=C1

InChI Identifier

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/b13-10+

InChI Key

DERZBLKQOCDDDZ-JLHYYAGUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Styrene
Aralkylamine
N-alkylpiperazine
1,4-diazinane
Piperazine
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

N-alkylpiperazine (CHEBI:31403 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0017 g/L	ALOGPS
logP	5.19	ALOGPS
logP	5.88	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	8.17	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	119.86 m³·mol⁻¹	ChemAxon
Polarizability	43.56 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0219000000-675f13add4c10c3ad62f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-1943000000-f6590cd5feec75a73b61	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-1900000000-a9c864770658b441961c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0009000000-deec46756ddbeb96cde8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0gb9-0179000000-30d60e48e3225ac9d20e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006x-7940000000-df85bd89cf9513a96383	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
833.0	Log mg/kg	[470:1500]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
496	Fencing	Building & Construction	Not Available
505	Amplifiers	Electrical & Electronic Equipment	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
509	Colour Television Systems	Electrical & Electronic Equipment	Not Available
516	Electric Hearing Aids	Electrical & Electronic Equipment	Not Available
525	Line Transmission Systems	Electrical & Electronic Equipment	Not Available
531	Relays	Electrical & Electronic Equipment	Not Available
533	Sparking Plugs	Electrical & Electronic Equipment	Not Available
536	Superconductive Or Hyperconductive Conductors Cables Or Transmission Lines	Electrical & Electronic Equipment	Not Available
538	Thin Magnetic Films	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
551	Processing Fish	Food, food processing & cookware	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
579	Manufacture Of Iron Or Steel	Industrial manufacturing & chemical processing	Not Available
585	Canoes And Kayaks	Marine, shipping & aquaculture	Not Available
592	Marine Propulsion Or Steering	Marine, shipping & aquaculture	Not Available
593	Nautical Instruments	Marine, shipping & aquaculture	Not Available
594	Ship Hulls	Marine, shipping & aquaculture	Not Available
599	Harvesters For Peanuts	Agriculture & land management	Not Available
612	Body Washing Or Cleaning Implements	Personal care & cosmetics	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available
652	Ropes	Textiles, leather & furnishings	Not Available
653	Sewing	Textiles, leather & furnishings	Not Available
656	Snap Fasteners	Textiles, leather & furnishings	Not Available

Pathways

6 pathways

Cinnarizine H1-Antihistamine Action

Cinnarizine Calcium Channel Vasodilation Action Pathway

Cinnarizine Drug Metabolism Action Pathway

Cinnarizine H1 Antihistamine Smooth Muscle Relaxation Action Pathway

Cinnarizine H1-Antihistamine Blood Vessel Constriction Action Pathway

Cinnarizine H1-Antihistamine Immune Response Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	11.5995
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	8.64126
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	3.58106
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	5.29375
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	24.6004
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	5.44945
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	8.87481
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	3.97031
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	31.2954
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	1.79053
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	3.58106
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Predicted (SEA)	2.72472
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	7.62922
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	7.23998
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	3.81461
Click to view 3D structure	Alpha-1D adrenergic receptor	P25100	Humans	Predicted (SEA)	4.20386
Click to view 3D structure	Alpha-1B adrenergic receptor	P15823	Rattus norvegicus	Predicted (SEA)	1.40129
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	5.99439
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	28.3371
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	4.5931
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	9.41976
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	34.3315
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	48.4222
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	114.75
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	154.92