Cyclizine (CED0008274)

Record Information

Version

1.0

Creation Date

2016-05-25 18:25:46 UTC

Update Date

2026-08-20 00:45:41 UTC

Accession Number

CHEM022255

Identification

Common Name

Cyclizine

Class

Small Molecule

Description

Cyclizine is an organic compound with the formula C18H22N2 and an average molecular weight of 266.38 g/mol. Cyclizine belongs to the diphenylmethanes, a subclass of benzene and substituted derivatives within the organic compounds. This compound is associated with six recorded sources, including healthcare, pharmaceuticals and veterinary products as antihistamines, as well as indoor air within air, dust and atmospheric transport. Other sources include household cleaning and consumer products, specifically tobacco smoke filters and non electric simulated smoking devices, and electrical and electronic equipment, such as electrically stimulated smoking devices and electric hearing aids. Recorded exposure routes for cyclizine include oral, intravenous, intramuscular, and inhalation. In terms of biological activity, cyclizine has two recorded protein targets. It acts as an antagonist or inhibitor of the Histamine H1 receptor (HRH1) and Sulfotransferase 1E1 (SULT1E1).

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-1-Diphenylmethyl-4-methylpiperazine	ChEBI
(N-Benzhydryl)(n'-methyl)diethylenediamine	ChEBI
1-(Diphenylmethyl)-4-methylpiperazine	ChEBI
1-Benzhydryl-4-methylpiperazin	ChEBI
Ciclizina	ChEBI
Cyclizinum	ChEBI
N-Benzhydryl-n'-methylpiperazine	ChEBI
N-Methyl-n'-benzhydrylpiperazine	ChEBI
Cyclizine chloride	HMDB
Cyclizine hydrochloride	HMDB
HCL, Cyclizine	HMDB
Marezine	HMDB
Cyclizine HCL	HMDB
Hydrochloride, cyclizine	HMDB

Chemical Formula

C₁₈H₂₂N₂

Average Molecular Mass

266.381 g/mol

Monoisotopic Mass

266.178 g/mol

CAS Registry Number

82-92-8

IUPAC Name

1-(diphenylmethyl)-4-methylpiperazine

Traditional Name

cyclizine

SMILES

CN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H22N2/c1-19-12-14-20(15-13-19)18(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18H,12-15H2,1H3

InChI Key

UVKZSORBKUEBAZ-UHFFFAOYSA-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
Aralkylamine
N-alkylpiperazine
N-methylpiperazine
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:3994 )

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	0.075 g/L	ALOGPS
logP	3.55	ALOGPS
logP	3.55	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	8.51	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	3	ChemAxon
Refractivity	84.93 m³·mol⁻¹	ChemAxon
Polarizability	31.53 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum	splash10-0aos-9620000000-ed8810ea85a4b69f8507	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-0aos-9620000000-ed8810ea85a4b69f8507	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-014r-6920000000-1ddcd42966325717db73	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gb9-0900000000-d6c91a9722832a6aa738	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-4b42cb223e1f1f2e4e90	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-2900000000-543bd0eeb1ff13d335d4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gb9-0900000000-bec36f8829bd4780e1cb	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gb9-0900000000-009d1551a59545ae449f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0uxr-0900000000-361d751c7870eb29ba4e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-240a440d2dd63341247d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gb9-0900000000-4afdf8368a89122da2f0	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gb9-0900000000-a86e695095f2ce184b7c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gb9-0900000000-bd83a5179314abf6afc5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-07a74edb751eeb230f23	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-0323096b4a21e2a8db23	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-4866511b3bef8af755b2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-748187bceefb902de284	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-0377cce0b27805d479b5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gb9-0900000000-9b7722ff0880ab6ea3f6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-2900000000-eceae62b15337b573a02	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gb9-0900000000-07d26fc06a38dc6e874d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-3265205697ae7aa25720	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0910000000-85378cd4451503da31c5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-12b4c9048e3545dd5c68	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-36e5889afe30a321f15f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gb9-0900000000-ac7a184256d570540fd8	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-b35c789712db971f718d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-88c9861f98aefb17cc2b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-15caec35b8655051737b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gb9-0900000000-c6b4d0d4c34c43457c29	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-4e5f6c6ae4c75d633e5f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0910000000-563b13a09160b70c05fe	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-de872e048c7e12cef490	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-7f774aff4a3fcaf4962e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-c42b108833a66bbcb4f3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-8d36d47772ee1d63ef7c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-847315cdef006cc8a851	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-3278e69a4bad6f9ed768	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-e68c610df6df6e05ddb3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-34b1369ae8e04ed5c597	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-2986187e3f7d56240593	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-9d40a8558c6c8fe414d8	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-c4f813db79eabc38e2b7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-d4894e4ed43055c2ad98	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-828e399294f0eff98273	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gb9-0900000000-094747f257114a704e45	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0190000000-f7a13fb94d177c5350a9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-1690000000-881d405f0ad451201d6b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-5910000000-f9a37fa63dc7990a9a89	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0090000000-6f0c5476da21d301550c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-1090000000-c691b21d5e972ebf73a2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9830000000-c56f9fb789eebf207dba	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0900000000-c692fb05e504a5da303a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0900000000-c692fb05e504a5da303a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-1900000000-82c81c9f93df24e66b55	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0090000000-3eabb2a4cedb6ab1b611	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0490000000-a52a4e907099f4888b8a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-1920000000-cedf20063b363fd3323d	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
232.0	Log mg/kg	[130:410]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
10	Insecticides	Agriculture & land management	Not Available
19	Indoor air	Air, dust & atmospheric transport	Not Available
393	Antihistamines	Healthcare, pharmaceuticals & veterinary products	Not Available
516	Electric Hearing Aids	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
596	Acaricides	Agriculture & land management	Not Available
600	Herbicides And Algicides	Agriculture & land management	Not Available
603	Nematocides	Agriculture & land management	Not Available
606	Plant Growth Regulators	Agriculture & land management	Not Available
607	Rodenticides(1)	Agriculture & land management	Not Available
608	Rodenticides	Agriculture & land management	Not Available
610	Aftersun Products	Personal care & cosmetics	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
614	Essential Oils Or Perfumes	Personal care & cosmetics	Not Available
615	Eye Makeup Products	Personal care & cosmetics	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available
618	Lip Makeup Products	Personal care & cosmetics	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available
642	Footwear	Textiles, leather & furnishings	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available

Pathways

6 pathways

Cyclizine H1-Antihistamine Action

Cyclizine Drug Metabolism Action Pathway

Cyclizine H1 Antihistamine Neurological Sleep Action Pathway

Cyclizine H1 Antihistamine Smooth Muscle Relaxation Action Pathway

Cyclizine H1-Antihistamine Blood Vessel Constriction Action Pathway

Cyclizine 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)	29.7384
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	17.4382
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	34.0201
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	14.3243
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	10.5875
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	8.01847
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	2.64687
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	5.13805
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	16.1926
Click to view 3D structure	Alpha-1D adrenergic receptor	P25100	Humans	Predicted (SEA)	6.53933
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Predicted (SEA)	4.20386
Click to view 3D structure	Alpha-1B adrenergic receptor	P15823	Rattus norvegicus	Predicted (SEA)	2.25763
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	10.1982
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	40.5594
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	8.95266
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	199.294
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	45.7753
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	132.11
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	47.8773
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	70.8428
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	58.854
Click to view 3D structure	Excitatory amino acid transporter 2	P43004	Humans	Predicted (SEA)	1.32344
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	248.339
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	146.746
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	398.822