ContaminantDB: Meclizine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:31 UTC

Update Date

2026-05-14 16:47:30 UTC

Accession Number

CHEM002261

Identification

Common Name

Meclizine

Class

Small Molecule

Description

Meclizine is only found in individuals that have used or taken this drug. It is a histamine H1 antagonist used in the treatment of motion sickness, vertigo, and nausea during pregnancy and radiation sickness. [PubChem]Along with its actions as an antagonist at H₁-receptors, meclizine also possesses anticholinergic, central nervous system depressant, and local anesthetic effects. Meclizine depresses labyrinth excitability and vestibular stimulation and may affect the medullary chemoreceptor trigger zone.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amine
Anti-Allergic Agent
Antiemetic
Drug
Histamine Antagonist
Histamine H1 Antagonist
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Nevidoxine	Kegg
Meclozine	Kegg
Bonamine	MeSH, HMDB
Chiclida	MeSH, HMDB
Dihydrochloride, meclizine	MeSH, HMDB
Histametizyn	MeSH, HMDB
Hydrochloride, meclizine	MeSH, HMDB
Meclizine dihydrochloride	MeSH, HMDB
Monohydrochloride, meclizine	MeSH, HMDB
Parachloramine	MeSH, HMDB
Pfizer brand 1 OF meclizine dihydrochloride	MeSH, HMDB
Pfizer brand 2 OF meclizine dihydrochloride	MeSH, HMDB
Ru vert m	MeSH, HMDB
Bonine	MeSH, HMDB
Meclizine hydrochloride	MeSH, HMDB
Meclizine monohydrochloride	MeSH, HMDB
Antivert	MeSH, HMDB
D Vert	MeSH, HMDB
D-Vert	MeSH, HMDB
DVert	MeSH, HMDB
Pfizer consumer healthcare brand OF meclizine dihydrochloride	MeSH, HMDB
Ru-vert-m	MeSH, HMDB
Torrens brand OF meclizine dihydrochloride	MeSH, HMDB
Vedim brand OF meclizine dihydrochloride	MeSH, HMDB
Agyrax	MeSH, HMDB
Roberts brand OF meclizine dihydrochloride	MeSH, HMDB
RuVertM	MeSH, HMDB

Chemical Formula

C₂₅H₂₇ClN₂

Average Molecular Mass

390.948 g/mol

Monoisotopic Mass

390.186 g/mol

CAS Registry Number

569-65-3

IUPAC Name

1-[(4-chlorophenyl)(phenyl)methyl]-4-[(3-methylphenyl)methyl]piperazine

Traditional Name

meclizine

SMILES

CC1=CC(CN2CCN(CC2)C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)=CC=C1

InChI Identifier

InChI=1S/C25H27ClN2/c1-20-6-5-7-21(18-20)19-27-14-16-28(17-15-27)25(22-8-3-2-4-9-22)23-10-12-24(26)13-11-23/h2-13,18,25H,14-17,19H2,1H3

InChI Key

OCJYIGYOJCODJL-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
Benzylamine
Phenylmethylamine
Chlorobenzene
Halobenzene
Aralkylamine
N-alkylpiperazine
Toluene
Aryl chloride
Aryl halide
1,4-diazinane
Piperazine
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Amine
Organopnictogen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

diarylmethane (CHEBI:6709 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	217-224°C
Boiling Point	Not Available
Solubility	0.1gm/100ml

Predicted Properties

Property	Value	Source
Water Solubility	0.001 g/L	ALOGPS
logP	5.59	ALOGPS
logP	6.39	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Basic)	8.16	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	5	ChemAxon
Refractivity	119.39 m³·mol⁻¹	ChemAxon
Polarizability	44.87 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052r-1920000000-da1d25573308648315fa	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052r-1920000000-da1d25573308648315fa	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01t9-1984000000-59561fa9a23e78a4a1c9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udi-0090000000-66c42b235873c2a66976	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udi-0090000000-02a85fbc5761853f587f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0uxr-0590000000-4633d1c1f89a98d9a694	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0gb9-0940000000-38b1d47fb87eb43db9bd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0910000000-0787c462628db9403567	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0900000000-9b3d5063cf1e4fd0ecda	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0udi-0390000000-10b11855a2539537e5af	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0gb9-0940000000-5877f50e2fa5ed23d00a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-014i-0910000000-f238a0747a77e83f6f98	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0udi-0090000000-e341c3ea9d734714365b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0uxr-0590000000-0427308d1872c2c3ac2f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0udi-0090000000-d0c038e50dc835b3724b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0019000000-eaefbd608e93c9f35478	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f6x-0298000000-d9fdac408e87b3c2dc8c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-1951000000-c1876845b9081d546d74	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-5a909f49cbcdca666c0e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0109000000-3c2989c5c8f415a9591f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9763000000-8429b322587128ad3a44	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f6x-0049000000-3036ced88eac29b14a8d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0090000000-cde3cef2a87633ad0dcd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0980000000-73c4f8f44a2692d293c9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-64dce0b80fb1d839019b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0109000000-3b07e66adf588403a15b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0036-3392000000-a48c57ae3e49c939767e	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0ap0-1910000000-a39cf62803f22b3df281	Spectrum

Toxicity Profile

Route of Exposure

Oral. Well absorbed

Mechanism of Toxicity

Along with its actions as an antagonist at H₁-receptors, meclizine also possesses anticholinergic, central nervous system depressant, and local anesthetic effects. Meclizine depresses labyrinth excitability and vestibular stimulation and may affect the medullary chemoreceptor trigger zone.

Metabolism

Hepatic Half Life: 6 hours

Toxicity Values

LD50: 1600 mg/kg (oral) (1) LD50: 659 mg/kg (i.p.) (1)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the prevention and treatment of nausea, vomiting, or dizziness associated with motion sickness.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of overdose include drowsiness and anticholinergic effects.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00737

HMDB ID

HMDB0259570

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Meclizine

Chemspider ID

3894

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

C07116

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

U.S. Patent 2,709,169.

MSDS

Not Available

General References

Not Available

Meclizine (CHEM002261)

Structure for CHEM002261: Meclizine