ContaminantDB: Orphenadrine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (16)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:31 UTC

Update Date

2026-03-31 17:46:10 UTC

Accession Number

CHEM002363

Identification

Common Name

Orphenadrine

Class

Small Molecule

Description

Orphenadrine is only found in individuals that have used or taken this drug. It is a muscarinic antagonist used to treat drug-induced parkinsonism and to relieve pain from muscle spasm. [PubChem] Orphenadrine binds and inhibits both histamine H1 receptors and NMDA receptors. It restores the motor disturbances induced by neuroleptics, in particular the hyperkinesia. The dopamine deficiency in the striatum increases the stimulating effects of the cholinergic system. This stimulation is counteracted by the anticholinergic effect of orphenadrine. It may have a relaxing effect on skeletal muscle spasms and it has a mood elevating effect.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amine
Antidyskinetic
Antiparkinson Agent
Drug
Ether
Metabolite
Muscarinic Antagonist
Muscle Relaxant, Central
Muscle Relaxant, Skeletal
Organic Compound
Parasympatholytic
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2-(Phenyl-O-tolylmethoxy)ethyldimethylamine	ChEBI
2-Methyldiphenhydramine	ChEBI
beta-Dimethylaminoethyl 2-methylbenzhydryl ether	ChEBI
Dimethyl-[2-(phenyl-O-tolyl-methoxy)-ethyl]-amine	ChEBI
N,N-Dimethyl-2-(alpha-2-tolylbenzoyloxy)ethylamine	ChEBI
N,N-Dimethyl-2-(phenyl(O-tolyl)methoxy)ethanamine	ChEBI
N,N-Dimethyl-2-[(O-methyl-alpha-phenylbenzyl)oxy]ethylamine	ChEBI
O-Methyldiphenhydramine	ChEBI
O-Monomethyldiphenhydramine	ChEBI
Orfenadrina	ChEBI
Orphenadrinum	ChEBI
Phenyl-O-tolylmethyl dimethyaminoethyl ether	ChEBI
Mialgin	Kegg
b-Dimethylaminoethyl 2-methylbenzhydryl ether	Generator
Β-dimethylaminoethyl 2-methylbenzhydryl ether	Generator
N,N-Dimethyl-2-(a-2-tolylbenzoyloxy)ethylamine	Generator
N,N-Dimethyl-2-(α-2-tolylbenzoyloxy)ethylamine	Generator
N,N-Dimethyl-2-[(O-methyl-a-phenylbenzyl)oxy]ethylamine	Generator
N,N-Dimethyl-2-[(O-methyl-α-phenylbenzyl)oxy]ethylamine	Generator
Mephenamine	HMDB
Orphenadine	HMDB
Orphenadrin	HMDB
Orphenadrine citrate	HMDB
Orphenate	HMDB
Orphenedrine	HMDB
Lysantin	HMDB
Mefenamine, sodium	HMDB
Norflex orphenadrine citrate	HMDB
Citrate, orphenadrine	HMDB
Disipal	HMDB
Methyldiphenylhydramine	HMDB
Norflex	HMDB
Citrate, norflex orphenadrine	HMDB
Hydrochloride, orphenadrine	HMDB
Mefenamine	HMDB
Orphenadrine citrate, norflex	HMDB
Sodium mefenamine	HMDB
Orphenadrine hydrochloride	HMDB

Chemical Formula

C₁₈H₂₃NO

Average Molecular Mass

269.381 g/mol

Monoisotopic Mass

269.178 g/mol

CAS Registry Number

83-98-7

IUPAC Name

dimethyl({2-[(2-methylphenyl)(phenyl)methoxy]ethyl})amine

Traditional Name

orphenadrine

SMILES

CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1C

InChI Identifier

InChI=1S/C18H23NO/c1-15-9-7-8-12-17(15)18(20-14-13-19(2)3)16-10-5-4-6-11-16/h4-12,18H,13-14H2,1-3H3

InChI Key

QVYRGXJJSLMXQH-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
Benzylether
Toluene
Tertiary aliphatic amine
Tertiary amine
Ether
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:7789 )
ether (CHEBI:7789 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	< 25°C
Boiling Point	195°C at 1.20E+01 mm Hg
Solubility	Sparingly soluble in water

Predicted Properties

Property	Value	Source
Water Solubility	0.03 g/L	ALOGPS
logP	3.5	ALOGPS
logP	4.17	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	8.87	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.97 m³·mol⁻¹	ChemAxon
Polarizability	31.83 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	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	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-7900000000-1125d9172d3a93e92a56	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	splash10-001i-0900000000-e233c4258b887b1c4d95	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0900000000-6eb16a45ba9f222e4a96	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0900000000-46ad662bd87fac31bf96	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0900000000-1e90246098db8159dcdd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0900000000-98528e097df59735a4a2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0900000000-b09cb35d4c4d1563eab0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0900000000-98fb2ac7e2a7b5389c76	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0900000000-f5b29d73b614d9a50c8c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-02t9-2900000000-5e46822ba471971d2ed4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00lr-0900000000-02f47ad2686722a25761	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00lr-0900000000-c646cee3a03cb818670b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-001i-0900000000-2e9d76988136705f609e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-0900000000-a72a380e118fb835fb66	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-014i-0900000000-a46666f03d45f46ab715	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-014i-0900000000-ea0698765985111d4210	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-001i-0900000000-97f69ccd350138f79526	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-014i-0900000000-4c978347af9b3509fd28	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-2190000000-9a5752136bf30980fbbf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-6690000000-440a3e9a238f42556d6c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9400000000-0d0ab00b78797f30d9ee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2290000000-9e0be4c70dbfcc9eb72e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-4790000000-bb9cc76650057f164459	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004m-9300000000-9fb3bdd2df4cd0bec407	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1690000000-307a51968b21b4478b96	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-1900000000-40275912271dbc75f9aa	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9200000000-213fd17f1f5014e79c8b	Spectrum

Toxicity Profile

Route of Exposure

Orphenadrine is almost completely absorbed in the gastrointestinal tract.

Mechanism of Toxicity

Orphenadrine binds and inhibits both histamine H1 receptors and NMDA receptors. It restores the motor disturbances induced by neuroleptics, in particular the hyperkinesia. The dopamine deficiency in the striatum increases the stimulating effects of the cholinergic system. This stimulation is counteracted by the anticholinergic effect of orphenadrine. It may have a relaxing effect on skeletal muscle spasms and it has a mood elevating effect.

Metabolism

Biotransformation occurs mainly in the liver. Pharmacologically active metabolites are N-demethyl orphenadrine and N,N-didemethyl orphenadrine. Half Life: 13-20 hours

Toxicity Values

LD50: 100 mg/kg (Oral, Mouse) (1) LD50: 255 mg/kg (Oral, Rat) (1)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

Indicated for the treatment of Parkinson's disease.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Treatment for orphenadrine overdose is evacuation of stomach contents (when necessary), charcoal at repeated doses, intensive monitoring, and appropriate supportive treatment of any emergent anticholinergic effects. (4)

Concentrations

Not Available

External Links

DrugBank ID

DB01173

HMDB ID

HMDB0015304

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID