CHEBI:7789 - orphenadrine

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ChEBI Name orphenadrine
ChEBI ID CHEBI:7789
Definition A tertiary amino compound which is the phenyl-o-tolylmethyl ether of 2-(dimethylamino)ethanol.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:177779
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Formula C18H23NO
Net Charge 0
Average Mass 269.38130
Monoisotopic Mass 269.178
InChI 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
InChIKey QVYRGXJJSLMXQH-UHFFFAOYSA-N
SMILES CN(C)CCOC(c1ccccc1)c1ccccc1C
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): NMDA receptor antagonist
Any substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs.
H1-receptor antagonist
H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
parasympatholytic
Any cholinergic antagonist that inhibits the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the muscarinic antagonists.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
Application(s): antidyskinesia agent
Any compound which can be used to treat or alleviate the symptoms of dyskinesia.
H1-receptor antagonist
H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
antiparkinson drug
A drug used in the treatment of Parkinson's disease.
parasympatholytic
Any cholinergic antagonist that inhibits the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the muscarinic antagonists.
muscle relaxant
A drug used to produce muscle relaxation (excepting neuromuscular blocking agents). Its primary clinical and therapeutic use is the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. Also used for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in multiple sclerosis.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
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ChEBI Ontology
Outgoing orphenadrine (CHEBI:7789) has role antidyskinesia agent (CHEBI:66956)
orphenadrine (CHEBI:7789) has role antiparkinson drug (CHEBI:48407)
orphenadrine (CHEBI:7789) has role H1-receptor antagonist (CHEBI:37955)
orphenadrine (CHEBI:7789) has role muscarinic antagonist (CHEBI:48876)
orphenadrine (CHEBI:7789) has role muscle relaxant (CHEBI:51371)
orphenadrine (CHEBI:7789) has role NMDA receptor antagonist (CHEBI:60643)
orphenadrine (CHEBI:7789) has role parasympatholytic (CHEBI:50370)
orphenadrine (CHEBI:7789) is a ether (CHEBI:25698)
orphenadrine (CHEBI:7789) is a tertiary amino compound (CHEBI:50996)
Incoming orphenadrine citrate (CHEBI:7790) has part orphenadrine (CHEBI:7789)
orphenadrine hydrochloride (CHEBI:60902) has part orphenadrine (CHEBI:7789)
IUPAC Name
N,N-dimethyl-2-[(2-methylphenyl)(phenyl)methoxy]ethanamine
INNs Sources
orfenadrina ChemIDplus
orphenadrine ChemIDplus
orphenadrinum ChemIDplus
Synonyms Sources
2-(phenyl-o-tolylmethoxy)ethyldimethylamine ChemIDplus
2-methyldiphenhydramine ChemIDplus
β-dimethylaminoethyl 2-methylbenzhydryl ether ChemIDplus
Dimethyl-[2-(phenyl-o-tolyl-methoxy)-ethyl]-amine ChEMBL
N,N-dimethyl-2-(α-2-tolylbenzoyloxy)ethylamine ChemIDplus
N,N-dimethyl-2-(phenyl(o-tolyl)methoxy)ethanamine ChEMBL
N,N-dimethyl-2-[(o-methyl-α-phenylbenzyl)oxy]ethylamine NIST Chemistry WebBook
o-methyldiphenhydramine ChemIDplus
o-monomethyldiphenhydramine ChemIDplus
ORPHENADRINE ChEMBL
Orphenadrine KEGG COMPOUND
phenyl-o-tolylmethyl dimethyaminoethyl ether ChemIDplus
Manual Xrefs Databases
1999 DrugCentral
C07935 KEGG COMPOUND
D08305 KEGG DRUG
DB01173 DrugBank
LSM-1630 LINCS
Orphenadrine Wikipedia
US2567351 Patent
US2991225 Patent
View more database links
Registry Numbers Types Sources
1885151 Reaxys Registry Number Reaxys
83-98-7 CAS Registry Number ChemIDplus
83-98-7 CAS Registry Number NIST Chemistry WebBook
Last Modified
22 February 2017
General Comment
2010-12-14 Orphenadrine is an anticholinergic with a predominantly central effect and only a weak peripheral effect. In addition, it has mild antihistaminic and local anaesthetic properties. The hydrochloride salt is used for the symptomatic treatment of parkinsonism, while the dihydrogen citrate salt is used to relieve pain due to skeletal muscle spasm.