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Substance Name: Orphenadrine [INN:BAN]
RN: 83-98-7
UNII: AL805O9OG9
InChIKey: QVYRGXJJSLMXQH-UHFFFAOYSA-N

Note

  • A muscarinic antagonist used to treat drug-induced parkinsonism and to relieve pain from muscle spasm.

Molecular Formula

  • C18-H23-N-O

Molecular Weight

  • 269.386
 

Classification Codes

  • Anti-Dyskinesia Agents
  • Antiparkinson Agents
  • Autonomic Agents
  • Central Nervous System Agents
  • Cholinergic Agents
  • Cholinergic Antagonists
  • Cytochrome P-450 CYP2B6 Inhibitors
  • Cytochrome P-450 Enzyme Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Metabolic Side Effects of Drugs and Substances
  • Muscarinic Antagonists
  • Muscle Relaxants, Central
  • Neuromuscular Agents
  • Neurotransmitter Agents
  • Parasympatholytics
  • Peripheral Nervous System Agents

Names and Synonyms

Results Name

  • Orphenadrine [INN:BAN]

Name of Substance

  • Orphenadrine
  • Orphenadrine [INN:BAN]

MeSH Heading

  • Orphenadrine

Synonyms

  • 2-(Phenyl-o-tolylmethoxy)ethyldimethylamine
  • 2-Methyldiphenhydramine
  • 4-06-00-04727 (Beilstein Handbook Reference)
  • beta-Dimethylaminoethyl 2-methylbenzhydryl ether
  • beta-Dimethylaminoethyl-2-methylbenzhydryl ether
  • Biorphen
  • BRN 1885151
  • Brocadisipal
  • BS 5930
  • Disipal
  • EINECS 201-509-2
  • HSDB 3139
  • N,N-Dimethyl-2-(alpha-2-tolylbenzoyloxy)ethylamin
  • N,N-Dimethyl-2-(o-methyl-alpha-phenylbenzyl)oxy)ethylamine
  • o-Methyldiphenhydramine
  • o-Monomethyldiphenhydramine
  • Orfenadrina
  • Orfenadrina [INN-Spanish]
  • ORP
  • Orphenadine
  • Orphenadinum
  • Orphenadrin
  • Orphenadrine
  • Orphenadrinum
  • Orphenadrinum [INN-Latin]
  • Orphenedrine
  • Phenyl-o-tolylmethyl dimethyaminoethyl ether
  • UNII-AL805O9OG9
  • WS 2434

Systematic Names

  • Ethanamine, N,N-dimethyl-2-((2-methylphenyl)phenylmethoxy)-
  • Ethylamine, N,N-dimethyl-2-((o-methyl-alpha-phenylbenzyl)oxy)-
  • Orphenadrine

Registry Numbers

CAS Registry Number

  • 83-98-7

FDA UNII

  • AL805O9OG9

Related Registry Numbers

  • 341-69-5 (hydrochloride)
  • 4682-36-4 (citrate)

System Generated Number

  • 0000083987

Structure Descriptors

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

c1([C@@H](c2ccccc2)OCCN(C)C)c(cccc1)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 14mg/kg (14mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
Acta Pharmacologica et Toxicologica, Supplementun. Vol. 41(2), Pg. 137, 1977.
human TDLo oral 7143mg/kg (7143mg/kg) BEHAVIORAL: COMA

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION
Archives of Toxicology, Supplement. Vol. 4, Pg. 425, 1980.
mouse LD50 intraperitoneal 80mg/kg (80mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Archives Internationales de Pharmacodynamie et de Therapie. Vol. 138, Pg. 62, 1962.
mouse LD50 intravenous 33mg/kg (33mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Archives Internationales de Pharmacodynamie et de Therapie. Vol. 138, Pg. 62, 1962.
mouse LD50 oral 125mg/kg (125mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Archives Internationales de Pharmacodynamie et de Therapie. Vol. 138, Pg. 62, 1962.
mouse LD50 subcutaneous 150mg/kg (150mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Archives Internationales de Pharmacodynamie et de Therapie. Vol. 138, Pg. 62, 1962.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point < 25 deg C   EXP
pKa Dissociation Constant 8.91 (none)   EXP
log P (octanol-water) 3.77 (none)   EXP
Water Solubility 113 mg/L 25 EST
Vapor Pressure 1.36E-05 mm Hg 25 EST
Henry's Law Constant 4.08E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.29E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.