Benzatropine (CHEM002151)

Record Information
Version1.0
Creation Date2009-07-21 20:26:23 UTC
Update Date2026-05-14 16:24:54 UTC
Accession NumberCHEM002151
Identification
Common NameBenzatropine
ClassSmall Molecule
Description
Benzotropine is a centrally-acting, antimuscarinic agent used as an adjunct in the treatment of Parkinson's disease. It may also be used to treat extrapyramidal reactions, such as dystonia and Parkinsonism, caused by antipsychotics (e.g. phenothiazines). Symptoms of Parkinson's disease and extrapyramidal reactions arise from decreases in dopaminergic activity which creates an imbalance between dopaminergic and cholinergic activity. Anticholinergic therapy is thought to aid in restoring this balance leading to relief of symptoms. In addition to its anticholinergic effects, benztropine also inhibits the reuptake of dopamine at nerve terminals via the dopamine transporter. Benzotropine also produces antagonistic effects at the histamine H1 receptor.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Antidyskinetic
  • Antiparkinson Agent
  • Dopamine Uptake Inhibitor
  • Drug
  • Ether
  • Metabolite
  • Muscarinic Antagonist
  • Organic Compound
  • Parasympatholytic
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3alpha-(Diphenylmethoxy)-1alphah,5alphah-tropaneChEBI
3alpha-(Diphenylmethoxy)tropaneChEBI
3alpha-Benzhydryloxy-8-methyl-8-azabicyclo[3.2.1]octaneChEBI
3ENdo-benzhydryloxytropaneChEBI
BenzatropinaChEBI
BenzatropinumChEBI
Benzhydryl 8-methyl-8-azabicyclo[3.2.1]oct-3-yl etherChEBI
BenztropineChEBI
Tropine benzohydryl etherChEBI
3a-(Diphenylmethoxy)-1alphah,5alphah-tropaneGenerator
3Α-(diphenylmethoxy)-1alphah,5alphah-tropaneGenerator
3a-(Diphenylmethoxy)tropaneGenerator
3Α-(diphenylmethoxy)tropaneGenerator
3a-Benzhydryloxy-8-methyl-8-azabicyclo[3.2.1]octaneGenerator
3Α-benzhydryloxy-8-methyl-8-azabicyclo[3.2.1]octaneGenerator
Benzatropine mesilateHMDB
BenztropinumHMDB
Chemical FormulaC21H25NO
Average Molecular Mass307.429 g/mol
Monoisotopic Mass307.194 g/mol
CAS Registry Number86-13-5
IUPAC Name(1R,3R,5S)-3-(diphenylmethoxy)-8-methyl-8-azabicyclo[3.2.1]octane
Traditional Namebenzatropina
SMILES[H][C@]12CC[C@]([H])(C[C@@]([H])(C1)OC(C1=CC=CC=C1)C1=CC=CC=C1)N2C
InChI IdentifierInChI=1S/C21H25NO/c1-22-18-12-13-19(22)15-20(14-18)23-21(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-21H,12-15H2,1H3/t18-,19+,20+
InChI KeyGIJXKZJWITVLHI-PMOLBWCYSA-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Benzylether
  • Tropane alkaloid
  • Piperidine
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary amine
  • Tertiary aliphatic amine
  • Dialkyl ether
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point138-140°C
Boiling PointNot Available
SolubilityVery soluble
Predicted Properties
PropertyValueSource
Water Solubility0.0012 g/LALOGPS
logP4.47ALOGPS
logP4.19ChemAxon
logS-5.4ALOGPS
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity94.24 m³·mol⁻¹ChemAxon
Polarizability35.42 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureIntravenous, Oral. Onset of action is 1-2 hours following oral administration. The onset of action is within minutes when administered by IM or IV injection.
Mechanism of ToxicityBenztropine is a selective M1 muscarinic acetylcholine receptor antagonist. It is able to discriminate between the M1 (cortical or neuronal) and the peripheral muscarinic subtypes (cardiac and glandular). Benztropine partially blocks cholinergic activity in the CNS, which is responsible for the symptoms of Parkinson's disease. It is also thought to increase the availability of dopamine, a brain chemical that is critical in the initiation and smooth control of voluntary muscle movement.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor use as an adjunct in the therapy of all forms of parkinsonism and also for use in the control of extrapyramidal disorders due to neuroleptic drugs.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSigns of overdose include confusion, nervousness, listlessness, hallucinations, dizziness; muscle weakness, ataxia, dry mouth, mydriasis, blurred vision, palpitations, tachycardia, elevated blood pressure, nausea, vomiting, dysuria, numbness of fingers, headache, delirium, coma, shock, convulsions, respiratory arrest, anhidrosis, hyperthermia, glaucoma, and constipation.
TreatmentPhysostigmine salicylate, 1 to 2 mg, SC or IV, reportedly will reverse symptoms of anticholinergic intoxication. A second injection may be given after 2 hours if required. Otherwise treatment is symptomatic and supportive. Induce emesis or perform gastric lavage (contraindicated in precomatose, convul-sive, or psychotic states). Maintain respiration. A short-acting barbiturate may be used for CNS excitement, but with caution to avoid subsequent depression; supportive care for depression (avoid convulsant stimulants such as picrotoxin, pentylenetetrazol, or bemegride); artificial respiration for severe respiratory depression; a local miotic for mydriasis and cycloplegia; ice bags or other cold applications and alcohol sponges for hyperpyrexia, a vasopressor and fluids for circulatory collapse. Darken room for photophobia. (4)
Concentrations
Not Available
External Links
DrugBank IDDB00245
HMDB IDHMDB0014390
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBenzatropine
Chemspider ID16736541
ChEBI ID3048
PubChem Compound IDNot Available
Kegg Compound IDC06846
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Phillips, R.F.; US. Patent 2,595,405; May 6, 1952; assigned to Merck & Co., Inc.

MSDSLink
General References
1. van Harten PN, Hoek HW, Matroos GE, Koeter M, Kahn RS: Intermittent neuroleptic treatment and risk for tardive dyskinesia: Curacao Extrapyramidal Syndromes Study III. Am J Psychiatry. 1998 Apr;155(4):565-7.
2. Wszola BA, Newell KM, Sprague RL: Risk factors for tardive dyskinesia in a large population of youths and adults. Exp Clin Psychopharmacol. 2001 Aug;9(3):285-96.