Trihexyphenidyl (CHEM002183)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (5)XML
Record Information
Version1.0
Creation Date2009-07-21 20:26:45 UTC
Update Date2016-11-09 01:08:42 UTC
Accession NumberCHEM002183
Identification
Common NameTrihexyphenidyl
ClassSmall Molecule
DescriptionTrihexyphenidyl is only found in individuals that have used or taken this drug. It is one of the centrally acting muscarinic antagonists used for treatment of parkinsonian disorders and drug-induced extrapyramidal movement disorders and as an antispasmodic. Trihexyphenidyl 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). Trihexyphenidyl 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Antidyskinetic
  • Antiparkinson Agent
  • Drug
  • Metabolite
  • Muscarinic Antagonist
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Apo-trihexKegg
TrihexylphenidylHMDB
TrihexylphenidyleHMDB
TrihexylphenizylHMDB
TrihexyphenidyleHMDB
TriphenidylHMDB
AHP brand OF trihexyphenidyl hydrochlorideMeSH, HMDB
ApoTrihexMeSH, HMDB
Eisai brand OF trihexyphenidyl hydrochlorideMeSH, HMDB
HipokinonMeSH, HMDB
ParkopanMeSH, HMDB
Trihexyphenidyl hydrochlorideMeSH, HMDB
Trihexyphenidyl wyeth brandMeSH, HMDB
apo TrihexMeSH, HMDB
ArtaneMeSH, HMDB
BenzhexolMeSH, HMDB
Cypress brand OF trihexyphenidyl hydrochlorideMeSH, HMDB
Lederle brand OF trihexyphenidyl hydrochlorideMeSH, HMDB
ParkinaneMeSH, HMDB
Psicofarma brand OF trihexyphenidyl hydrochlorideMeSH, HMDB
Rugby brand OF trihexyphenidyl hydrochlorideMeSH, HMDB
Trihexidyl hydrochlorideMeSH, HMDB
Wyeth brand OF trihexyphenidylMeSH, HMDB
Wyeth brand OF trihexyphenidyl hydrochlorideMeSH, HMDB
Apotex brand OF trihexyphenidyl hydrochlorideMeSH, HMDB
Aventis brand OF trihexyphenidyl hydrochlorideMeSH, HMDB
Schrein brand OF trihexyphenidyl hydrochlorideMeSH, HMDB
CyclodolMeSH, HMDB
Hexal brand OF trihexyphenidyl hydrochlorideMeSH, HMDB
Liquipharm brand OF trihexyphenidyl hydrochlorideMeSH, HMDB
Pharmaceutical associates brand OF trihexyphenidyl hydrochlorideMeSH, HMDB
TrihexaneMeSH, HMDB
Trihexyphenidyl hydrochloride elixirMeSH, HMDB
Chemical FormulaC20H31NO
Average Molecular Mass301.466 g/mol
Monoisotopic Mass301.241 g/mol
CAS Registry Number144-11-6
IUPAC Name1-cyclohexyl-1-phenyl-3-(piperidin-1-yl)propan-1-ol
Traditional Nametrihexyphenidyl
SMILESOC(CCN1CCCCC1)(C1CCCCC1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C20H31NO/c22-20(18-10-4-1-5-11-18,19-12-6-2-7-13-19)14-17-21-15-8-3-9-16-21/h1,4-5,10-11,19,22H,2-3,6-9,12-17H2
InChI KeyHWHLPVGTWGOCJO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Monocyclic benzene moiety
  • Piperidine
  • Benzenoid
  • 1,3-aminoalcohol
  • Tertiary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organopnictogen compound
  • Aromatic alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point258.5°C
Boiling PointNot Available
Solubility3.14e-03 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.0031 g/LALOGPS
logP4.93ALOGPS
logP4.23ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)13.84ChemAxon
pKa (Strongest Basic)9.32ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.21 m³·mol⁻¹ChemAxon
Polarizability36.73 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4j-9520000000-9a2c379908fc40e03fe2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-08gm-8291000000-e91e4f7026454f2df547Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-4119000000-9ed82688d3c1b39f26ebSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-1190000000-eb1d6e20e193aabe8331Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004r-9440000000-9b8665d040c0679d223dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-009i-6950000000-12b0f3e5468353070296Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-1096000000-d3df91688ef1945d673eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9130000000-5c5ffd9794999341adecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mn-9210000000-f0b1224b58d81bff09deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-7ed6535dacec03b4f64eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-9145000000-5ef99bbb769978df62bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9010000000-ee7ed12c77da3bd0134fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3009000000-cd1bde8ffe3dde655051Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9001000000-edf90121115e0df0494dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9020000000-c9173163c6667307ea2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-2b5232fe5f3af3692a07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0319000000-5b77372872ee2d4b2758Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0390000000-a4123a20c113e31a331fSpectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9200000000-2092a098302f5e63b76cSpectrum
Toxicity Profile
Route of ExposureOral. Trihexyphenidyl is rapidly absorbed from the gastrointestinal tract.
Mechanism of ToxicityTrihexyphenidyl 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). Trihexyphenidyl 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.
MetabolismHalf Life: 3.3-4.1 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesIndicated for the treatment of parkinson's disease and extrapyramidal reactions caused by drugs.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include mydriasis, dryness of mucous membranes, red face, atonic states of bowels and bladder, and hyperthermia in high doses. Central consequences are agitation, confusion, and hallucinations.
TreatmentTreatment of acute overdose involves symptomatic and supportive therapy. Gastric lavage or other methods to limit absorption should be instituted. A small dose of diazepam or a short-acting barbiturate may be administered if CNS excitation is observed. Phenothiazines are contraindicated because the toxicity may be intensified due to their antimuscarinic action, causing coma. Respiratory support, artificial respiration or vasopressor agents may be necessary. Hyperpyrexia must be reversed, fluid volume replaced and acid-balance maintained. Urinary catheterization may be necessary. It is not known if Trihexyphenidyl is dialyzable. (2)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID5371
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDC07171
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available