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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:39 UTC
HMDB IDHMDB0014520
Secondary Accession Numbers
  • HMDB14520
Metabolite Identification
Common NameTrihexyphenidyl
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. [PubChem]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.
Structure
Data?1582753188
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 Weight301.4662
Monoisotopic Molecular Weight301.240564619
IUPAC Name1-cyclohexyl-1-phenyl-3-(piperidin-1-yl)propan-1-ol
Traditional Nametrihexyphenidyl
CAS Registry Number144-11-6
SMILES
OC(CCN1CCCCC1)(C1CCCCC1)C1=CC=CC=C1
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point258.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0031 g/LNot Available
LogP4.5Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.31931661259
DarkChem[M-H]-166.41231661259
DeepCCS[M+H]+174.30530932474
DeepCCS[M-H]-171.94730932474
DeepCCS[M-2H]-204.83430932474
DeepCCS[M+Na]+180.39830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TrihexyphenidylOC(CCN1CCCCC1)(C1CCCCC1)C1=CC=CC=C12407.4Standard polar33892256
TrihexyphenidylOC(CCN1CCCCC1)(C1CCCCC1)C1=CC=CC=C12254.3Standard non polar33892256
TrihexyphenidylOC(CCN1CCCCC1)(C1CCCCC1)C1=CC=CC=C12227.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Trihexyphenidyl,1TMS,isomer #1C[Si](C)(C)OC(CCN1CCCCC1)(C1=CC=CC=C1)C1CCCCC12421.9Semi standard non polar33892256
Trihexyphenidyl,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(CCN1CCCCC1)(C1=CC=CC=C1)C1CCCCC12656.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Trihexyphenidyl GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4j-9520000000-9a2c379908fc40e03fe22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trihexyphenidyl GC-MS (1 TMS) - 70eV, Positivesplash10-08gm-8291000000-e91e4f7026454f2df5472017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trihexyphenidyl GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trihexyphenidyl GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trihexyphenidyl GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9200000000-2092a098302f5e63b76c2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Trihexyphenidyl , positive-QTOFsplash10-0udi-4119000000-9ed82688d3c1b39f26eb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trihexyphenidyl 10V, Negative-QTOFsplash10-00di-1190000000-eb1d6e20e193aabe83312021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trihexyphenidyl 40V, Negative-QTOFsplash10-004r-9440000000-9b8665d040c0679d223d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trihexyphenidyl 20V, Negative-QTOFsplash10-009i-6950000000-12b0f3e54683530702962021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trihexyphenidyl 10V, Positive-QTOFsplash10-0f89-1096000000-d3df91688ef1945d673e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trihexyphenidyl 20V, Positive-QTOFsplash10-0002-9130000000-5c5ffd9794999341adec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trihexyphenidyl 40V, Positive-QTOFsplash10-05mn-9210000000-f0b1224b58d81bff09de2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trihexyphenidyl 10V, Negative-QTOFsplash10-0udi-0019000000-7ed6535dacec03b4f64e2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trihexyphenidyl 20V, Negative-QTOFsplash10-0f89-9145000000-5ef99bbb769978df62bd2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trihexyphenidyl 40V, Negative-QTOFsplash10-001i-9010000000-ee7ed12c77da3bd0134f2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trihexyphenidyl 10V, Positive-QTOFsplash10-0udi-3009000000-cd1bde8ffe3dde6550512021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trihexyphenidyl 20V, Positive-QTOFsplash10-0002-9001000000-edf90121115e0df0494d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trihexyphenidyl 40V, Positive-QTOFsplash10-0002-9020000000-c9173163c6667307ea2f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trihexyphenidyl 10V, Negative-QTOFsplash10-0udi-0009000000-2b5232fe5f3af3692a072021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trihexyphenidyl 20V, Negative-QTOFsplash10-0udi-0319000000-5b77372872ee2d4b27582021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trihexyphenidyl 40V, Negative-QTOFsplash10-0002-0390000000-a4123a20c113e31a331f2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00376 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00376 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5371
KEGG Compound IDC07171
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular weight:
66127.4
References
  1. Bognar IT, Altes U, Beinhauer C, Kessler I, Fuder H: A muscarinic receptor different from the M1, M2, M3 and M4 subtypes mediates the contraction of the rabbit iris sphincter. Naunyn Schmiedebergs Arch Pharmacol. 1992 Jun;345(6):611-8. [PubMed:1635586 ]
  2. Dorje F, Wess J, Lambrecht G, Tacke R, Mutschler E, Brann MR: Antagonist binding profiles of five cloned human muscarinic receptor subtypes. J Pharmacol Exp Ther. 1991 Feb;256(2):727-33. [PubMed:1994002 ]
  3. Freedman SB, Beer MS, Harley EA: Muscarinic M1, M2 receptor binding. Relationship with functional efficacy. Eur J Pharmacol. 1988 Oct 26;156(1):133-42. [PubMed:3208836 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular weight:
51420.4
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Prus AJ, Pehrson AL, Philibin SD, Wood JT, Vunck SA, Porter JH: The role of M1 muscarinic cholinergic receptors in the discriminative stimulus properties of N-desmethylclozapine and the atypical antipsychotic drug clozapine in rats. Psychopharmacology (Berl). 2009 Apr;203(2):295-301. doi: 10.1007/s00213-008-1262-0. Epub 2008 Aug 7. [PubMed:18685832 ]
  4. Giachetti A, Giraldo E, Ladinsky H, Montagna E: Binding and functional profiles of the selective M1 muscarinic receptor antagonists trihexyphenidyl and dicyclomine. Br J Pharmacol. 1986 Sep;89(1):83-90. [PubMed:2432979 ]
  5. Tanda G, Katz JL: Muscarinic preferential M(1) receptor antagonists enhance the discriminative-stimulus effects of cocaine in rats. Pharmacol Biochem Behav. 2007 Oct;87(4):400-4. Epub 2007 Jun 2. [PubMed:17631384 ]
  6. Dorje F, Wess J, Lambrecht G, Tacke R, Mutschler E, Brann MR: Antagonist binding profiles of five cloned human muscarinic receptor subtypes. J Pharmacol Exp Ther. 1991 Feb;256(2):727-33. [PubMed:1994002 ]
  7. Freedman SB, Beer MS, Harley EA: Muscarinic M1, M2 receptor binding. Relationship with functional efficacy. Eur J Pharmacol. 1988 Oct 26;156(1):133-42. [PubMed:3208836 ]
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular weight:
51714.6
References
  1. Bognar IT, Altes U, Beinhauer C, Kessler I, Fuder H: A muscarinic receptor different from the M1, M2, M3 and M4 subtypes mediates the contraction of the rabbit iris sphincter. Naunyn Schmiedebergs Arch Pharmacol. 1992 Jun;345(6):611-8. [PubMed:1635586 ]
  2. Dorje F, Wess J, Lambrecht G, Tacke R, Mutschler E, Brann MR: Antagonist binding profiles of five cloned human muscarinic receptor subtypes. J Pharmacol Exp Ther. 1991 Feb;256(2):727-33. [PubMed:1994002 ]
  3. Freedman SB, Beer MS, Harley EA: Muscarinic M1, M2 receptor binding. Relationship with functional efficacy. Eur J Pharmacol. 1988 Oct 26;156(1):133-42. [PubMed:3208836 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase
Gene Name:
CHRM4
Uniprot ID:
P08173
Molecular weight:
53048.7
References
  1. Bognar IT, Altes U, Beinhauer C, Kessler I, Fuder H: A muscarinic receptor different from the M1, M2, M3 and M4 subtypes mediates the contraction of the rabbit iris sphincter. Naunyn Schmiedebergs Arch Pharmacol. 1992 Jun;345(6):611-8. [PubMed:1635586 ]
  2. Dorje F, Wess J, Lambrecht G, Tacke R, Mutschler E, Brann MR: Antagonist binding profiles of five cloned human muscarinic receptor subtypes. J Pharmacol Exp Ther. 1991 Feb;256(2):727-33. [PubMed:1994002 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM5
Uniprot ID:
P08912
Molecular weight:
60073.2
References
  1. Bognar IT, Altes U, Beinhauer C, Kessler I, Fuder H: A muscarinic receptor different from the M1, M2, M3 and M4 subtypes mediates the contraction of the rabbit iris sphincter. Naunyn Schmiedebergs Arch Pharmacol. 1992 Jun;345(6):611-8. [PubMed:1635586 ]
  2. Dorje F, Wess J, Lambrecht G, Tacke R, Mutschler E, Brann MR: Antagonist binding profiles of five cloned human muscarinic receptor subtypes. J Pharmacol Exp Ther. 1991 Feb;256(2):727-33. [PubMed:1994002 ]