ContaminantDB: Trihexyphenidyl

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (5)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:45 UTC

Update Date

2026-03-27 00:51:48 UTC

Accession Number

CHEM002183

Identification

Common Name

Trihexyphenidyl

Class

Small Molecule

Description

Trihexyphenidyl 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Apo-trihex	Kegg
Trihexylphenidyl	HMDB
Trihexylphenidyle	HMDB
Trihexylphenizyl	HMDB
Trihexyphenidyle	HMDB
Triphenidyl	HMDB
AHP brand OF trihexyphenidyl hydrochloride	MeSH, HMDB
ApoTrihex	MeSH, HMDB
Eisai brand OF trihexyphenidyl hydrochloride	MeSH, HMDB
Hipokinon	MeSH, HMDB
Parkopan	MeSH, HMDB
Trihexyphenidyl hydrochloride	MeSH, HMDB
Trihexyphenidyl wyeth brand	MeSH, HMDB
apo Trihex	MeSH, HMDB
Artane	MeSH, HMDB
Benzhexol	MeSH, HMDB
Cypress brand OF trihexyphenidyl hydrochloride	MeSH, HMDB
Lederle brand OF trihexyphenidyl hydrochloride	MeSH, HMDB
Parkinane	MeSH, HMDB
Psicofarma brand OF trihexyphenidyl hydrochloride	MeSH, HMDB
Rugby brand OF trihexyphenidyl hydrochloride	MeSH, HMDB
Trihexidyl hydrochloride	MeSH, HMDB
Wyeth brand OF trihexyphenidyl	MeSH, HMDB
Wyeth brand OF trihexyphenidyl hydrochloride	MeSH, HMDB
Apotex brand OF trihexyphenidyl hydrochloride	MeSH, HMDB
Aventis brand OF trihexyphenidyl hydrochloride	MeSH, HMDB
Schrein brand OF trihexyphenidyl hydrochloride	MeSH, HMDB
Cyclodol	MeSH, HMDB
Hexal brand OF trihexyphenidyl hydrochloride	MeSH, HMDB
Liquipharm brand OF trihexyphenidyl hydrochloride	MeSH, HMDB
Pharmaceutical associates brand OF trihexyphenidyl hydrochloride	MeSH, HMDB
Trihexane	MeSH, HMDB
Trihexyphenidyl hydrochloride elixir	MeSH, HMDB

Chemical Formula

C₂₀H₃₁NO

Average Molecular Mass

301.466 g/mol

Monoisotopic Mass

301.241 g/mol

CAS Registry Number

144-11-6

IUPAC Name

1-cyclohexyl-1-phenyl-3-(piperidin-1-yl)propan-1-ol

Traditional Name

trihexyphenidyl

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 Key

HWHLPVGTWGOCJO-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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Aralkylamines

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

amine (CHEBI:9720 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	258.5°C
Boiling Point	Not Available
Solubility	3.14e-03 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.0031 g/L	ALOGPS
logP	4.93	ALOGPS
logP	4.23	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	13.84	ChemAxon
pKa (Strongest Basic)	9.32	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	93.21 m³·mol⁻¹	ChemAxon
Polarizability	36.73 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-9520000000-9a2c379908fc40e03fe2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-08gm-8291000000-e91e4f7026454f2df547	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0udi-4119000000-9ed82688d3c1b39f26eb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1190000000-eb1d6e20e193aabe8331	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004r-9440000000-9b8665d040c0679d223d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-009i-6950000000-12b0f3e5468353070296	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-1096000000-d3df91688ef1945d673e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9130000000-5c5ffd9794999341adec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mn-9210000000-f0b1224b58d81bff09de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0019000000-7ed6535dacec03b4f64e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f89-9145000000-5ef99bbb769978df62bd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9010000000-ee7ed12c77da3bd0134f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-3009000000-cd1bde8ffe3dde655051	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9001000000-edf90121115e0df0494d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9020000000-c9173163c6667307ea2f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-2b5232fe5f3af3692a07	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0319000000-5b77372872ee2d4b2758	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-0390000000-a4123a20c113e31a331f	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9200000000-2092a098302f5e63b76c	Spectrum

Toxicity Profile

Route of Exposure

Oral. Trihexyphenidyl is rapidly absorbed from the gastrointestinal tract.

Mechanism of Toxicity

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.

Metabolism

Half Life: 3.3-4.1 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Indicated for the treatment of parkinson's disease and extrapyramidal reactions caused by drugs.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms 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.

Treatment

Treatment 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

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

5371

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

C07171

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Trihexyphenidyl (CHEM002183)

Structure for CHEM002183: Trihexyphenidyl