You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-09-27 08:27:46 UTC
HMDB IDHMDB0014947
Secondary Accession Numbers
  • HMDB14947
Metabolite Identification
Common NameTropicamide
DescriptionTropicamide is only found in individuals that have used or taken this drug. It is one of the muscarinic antagonists with pharmacologic action similar to atropine and used mainly as an ophthalmic parasympatholytic or mydriatic. [PubChem]Tropicamide binds to and blocks the receptors in the muscles of the eye (muscarinic receptor M4). Tropicamide acts by blocking the responses of the iris sphincter muscle to the iris and ciliary muscles to cholinergic stimulation, producing dilation of the pupil and paralysis of the ciliary muscle.
Structure
Thumb
Synonyms
ValueSource
MydriacylKegg
Medical ophthalmics brand OF tropicamideMeSH
MydrumMeSH
Novartis brand OF tropicamideMeSH
OcuTropicMeSH
Ocusoft brand OF tropicamideMeSH
Tropicamide chauvin brandMeSH
Tropicamide, (R)-isomerMeSH
Colircusi tropicamidaMeSH
Minims tropicamideMeSH
N-Ethyl-alpha-(hydroxymethyl)-N-(4-pyridinylmethyl)benzeneacetamideMeSH
Ocu-tropicMeSH
Stulln brand 1 OF tropicamideMeSH
Triaminic DMMeSH
Tropicamide faureMeSH
Tropicamide minimsMeSH
Tropicamide monohydrochloride, (S)-isomerMeSH
Tropicamide ocumed brandMeSH
Alcon brand OF tropicamideMeSH
MydriafairMeSH
MydriaticumMeSH
Ocu tropicMeSH
Ocumed brand OF tropicamideMeSH
Pharmafair brand OF tropicamideMeSH
Rivex brand OF tropicamideMeSH
Stulln brand 2 OF tropicamideMeSH
TropicacylMeSH
Tropicamide monofreeMeSH
Tropicamide monohydrochloride, (R)-isomerMeSH
Tropicamide novartis brandMeSH
Akorn brand OF tropicamideMeSH
Bournonville brand OF tropicamideMeSH
Cahill may roberts brand OF tropicamideMeSH
Chauvin brand OF tropicamideMeSH
MydralMeSH
N-Ethyl-N-(4-pyridylmethyl)tropamideMeSH
Tropicamide alcon brandMeSH
Tropicamide pharmafair brandMeSH
Tropicamide rivex brandMeSH
Tropicamide, (+-)-isomerMeSH
Tropicamide, (S)-isomerMeSH
Chemical FormulaC17H20N2O2
Average Molecular Weight284.3529
Monoisotopic Molecular Weight284.152477894
IUPAC NameN-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide
Traditional Nametropicamide
CAS Registry Number1508-75-4
SMILES
CCN(CC1=CC=NC=C1)C(=O)C(CO)C1=CC=CC=C1
InChI Identifier
InChI=1S/C17H20N2O2/c1-2-19(12-14-8-10-18-11-9-14)17(21)16(13-20)15-6-4-3-5-7-15/h3-11,16,20H,2,12-13H2,1H3
InChI KeyBGDKAVGWHJFAGW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylacetamides. These are amide derivatives of phenylacetic acids.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentPhenylacetamides
Alternative Parents
Substituents
  • Phenylacetamide
  • Pyridine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point96.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.38 g/LNot Available
LogP1.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.38 g/LALOGPS
logP1.42ALOGPS
logP1.38ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)15.18ChemAxon
pKa (Strongest Basic)5.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area53.43 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity82.53 m³·mol⁻¹ChemAxon
Polarizability29.78 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4r-4930000000-ca3db93b017c3a6fb89bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0290000000-8c6533b9c36099d52c7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-1390000000-cf89fdf233a948aed049View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4r-4930000000-ca3db93b017c3a6fb89bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0190000000-e4250eb8b747f7189470View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014s-0790000000-468755f6d0acd4a9ce7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fba-6900000000-a079daea4b21e265a60fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-871b570074f2f5c65681View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w29-1590000000-c4843861d8def887b97bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-5930000000-9c4b08cf568ef559cf0cView in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00809 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00809 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00809
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5391
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTropicamide
METLIN IDNot Available
PubChem Compound5593
PDB IDNot Available
ChEBI ID774555
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. Betz AJ, McLaughlin PJ, Burgos M, Weber SM, Salamone JD: The muscarinic receptor antagonist tropicamide suppresses tremulous jaw movements in a rodent model of parkinsonian tremor: possible role of M4 receptors. Psychopharmacology (Berl). 2007 Oct;194(3):347-59. Epub 2007 Jun 27. [PubMed:17594079 ]
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. Betz AJ, McLaughlin PJ, Burgos M, Weber SM, Salamone JD: The muscarinic receptor antagonist tropicamide suppresses tremulous jaw movements in a rodent model of parkinsonian tremor: possible role of M4 receptors. Psychopharmacology (Berl). 2007 Oct;194(3):347-59. Epub 2007 Jun 27. [PubMed:17594079 ]
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. Betz AJ, McLaughlin PJ, Burgos M, Weber SM, Salamone JD: The muscarinic receptor antagonist tropicamide suppresses tremulous jaw movements in a rodent model of parkinsonian tremor: possible role of M4 receptors. Psychopharmacology (Berl). 2007 Oct;194(3):347-59. Epub 2007 Jun 27. [PubMed:17594079 ]
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. 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. Betz AJ, McLaughlin PJ, Burgos M, Weber SM, Salamone JD: The muscarinic receptor antagonist tropicamide suppresses tremulous jaw movements in a rodent model of parkinsonian tremor: possible role of M4 receptors. Psychopharmacology (Berl). 2007 Oct;194(3):347-59. Epub 2007 Jun 27. [PubMed:17594079 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]