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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:48 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
Data?1582753239
Synonyms
ValueSource
MydriacylKegg
Medical ophthalmics brand OF tropicamideMeSH, HMDB
MydrumMeSH, HMDB
Novartis brand OF tropicamideMeSH, HMDB
OcuTropicMeSH, HMDB
Ocusoft brand OF tropicamideMeSH, HMDB
Tropicamide chauvin brandMeSH, HMDB
Tropicamide, (R)-isomerMeSH, HMDB
Colircusi tropicamidaMeSH, HMDB
Minims tropicamideMeSH, HMDB
N-Ethyl-alpha-(hydroxymethyl)-N-(4-pyridinylmethyl)benzeneacetamideMeSH, HMDB
Ocu-tropicMeSH, HMDB
Stulln brand 1 OF tropicamideMeSH, HMDB
Triaminic DMMeSH, HMDB
Tropicamide faureMeSH, HMDB
Tropicamide minimsMeSH, HMDB
Tropicamide monohydrochloride, (S)-isomerMeSH, HMDB
Tropicamide ocumed brandMeSH, HMDB
Alcon brand OF tropicamideMeSH, HMDB
MydriafairMeSH, HMDB
MydriaticumMeSH, HMDB
Ocu tropicMeSH, HMDB
Ocumed brand OF tropicamideMeSH, HMDB
Pharmafair brand OF tropicamideMeSH, HMDB
Rivex brand OF tropicamideMeSH, HMDB
Stulln brand 2 OF tropicamideMeSH, HMDB
TropicacylMeSH, HMDB
Tropicamide monofreeMeSH, HMDB
Tropicamide monohydrochloride, (R)-isomerMeSH, HMDB
Tropicamide novartis brandMeSH, HMDB
Akorn brand OF tropicamideMeSH, HMDB
Bournonville brand OF tropicamideMeSH, HMDB
Cahill may roberts brand OF tropicamideMeSH, HMDB
Chauvin brand OF tropicamideMeSH, HMDB
MydralMeSH, HMDB
N-Ethyl-N-(4-pyridylmethyl)tropamideMeSH, HMDB
Tropicamide alcon brandMeSH, HMDB
Tropicamide pharmafair brandMeSH, HMDB
Tropicamide rivex brandMeSH, HMDB
Tropicamide, (+-)-isomerMeSH, HMDB
Tropicamide, (S)-isomerMeSH, HMDB
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
Description Belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetamides
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

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point96.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.38 g/LNot Available
LogP1.3Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available169.469http://allccs.zhulab.cn/database/detail?ID=AllCCS00000791
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+167.01431661259
DarkChem[M-H]-166.99731661259
DeepCCS[M+H]+171.97830932474
DeepCCS[M-H]-169.6230932474
DeepCCS[M-2H]-202.50630932474
DeepCCS[M+Na]+178.07130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TropicamideCCN(CC1=CC=NC=C1)C(=O)C(CO)C1=CC=CC=C13145.3Standard polar33892256
TropicamideCCN(CC1=CC=NC=C1)C(=O)C(CO)C1=CC=CC=C12369.6Standard non polar33892256
TropicamideCCN(CC1=CC=NC=C1)C(=O)C(CO)C1=CC=CC=C12327.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tropicamide,1TMS,isomer #1CCN(CC1=CC=NC=C1)C(=O)C(CO[Si](C)(C)C)C1=CC=CC=C12343.2Semi standard non polar33892256
Tropicamide,1TBDMS,isomer #1CCN(CC1=CC=NC=C1)C(=O)C(CO[Si](C)(C)C(C)(C)C)C1=CC=CC=C12579.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tropicamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9820000000-fca35b01c8f465360cd22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tropicamide GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9721000000-742d6fa00b915c8fa0862017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tropicamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tropicamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tropicamide GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tropicamide LC-ESI-qTof , Positive-QTOFsplash10-0a4r-4930000000-ca3db93b017c3a6fb89b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tropicamide , positive-QTOFsplash10-000i-0290000000-8c6533b9c36099d52c7c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tropicamide , positive-QTOFsplash10-000i-1390000000-cf89fdf233a948aed0492017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tropicamide , positive-QTOFsplash10-0a4r-4930000000-ca3db93b017c3a6fb89b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tropicamide 20V, Positive-QTOFsplash10-000i-4980000000-4a3ea42a69997c4e3c002021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tropicamide 40V, Positive-QTOFsplash10-0006-9700000000-0950384cf8ce560459b52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tropicamide 10V, Positive-QTOFsplash10-000i-0390000000-ce170bc65ec79ef3bed22021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropicamide 10V, Positive-QTOFsplash10-00kr-0190000000-e4250eb8b747f71894702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropicamide 20V, Positive-QTOFsplash10-014s-0790000000-468755f6d0acd4a9ce7c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropicamide 40V, Positive-QTOFsplash10-0fba-6900000000-a079daea4b21e265a60f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropicamide 10V, Negative-QTOFsplash10-001i-0090000000-871b570074f2f5c656812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropicamide 20V, Negative-QTOFsplash10-0w29-1590000000-c4843861d8def887b97b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropicamide 40V, Negative-QTOFsplash10-004i-5930000000-9c4b08cf568ef559cf0c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropicamide 10V, Positive-QTOFsplash10-000i-0190000000-a225d76819664a23f7a92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropicamide 20V, Positive-QTOFsplash10-000l-4690000000-50a111b95455fdaed7742021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropicamide 40V, Positive-QTOFsplash10-0006-9500000000-d8ba943b9c3c115764b52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropicamide 10V, Negative-QTOFsplash10-001i-0090000000-6d0c245194763db75c7f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropicamide 20V, Negative-QTOFsplash10-0udi-4690000000-c0ddc3dfc09b260cca002021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropicamide 40V, Negative-QTOFsplash10-0fxx-6950000000-7f274342c49f842dcd292021-10-11Wishart 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 DB00809 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00809 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00809
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5391
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTropicamide
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)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 ]