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Physostigmine (CHEM003968)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 01:30:59 UTC
Update Date2016-11-09 01:09:15 UTC
Accession NumberCHEM003968
Identification
Common NamePhysostigmine
ClassSmall Molecule
DescriptionA cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity.
Contaminant Sources
  • Clean Air Act Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AntiliriumChEBI
EserineChEBI
PhysostolChEBI
ErserineHMDB
Eserine sulfateHMDB
Eserolein, methylcarbamateHMDB
Chemical FormulaC15H21N3O2
Average Molecular Mass275.346 g/mol
Monoisotopic Mass275.163 g/mol
CAS Registry Number57-47-6
IUPAC Name(3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate
Traditional Namephysostigmine
SMILES[H][C@]12N(C)CC[C@@]1(C)C1=C(C=CC(OC(=O)NC)=C1)N2C
InChI IdentifierInChI=1S/C15H21N3O2/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2/h5-6,9,13H,7-8H2,1-4H3,(H,16,19)/t13-,15+/m1/s1
InChI KeyPIJVFDBKTWXHHD-HIFRSBDPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyrroloindoles
Direct ParentPyrroloindoles
Alternative Parents
Substituents
  • Pyrroloindole
  • Indole
  • Dialkylarylamine
  • Benzenoid
  • N-alkylpyrrolidine
  • Pyrrole
  • Pyrrolidine
  • Carbamic acid ester
  • Carbonic acid derivative
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.99 g/LALOGPS
logP1.8ALOGPS
logP2.23ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)14.77ChemAxon
pKa (Strongest Basic)6.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.81 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity78.4 m³·mol⁻¹ChemAxon
Polarizability30.62 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001j-1590000000-508da23acfe2c8a2f568Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00ea-6790000000-c7dad12610a8d73fb915Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001j-1590000000-508da23acfe2c8a2f568Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00ea-6790000000-c7dad12610a8d73fb915Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ea-3290000000-ff0ad85b80701aa56609Spectrum
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03dj-2900000000-b9d164a9a3afaf8a17cfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00or-0090000000-1f322550abc600bd72a9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0490000000-e4a06a93b3b18d738157Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-d9ddac609ada184032acSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-ef8f7c2ddbdba70fe1d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01ot-0900000000-daf3030c2c85de1db72eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-014i-0090000000-8a9155530ad88f483e2eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03dj-2900000000-b9d164a9a3afaf8a17cfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03di-0900000000-d3eb59c5c9b1e38fcb05Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03xr-0960000000-5c126e885fa694d4eeacSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-0900000000-a1155e879f5d35d96bb7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-016r-0090000000-5864a0721423095f52acSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-016r-0090000000-5fdb9bd8096eedcd6a56Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0002-0900000000-d4927334d1d827874b42Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03xr-0960000000-11d52cd0d5583d0e2c27Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03xr-0950000000-e238974d00c6c1a74ff8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03di-0910000000-f5b98a709049c6a598e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-014i-0190000000-5bee8bebe8f73ca69075Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-016r-0090000000-77bf45d5232f86cce363Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-3090000000-4d4b520473a9f2047c89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-3090000000-a96a130ca2964214aa50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-9440000000-97f447b7b63d60cd222bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-8090000000-c4df4baeb1b2ed495e64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-6090000000-03d5fd62a0bf34c26c01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9380000000-7df539c4225faf494471Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00981
HMDB IDHMDB0015116
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00001757
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPhysostigmine
Chemspider ID5763
ChEBI ID27953
PubChem Compound ID5983
Kegg Compound IDC06535
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available