Atropine (CHEM016234)

Record Information
Version1.0
Creation Date2016-05-22 03:23:50 UTC
Update Date2026-05-14 16:42:43 UTC
Accession NumberCHEM016234
Identification
Common NameAtropine
ClassSmall Molecule
Description
An alkaloid, originally from Atropa belladonna, but found in other plants, mainly solanaceae.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Human Neurotoxin
  • PFAS
  • Phytotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-AtropineChEBI
(+-)-HyoscyamineChEBI
(+,-)-Tropyl tropateChEBI
(3-endo)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropateChEBI
8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoateChEBI
8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropateChEBI
[(1S,5R)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-hydroxy-2-phenyl-propanoateChEBI
AtropinChEBI
AtropinaChEBI
DL-HyoscyamineChEBI
DL-TropyltropateChEBI
Tropine tropateChEBI
AtropenKegg
(+,-)-Tropyl tropic acidGenerator
(3-endo)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropic acidGenerator
8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoic acidGenerator
8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropic acidGenerator
[(1S,5R)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-hydroxy-2-phenyl-propanoic acidGenerator
DL-Tropyltropic acidGenerator
Tropine tropic acidGenerator
Atropine sulfateHMDB
DL-Tropyl tropateHMDB
Chemical FormulaC17H23NO3
Average Molecular Mass289.369 g/mol
Monoisotopic Mass289.168 g/mol
CAS Registry Number51-55-8
IUPAC Name(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
Traditional Name(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
SMILESCN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)C1=CC=CC=C1
InChI IdentifierInChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16?
InChI KeyRKUNBYITZUJHSG-SPUOUPEWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassTropane alkaloids
Sub ClassNot Available
Direct ParentTropane alkaloids
Alternative Parents
Substituents
  • Tropane alkaloid
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Piperidine
  • Benzenoid
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Primary alcohol
  • 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 Solubility2.52 g/LALOGPS
logP2.19ALOGPS
logP1.57ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)15.15ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.77 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity80.82 m³·mol⁻¹ChemAxon
Polarizability31.28 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
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
External Links
DrugBank IDDB00572
HMDB IDHMDB0014712
FooDB IDFDB004090
Phenol Explorer IDNot Available
KNApSAcK IDC00002277
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAtropine
Chemspider ID10194105
ChEBI ID16684
PubChem Compound IDNot Available
Kegg Compound IDC01479
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Thomson R: Side effects and placebo amplification. Br J Psychiatry. 1982 Jan;140:64-8.
2. Hervada AR, Feit E, Sagraves R: Drugs in breast milk. Perinat Care. 1978 Sep;2(8):19-25.
3. Brodie MS, Proudfit HK: Hypoalgesia induced by the local injection of carbachol into the nucleus raphe magnus. Brain Res. 1984 Jan 23;291(2):337-42.
4. Bryant KR, Rothwell NJ, Stock MJ, Wyllie MG: Parasympathethic effects on diet-induced thermogenesis. Eur J Pharmacol. 1983 Nov 25;95(3-4):291-4.
5. Yamazaki Z, Tagaya I: Antiviral effects of atropine and caffeine. J Gen Virol. 1980 Oct;50(2):429-31.
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15374592
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=18369575