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Showing Compound Atropine (FDB004090)

Record Information
Version1.0
Creation date2010-04-08 22:06:05 UTC
Update date2019-11-26 02:59:48 UTC
Primary IDFDB004090
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAtropine
DescriptionAtropine, a naturally occurring belladonna alkaloid, is a racemic mixture of equal parts of d- and l-hyoscyamine, whose activity is due almost entirely to the levo isomer of the drug. Atropine is commonly classified as an anticholinergic or antiparasympathetic (parasympatholytic) drug. More precisely, however, it is termed an antimuscarinic agent since it antagonizes the muscarine-like actions of acetylcholine and other choline esters. Adequate doses of atropine abolish various types of reflex vagal cardiac slowing or asystole. The drug also prevents or abolishes bradycardia or asystole produced by injection of choline esters, anticholinesterase agents or other parasympathomimetic drugs, and cardiac arrest produced by stimulation of the vagus. Atropine may also lessen the degree of partial heart block when vagal activity is an etiologic factor. Atropine in clinical doses counteracts the peripheral dilatation and abrupt decrease in blood pressure produced by choline esters. However, when given by itself, atropine does not exert a striking or uniform effect on blood vessels or blood pressure. Atropine is found in burdock.
CAS Number51-55-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
AnaspazHMDB
CytospazHMDB
Atropine sulfate, 3(S)-endo-isomerHMDB
HyoscyamineHMDB
Hyoscyamine hydrobromideHMDB
Hyoscyamine hydrochlorideHMDB
Atropine, 3(S)-endo-isomerHMDB
Hyoscyamine sulfateHMDB
Hyoscyamine sulfate anhydrousHMDB
(±)-atropinebiospider
(±)-hyoscyaminebiospider
(+-)-atropinebiospider
(+-)-hyoscyaminebiospider
(+,-)-tropyl tropatebiospider
(+,-)-Tropyl tropic acidGenerator
(+/-)-atropinebiospider
(+/-)-hyoscyaminebiospider
(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl tropatebiospider
(3-Endo)-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-propanoateChEBI
[(1S,5R)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-hydroxy-2-phenyl-propanoic acidGenerator
1-α-H,5-α-H-Tropan-3-α-ol (.+/-.)-tropatebiospider
1-alpha-H,5-alpha-H-Tropan-3-alpha-ol (+-)-tropate (ester)biospider
1αH,5αH-Tropan-3α-ol (±)-tropatebiospider
1alphaH,5alphaH-Tropan-3alpha-ol (+-)-tropate (ester)biospider
2-Phenylhydracrylic acid 3-α-tropanyl esterbiospider
2-Phenylhydracrylic acid 3-alpha-tropanyl esterbiospider
51-55-8 (FREE BASE)biospider
5908-99-6 (SULFATE(2:1), MONOHYDRATE)biospider
8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoateChEBI
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 tropatebiospider
8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropic acidGenerator
Atnaabiospider
Atropenbiospider
Atropen (TN)biospider
Atropinbiospider
Atropin-flexiolenbiospider
Atropinabiospider
Atropinebiospider
Atropine (usp)biospider
Atropine [ban]biospider
Atropine Ont 1%biospider
Atropine sulfatebiospider
Atropine sulfate ansyr plastic syringebiospider
Atropinolbiospider
Atropinumbiospider
Atropisolbiospider
Atroptbiospider
Belladenalbiospider
Bellergal-sbiospider
Butibelbiospider
DL-hyoscyaminebiospider
DL-Tropanyl 2-hydroxy-1-phenylpropionatebiospider
DL-tropyl tropatebiospider
DL-tropyltropatebiospider
DL-Tropyltropic acidGenerator
Donnagelbiospider
Donnatalbiospider
Eyesulesbiospider
Hycodanbiospider
Isopto Atropine 1%biospider
Isopto-atropinebiospider
Lomotilbiospider
Lonoxbiospider
Minimsbiospider
Minims Atropine Sulphate 1%biospider
Neo-diophenbiospider
Protamine + atropinebiospider
Protamine and atropinebiospider
tropan-3alpha-yl 3-hydroxy-2-phenylpropanoatebiospider
Tropic acid, 3-α-tropanyl esterbiospider
Tropic acid, 3-alpha-tropanyl esterbiospider
Tropic acid, ester with tropinebiospider
Tropine (+/-)-tropatebiospider
Tropine tropatebiospider
Tropine tropic acidGenerator
Tropine, tropate (ester)biospider
Troyl tropatebiospider
Urisedbiospider
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
Polarizability31.97 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H23NO3
IUPAC name8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
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
InChI KeyRKUNBYITZUJHSG-UHFFFAOYSA-N
Isomeric SMILESCN1C2CCC1CC(C2)OC(=O)C(CO)C1=CC=CC=C1
Average Molecular Weight289.3694
Monoisotopic Molecular Weight289.167793607
Classification
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 DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point118.5 oC
Boiling PointNot Available
Experimental Water Solubility2.2 mg/mL at 25 oCDEHN,WM (1917)
Experimental logP1.83HANSCH,C ET AL. (1995)
Experimental pKa9.43
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAtropine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-5900000000-f705f96b0219dcd47d66Spectrum
Predicted GC-MSAtropine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-0090000000-7255a458bf0a1174db0e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-0290000000-0fa7c3e676abe6d74e1b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-0290000000-5dc90a665e979b22b90d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-9400000000-6ffeab7f3dd99dda689d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-0090000000-f1c38996b983b5e391f42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00di-0900000000-cbd0badb88e127ba2c672021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-0090000000-b69f630a2e01f48f80712021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-9400000000-60b9b888396fac61f0632021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00dl-5910000000-7cff8eefb7a301a7d60e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-0290000000-2a780a90ba94dfbaeae42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0950000000-de8a9c1c6040f15073112021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0190000000-f263fc3f7ab75b62bc3d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00dl-5900000000-cc1c307e3cefc38754072021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00dl-5910000000-d0ef371a67863ce071d72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-0290000000-17af349d5d2a4c2433482021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-9400000000-f8615194729e261a02312021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0790000000-b3809a4d9f3d534726262016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1920000000-5cf6a284aa0360bfa6f52016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g02-2900000000-03a359b67b71a8d41b5a2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0490000000-42268e6db552a2d85a662016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05g3-1960000000-db1243e11ae5ea609f092016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00bc-5900000000-3453e9ae42b1ccba243c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-38746560650547c38a282021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-1590000000-abf830c79515feb657d22021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006y-9500000000-28e9eb9a8330fa4c60d92021-10-12View Spectrum
NMRNot Available
ChemSpider ID10194105
ChEMBL IDCHEMBL517712
KEGG Compound IDC01479
Pubchem Compound ID174174
Pubchem Substance IDNot Available
ChEBI ID16684
Phenol-Explorer IDNot Available
DrugBank IDDB00572
HMDB IDHMDB14712
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDATROPINE
BIGG IDNot Available
KNApSAcK IDC00002277
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anestheticDUKE
anhydroticDUKE
anti anoxic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti arrhythmic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti asthmatic49167 A drug used to treat asthma.DUKE
anti bradycardic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti cholinergic38323 Any drug used for its actions on cholinergic systems. Included here are agonists and antagonists, drugs that affect the life cycle of acetylcholine, and drugs that affect the survival of cholinergic neurons.DUKE
antidote50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti emetic50919 A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.DUKE
anti emphysemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti enureticDUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti iriticDUKE
anti muscarinic48876 A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.DUKE
anti Parkinsonian48407 A drug used in the treatment of Parkinson's disease.DUKE
anti peristalticDUKE
anti perspirantDUKE
anti pertussic33282 A substance that kills or slows the growth of bacteria.DUKE
anti polio22587 A substance that destroys or inhibits replication of viruses.DUKE
anti sialogogueDUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
anti uveiticDUKE
anti vertigo52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
bronchodilator35523 An agent that causes an increase in the expansion of a bronchus or bronchial tubes.DUKE
cholereticDUKE
central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
central nervous system stimulant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
hyperpyrexicDUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
mydriatic50513 Agent that dilates the pupil. Used in eye diseases and to facilitate eye examination. It may be either a sympathomimetic or parasympatholytic. The latter cause cycloplegia or paralysis of accommodation at high doses and may precipitate glaucoma.DUKE
myorelaxantDUKE
neurotoxic50910 A poison that interferes with the functions of the nervous system.DUKE
paralyticDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
psychotomimetic35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
tachycardic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
transdermalDUKE
tumorigenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).