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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-12-07 02:47:02 UTC
HMDB IDHMDB0014712
Secondary Accession Numbers
  • HMDB14712
  • HMDB31435
Metabolite Identification
Common NameAtropine
DescriptionAtropine is found in burdock. Atropine is a naturally occurring belladonna alkaloid originally from Atropa belladonna, but found in other plants, mainly solanaceae. It 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. Atropine binds to and inhibit muscarinic acetylcholine receptors, producing a wide range of anticholinergic effects. 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 has been shown to exhibit anti-depressant, laxative, nociceptive, thermogenic and anti-viral functions (PMID 7037102 , 12311408 , 6697194 , 6653675 , 6257827 ). Atropine belongs to the family of Phenylacetic Acid Derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
Structure
Thumb
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
(+,-)-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 Weight289.3694
Monoisotopic Molecular Weight289.167793607
IUPAC Name(1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
Traditional Nameatropine
CAS Registry Number51-55-8
SMILES
CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)C1=CC=CC=C1
InChI Identifier
InChI=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
DescriptionThis compound belongs to the class of chemical entities known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane.
KingdomChemical entities
Super ClassOrganic compounds
ClassAlkaloids and derivatives
Sub ClassTropane alkaloids
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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Role

Industrial application:

  Pharmaceutical industry:

    Cardiovascular drug:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point118.5 °CPhysProp
Boiling PointNot AvailableNot Available
Water Solubility2200 mg/L (at 25 °C)DEHN,WM (1917)
LogP1.83HANSCH,C ET AL. (1995)
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
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, Positivesplash10-00di-5900000000-f705f96b0219dcd47d66View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-4900000000-d0c3228da9df55297f7bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-006x-6951100000-dad9042cce0338579e31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0090000000-b8bc13dbb3c507a0f6b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0190000000-c8603eb138fb8f0e3404View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00dl-3940000000-da1a38da6babdc138c49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-006x-9700000000-2f9f7ce546a61df93bfaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-9300000000-6a976c404c7b299bbdd6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-9200000000-0eb0ff987d891c85a047View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0090000000-59d025c22f64675dc295View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0090000000-661bc87f4d92ae6353d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-1960000000-dafd68e61cc5909f5decView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-7900000000-48d355c9eef2af0979ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9300000000-659231292b6eba371158View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-00di-2900000000-3d5f34ceb343969b3c91View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , positivesplash10-00fr-0900000000-a216bda74712aba9b341View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-006x-6951100000-dad9042cce0338579e31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0790000000-b3809a4d9f3d53472626View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1920000000-5cf6a284aa0360bfa6f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g02-2900000000-03a359b67b71a8d41b5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0490000000-42268e6db552a2d85a66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05g3-1960000000-db1243e11ae5ea609f09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00bc-5900000000-3453e9ae42b1ccba243cView in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00572 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00572 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00572
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB004090
KNApSAcK IDC00002277
Chemspider ID10194105
KEGG Compound IDC01479
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAtropine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID16684
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Thomson R: Side effects and placebo amplification. Br J Psychiatry. 1982 Jan;140:64-8. [PubMed:7037102 ]
  2. Hervada AR, Feit E, Sagraves R: Drugs in breast milk. Perinat Care. 1978 Sep;2(8):19-25. [PubMed:12311408 ]
  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. [PubMed:6697194 ]
  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. [PubMed:6653675 ]
  5. Yamazaki Z, Tagaya I: Antiviral effects of atropine and caffeine. J Gen Virol. 1980 Oct;50(2):429-31. [PubMed:6257827 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]
  2. 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 ]
  3. 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 ]
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. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]
  2. 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 ]
  3. 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 ]
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. Roman S, Badia A, Camps P, Munoz-Torrero D, Clos MV: Nicotinic-receptor potentiator drugs, huprine X and galantamine, increase ACh release by blocking AChE activity but not acting on nicotinic receptors. Brain Res. 2005 Nov 9;1061(2):73-9. Epub 2005 Oct 24. [PubMed:16248990 ]
  2. Minaba M, Ichiyama S, Kojima K, Ozaki M, Kato Y: Activation of nematode G protein GOA-1 by the human muscarinic acetylcholine receptor M2 subtype. Functional coupling of G-protein-coupled receptor and G protein originated from evolutionarily distant animals. FEBS J. 2006 Dec;273(24):5508-16. Epub 2006 Nov 3. [PubMed:17087737 ]
  3. May LT, Lin Y, Sexton PM, Christopoulos A: Regulation of M2 muscarinic acetylcholine receptor expression and signaling by prolonged exposure to allosteric modulators. J Pharmacol Exp Ther. 2005 Jan;312(1):382-90. Epub 2004 Aug 27. [PubMed:15333678 ]
  4. Cembala TM, Forde SC, Appadu BL, Lambert DG: Allosteric interaction of the neuromuscular blockers vecuronium and pancuronium with recombinant human muscarinic M2 receptors. Eur J Pharmacol. 2007 Aug 13;569(1-2):37-40. Epub 2007 May 22. [PubMed:17588565 ]
  5. Nelson CP, Nahorski SR, Challiss RA: Constitutive activity and inverse agonism at the M2 muscarinic acetylcholine receptor. J Pharmacol Exp Ther. 2006 Jan;316(1):279-88. Epub 2005 Sep 27. [PubMed:16188951 ]
  6. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]
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. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]
  2. 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 ]
  3. 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 ]
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:
CHRM5
Uniprot ID:
P08912
Molecular weight:
60073.2
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]
  2. 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 ]
  3. 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 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]