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Compound Summary

General Compound Information

Atropine

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Description

Atropine is a racemate composed of equimolar concentrations of (S)- and (R)-atropine. It is obtained from deadly nightshade (Atropa belladonna) and other plants of the family Solanaceae. It has a role as a muscarinic antagonist, an anaesthesia adjuvant, an anti-arrhythmia drug, a mydriatic agent, a parasympatholytic, a bronchodilator agent, a plant metabolite, an antidote to sarin poisoning and a oneirogen. It contains a (S)-atropine and a (R)-atropine.

Synonyms

ATROPINE; dl-Hyoscyamine; 51-55-8; Tropine tropate; Atropen;

Atropin;dl-Tropyltropate;Atropinol;Eyesules;Isopto-atropine;Troyl tropate;hyoscyamine;Atropina;Atropin-flexiolen;(+,-)-Tropyl tropate;Atropin [German];Atropina [Italian];(+-)-hyoscyamine;Tropine, tropate (ester);(+-)-atropine;Tropic acid, ester with tropine;(+/-)-Atropine;(+/-)-Hyoscyamine;CCRIS 3080;Atropine (USP);Tropic acid, 3-alpha-tropanyl ester;Atropinum;HSDB 2199;DL-Tropanyl 2-hydroxy-1-phenylpropionate;2-Phenylhydracrylic acid 3-alpha-tropanyl ester;AI3-60219;beta-Phenyl-gamma-oxypropionsaure-tropyl-ester [German];DL-Tropyl tropate;(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoate;1alphaH,5alphaH-Tropan-3alpha-ol (+-)-tropate (ester);beta-Phenyl-gamma-oxypropionsaeure-tropyl-ester [German];(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl tropate;tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate;8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropate;MLS000069795;Tropine tropate;DL-Hyoscyamine;DTXSID4020113;CHEBI:16684;7C0697DR9I;8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoate;[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-hydroxy-2-phenyl-propanoate;alpha-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester;endo-(+/-)-alpha-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester;Benzeneacetic acid, alpha-(hydroxymethyl)-8-methyl-8-azabicyclo(3,2,1)oct-3-yl ester, endo-(+-)-;NCGC00017333-03;SMR000058248;AB00694549-11;Benzeneacetic acid, alpha-(hydroxymethyl)-, 8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester, endo-(+-)-;DTXCID20113;CAS-51-55-8;Atropen (TN);Protamine & Atropine;Atropine [USP:BAN];5908-99-6;EINECS 200-104-8;Tropine (+/-)-tropate;ropine tropate;UNII-7C0697DR9I;(3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL TROPATE;NCGC00159345-02;3-tropoyloxytropane;1-alpha-H,5-alpha-H-Tropan-3-alpha-ol (+-)-tropate (ester);ATROPINE [MI];ATROPINE [VANDF];ATROPINUM [HPUS];Opera_ID_1088;ATROPINE [MART.];beta-Phenyl-gamma-oxypropionsaure-tropyl-ester;ATROPINE [USP-RS];ATROPINE [WHO-DD];bmse000649;beta-Phenyl-gamma-oxypropionsaeure-tropyl-ester;SCHEMBL2812;[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate;Atropine, analytical standard;GTPL320;Benzeneacetic acid, alpha-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester;MLS001148094;MLS002695888;ATROPINE [GREEN BOOK];ATNAA COMPONENT ATROPINE;ATROPINE [EP IMPURITY];ATROPINE [ORANGE BOOK];CHEMBL254656;CHEMBL475124;CHEMBL517712;cid_174174;MEGxp0_001878;Atropine ((+/-)-Hyoscyamin);ATROPINE [EP MONOGRAPH];ATROPINE [USP MONOGRAPH];ATROPINE, (+/-)-;ACon1_000046;CHEBI:78734;DUODOTE COMPONENT ATROPINE;(1R,3r,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate;ATROPINE ((+/-)-);Atropine, >=95.0% (NT);ATROPINE COMPONENT OF ATNAA;BDBM200229;DTXSID601141720;HMS2089A16;HMS2231G17;HMS3259M13;BCP15060;HY-B1205;ATROPINE COMPONENT OF DUODOTE;Atropine, >=99% (TLC), powder;Tox21_110816;Tox21_111590;Tox21_200487;1-alpha-H,5-alpha-H-Tropan-3-alpha-ol (+-)-tropate (ester) (8CI);BDBM50403547;s4713;AKOS015955538;CS-4834;DB00572;NC00493;NCGC00017333-02;NCGC00017333-04;NCGC00017333-05;NCGC00017333-06;NCGC00142514-01;NCGC00142514-03;NCGC00258041-01;NCGC00385525-01;AS-56020;Benzeneacetic acid, alpha-(hydroxymethyl)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester, endo-(+-)-;Atropine, meets USP testing specifications;C1504;FT-0627165;C01479;D00113;Q26272;AB00694549-12;AB00694549_14;rac-tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate;BRD-A27290375-001-01-8;BRD-A27290375-330-01-1;Atropine, European Pharmacopoeia (EP) Reference Standard;HOMATROPINE HYDROBROMIDE IMPURITY D [EP IMPURITY];1.ALPHA.H,5.ALPHA.H-TROPAN-3.ALPHA.-OL (+/-)-TROPATE (ESTER);(3-exo)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl alpha-(hydroxymethyl)benzeneacetate;[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenyl-propanoate;[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenyl-propanoate;alpha-Hydroxymethylphenylacetic acid (1R,5S)-8-methyl-8-azabicyclo[3.2.1]octane-3-yl ester;Atropine for peak identification, European Pharmacopoeia (EP) Reference Standard;rac-(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoate;(1beta,3alpha,5beta)-3-[(3-Hydroxy-1-oxo-2-phenylpropyl)oxy]-8-methyl-8-azabicyclo[3.2.1]octane;16175-85-2;BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-(3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER;BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, ENDO-(+/-)-;Benzeneacetic acid, alpha-(hydroxymethyl)- (3-endo)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester;Benzeneacetic acid, alpha-(hydroxymethyl)-, 8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester, endo-(+/-)-;

FlavorDB ID

4235

PUBCHEM ID

Molecular Weight

289.4 Molecular Formula

C17H23NO3

Openeye Can Smiles

CN1C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3

IUPAC Inchikey

RKUNBYITZUJHSG-PJPHBNEVSA-N

Network

Similarity

Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database
Oral, mouse: LD50 = 75 mg/kg. Symptoms of overdose includes widespread paralysis of parasympathetically innervated organs. Dry mucous membranes, widely dilated and nonresponsive pupils, tachycardia, fever and cutaneous flush are especially prominent, as are mental and neurological symptoms. In instances of severe intoxication, respiratory depression, coma, circulatory collapse and death may occur.
Source: DrugBank or Hazardous Substances Data Bank (HSDB)

EFSA's chemical Hazards Database : OpenFoodTox
This compound is found in OpenFoodTox with the name: Atropine

Reference point : Defined point on an experimental dose–response relationship for the critical effect. This term is synonymous to Point of departure (USA). Reference points include the lowest or no observed adverse effect level (LOAEL/NOAEL) or benchmark dose lower confidence limit (BDML), used to derive a reference value or Margin of Exposure in human and animal health risk assessment. In the ecological area, these include lethal dose (LD50), effect concentration (EC5/ECx), no (adverse) effect concentration/dose (NOEC/NOAEC/NOAED), no (adverse) effect level (NEL/NOAEL), hazard concentration (HC5/HCx) derived from a Species Sensitivity Distributions (SSD) for the ecosystem (EFSA Scientific Committee,2018). Citation: DOI 10.5281/zenodo.4740174

Reference point information of this compound is not available!

Reference Value

Reference Value : The estimated maximum dose (on a body mass basis) or the concentration of an agent to which an individual may be exposed over a specified period without appreciable risk. Reference values are established by applying an uncertainty factor to the reference point. Examples of reference values in human health include acceptable daily intake (ADI) for food and feed additives, and pesticides, tolerable upper intake levels (UL) for vitamins and minerals, and tolerable daily intake (TDI) for contaminants and food contact materials. For acute effects and operators, the acute reference dose (ARfD) and the acceptable operator exposure level (AOEL). In animal health and the ecological area, these include safe feed concentrations and the Predicted no effect concentration (PNEC) respectively (EFSA Scientific Committee, 2018). Citation: DOI 10.5281/zenodo.4740174

Reference value information of this compound is not available!

Genotoxicity

Author	YEAR	OUTPUT ID	Genotoxicity
EFSA CONTAM	2008	103	Negative
EFSA CONTAM	2013	2396	Negative

EFSA Outputs

Output ID	Title	DOI	Published
103	Tropane alkaloids (from Datura sp)as undesirable substances in animal feed	doi:10.2903/j.efsa.2008.691	05Aug2008
2396	Scientific Opinion on Tropane alkaloids in food and feed.	doi:10.2903/j.efsa.2013.3386	15Oct2013

Receptors

Receptor	REFERENCE	EC50 [µM]	Effective Concentration [µM]
TAS2R10	details	Activated	100.00
TAS2R46	details	Activated	100.00

Consensus Spectra

Spectrum Type	Spectrum View	Description	Polarity
Experimental GCMS	view	GCMS	positive
Experimental LCMS	view	LCMS_Positive	positive
Experimental LCMS	view	LCMS_Negative	negative

Content

Compound Summary

Atropine

Description

Synonyms

ATROPINE; dl-Hyoscyamine; 51-55-8; Tropine tropate; Atropen;

FlavorDB ID

4235

PUBCHEM ID

174174

Molecular Weight

289.4

Molecular Formula

C17H23NO3

Openeye Can Smiles

CN1C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3

IUPAC Inchikey

RKUNBYITZUJHSG-PJPHBNEVSA-N

Network

Shown in network

Similarity

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Content

Compound Summary

Atropine

Description

Synonyms

ATROPINE; dl-Hyoscyamine; 51-55-8; Tropine tropate; Atropen;

FlavorDB ID

4235

PUBCHEM ID

174174

Molecular Weight

289.4

Molecular Formula

C17H23NO3

Openeye Can Smiles

CN1C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3

IUPAC Inchikey

RKUNBYITZUJHSG-PJPHBNEVSA-N

Network

Shown in network

Similarity

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OpenFoodTox: component Atropine

Reference Details

Reference Details

GC-MS Spectrum

GC-MS Spectrum

GC-MS Spectrum