Atropine

Parasympatholytic, Muscarinic antagonist || Purified from Atropa belladonna, Datura stramonium...but found in other plants, mainly solanaceae, anticholinergic (muscarinic)competitive antagonist at central and peripheral cholinergic synapses. || sulfate salt (C17H23NO3)2.H2SO4 MW 676.8 cas 5908-99-6. || 1-hyoscyamine is the name of the active enantiomer

General

Type : Not A\/B H target, Muscarinic antagonist, Drug, Alkaloid, Natural, Azabicyclo, Propionate

Chemical_Nomenclature : endo-(+\/-)-alpha-(Hydroxymethyl)benzene-acetic acid 8-azabicyclo[3.2.1]oct-3-yl ester

Canonical SMILES :

InChI :

InChIKey :

Other name(s) : Ekomine  ||  Harvatrat  ||  Sulfatropinol  ||  hyoscyamine  ||  genatropin  ||  barbidonna  ||  atropen  ||  eyesules  ||  atropine metonitrate  ||  pylostropin  ||  Hyoscyamine (D)-  ||  HSDB 3553  ||  (+)-Atropine  ||  R-(+)-Hyoscyamine  ||  BRN 0091258  ||  (+)-Hyoscyamine  ||  Tropan-3alpha-yl  ||  (2R)-3-hydroxy-2-phenylpropanoate  ||  (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl  ||  1-hyoscyamine


MW : 289.4

Formula : C17H23NO3

CAS_number : 51-55-8

PubChem : 17184,    25817,    637577,    481107725

UniChem :

IUPHAR : 320

Wikipedia : Atropine

Target

Structures : No structure

Families : BCHE, AlphaBeta_hydrolase

References (28)

Title : Human Plasma Butyrylcholinesterase Hydrolyzes Atropine: Kinetic and Molecular Modeling Studies - Mukhametgalieva_2024_Molecules_29_2140
Author(s) : Mukhametgalieva A , Mir SA , Shaihutdinova Z , Masson P
Ref : Molecules , 29 : , 2024
Abstract :
PubMedSearch : Mukhametgalieva_2024_Molecules_29_2140
PubMedID: 38731631

Title : Application of an enantioselective LC-ESI MS\/MS procedure to determine R- and S-hyoscyamine following intravenous atropine administration in swine - John_2012_Drug.Test.Anal_4_194
Author(s) : John H , Mikler J , Worek F , Thiermann H
Ref : Drug Test Anal , 4 :194 , 2012
Abstract :
PubMedSearch : John_2012_Drug.Test.Anal_4_194
PubMedID: 21964777

Title : High-performance liquid-chromatographic tandem-mass spectrometric methods for atropinesterase-mediated enantioselective and chiral determination of R- and S-hyoscyamine in plasma - John_2010_Anal.Chim.Acta_680_32
Author(s) : John H , Eyer F , Zilker T , Thiermann H
Ref : Anal Chim Acta , 680 :32 , 2010
Abstract :
PubMedSearch : John_2010_Anal.Chim.Acta_680_32
PubMedID: 20969988

Title : The presence of atropinesterase activity in animal plasma - Harrison_2006_Naunyn.Schmiedebergs.Arch.Pharmacol_373_230
Author(s) : Harrison PK , Tattersall JE , Gosden E
Ref : Naunyn Schmiedebergs Arch Pharmacol , 373 :230 , 2006
Abstract :
PubMedSearch : Harrison_2006_Naunyn.Schmiedebergs.Arch.Pharmacol_373_230
PubMedID: 16736160

Title : The influence of peripheral site ligands on the reaction of symmetric and chiral organophosphates with wildtype and mutant acetylcholinesterases - Radic_1999_Chem.Biol.Interact_119-120_111
Author(s) : Radic Z , Taylor P
Ref : Chemico-Biological Interactions , 119-120 :111 , 1999
Abstract :
PubMedSearch : Radic_1999_Chem.Biol.Interact_119-120_111
PubMedID: 10421444

Title : Nerve agent poisoning in primates: antilethal, anti-epileptic and neuroprotective effects of GK-11 - Lallement_1998_Arch.Toxicol_72_84
Author(s) : Lallement G , Clarencon D , Masqueliez C , Baubichon D , Galonnier M , Burckhart MF , Peoc'h M , Mestries JC
Ref : Archives of Toxicology , 72 :84 , 1998
Abstract :
PubMedSearch : Lallement_1998_Arch.Toxicol_72_84
PubMedID: 9456079

Title : Effects of four anticholinesterase-anticholinergic combinations and tracheal extubation on QTc interval of the ECG, heart rate and arterial pressure - Saarnivaara_1998_Acta.Anaesthesiol.Scand_42_460
Author(s) : Saarnivaara L , Simola M
Ref : Acta Anaesthesiologica Scandinavica , 42 :460 , 1998
Abstract :
PubMedSearch : Saarnivaara_1998_Acta.Anaesthesiol.Scand_42_460
PubMedID: 9563867

Title : Paraoxon: cholinesterase-independent stimulation of transmitter release and selective block of ligand-gated ion channels in cultured hippocampal neurons - Rocha_1996_J.Pharmacol.Exp.Ther_278_1175
Author(s) : Rocha ES , Swanson KL , Aracava Y , Goolsby JE , Maelicke A , Albuquerque EX
Ref : Journal of Pharmacology & Experimental Therapeutics , 278 :1175 , 1996
Abstract :
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PubMedID: 8819500

Title : Cholinergic regulation of neurite outgrowth from isolated chick sympathetic neurons in culture - Small_1995_J.Neurosci_15_144
Author(s) : Small DH , Reed G , Whitefield B , Nurcombe V
Ref : Journal of Neuroscience , 15 :144 , 1995
Abstract :
PubMedSearch : Small_1995_J.Neurosci_15_144
PubMedID: 7823125

Title : Effect of atropine and bispyridinium oximes on respiratory and circulatory function in guinea-pigs poisoned by sarin - Worek_1995_Toxicology_95_123
Author(s) : Worek F , Kirchner T , Szinicz L
Ref : Toxicology , 95 :123 , 1995
Abstract :
PubMedSearch : Worek_1995_Toxicology_95_123
PubMedID: 7825179

Title : Accumulation of enkephalin, proenkephalin mRNA, and neuropeptide Y in immunologically denervated rat adrenal glands: evidence for divergent peptide regulation - Brimijoin_1995_J.Neurochem_64_1281
Author(s) : Brimijoin S , Dagerlind A , Rao R , McKinzie S , Hammond P
Ref : Journal of Neurochemistry , 64 :1281 , 1995
Abstract :
PubMedSearch : Brimijoin_1995_J.Neurochem_64_1281
PubMedID: 7861161

Title : Prognostic value of serum cholinesterase in organophosphate poisoning - Nouira_1994_Chest_106_1811
Author(s) : Nouira S , Abroug F , Elatrous S , Boujdaria R , Bouchoucha S
Ref : Chest , 106 :1811 , 1994
Abstract :
PubMedSearch : Nouira_1994_Chest_106_1811
PubMedID: 7988206

Title : Correlation of time course of blood cholinesterase activity and toxic manifestations of acute methylparathion in antidote treated rats - Venkataraman_1994_Ind.J.Physiol.Pharmacol_38_214
Author(s) : Venkataraman BV , Rani MA , Andrade C , Joseph T
Ref : Indian Journal of Physiology & Pharmacology , 38 :214 , 1994
Abstract :
PubMedSearch : Venkataraman_1994_Ind.J.Physiol.Pharmacol_38_214
PubMedID: 7814086

Title : Emergency care of insecticide poisonings - Hillman_1994_J.Florida.Med.Assoc_81_750
Author(s) : Hillman JV
Ref : Journal of the Florida Medical Association , 81 :750 , 1994
Abstract :
PubMedSearch : Hillman_1994_J.Florida.Med.Assoc_81_750
PubMedID: 7815041

Title : Study of respiratory failure in organophosphate and carbamate poisoning - Goswamy_1994_Heart.Lung_23_466
Author(s) : Goswamy R , Chaudhuri A , Mahashur AA
Ref : Heart & Lung , 23 :466 , 1994
Abstract :
PubMedSearch : Goswamy_1994_Heart.Lung_23_466
PubMedID: 7852061

Title : Primate performance decrements following acute soman exposure: failure of chemical countermeasures - Blick_1994_Pharmacol.Biochem.Behav_49_503
Author(s) : Blick DW , Murphy MR , Brown GC , Hartgraves SL
Ref : Pharmacology, Biochemistry & Behavior , 49 :503 , 1994
Abstract :
PubMedSearch : Blick_1994_Pharmacol.Biochem.Behav_49_503
PubMedID: 7862701

Title : Age-related changes of cholinergic markers in the rat brain - Yufu_1994_Japan.J.Pharmacol_66_247
Author(s) : Yufu F , Egashira T , Yamanaka Y
Ref : Japanese Journal of Pharmacology , 66 :247 , 1994
Abstract :
PubMedSearch : Yufu_1994_Japan.J.Pharmacol_66_247
PubMedID: 7869609

Title : Effect of atropine, HLo 7 and HI 6 on respiratory and circulatory function in guinea-pigs poisoned by O-ethyl S-[2-(diisopropylamino) ethyl] methylphosponothioate (VX) - Worek_1994_Pharmacol.Toxicol_75_302
Author(s) : Worek F , Kirchner T , Szinicz L
Ref : Pharmacol Toxicol , 75 :302 , 1994
Abstract :
PubMedSearch : Worek_1994_Pharmacol.Toxicol_75_302
PubMedID: 7870702

Title : SR 46559A: a novel and potent muscarinic compound with no cholinergic syndrome - Kan_1993_Psychopharmacology_112_219
Author(s) : Kan JP , Steinberg R , Oury-Donat F , Michaud JC , Thurneyssen O , Terranova JP , Gueudet C , Souilhac J , Brodin R , Boigegrain R , et al.
Ref : Psychopharmacology , 112 :219 , 1993
Abstract :
PubMedSearch : Kan_1993_Psychopharmacology_112_219
PubMedID: 7871023

Title : [A study on acute organophosphorus poisoning--changes in the activity and isoenzyme patterns of serum cholinesterase in human poisoning]. [Japanese] - Yamanaka_1993_Japanese.J.Hyg_48_955
Author(s) : Yamanaka S , Yoshida M , Yamamura Y , Nishimura M , Takaesu Y
Ref : Nippon Eiseigaku Zasshi Japanese Journal of Hygiene , 48 :955 , 1993
Abstract :
PubMedSearch : Yamanaka_1993_Japanese.J.Hyg_48_955
PubMedID: 8107298

Title : Structure-activity relationship of reversible cholinesterase inhibitors including paraquat - Seto_1988_Arch.Toxicol_62_37
Author(s) : Seto Y , Shinohara T
Ref : Archives of Toxicology , 62 :37 , 1988
Abstract :
PubMedSearch : Seto_1988_Arch.Toxicol_62_37
PubMedID: 3190453

Title : Hydrodynamic characterization of the size and shape of atropinesterase from Pseudomonas putida - van der Drift_1987_Biochim.Biophys.Acta_912_167
Author(s) : van der Drift AC , Sluiter W , Berends F
Ref : Biochimica & Biophysica Acta , 912 :167 , 1987
Abstract :
PubMedSearch : van der Drift_1987_Biochim.Biophys.Acta_912_167
PubMedID: 3828356

Title : Comparison of the active sites of atropinesterase and some serine proteases by spin-labeling - van der Drift_1985_Biochemistry_24_5333
Author(s) : van der Drift AC , Moes GW , van der Drift E , Rousseeuw BA
Ref : Biochemistry , 24 :5333 , 1985
Abstract :
PubMedSearch : van der Drift_1985_Biochemistry_24_5333
PubMedID: 3000432

Title : P NMR and mass spectrometry of atropinesterase and some serine proteases phosphorylated with a transition-state analogue - van der Drift_1985_Biochemistry_24_6894
Author(s) : van der Drift AC , Beck HC , Dekker WH , Hulst AG , Wils ER
Ref : Biochemistry , 24 :6894 , 1985
Abstract :
PubMedSearch : van der Drift_1985_Biochemistry_24_6894
PubMedID: 3907704

Title : In vivo detection of rabbit atropinesterase - Linn_1979_Lab.Anim.Sci_29_335
Author(s) : Linn JM , Liebenberg SP
Ref : Lab Anim Sci , 29 :335 , 1979
Abstract :
PubMedSearch : Linn_1979_Lab.Anim.Sci_29_335
PubMedID: 502459

Title : Resolution, purification and characterization of rabbit serum atropinesterase and cocainesterase -
Author(s) : Cauthen SE , Ellis RD , Larrison SB , Kidd MR
Ref : Biochemical Pharmacology , 25 :181 , 1976
PubMedID: 4075

Title : Genetic polymorphism of plasma carboxylesterases in the rabbit: correlation with pharmacologic and toxicologic effects -
Author(s) : Ecobichon DJ , Comeau AM
Ref : Toxicol Appl Pharmacol , 27 :28 , 1974
PubMedID: 4852152

Title : Serum esterase genetics in rabbits. I. Phenotypic variation of the prealbumin esterases and classification of atropinesterase and cocainesterase -
Author(s) : Van Zutphen LF
Ref : Biochemical Genetics , 12 :309 , 1974
PubMedID: 4441364