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Merck

A0257

Atropine sulfate salt monohydrate

≥97% (TLC), crystalline, cholinergic receptor antagonist

Synonym(s):

α-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, Tropine tropate

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About This Item

Linear Formula:
(C17H23NO3)2 · H2SO4 · H2O
CAS Number:
5908-99-6
Molecular Weight:
694.83
NACRES:
NA.32
PubChem Substance ID:
57653815
UNSPSC Code:
12352210
EC Number:
200-235-0
MDL number:
MFCD00074815
Beilstein/REAXYS Number:
6109275

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Product Name

Atropine sulfate salt monohydrate, ≥97% (TLC), crystalline

InChI key

JPKKQJKQTPNWTR-CHYDPLAESA-N

InChI

1S/2C17H23NO3.H2O4S.H2O/c2*1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12;1-5(2,3)4;/h2*2-6,13-16,19H,7-11H2,1H3;(H2,1,2,3,4);1H2/t2*13-,14+,15+,16?;;

SMILES string

O.OS(O)(=O)=O.CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)c3ccccc3.CN4[C@H]5CC[C@@H]4C[C@@H](C5)OC(=O)C(CO)c6ccccc6

assay

≥97% (TLC)

form

crystalline

color

white

mp

189-192 °C (A) (lit.)

solubility

ethanol: 200 mg/mL (stable for several days at 4 °C.)
glycerol: 400 mg/mL (stable for several days at 4 °C.)
H2O: 50 mg/mL (stable for several days at 4 °C.)

Quality Level

200

Gene Information

human ... CHRM1(1128), CHRM2(1129), CHRM3(1131), CHRM4(1132), CHRM5(1133)

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Application

Atropine sulfate salt hydrate has been used:
  • to assay specific binding of high-affinity 3-quinuclidinyl benzilate-3H ([3H]QNB) to the muscarinic acetylcholine receptor (mAChR)
  • to block the recovery phase of the aldicarb (Ald) response
  • as an analyte for liquid chromatography with tandem mass spectrometry (LC-MS/MS)
  • as a mAChR antagonist to block acetylcholine receptor

Biochem/physiol Actions

Competitive nonselective antagonist at central and peripheral muscarinic acetylcholine receptors.

General description

Atropine is isolated from Atropa belladonna, Datura stramonium and Mandragora officinarum. It is a tertiary amine, which acts as a cholinergic receptor antagonist.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF7835V
WXBF5209V
WXBF1811V
BCCJ0141
BCCG8993

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Faust's Anesthesiology Review E-Book (2014)
Spinalization and locomotor training differentially affect muscarinic acetylcholine receptor type 2 abutting on alpha-motoneurons innervating the ankle extensor and flexor muscles
Wikeckowska A, et al.
Journal of Neurochemistry, 147(3), 361-379 (2018)
Acute effects of drugs on C. elegans movement reveal complex responses and plasticity
Spensley MA, et al.
G3 (Bethesda, Md.), 299719-299719 (2018)
Method validation for simultaneous determination of atropine, pralidoxime and 12 organophosphorus compounds in blood samples by means of high-performance liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS).
<BIG>Marques GLM, et al</BIG>.
Journal of Chromatography. B, Biomedical Sciences and Applications, 1097, 44-53 (2018)
Laxmikant S Deshpande et al.
Toxicological sciences : an official journal of the Society of Toxicology, 116(2), 623-631 (2010-05-26)
Organophosphate (OP) compounds are among the most lethal chemical weapons ever developed and are irreversible inhibitors of acetylcholinesterase. Exposure to majority of OP produces status epilepticus (SE) and severe cholinergic symptoms that if left untreated are fatal. Survivors of OP
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