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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
Assay:
≥97% (TLC)
Form:
crystalline
Quality level:
200

Key Documents

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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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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)
Faust's Anesthesiology Review E-Book (2014)
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)
Ian De Proost et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 23(4), 1153-1160 (2008-12-04)
Pulmonary neuroepithelial bodies (NEBs) are densely innervated groups of complex sensory airway receptors involved in the regulation of breathing. Together with their surrounding Clara-like cells, they exhibit stem cell potential through their capacity to regenerate depopulated areas of the epithelium
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