A0132

Sigma-Aldrich

Atropine

≥99% (TLC), powder

Synonym(s):
endo-(±)-α-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, Hyoscyamine, Tropine tropate
Empirical Formula (Hill Notation):
C17H23NO3
CAS Number:
Molecular Weight:
289.37
Beilstein/REAXYS Number:
91260
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥99% (TLC)

form

powder

color

white

solubility

H2O: 2 mg/mL
dilute aqueous acid: soluble
ethanol: soluble

originator

Pfizer

SMILES string

CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)c3ccccc3

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 key

RKUNBYITZUJHSG-SPUOUPEWSA-N

Gene Information

human ... CHRM1(1128), CHRM2(1129), CHRM3(1131), CHRM4(1132), CHRM5(1133), LOC730413(730413)
mouse ... Chrm1(12669)
rat ... Chrm1(25229), Chrm2(81645), Chrm3(24260), Drd2(24318), Htr1a(24473)

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General description

Atropine, a belladonna alkaloid, is an anti-muscarinic drug. It is extracted from Atropa belladonna. Atropine is an anticholinergic agent, which is linked to passive mydriasis. It blocks acetylcholine receptors in brain and has hallucinogenic effects. Atropine eye drops are used to treat uveitis and early amblyopia. It is also used to treat nerve agents.

Application

Atropine has been used:
  • as a tastant to analyse the bitter taste perception in Drosophila larvae
  • as a muscarinic acetylcholine autoreceptors (mAChRs) antagonist to investigate the involvement of individual mAChR subtypes in the control of synapse elimination
  • to investigate the pathways of serotonin (5-HT) action in zebrafish hearts

Atropine has been used to study it′s in vitro cytotoxicity, antiviral and antimicrobial activities. It has also used to antagonize acetylcholine induced K+ current.

Packaging

1, 5, 25, 100 g in glass bottle

Biochem/physiol Actions

Atropine is used to treat myopia and ocular axial elongation in Asian children. Small dosage of atropine is used to slow down the heart rate.
Competitive nonselective antagonist at central and peripheral muscarinic acetylcholine receptors.

Reconstitution

Solutions stable for several days at 4 °C.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 1544PSN1 6.1 / PGII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Atropine for the treatment of childhood myopia
Chua WA, et al.
Ophthalmology, 113(12), 2285-2291 (2006)
Weapons of Mass Destruction: An Encyclopedia of Worldwide Policy, Technology, and History, Volume 2 (2005)
Presynaptic muscarinic acetylcholine autoreceptors (M 1, M 2 and M 4 subtypes), adenosine receptors (A 1 and A 2A) and tropomyosin-related kinase B receptor (TrkB) modulate the developmental synapse elimination process at the neuromuscular junction
Nadal L, et al.
Molecular Brain, 9(1), 67-67 (2016)
Pharmacology: Prep Manual for Undergraduates (2011)
Drug Use and Abuse (2007)

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