U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry EPIMERIC
Molecular Formula C17H23NO3
Molecular Weight 289.3694
Optical Activity ( + / - )
Defined Stereocenters 3 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ATROPINE

SMILES

CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)C3=CC=CC=C3

InChI

InChIKey=RKUNBYITZUJHSG-SPUOUPEWSA-N
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?

HIDE SMILES / InChI

Description

Atropine inhibits the muscarinic actions of acetylcholine on structures innervated by postganglionic cholinergic nerves, and on smooth muscles which respond to endogenous acetylcholine but are not so innervated. As with other antimuscarinic agents, the major action of atropine is a competitive or surmountable antagonism which can be overcome by increasing the concentration of acetylcholine at receptor sites of the effector organ (e.g., by using anticholinesterase agents which inhibit the enzymatic destruction of acetylcholine). The receptors antagonized by atropine are the peripheral structures that are stimulated or inhibited by muscarine (i.e., exocrine glands and smooth and cardiac muscle). Responses to postganglionic cholinergic nerve stimulation also may be inhibited by atropine but this occurs less readily than with responses to injected (exogenous) choline esters. Atropine is relatively selective for muscarinic receptors. Its potency at nicotinic receptors is much lower, and actions at non-muscarinic receptors are generally undetectable clinically. Atropine does not distinguish among the M1, M2, and M3 subgroups of muscarinic receptors.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Nicotine potentiates sulpiride-induced catalepsy in mice.
1998
The incidence of systemic side-effects following subconjunctival Mydricaine no. 1 injection.
1999 Dec
TIVA with propofol and remifentanil.
1999 May
Effects of topical glucocorticoids on in vitro lactoferrin glandular secretion: comparison between human upper and lower airways.
2000 Dec
Focal microinjection of carbachol into the periaqueductal gray induces seizures in the forebrain of the rat.
2000 Dec
Effect of alpha-2 adrenoceptor antagonists on colonic function in rats.
2000 Jun
Near fatal case of atrio-ventricular block induced by amitriptyline at therapeutic dose.
2000 Sep
SCH 23390 affords protection against soman-evoked seizures in the freely moving guinea-pig: a concomitant neurochemical, electrophysiological and behavioural study.
2001
Influence of nitric oxide donors and of the alpha(2)-agonist UK-14,304 on acetylcholine release in the pig gastric fundus.
2001
Endothelin receptors in human and guinea-pig gallbladder muscle.
2001 Apr 20
Localisation and neural control of the release of calcitonin gene-related peptide (CGRP) from the isolated perfused porcine ileum.
2001 Apr 20
Accelerated dobutamine stress testing: safety and feasibility in patients with known or suspected coronary artery disease.
2001 Feb
On the mechanisms of cholinergic control of the sinoatrial node discharge.
2001 Feb
Muscarinic receptor subtypes and calcium signaling in Fischer rat thyroid cells.
2001 Feb 1
Acetylcholine-evoked calcium increases in Deiters' cells of the guinea pig cochlea suggest alpha9-like receptors.
2001 Feb 1
Characterisation of the prejunctional inhibitory muscarinic receptor on cholinergic nerves in the rat urinary bladder.
2001 Feb 16
Facilitation of transmitter release in the urinary bladders of neonatal and adult rats via alpha1-adrenoceptors.
2001 Feb 23
Photochemical N-demethylation of alkaloids.
2001 Feb 26
[Availability of antidotes in French emergency medical aid units].
2001 Feb 3
[Experiences with cycloplegic drops in German-speaking centers of pediatric ophthalmology and stabology--results of a 1999 survey].
2001 Jan
Preanaesthetic use of atropine in small animals.
2001 Jan
Mechanisms of acetylcholine-induced vasorelaxation in high K+-stimulated rabbit renal arteries.
2001 Jan
High concentration sevoflurane induction of anesthesia accelerates onset of vecuronium neuromuscular blockade.
2001 Jan
[Marked bradycardia during anesthetic induction treated with temporary cardiac pacing in a patient with latent sick sinus syndrome].
2001 Jan
Tris(2,2'-bipyridine)ruthenium(II) electrogenerated chemiluminescence of alkaloid type drugs with solid phase extraction sample preparation.
2001 Jan
Spectral analysis of circadian rhythms in heart rate variability of dogs.
2001 Jan
Unplanned administration of atropine, succinylcholine and lidocaine.
2001 Jan
Age-related changes in cholinergic and purinergic neurotransmission in human isolated bladder smooth muscles.
2001 Jan
Characterization of a novel mechanism accounting for the adverse cholinergic effects of the anticancer drug irinotecan.
2001 Jan
Eruptive pruritic syringomas: treatment with topical atropine.
2001 Jan
Administration of atropine in the setting of acute myocardial infarction: potentiation of the ischemic process?
2001 Jan
Assessment of autonomic cardiovascular indices in non-stationary data in rats.
2001 Jan
Relaxant effect of Pimpinella anisum on isolated guinea pig tracheal chains and its possible mechanism(s).
2001 Jan
Secretion and gene expression of secretory leukocyte protease inhibitor by human airway submucosal glands.
2001 Jan
Effects of preemptive atropine administration on incidence of medetomidine-induced bradycardia in dogs.
2001 Jan 1
[Atropine. Principles and rules of utilization].
2001 Jan 15
Upregulation of immunoreactive angiotensin II release and angiotensinogen mRNA expression by high-frequency preganglionic stimulation at the canine cardiac sympathetic ganglia.
2001 Jan 19
The effect of nitrate and ammonium concentrations on growth and alkaloid accumulation of Atropa belladonna hairy roots.
2001 Jan 23
Determination of scopolamine in human serum and microdialysis samples by liquid chromatography-tandem mass spectrometry.
2001 Jan 5
Neural-epithelial cell interplay: in vitro evidence that vagal mediators increase PGE2 production by human nasal epithelial cells.
2001 Jan-Feb
Evidence of alpha-adrenoceptor-mediated chronotropic action in children.
2001 Jan-Feb
Activation of the parasympathetic nervous system is necessary for normal meal-induced insulin secretion in rhesus macaques.
2001 Mar
From 'captive' agonism to insurmountable antagonism: demonstrating the power of analytical pharmacology.
2001 Mar
Pharmacological characterization of locomotor sensitization induced by chronic phencyclidine administration.
2001 Mar
Respective roles of carbamylcholine and cyclic adenosine monophosphate in their synergistic regulation of cell cycle in thyroid primary cultures.
2001 Mar
Initiation of distension-induced descending peristaltic reflex in opossum esophagus: role of muscle contractility.
2001 Mar
Muscarinic stimulation increases basal Ca(2+) and inhibits spontaneous Ca(2+) transients in murine colonic myocytes.
2001 Mar
5-Hydroxytryptamine and atropine inhibit nicotinic receptors in submucosal neurons.
2001 Mar 2
Evidence for a direct action of Tityus serrulatus scorpion venom on the cardiac muscle.
2001 May
The role of nitric oxide on the relaxations of rabbit corpus cavernosum induced by Androctonus australis and Buthotus judaicus scorpion venoms.
2001 May
Patents

Sample Use Guides

In Vivo Use Guide
Atropine as an antisialagogue or for antivagal effects: initial single dose of 0.5 mg to 1 mg; as an antidote for organophosporous or muscarinic mushroom poisoning: initial single dose of 2 mg to 3 mg, repeated every 20­-30 minutes; for bradyasystolic cardiac arrest: 1 mg dose, repeated every 3-5 minutes if asystole persists; in patients with coronary artery disease: total dose should not exceed 0.03 mg/kg to 0.04 mg/kg.
Route of Administration: intravenous; intramuscular; subcuatenous; endotracheal
In Vitro Use Guide
Atropine in doses -5.44 to -4.74 log mol/L totally inhibited the contraction induced by acetylcholine and carbachol in segmental pulmonary artery specimens taken from the patients undergoing thoracic surgery.
Name Type Language
ATROPINE
EP   GREEN BOOK   HSDB   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
Common Name English
ATROPINE [USP]
Common Name English
ATROPINE [VANDF]
Common Name English
ATROPINE COMPONENT OF ATNAA
Common Name English
ATROPINE [HSDB]
Common Name English
(+/-)-HYOSCYAMINE
Common Name English
BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-(3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER
Common Name English
ATROPEN
Brand Name English
ATROPINE [WHO-DD]
Common Name English
HOMATROPINE HYDROBROMIDE IMPURITY D [EP]
Common Name English
ATROPINUM [HPUS]
Common Name English
ATROPINE COMPONENT OF DUODOTE
Common Name English
ATROPINE [ORANGE BOOK]
Common Name English
DUODOTE COMPONENT ATROPINE
Common Name English
ATROPINE ((+/-))
Common Name English
(3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL TROPATE
Common Name English
ATROPINE [MI]
Common Name English
ATROPINE, (+/-)-
Common Name English
ATNAA COMPONENT ATROPINE
Common Name English
ATROPINE [GREEN BOOK]
Common Name English
ATROPINE [MART.]
Common Name English
ATROPINUM
HPUS  
Common Name English
BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, ENDO-(+/-)-
Common Name English
ATROPINE [EP]
Common Name English
1.ALPHA.H,5.ALPHA.H-TROPAN-3.ALPHA.-OL (+/-)-TROPATE (ESTER)
Common Name English
DL-HYOSCYAMINE
Common Name English
Classification Tree Code System Code
NDF-RT N0000175370
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
NDF-RT N0000000125
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
WHO-ATC A03CB03
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
WHO-VATC QA03BA01
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
LIVERTOX 74
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
NDF-RT N0000175574
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
WHO-ATC S01FA01
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
NDF-RT N0000000125
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
NDF-RT N0000000125
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
NCI_THESAURUS C29704
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
WHO-ATC A03BA01
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
WHO-VATC QS01FA01
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
CFR 21 CFR 310.533
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 4.2
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
CFR 21 CFR 520.2520A
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
WHO-VATC QA03CB03
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 21.5
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 1.3
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
WHO-ATC S01BB01
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
NDF-RT N0000175700
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
Code System Code Type Description
MESH
D001285
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
PRIMARY
CAS
51-55-8
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
PRIMARY
WIKIPEDIA
ATROPINE
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
PRIMARY
NCI_THESAURUS
C28840
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
PRIMARY
LactMed
51-55-8
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
PRIMARY
EVMPD
SUB00621MIG
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
PRIMARY
ChEMBL
CHEMBL517712
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-104-8
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
PRIMARY
DRUG BANK
DB00572
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
PRIMARY
HSDB
51-55-8
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
PRIMARY
MERCK INDEX
M2136
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
PRIMARY Merck Index
RXCUI
1223
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
PRIMARY RxNorm
EPA CompTox
51-55-8
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
PRIMARY
IUPHAR
320
Created by admin on Tue Oct 22 00:49:22 UTC 2019 , Edited by admin on Tue Oct 22 00:49:22 UTC 2019
PRIMARY