ChemFOnt: Showing chemical card for Atropine (CFc000009063)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:05 UTC

Chemfont ID

CFc000009063

Molecule Identification

Common Name

Atropine

Definition

Atropine is found in burdock. Atropine is a naturally occurring belladonna alkaloid originally from Atropa belladonna, but found in other plants, mainly solanaceae. It is a racemic mixture of equal parts of d- and l-hyoscyamine, whose activity is due almost entirely to the levo isomer of the drug. Atropine is commonly classified as an anticholinergic or antiparasympathetic (parasympatholytic) drug. More precisely, however, it is termed an antimuscarinic agent since it antagonizes the muscarine-like actions of acetylcholine and other choline esters. Atropine binds to and inhibit muscarinic acetylcholine receptors, producing a wide range of anticholinergic effects. Adequate doses of atropine abolish various types of reflex vagal cardiac slowing or asystole. The drug also prevents or abolishes bradycardia or asystole produced by injection of choline esters, anticholinesterase agents or other parasympathomimetic drugs, and cardiac arrest produced by stimulation of the vagus. Atropine may also lessen the degree of partial heart block when vagal activity is an etiologic factor. Atropine in clinical doses counteracts the peripheral dilatation and abrupt decrease in blood pressure produced by choline esters. However, when given by itself, atropine does not exert a striking or uniform effect on blood vessels or blood pressure. Atropine has been shown to exhibit anti-depressant, laxative, nociceptive, thermogenic and anti-viral functions (PMID 7037102 , 12311408 , 6697194 , 6653675 , 6257827 ). Atropine belongs to the family of Phenylacetic Acid Derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Atropine	ChEBI
(-)-Hyoscyamine	ChEBI
(S)-(-)-Hyoscyamine	ChEBI
[3(S)-endo]-alpha-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester	ChEBI
Daturine	ChEBI
Duboisine	ChEBI
L-Hyoscyamine	ChEBI
L-Tropine tropate	ChEBI
Tropine, (-)-tropate	ChEBI
[3(S)-endo]-a-(Hydroxymethyl)benzeneacetate 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester	Generator
[3(S)-endo]-a-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester	Generator
[3(S)-endo]-alpha-(Hydroxymethyl)benzeneacetate 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester	Generator
[3(S)-endo]-Α-(hydroxymethyl)benzeneacetate 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester	Generator
[3(S)-endo]-Α-(hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester	Generator
L-Tropine tropic acid	Generator
Tropine, (-)-tropic acid	Generator
(Leo)-atropine	HMDB
(Leo)-hyoscyamine	HMDB
(S)-(Leo)-hyoscyamine	HMDB
(S)Atropine	HMDB
Hyocyamine	HMDB
L-Atropine	HMDB
L-Hyopscyamine	HMDB
L-Hyoscamine	HMDB
Hyoscyamine	ChEBI

Chemical Formula

C₁₇H₂₃NO₃

Average Molecular Weight

289.3694

Monoisotopic Molecular Weight

289.167793607

IUPAC Name

(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2S)-3-hydroxy-2-phenylpropanoate

Traditional Name

L-hyoscyamine

CAS Registry Number

101-31-5

SMILES

CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)[C@H](CO)C1=CC=CC=C1

InChI Identifier

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-/m1/s1

InChI Key

RKUNBYITZUJHSG-FXUDXRNXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Tropane alkaloids

Sub Class

Not Available

Direct Parent

Tropane alkaloids

Alternative Parents

Substituents

Tropane alkaloid
Beta-hydroxy acid
Monocyclic benzene moiety
Hydroxy acid
Piperidine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate (CHEBI:17486 )
Tropane alkaloids (C02046 )
Tropan alkaloids (C02046 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014712)

Source

Exogenous

Exogenous (HMDB: HMDB0014712)

Food

Vegetable

Root vegetable

Burdock (FooDB: FOOD00017)

Endogenous

Endogenous (HMDB: HMDB0014712)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Analgesic (HMDB: HMDB0014712)
Antimuscarinic (HMDB: HMDB0014712)

Antiviral agent (HMDB: HMDB0014712)
Bronchodilator agent (HMDB: HMDB0014712)
Central nervous system depressant (HMDB: HMDB0014712)
Central nervous system stimulant (HMDB: HMDB0014712)
Mydriatic agent (HMDB: HMDB0014712)
Vasodilator agent (HMDB: HMDB0014712)

Pharmaceutical industry

Agriculture

Pesticide

Insecticide (HMDB: HMDB0014712)

Pesticide (HMDB: HMDB0014712)

Biological role

Indirect biological role

Metabotoxin

Neurotoxin (HMDB: HMDB0014712)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.52 g/L	ALOGPS
logP	2.19	ALOGPS
logP	1.57	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	15.15	ChemAxon
pKa (Strongest Basic)	9.39	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.82 m³·mol⁻¹	ChemAxon
Polarizability	31.74 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon