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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H23NO4.BrH
Molecular Weight 386.281
Optical Activity ( - )
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANISODAMINE HYDROBROMIDE

SMILES

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

InChI

InChIKey=KMYQCELRVANQNG-YXGOVGSCSA-N
InChI=1S/C17H23NO4.BrH/c1-18-12-7-13(9-15(18)16(20)8-12)22-17(21)14(10-19)11-5-3-2-4-6-11;/h2-6,12-16,19-20H,7-10H2,1H3;1H/t12-,13-,14+,15+,16-;/m0./s1

HIDE SMILES / InChI

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C17H23NO4
Molecular Weight 305.3688
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27010563

Anisodamine is a naturally occurring atropine derivative that has been isolated, synthesized and characterized by scientists in the People's Republic of China. Anisodamine is a non-specific cholinergic antagonist. Anisodamine has been shown to interact with and disrupt liposome structure which may reflect its effects on cellular membranes. Experimental evidence implicates anisodamine as an anti-oxidant that may protect against free radical-induced cellular damage. Its cardiovascular properties include depression of cardiac conduction and the ability to protect against arrhythmia induced by various agents. Anisodamine is a relatively weak alpha(1) adrenergic antagonist which may explain its vasodilating activity. Its anti-thrombotic activity may be a result of inhibition of thromboxane synthesis. Numerous therapeutic uses of anisodamine have been proposed including treatment of septic shock, various circulatory disorders, organophosphorus (OP) poisoning, migraine, gastric ulcers, gastrointestinal colic, acute glomerular nephritis, eclampsia, respiratory diseases, rheumatoid arthritis, obstructive jaundice, opiate addiction, snake bite and radiation damage protection. The primary therapeutic use of anisodamine has been for the treatment of septic shock. Several mechanisms have been proposed to explain its beneficial effect though most mechanisms are based upon the assumption that anisodamine ultimately acts by an improvement of blood flow in the microcirculation. Preliminary studies suggest another important therapeutic use of anisodamine is for the treatment of OP poisoning. Anisodamine has been employed therapeutically since 1965 in the People’s Republic of China primarily to improve blood flow in circulatory disorders such as septic shock, disseminated intravascular coagulation (DIC) and as an antidote to organophosphate poisoning.

CNS Activity

Curator's Comment: Anisodamine hardly influenced cognition at normal doses due to its extremely low blood–brain barrier permeability. Anisodamine counteracts cholinergic adverse effects and facilitates cognitive amelioration of rivastigmine. Anisodamine displays less CNS toxicity than scopolamine.

Originator

Curator's Comment: Anisodamine is a naturally occurring atropine derivative that has been isolated, synthesized and characterized by scientists in the People's Republic of China.

Approval Year

Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
PubMed

PubMed

TitleDatePubMed
A combination of neostigmine and anisodamine protects against ischemic stroke by activating α7nAChR.
2015 Jul
Establishment, Culture, and Scale-up of Brugmansia candida Hairy Roots for the Production of Tropane Alkaloids.
2016
Possible role for anisodamine in organophosphate poisoning.
2016 Jun
Patents

Patents

Sample Use Guides

Anisodamine will be given first as bolus of 10 mg, followed by 0.1-0.5mg/kg/hr.
Route of Administration: Parenteral
Anisodamine at 50 ug/ml suppressed TNF-a production in human monocytic cells after 24 hr. Anisodamine at concentration 400 ug/ml inhibited Stx2-induced TNF-a production completely.
Substance Class Chemical
Created
by admin
on Sat Dec 16 02:48:34 GMT 2023
Edited
by admin
on Sat Dec 16 02:48:34 GMT 2023
Record UNII
4RKP5CSA1O
Record Status Validated (UNII)
Record Version
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Name Type Language
ANISODAMINE HYDROBROMIDE
WHO-DD  
Common Name English
L-TROPIC ACID, 6.BETA.-HYDROXY-3.ALPHA.-TROPANYL ESTER, HYDROBROMIDE
Common Name English
(-)-6-HYDROXYHYOSCYAMINE HYDROBROMIDE
Common Name English
BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-, 6-HYDROXY-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, HYDROBROMIDE, (1R-(1.ALPHA.,3.BETA.(S*),5.ALPHA.,6.ALPHA.))-
Common Name English
HYOSCYAMINE, 6-HYDROXY-, HYDROBROMIDE
Common Name English
BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-, (1R,3S,5R,6S)-6-HYDROXY-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, HYDROBROMIDE (1:1), (.ALPHA.S)-
Common Name English
BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-, (1R,3S,5R,6S)-6-HYDROXY-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, HYDROBROMIDE, (.ALPHA.S)-
Common Name English
Anisodamine hydrobromide [WHO-DD]
Common Name English
Code System Code Type Description
SMS_ID
300000010107
Created by admin on Sat Dec 16 02:48:34 GMT 2023 , Edited by admin on Sat Dec 16 02:48:34 GMT 2023
PRIMARY
PUBCHEM
118856046
Created by admin on Sat Dec 16 02:48:34 GMT 2023 , Edited by admin on Sat Dec 16 02:48:34 GMT 2023
PRIMARY
FDA UNII
4RKP5CSA1O
Created by admin on Sat Dec 16 02:48:34 GMT 2023 , Edited by admin on Sat Dec 16 02:48:34 GMT 2023
PRIMARY
CAS
55449-49-5
Created by admin on Sat Dec 16 02:48:34 GMT 2023 , Edited by admin on Sat Dec 16 02:48:34 GMT 2023
PRIMARY