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

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H19NO3.BrH
Molecular Weight 354.239
Optical Activity ( + )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of β-Erythroidine hydrobromide

SMILES

Br.CO[C@@H]1C[C@]23N(CC=C2C=C1)CCC4=C3CC(=O)OC4

InChI

InChIKey=MSKKVYOXYGLFTO-LINSIKMZSA-N
InChI=1S/C16H19NO3.BrH/c1-19-13-3-2-12-5-7-17-6-4-11-10-20-15(18)8-14(11)16(12,17)9-13;/h2-3,5,13H,4,6-10H2,1H3;1H/t13-,16-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C16H19NO3
Molecular Weight 273.327
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Beta-erythroidine is an organic heterotetracyclic indole alkaloid isolated from the seeds and other parts of Erythrina species. A drug used to produce muscle relaxation (excepting neuromuscular blocking agents). Its primary clinical and therapeutic use is the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. Also used for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in multiple sclerosis. Beta-erythroidine is a neuronal nicotinic acetylcholine receptor antagonist. The beta-erythroidine and its more potent derivative (2,7-dihydro) have been used as muscular relaxants in numerous clinical applications. This activity is attributed to a antagonistic action of the dihydro-beta-erythroidine with the nicotinic receptors of acetyl choline.

CNS Activity

Curator's Comment: Beta-erythroidine diminished the aggressive behavior in rats

Approval Year

PubMed

PubMed

TitleDatePubMed
An hypothesis concerning the molecular structure of the nicotinic acetylcholine receptor.
1980 Sep
Erythroidine alkaloids: a novel class of phytoestrogens.
2014 Jul
Patents

Sample Use Guides

Mice: b-erythroidine (i.p.) has a more potent action where the LD50 was 24 mg/kg and 29.5 mg/kg
Route of Administration: Intraperitoneal
Beta-erythroidine is void of cytotoxicity in doses up to 10 uM. Beta-erythroidine induced significant estrogenic activity starting from 1 uM. Beta-erythroidine induced a significant and dose-dependent activation of luciferase reporter gene activity in U2OS-ERα cells starting from 10 nM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 07:58:55 GMT 2023
Edited
by admin
on Sat Dec 16 07:58:55 GMT 2023
Record UNII
I4J80ABV1U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
β-Erythroidine hydrobromide
MI  
Common Name English
1H,12H-PYRANO(4',3':3,4)PYRIDO(2,1-I)INDOL-12-ONE, 2,6,8,9,10,13-HEXAHYDRO-2-METHOXY-, HYDROBROMIDE, (1:1) (2R,13BS)-
Systematic Name English
.BETA.-ERYTHROIDINE HYDROBROMIDE [MI]
Common Name English
.BETA.-ERYTHROIDINE HYDROBROMIDE, (+)-
Common Name English
Code System Code Type Description
FDA UNII
I4J80ABV1U
Created by admin on Sat Dec 16 07:58:56 GMT 2023 , Edited by admin on Sat Dec 16 07:58:56 GMT 2023
PRIMARY
PUBCHEM
76968615
Created by admin on Sat Dec 16 07:58:56 GMT 2023 , Edited by admin on Sat Dec 16 07:58:56 GMT 2023
PRIMARY
MERCK INDEX
m5008
Created by admin on Sat Dec 16 07:58:56 GMT 2023 , Edited by admin on Sat Dec 16 07:58:56 GMT 2023
PRIMARY Merck Index
CAS
297-82-5
Created by admin on Sat Dec 16 07:58:56 GMT 2023 , Edited by admin on Sat Dec 16 07:58:56 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE