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

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H19NO3
Molecular Weight 273.327
Optical Activity ( + )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of β-Erythroidine

SMILES

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

InChI

InChIKey=PXWINCSLFXUWBZ-BBRMVZONSA-N
InChI=1S/C16H19NO3/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/t13-,16-/m0/s1

HIDE SMILES / InChI

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
96.1 µM [IC50]
1.1 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.