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

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H21NO3.ClH
Molecular Weight 311.804
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIHYDRO-.BETA.-ERYTHROIDINE HYDROCHLORIDE

SMILES

Cl.CO[C@H]1CC=C2CCN3CCC4=C(CC(=O)OC4)[C@]23C1

InChI

InChIKey=KEWUQAPTUPWKSX-LINSIKMZSA-N
InChI=1S/C16H21NO3.ClH/c1-19-13-3-2-12-5-7-17-6-4-11-10-20-15(18)8-14(11)16(12,17)9-13;/h2,13H,3-10H2,1H3;1H/t13-,16-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C16H21NO3
Molecular Weight 275.3428
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27940077 | https://www.ncbi.nlm.nih.gov/pubmed/23561269 | https://www.ncbi.nlm.nih.gov/pubmed/24187998

Dihydro-β-erythroidine is a competitive nicotinic acetylcholine receptor antagonist with moderate selectivity for the neuronal α4 receptor subunit. Dihydro-β-erythroidine have curare-like effects at peripheral nicotinic receptors, which include severe respiratory depression. Thus in vivo behavioral studies using Dihydro-β-erythroidine are limited. Dihydro-β-erythroidine antagonizes behavioral effects of nicotine in vivo. After s.c. administration, Dihydro-β-erythroidine was potent in blocking nicotine's effects except for antinociception. Intrathecal injection of Dihydro-β-erythroidine was effective in blocking the antinociceptive effect of nicotine.

Originator

Sources: Journal of the American Pharmaceutical Association. American Pharmaceutical Association (1946), 35, 48.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Neonicotinic analogues: selective antagonists for α4β2 nicotinic acetylcholine receptors.
2013 May 15
Patents

Patents

Sample Use Guides

Single dose is 200 mg (total dose) and 6 mg per kg.
Route of Administration: Oral
In Vitro Use Guide
Oocytes were perfused at room temperature (20—25°C), in a 300-mkl chamber with perfusion solution [115 mM NaC1, 1.8 mM CaC12, 2.5 mM KC1, 10 mM HEPES (pH 7.2), and 1.0 mkM atropine 1. Perfusion was at a continuous rate of ~20 ml/min. ACh was diluted in perfusion solution, and the oocytes were exposed to ACh for ~10 s, using a solenoid valve. DH/3E sensitivity was tested by measuring the reduction of ACh-induced current responses when Dihydro-β-erythroidine was coapplied with ACh. The ACh-induced response recorded during coapplication with Dihydro-β-erythroidine is reported as a percentage of the response to ACh alone. Current responses to agonist application were measured under two-electrode voltage-clamp using a Knight Industrial Technologies (Miami, FL, U.S.A.) unit. All experiments were conducted at a holding potential of —70 mV, except for someof the ACh dose—responseand Dihydro-β-erythroidine dose—inhibition experiments involving alpha4/beta2 and alpha2/beta4, which were done at —30 mY. We have found that pharmacological measurements are identical at both holding potentials. Micropipettes were filled with 3 M KC1 and had resistances of 0.5—3.0 M. Agonist-induced responses were captured, stored, and analyzed on a Macintosh IIci computer using a data acquisition program written with LabVIEW (National Instruments) and LIBI (University of Arizona) software
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:32:54 GMT 2023
Edited
by admin
on Sat Dec 16 09:32:54 GMT 2023
Record UNII
03D77SZX4M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIHYDRO-.BETA.-ERYTHROIDINE HYDROCHLORIDE
MI  
Common Name English
1H,12H-BENZO(I)PYRANO(3,4-G)INDOLIZIN-12-ONE, 2,3,5,6,8,9,10,13-OCTAHYDRO-2-METHOXY-, HYDROCHLORIDE, (2S-(2R*,13BR*))-
Systematic Name English
2,7-DIHYDRO-.BETA.-ERYTHROIDINE HYDROCHLORIDE
Common Name English
DIHYDRO-.BETA.-ERYTHROIDINE HYDROCHLORIDE [MI]
Common Name English
Code System Code Type Description
MERCK INDEX
m4462
Created by admin on Sat Dec 16 09:32:54 GMT 2023 , Edited by admin on Sat Dec 16 09:32:54 GMT 2023
PRIMARY Merck Index
FDA UNII
03D77SZX4M
Created by admin on Sat Dec 16 09:32:54 GMT 2023 , Edited by admin on Sat Dec 16 09:32:54 GMT 2023
PRIMARY
CAS
1328-90-1
Created by admin on Sat Dec 16 09:32:54 GMT 2023 , Edited by admin on Sat Dec 16 09:32:54 GMT 2023
PRIMARY
PUBCHEM
23617475
Created by admin on Sat Dec 16 09:32:54 GMT 2023 , Edited by admin on Sat Dec 16 09:32:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID10927830
Created by admin on Sat Dec 16 09:32:54 GMT 2023 , Edited by admin on Sat Dec 16 09:32:54 GMT 2023
PRIMARY