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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H21NO3
Molecular Weight 275.3428
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

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

SMILES

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

InChI

InChIKey=ALSKYCOJJPXPFS-BBRMVZONSA-N
InChI=1S/C16H21NO3/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/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

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
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 09:13:05 GMT 2023
Edited
by admin
on Sat Dec 16 09:13:05 GMT 2023
Record UNII
RBN56W7U63
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIHYDRO-.BETA.-ERYTHROIDINE
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-, (2S,13BS)-
Systematic Name English
NSC-9965
Code English
DIHYDRO-.BETA.-ERYTHROIDINE [MI]
Common Name English
DHBE
Common Name English
2,7-DIHYDRO-.BETA.-ERYTHROIDINE
Common Name English
Code System Code Type Description
FDA UNII
RBN56W7U63
Created by admin on Sat Dec 16 09:13:05 GMT 2023 , Edited by admin on Sat Dec 16 09:13:05 GMT 2023
PRIMARY
MERCK INDEX
m4462
Created by admin on Sat Dec 16 09:13:05 GMT 2023 , Edited by admin on Sat Dec 16 09:13:05 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID80945945
Created by admin on Sat Dec 16 09:13:05 GMT 2023 , Edited by admin on Sat Dec 16 09:13:05 GMT 2023
PRIMARY
NSC
9965
Created by admin on Sat Dec 16 09:13:05 GMT 2023 , Edited by admin on Sat Dec 16 09:13:05 GMT 2023
PRIMARY
PUBCHEM
31762
Created by admin on Sat Dec 16 09:13:05 GMT 2023 , Edited by admin on Sat Dec 16 09:13:05 GMT 2023
PRIMARY
CAS
23255-54-1
Created by admin on Sat Dec 16 09:13:05 GMT 2023 , Edited by admin on Sat Dec 16 09:13:05 GMT 2023
PRIMARY