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Details

Stereochemistry ACHIRAL
Molecular Formula C22H29NO2.BrH
Molecular Weight 420.383
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOBELANIDINE HYDROBROMIDE

SMILES

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

InChI

InChIKey=MTGGITMQSKBNME-NRDKKTCLSA-N
InChI=1S/C22H29NO2.BrH/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18;/h2-7,9-12,19-22,24-25H,8,13-16H2,1H3;1H/t19-,20+,21-,22+;

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 C22H29NO2
Molecular Weight 339.4712
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
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/19217305 | https://www.ncbi.nlm.nih.gov/pubmed/17658751

Lobelanidine is one of lobelia alkaloids that are the constituents of Lobelia inflata. Lobelia Chinensis Lour. (L. chinensis) is a plant of the Campanulaceae family that is commonly known as "xi-mi-cao", and "she-she-cao". It has been widely used as an antidote, diuretic, and hemostat in traditional Chinese medicine for decades. Lobelanidine is known for its emetic and anticancer activity.

Originator

Sources: Annalen der Chemie, Justus Liebigs (1925), 444, 40-68.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Synthesis of (-)-lobeline via enzymatic desymmetrization of lobelanidine.
2009 Mar 1
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:06:11 GMT 2023
Edited
by admin
on Sat Dec 16 10:06:11 GMT 2023
Record UNII
MNQ83B2861
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LOBELANIDINE HYDROBROMIDE
MI  
Common Name English
LOBELANIDINE HYDROBROMIDE [MI]
Common Name English
2,6-PIPERIDINEDIETHANOL, 1-METHYL-.ALPHA.,.ALPHA.'-DIPHENYL-, HYDROBROMIDE, (2.ALPHA.(R*),6.ALPHA.(S*))-
Systematic Name English
Code System Code Type Description
MERCK INDEX
m280
Created by admin on Sat Dec 16 10:06:11 GMT 2023 , Edited by admin on Sat Dec 16 10:06:11 GMT 2023
PRIMARY Merck Index
PUBCHEM
90478427
Created by admin on Sat Dec 16 10:06:11 GMT 2023 , Edited by admin on Sat Dec 16 10:06:11 GMT 2023
PRIMARY
CAS
6112-87-4
Created by admin on Sat Dec 16 10:06:11 GMT 2023 , Edited by admin on Sat Dec 16 10:06:11 GMT 2023
PRIMARY
FDA UNII
MNQ83B2861
Created by admin on Sat Dec 16 10:06:11 GMT 2023 , Edited by admin on Sat Dec 16 10:06:11 GMT 2023
PRIMARY