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

Details

Stereochemistry RACEMIC
Molecular Formula C22H27NO2
Molecular Weight 337.4553
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOBELINE, (±)-

SMILES

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

InChI

InChIKey=MXYUKLILVYORSK-QHAWAJNXSA-N
InChI=1S/C22H27NO2/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/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H27NO2
Molecular Weight 337.4553
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Lobeline,(+)- is unnatural enantiomer of Lobeline. Lobeline is the main active alkaloid constituent of Lobelia inflata, a plant sometimes called “Indian tobacco” because it was initially used by Indians of North America as a tobacco substitute. The crude extract is toxic but has been widely recommended for treatment of respiratory illnesses such as asthma, bronchitis, pneumonia, and whooping cough.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.3 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Structures of Aplysia AChBP complexes with nicotinic agonists and antagonists reveal distinctive binding interfaces and conformations.
2005 Oct 19

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 08:52:33 GMT 2023
Edited
by admin
on Sat Dec 16 08:52:33 GMT 2023
Record UNII
73BJ3LA259
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LOBELINE, (±)-
Common Name English
ETHANONE, 2-((2R,6S)-6-((2S)-2-HYDROXY-2-PHENYLETHYL)-1-METHYL-2-PIPERIDINYL)-1-PHENYL-, REL-
Systematic Name English
LOBELIDINE
Brand Name English
(±)-LOBELINE
Common Name English
LOBELINE (±)-FORM [MI]
Common Name English
Code System Code Type Description
CAS
134-65-6
Created by admin on Sat Dec 16 08:52:33 GMT 2023 , Edited by admin on Sat Dec 16 08:52:33 GMT 2023
PRIMARY
PUBCHEM
5288703
Created by admin on Sat Dec 16 08:52:33 GMT 2023 , Edited by admin on Sat Dec 16 08:52:33 GMT 2023
PRIMARY
MERCK INDEX
m6879
Created by admin on Sat Dec 16 08:52:33 GMT 2023 , Edited by admin on Sat Dec 16 08:52:33 GMT 2023
PRIMARY Merck Index
FDA UNII
73BJ3LA259
Created by admin on Sat Dec 16 08:52:33 GMT 2023 , Edited by admin on Sat Dec 16 08:52:33 GMT 2023
PRIMARY