L0B

Alpha-Lobeline


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Chemical Component Summary

NameAlpha-Lobeline
Identifiers2-[(2R,6S)-1-methyl-6-[(2S)-2-oxidanyl-2-phenyl-ethyl]piperidin-2-yl]-1-phenyl-ethanone
FormulaC22 H27 N O2
Molecular Weight337.455
TypeNON-POLYMER
Isomeric SMILESCN1[C@@H](CCC[C@@H]1CC(=O)c2ccccc2)C[C@@H](c3ccccc3)O
InChIInChI=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-/m0/s1
InChIKeyMXYUKLILVYORSK-HBMCJLEFSA-N

Chemical Details

Formal Charge0
Atom Count52
Chiral Atom Count3
Bond Count54
Aromatic Bond Count12

Drug Info: DrugBank

DrugBank IDDB05137 
NameLobeline
Groups investigational
DescriptionAn alkaloid that has actions similar to nicotine on nicotinic cholinergic receptors but is less potent. It has been proposed for a variety of therapeutic uses including in respiratory disorders, peripheral vascular disorders, insomnia, and smoking cessation. [PubChem]
Synonyms
  • Lobeline
  • Lobelina
IndicationInvestigated for use/treatment in addictions.
Categories
  • Alkaloids
  • Autonomic Agents
  • Cholinergic Agents
  • Cholinergic Agonists
  • Ganglionic Stimulants
CAS number90-69-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Neuronal acetylcholine receptor subunit alpha-7MRCSPGGVWLALAASLLHVSLQGEFQRKLYKELVKNYNPLERPVANDSQP...unknown
Neuronal acetylcholine receptor subunit alpha-9MNWSHSCISFCWIYFAASRLRAAETADGKYAQKLFNDLFEDYSNALRPVE...unknown
Neuronal acetylcholine receptor subunit alpha-10MGLRSHHLSLGLLLLFLLPAECLGAEGRLALKLFRDLFANYTSALRPVAD...unknown
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL122270
PubChem 101616
ChEMBL CHEMBL122270
ChEBI CHEBI:48723
CCDC/CSD YIGQOV