Structure via PubChem · Public domain (PubChem)
lobeline
Sign in to saveLobeline is a piperidine alkaloid found in a variety of plants, particularly those in the genus Lobelia, including Indian tobacco (Lobelia inflata), Devil's tobacco (Lobelia tupa), great lobelia (Lobelia siphilitica), Lobelia chinensis, and Hippobroma longiflora. In its pure form, it is a white amorphous powder which is freely soluble in water.
Key facts
- Drug.ChemSpiderID
- 91814
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 458947626
- Drug.IUPAC_name
- 2-((2R,6S)-6-((S)-2-Hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethanone
- Drug.image
- Lobeline structure.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 225px
- Drug.CAS_number
- 90-69-7
- Drug.ATCvet
- yes
- Drug.ATC_prefix
- V04
- Drug.ATC_suffix
- CV01
- Drug.PubChem
- 101616
- Drug.ChEBI
- 48723
- Drug.DrugBank
- DB05137
- Drug.UNII
- D0P25S3P81
- Drug.KEGG
- D02364
- Drug.ChEMBL
- 2103769
via Wikipedia infobox
Chemical data
- Formula
- C22H27NO2
- Molecular weight
- 337.5 g/mol
- IUPAC name
- 2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone
- SMILES
- CN1[C@@H](CCC[C@@H]1CC(=O)C2=CC=CC=C2)C[C@@H](C3=CC=CC=C3)O
- InChIKey
- MXYUKLILVYORSK-HBMCJLEFSA-N
- XLogP
- 3.8
- Polar surface area
- 40.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
649 papers- Lobeline for smoking cessation.The Cochrane database of systematic reviews · 2000
- Lobeline for smoking cessation.The Cochrane database of systematic reviews · 2012
- Lobeline: A multifunctional alkaloid modulates cholinergic and glutamatergic activities.IUBMB life · 2023
- From cis-Lobeline to trans-Lobeline: Study on the Pharmacodynamics and Isomerization Factors.Molecules (Basel, Switzerland) · 2022
- A novel mechanism of action and potential use for lobeline as a treatment for psychostimulant abuse.Biochemical pharmacology · 2002
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 337.20417910400005
Show 6 more facts
- chemical formula
- C₂₂H₂₇NO₂
- canonical SMILES
- CN1C(CCCC1CC(=O)C2=CC=CC=C2)CC(C3=CC=CC=C3)O
- isomeric SMILES
- CN1[C@H](C[C@H](O)C2=CC=CC=C2)CCC[C@@H]1CC(=O)C3=CC=CC=C3
- NCI Thesaurus ID
- C93261
- found in taxon
- Lobelia berlandieri
- Commons category
- Lobeline
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
5 sectionsContents
- Potential uses
- Toxicity
- Pharmacology
- See also
- References
Lobeline is a piperidine alkaloid found in a variety of plants, particularly those in the genus Lobelia, including Indian tobacco (Lobelia inflata), Devil's tobacco (Lobelia tupa), great lobelia (Lobelia siphilitica), Lobelia chinensis, and Hippobroma longiflora. In its pure form, it is a white amorphous powder which is freely soluble in water.
==Potential uses== Lobeline has been sold, in tablet form, for use as a smoking cessation aid, but scientific research has not provided supporting evidence for this use. Lobeline has also been studied for the treatment of other drug addictions such as addiction to amphetamines, cocaine, or alcohol; however, there is limited clinical evidence of any efficacy.
Excerpted from Wikipedia’s “lobeline” article, available under the CC BY-SA 4.0 licence.