Structure via PubChem · Public domain (PubChem)
cytisine
Sign in to saveAlso known as cytisin, (-)-cytisine, baptitoxine, sophorine, laburnin, baptitoxin, sophorin, (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido[1,2a][1,5]diazocin-8-one
Cytisine, also known as baptitoxine, cytisinicline, or sophorine, is an alkaloid that occurs naturally in several plant genera, such as Laburnum and Cytisus of the family Fabaceae. It has been used medically to help with smoking cessation. It has been found effective in several randomized clinical trials, including in the United States and New Zealand, and is being investigated in additional trials in the United States and a non-inferiority trial in Australia in which it is being compared head-to-head with the smoking cessation aid varenicline (sold in the United States as Chantix). It has als
Key facts
- Drug.image
- (-)-Cytisine.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Cytisine 3D ball.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- TBX-Free
- Drug.DailyMedID
- Cytisine
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- N07
- Drug.ATC_suffix
- BA04
- Drug.CAS_number
- 485-35-8
- Drug.PubChem
- 10235
- Drug.IUPHAR_ligand
- 5347
- Drug.DrugBank
- DB09028
- Drug.ChemSpiderID
- 9818
- Drug.UNII
- 53S5U404NU
- Drug.ChEBI
- 4055
- Drug.ChEMBL
- 497939
- Drug.synonyms
- Cytisine; baptitoxine; sophorine
via Wikipedia infobox
Chemical data
- Formula
- C11H14N2O
- Molecular weight
- 190.24 g/mol
- IUPAC name
- (1R,9S)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
- SMILES
- C1[C@H]2CNC[C@@H]1C3=CC=CC(=O)N3C2
- InChIKey
- ANJTVLIZGCUXLD-DTWKUNHWSA-N
- XLogP
- 0.2
- Polar surface area
- 32.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Has part
- carbon
- Mass
- 190.111
- Has use
- medication
Show 10 more facts
- chemical formula
- C₁₁H₁₄N₂O
- isomeric SMILES
- C1[C@H]2CNC[C@@H]1C3=CC=CC(=O)N3C2
- canonical SMILES
- C1C2CNCC1C3=CC=CC(=O)N3C2
- discoverer or inventor
- Alphonse Chevallier
- Commons category
- Cytisine
- time of discovery or invention
- 1818-00-00
- boiling point
- 218
- melting point
- 152.5
- different from
- cytosine
- described by source
- Encyclopædia Britannica 11th edition
Sources (6)
via Wikidata · CC0
~4 min read
Encyclopedic overview
8 sectionsContents
- Uses
- Smoking cessation
- Recreational
- Reagent for organic chemistry
- Sources
- Toxicity
- References
- External links
Cytisine, also known as baptitoxine, cytisinicline, or sophorine, is an alkaloid that occurs naturally in several plant genera, such as Laburnum and Cytisus of the family Fabaceae. It has been used medically to help with smoking cessation. It has been found effective in several randomized clinical trials, including in the United States and New Zealand, and is being investigated in additional trials in the United States and a non-inferiority trial in Australia in which it is being compared head-to-head with the smoking cessation aid varenicline (sold in the United States as Chantix). It has also been used entheogenically via mescalbeans by some Native American groups, historically in the Rio Grande Valley predating even peyote.
Cytisine is on the World Health Organization's List of Essential Medicines.
Excerpted from Wikipedia’s “cytisine” article, available under the CC BY-SA 4.0 licence.