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Cytisine information


Cytisine
Clinical data
Other namesCytisine; Baptitoxine; Sophorine
License data
  • US DailyMed: Cytisine
ATC code
  • N07BA04 (WHO)
Identifiers
IUPAC name
  • (1R,5S)-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,3]diazocin-8-one
CAS Number
  • 485-35-8
PubChem CID
  • 10235
IUPHAR/BPS
  • 5347
DrugBank
  • DB09028
ChemSpider
  • 9818
UNII
  • 53S5U404NU
ChEBI
  • CHEBI:4055
ChEMBL
  • ChEMBL497939
CompTox Dashboard (EPA)
  • DTXSID00883395 Edit this at Wikidata
ECHA InfoCard100.006.924 Edit this at Wikidata
Chemical and physical data
FormulaC11H14N2O
Molar mass190.246 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point152 °C (306 °F)
Boiling point218 °C (424 °F)
SMILES
  • O=C1/C=C\C=C2/N1C[C@@H]3CNC[C@H]2C3
InChI
  • InChI=1S/C11H14N2O/c14-11-3-1-2-10-9-4-8(5-12-6-9)7-13(10)11/h1-3,8-9,12H,4-7H2/t8-,9+/m0/s1
  • Key:ANJTVLIZGCUXLD-DTWKUNHWSA-N

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.[1] Although widely used for smoking cessation in Eastern Europe, cytisine remains relatively unknown beyond it.[citation needed] However, it has been found effective in several randomized clinical trials, including some in the United States and a large one in New Zealand,[1] and is being investigated in additional trials in the United States (being conducted by Achieve Life Sciences) 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).[2] It has also been used entheogenically via mescalbeans by some Native American groups, historically in the Rio Grande Valley predating even peyote.[3]

  1. ^ a b Walker N, Howe C, Glover M, McRobbie H, Barnes J, Nosa V, et al. (December 2014). "Cytisine versus nicotine for smoking cessation". The New England Journal of Medicine. 371 (25): 2353–2362. doi:10.1056/nejmoa1407764. PMID 25517706. S2CID 13759117.
  2. ^ Thomas D, Farrell M, McRobbie H, Tutka P, Petrie D, West R, et al. (May 2019). "The effectiveness, safety and cost-effectiveness of cytisine versus varenicline for smoking cessation in an Australian population: a study protocol for a randomized controlled non-inferiority trial" (PDF). Addiction. 114 (5): 923–933. doi:10.1111/add.14541. PMID 30589984. S2CID 58621453.
  3. ^ Howard JH (1957). "The Mescal Bean Cult of the Central and Southern Plains: An Ancestor of the Peyote Cult". American Anthropologist. 59 (1): 75–87. doi:10.1525/aa.1957.59.1.02a00070. JSTOR 666531.

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Cytisine

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Cytisine, also known as baptitoxine, cytisinicline, or sophorine, is an alkaloid that occurs naturally in several plant genera, such as Laburnum and Cytisus...

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List of plants used for smoking

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Eschscholzia californica ~ California poppy Euchresta japonica Regel ~ Cytisine Eucommia ulmoides Fittonia albivenis Heimia montana Heimia myrtifolia Heimia...

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Varenicline

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led to use as a cessation aid in eastern Europe and extraction of cytisine. Cytisine analogs led to varenicline at Pfizer. Varenicline received a priority...

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Laburnum anagyroides

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The seeds are legumes with large numbers of black seeds that contain cytisine, an alkaloid somewhat poisonous to humans as well as goats and horses,...

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Nicotinic agonist

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endogenous agonist of nAChRs), choline, epibatidine, lobeline, varenicline and cytisine. Nicotine has been known for centuries for its intoxicating effect. It...

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Wisteria frutescens

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structure and in effects to the alkaloid cytisine, but less potent. It has a bittersweet taste. As with the cytisine-containing Laburnum, its leaves are sometimes...

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Quinolizidine alkaloids

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angustifoline the α-pyridone type with 25 structures, including anagyrine and cytisine the matrine type with 31 structures, including matrine and the ormosanin...

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Kentucky coffeetree

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miniature seedless pods. The beans are commonly thought to contain the toxin cytisine, although this has yet to be confirmed in a study. Bark: Tan or dark gray...

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Nicotine withdrawal

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Other medication used for quitting smoking include bupropion, varenicline, cytisine, nortriptyline, and clonidine and psychedelics. Treatments other than medication...

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Laburnum

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times the convulsions are markedly tetanic. The main toxin in the plant is cytisine, a nicotinic receptor agonist. It is used as a food plant by the larvae...

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Nicotine dependence

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medications (nicotine replacement therapy, bupropion, varenicline, or cytisine) and behavioral counseling, can double or triple a smoker's chances of...

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Cytisus scoparius

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relationship with Rhizobium bacteria. One of the main alkaloids of this plant is cytisine. The characteristic constituents are biogenic amines (mostly tyramine in...

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Styphnolobium japonicum

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and kaempferol-3-rhamnodiglucoside. The fruit also contain the alkaloids cytisine, N-methylcytisine, sophocarpine, matrine and stizolamine. "Styphnolobium...

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Cocaine

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ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543...

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MDMA

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ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543...

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Retama monosperma

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and Phyllonorycter spartocytisi feed on R. monosperma. The seeds contain cytisine, a toxic alkaloid. Fifteen other quinolizidine and three dipiperidine alkaloids...

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Ketamine

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hydroxynaphthoate Butinoline Butyrylcholine Carbachol Choline Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium...

Word Count : 11403

Cotinine

Last Update:

Anderson DJ, Arneric SP (March 1994). "Nicotinic receptor binding of [3H]cytisine, [3H]nicotine and [3H]methylcarbamylcholine in rat brain". European Journal...

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Retama

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incorporated into the genus Genista (see Genisteae). The species contain cytisine, a toxic alkaloid. In the Spanish language the name retama is commonly...

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Dermatophyllum secundiflorum

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but is also extremely toxic due to the presence of the bicyclic alkaloid cytisine, which is chemically related to nicotine. The consumption of a single seed...

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Methamphetamine

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ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543...

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Anticholinergic

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hydroxynaphthoate Butinoline Butyrylcholine Carbachol Choline Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium...

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Ginseng

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ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543...

Word Count : 3105

Quinolizidine

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is a nitrogen-containing heterocyclic compound. Some alkaloids (e.g. cytisine and sparteine) are derivatives of quinolizidine. Quinolizidine alkaloids...

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Methadone

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hydroxynaphthoate Butinoline Butyrylcholine Carbachol Choline Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium...

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List of poisonous plants

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are poisonous and can be lethal if consumed in excess. The main toxin is cytisine, a nicotinic receptor agonist. Symptoms of poisoning may include intense...

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Nitrous oxide

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hydroxynaphthoate Butinoline Butyrylcholine Carbachol Choline Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium...

Word Count : 10073

Caffeine

Last Update:

ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543...

Word Count : 19814

Dermatophyllum

Last Update:

All parts of the mescalbeans are very poisonous, containing the alkaloid cytisine (not mescaline, as suggested by the name). Nevertheless, evidence exists...

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