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C2899

Sigma-Aldrich

Cytisine

≥99%, powder

Synonyme(s) :

(−)-Cytisine, (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido[1,2a][1,5]diazocin-8-one, (1S,9S)-3,11-Diazatricyclo[7.3.1.03,8]trideca-5,7-dien-4-one, Baptitoxin, Laburnin, Sophorine, Ulexine

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About This Item

Formule empirique (notation de Hill):
C11H14N2O
Numéro CAS:
485-35-8
Poids moléculaire :
190.24
Numéro CE :
207-616-0
Numéro MDL:
MFCD00136048
Code UNSPSC :
12352210
ID de substance PubChem :
24892544
Nomenclature NACRES :
NA.77

Pureté

≥99%

Forme

powder

Couleur

light yellow

Point d'ébullition

218 °C/2 mmHg (lit.)

Pf

154-156 °C (lit.)

Chaîne SMILES 

O=C1C=CC=C2C3CNCC(C3)CN12

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

Clé InChI

ANJTVLIZGCUXLD-DTWKUNHWSA-N

Informations sur le gène

rat ... Chrna2(170945) , Chrna3(25101) , Chrna4(25590)

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Description générale

Cytisine is an alkaloid present in Cytisus laburnum, particularly in its seeds. It might be effective for smoking cessation. Cytisine is a natural insecticide. It has a molecular structure similar to nicotine. Cytisine may have antidepressant like properties.

Actions biochimiques/physiologiques

Potent agonist at α3β4 and α7 nicotinic acetylcholine receptors and partial agonist at α4β2 nicotinic acetylcholine receptors.

Caractéristiques et avantages

This compound is featured on the Acetylcholine Receptors (Nicotinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301 + H311 + H331

Classification des risques

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Bruno Tasso et al.
Journal of medicinal chemistry, 52(14), 4345-4357 (2009-06-25)
The availability of drug affecting neuronal nicotinic acetylcholine receptors (nAChRs) may have important therapeutic potential for the treatment of several CNS pathologies. Pursuing our efforts on the systematic structural modification of cytisine and N-arylalkyl and N-aroylalkyl cytisines were synthesized and
Michael J Marks et al.
Journal of neurochemistry, 130(2), 185-198 (2014-03-26)
Nicotinic acetylcholine receptors (nAChR) of the α6β2* subtype (where *indicates the possible presence of additional subunits) are prominently expressed on dopaminergic neurons. Because of this, their role in tobacco use and nicotine dependence has received much attention. Previous studies have
Edwin G Pérez et al.
Natural product reports, 29(5), 555-567 (2012-03-01)
Covering: up to the end of 2011. This review covers classical and modern structural modifications of the alkaloid, the more recent (since 2007) syntheses of cytisine and analogues, and the pharmacology of these compounds, with emphasis on their interactions with
Yann S Mineur et al.
Neuropharmacology, 52(5), 1256-1262 (2007-02-27)
The nicotine in tobacco is thought to modulate neuronal systems regulating mood. Moreover, it appears possible that blockade rather than activation of beta2-containing (beta2*) nicotinic acetylcholine receptors (nAChRs) may lead to antidepressant-like effects. We used cytisine, a partial agonist of
Mariaelvina Sala et al.
British journal of pharmacology, 168(4), 835-849 (2012-09-11)
Many of the addictive and rewarding effects of nicotine are due to its actions on the neuronal nicotinic ACh receptor (nAChR) subtypes expressed in dopaminergic mesocorticolimbic cells. The partial agonists, cytisine and varenicline, are helpful smoking cessation aids. These drugs
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