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712264

Sigma-Aldrich

Cytisine

≥99.0% (HPLC), ≥99%

Sinônimo(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

Fórmula empírica (Notação de Hill):
C11H14N2O
Número CAS:
485-35-8
Peso molecular:
190.24
Número CE:
207-616-0
Número MDL:
MFCD00136048
Código UNSPSC:
12352200
ID de substância PubChem:
329763123
NACRES:
NA.22

Nível de qualidade

100

Ensaio

≥99%
≥99.0% (HPLC)

Formulário

powder

atividade óptica

[α]/D -108±3°, c = 1% in ethanol

p.e.

218 °C/2 mmHg (lit.)

pf

154-156 °C (lit.)

cadeia de caracteres 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

chave InChI

ANJTVLIZGCUXLD-DTWKUNHWSA-N

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Descrição geral

Cystine ((1R,5S)-1,2,3,4,5,6-hexahydro-1,5-methano-8H-pyrido[1,2a][1,5]diazocin-8-one) displays classical antidepressant action in various animal models of antidepressant efficacy. Infrared and Raman spectral studies suggest that it has two stable conformers.
Cytisine was found to be more effective than nicotine-replacement therapy in helping smokers to quit smoking. It is an α4 β2 nicotinic receptor partial agonist. It is a plant alkaloid which is commercially extracted for use as a smoking cessation medication. Preparation of nicotine partial agonist cytisine via “in situ” Stille or Suzuki biaryl pyridine coupling has been reported. Cytisine is a competitive partial agonist at α4 subunit-containing nicotinic acetylcholine (nACh) receptors while at homomeric α7-nACh receptors it behaves as a full agonist with a relatively lower potency.

Aplicação

Cystine may be used as nicotine substitute in nicotine addiction therapy.
Cytisine is suitable for use in a study to compare the effects of varenicline and cytisine on ethanol consumption by rats bred for many generations as high ethanol drinkers.

Ações bioquímicas/fisiológicas

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

Embalagem

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictogramas

Skull and crossbones
GHS06

Palavra indicadora

Danger

Frases de perigo

H301 + H311 + H331

Classificações de perigo

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

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

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

Escolha uma das versões mais recentes:

Certificados de análise (COA)

Lot/Batch Number
BCCG6368
BCBZ9991
BCCD2663
BCBV0078
BCBR5357V

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Melatonina powder, ≥98% (TLC)

Sigma-Aldrich

M5250

Melatonina

Fluorescein (free acid) Dye content 95 %

Sigma-Aldrich

F2456

Fluorescein (free acid)

(−)-Nicotine ≥99% (GC), liquid

Sigma-Aldrich

N3876

(−)-Nicotine

B T O'Neill et al.
Organic letters, 2(26), 4201-4204 (2001-01-11)
[reaction:see text] The nicotine partial agonist cytisine was prepared in five steps featuring an "in situ" Stille or Suzuki biaryl pyridine coupling. Differentiation of the pyridyl rings was accomplished via selective benzylation and then reduction of a pyridinium ring. The
Ramón Sotomayor-Zárate et al.
Psychopharmacology, 227(2), 287-298 (2013-01-25)
Neuronal nicotinic acetylcholine receptors (nAChRs) are pharmacological targets that have recently been implicated in the reinforcing effects of many drugs of abuse, including ethanol. Varenicline and cytisine are nAChR partial agonists in clinical use as smoking cessation aids. However, their
Experimental (FT-IR and Raman) and theoretical (DFT) studies on the vibrational dynamics in cytisine.
Gornicka E, et al.
Vibrational Spectroscopy, 36(1), 105-115 (2004)
Y E Slater et al.
Neuropharmacology, 44(4), 503-515 (2003-03-21)
Cytisine (cy) is a potent and competitive partial agonist at alpha4 subunit-containing nicotinic acetylcholine (nACh) receptors while at homomeric alpha7-nACh receptors it behaves as a full agonist with a relatively lower potency. In the present study, we assessed the effects
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
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