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712264

Sigma-Aldrich

Cytisine

≥99.0% (HPLC), ≥99%

Sinónimos:

(−)-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 (notación de Hill):
C11H14N2O
Número de CAS:
485-35-8
Peso molecular:
190.24
Número CE:
207-616-0
Número MDL:
MFCD00136048
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
329763123
NACRES:
NA.22
En este momento no podemos mostrarle ni los precios ni la disponibilidad

Nivel de calidad

100

Ensayo

≥99%
≥99.0% (HPLC)

Formulario

powder

actividad óptica

[α]/D -108±3°, c = 1% in ethanol

bp

218 °C/2 mmHg (lit.)

mp

154-156 °C (lit.)

cadena 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

Clave InChI

ANJTVLIZGCUXLD-DTWKUNHWSA-N

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Descripción general

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.[1] Infrared and Raman spectral studies suggest that it has two stable conformers.[2]
Cytisine was found to be more effective than nicotine-replacement therapy in helping smokers to quit smoking.[3] 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.[4] Preparation of nicotine partial agonist cytisine via “in situ” Stille or Suzuki biaryl pyridine coupling has been reported.[5] 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.[6]

Aplicación

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.[7]

Acciones bioquímicas o fisiológicas

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

Envase

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictogramas

Skull and crossbones
GHS06

Palabra de señalización

Danger

Frases de peligro

H301 + H311 + H331

Clasificaciones de peligro

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

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

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

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Certificados de análisis (COA)

Lot/Batch Number
BCCJ3127
BCCG6368
BCBZ9991
BCCD2663
BCBV0078

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Fluorescein (free acid) Dye content 95 %

Sigma-Aldrich

F2456

Fluorescein (free acid)

(−)-Nicotina ≥99% (GC), liquid

Sigma-Aldrich

N3876

(−)-Nicotina

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
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
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
Natalie Walker et al.
BMC public health, 11, 880-880 (2011-11-23)
Smokers need effective support to maximise the chances of successful quit attempts. Current smoking cessation medications, such as nicotine replacement therapy (NRT), bupropion, nortriptyline or varenicline, have been shown to be effective in clinical trials but are underused by smokers
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