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C2899

Cytisine

Name: Cytisine
Brand: SIGMA

≥99%, powder

Synonym(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[7.3.1.0^3,8]trideca-5,7-dien-4-one, Baptitoxin, Laburnin, Sophorine, Ulexine

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About This Item

Empirical Formula (Hill Notation):

C₁₁H₁₄N₂O

CAS Number:

485-35-8

Molecular Weight:

190.24

NACRES:

NA.77

PubChem Substance ID:

24892544

UNSPSC Code:

12352210

EC Number:

207-616-0

MDL number:

MFCD00136048

Assay:

≥99%

Form:

powder

Quality level:

100

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Quality Level

100

assay

≥99%

form

powder

color

light yellow

bp

218 °C/2 mmHg (lit.)

mp

154-156 °C (lit.)

SMILES string

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

InChI key

ANJTVLIZGCUXLD-DTWKUNHWSA-N

Gene Information

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

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Bioactive Small Molecule Agonists

General description

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.

Biochem/physiol Actions

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

Features and Benefits

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.

pictograms

GHS06

signalword

Danger

hcodes

H301 + H311 + H331

pcodes

P261 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311

Hazard Classifications

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

Storage Class

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Information

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Differences in neonatal neurotoxicity of brominated flame retardants, PBDE 99 and TBBPA, in mice.

Henrik Viberg et al.

Toxicology, 289(1), 59-65 (2011-08-09)

Flame retardants such as polybrominated diphenyl ethers (PBDE) and tetrabromobisphenol A are used as flame retardants and detected in the environmental, wildlife species and human tissues. Exposure to PBDEs during the neonatal development of the brain has been shown to

11C-NS14492 as a novel PET radioligand for imaging cerebral alpha7 nicotinic acetylcholine receptors: in vivo evaluation and drug occupancy measurements.

Anders Ettrup et al.

Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 52(9), 1449-1456 (2011-08-11)

Small-molecule α(7) nicotinic acetylcholine receptor (α(7)nAChR) agonists are currently validated for use as treatment for cognitive disturbances in schizophrenia and in Alzheimer disease. A suitable radiolabeled α(7)nAChR PET tracer would be important for in vivo quantification of α(7)nAChR binding in

Nicotine decreases food intake through activation of POMC neurons.

Yann S Mineur et al.

Science (New York, N.Y.), 332(6035), 1330-1332 (2011-06-11)

Smoking decreases appetite, and smokers often report that they smoke to control their weight. Understanding the neurobiological mechanisms underlying the anorexic effects of smoking would facilitate the development of novel treatments to help with smoking cessation and to prevent or

Synthesis, binding, and modeling studies of new cytisine derivatives, as ligands for neuronal nicotinic acetylcholine receptor subtypes.

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

Efficacy of cytisine in helping smokers quit: systematic review and meta-analysis.

Peter Hajek et al.

Thorax, 68(11), 1037-1042 (2013-02-14)

A recent rigorous study has shown that cytisine, a low-cost drug, is effective for smoking cessation. A number of earlier studies exist, mostly from former communist countries where cytisine has been used since the 1960s. The key question now is

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Global Trade Item Number

SKU	GTIN
C2899-25MG	04061832941028
C2899-100MG	04061832941011
C2899-250MG	04061832283678
C2899-5MG	04061833484814

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