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C2899

Sigma-Aldrich

Cytisine

≥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[7.3.1.03,8]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
EC Number:
207-616-0
MDL number:
MFCD00136048
UNSPSC Code:
12352210
PubChem Substance ID:
24892544
NACRES:
NA.77

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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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

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301 + H311 + H331

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Kate Cahill et al.
The Cochrane database of systematic reviews, 4(4), CD006103-CD006103 (2012-04-20)
Nicotine receptor partial agonists may help people to stop smoking by a combination of maintaining moderate levels of dopamine to counteract withdrawal symptoms (acting as an agonist) and reducing smoking satisfaction (acting as an antagonist). The primary objective of this
Jean-François Etter
Archives of internal medicine, 166(15), 1553-1559 (2006-08-16)
Cytisine is an agonist of nicotinic receptors; in particular, it binds strongly with alpha(4)beta(2) nicotinic receptors. Cytisine has been used to treat tobacco dependence for 40 years in Eastern Europe. The objective of this study was to review the literature
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
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
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
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