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712264

Sigma-Aldrich

Cytisine

≥99.0% (HPLC), ≥99%

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:
12352200
PubChem Substance ID:
329763123
NACRES:
NA.22

Assay

≥99%
≥99.0% (HPLC)

form

powder

optical activity

[α]/D -108±3°, c = 1% in ethanol

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

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General description

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.

Application

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.

Biochem/physiol Actions

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

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ3127
BCCG6368
BCBZ9991
BCCD2663
BCBV0078

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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
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)
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
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
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
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