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712264

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
NACRES:
NA.22
PubChem Substance ID:
329763123
UNSPSC Code:
12352200
EC Number:
207-616-0
MDL number:
MFCD00136048
Assay:
≥99%, ≥99.0% (HPLC)
Form:
powder
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Quality Level

100

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

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.

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pictograms

Skull and crossbones
GHS06

signalword

Danger

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

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Articles

(+)-Sparteine Surrogate

Sigma-Aldrich.com presents an article concerning (+)-Sparteine Surrogate.

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)
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Global Trade Item Number

SKUGTIN
712264-100MG04061832844046
712264-500MG04061833228807