An alkaloid and a partial agonist of nAChRs
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Cytisine

Item No. 26437

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,5S)-1,2,3,4,5,6-hexahydro-1,5-methano-8H-pyrido[1,2-a][1,5]diazocin-8-one
CAS Number
485-35-8
Synonyms
  • Baptitoxine
  • Cytiton
  • Laburnin
  • Sophorine
  • Tsitafat
Molecular Formula
C11H14N2O
Formula Weight
190.2
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 5 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
234, 309 nm
SMILES
O=C1N2C[C@]3([H])CNC[C@](C3)([H])C2=CC=C1
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

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    Product Description

    Cytisine is an alkaloid that has been found in C. laburnum.1 It is a partial agonist of nicotinic acetylcholine receptors (nAChRs) with an EC50 value of approximately 1 µM for increasing current in Xenopus oocytes expressing α4β2 subunit-containing nAChRs. Cytisine (20 nM) inhibits current induced by acetylcholine (Item No. 23829) by 50% in Xenopus oocytes expressing α4β2-subunit containing nAChRs. It binds to α2β2, α2β4, α3β2, α3β4, α4β2, and α4β4 nAChR subunits expressed in HEK293 cells with Ki values of 1.1, 5.4, 37, 220, 1.5, and 2.1 nM, respectively.2 Cytisine (3 mg/kg) reduces increases in the intracranial self-stimulation (ICSS) threshold of rats withdrawing from nicotine self-administration, indicating a decrease in the dysphoric state induced by nicotine withdrawal.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Papke, R.L., and Heinemann, S.F. Partial agonist properties of cytisine on neuronal nicotinic receptors containing the β2 subunit. Mol. Pharmacol. 45(1), 142-149 (1994).

    2. Xiao, Y., and Kellar, K.J. The comparative pharmacology and up-regulation of rat neuronal nicotinic receptor subtype binding sites stably expressed in transfected mammalian cells. J. Pharmacol. Exp. Ther. 310(1), 98-107 (2004).

    3. Igari, M., Alexander, J.C., Ji, Y., et al. Varenicline and cytisine diminish the dysphoric-like state associated with spontaneous nicotine withdrawal in rats. Neuropsychopharmacology 39(2), 455-465 (2014).