Cytisinicline
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MedKoo CAT#: 540097

CAS#: 485-35-8

Description: Cytisinicline, also known as Cytisine, is an α3β4 nAChR agonist and an α4β2 nAChR partial agonist found in Laburnum, and Cytisus. It decreases depression-like behaviors and increases smoking cessation rates.

Chemical Structure

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Cytisinicline
CAS# 485-35-8
Instruction

Theoretical Analysis

MedKoo Cat#: 540097
Name: Cytisinicline
CAS#: 485-35-8
Chemical Formula: C11H14N2O
Exact Mass: 190.11
Molecular Weight: 190.240
Elemental Analysis: C, 69.45; H, 7.42; N, 14.73; O, 8.41

Price and Availability

Size Price Availability Quantity
1g USD 250 2 Weeks
2g USD 400 2 Weeks
5g USD 750 2 Weeks
10g USD 1250 2 Weeks
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Synonym: Baptitoxin; Citizin; HSDB 3560; HSDB3560; HSDB-3560; Laburnin; NSC 407282; NSC407282; NSC-407282; Sophorin; Cytisine; Cytisinicline

IUPAC/Chemical Name: (1R,5S)-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one

InChi Key: ANJTVLIZGCUXLD-DTWKUNHWSA-N

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

SMILES Code: O=C1C=CC=C2N1C[C@]3([H])CNC[C@@]2([H])C3

Appearance: Solid powder

Purity: >97% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 190.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Walker N, Howe C, Glover M, McRobbie H, Barnes J, Nosa V, Parag V, Bassett B, Bullen C. Cytisine versus nicotine for smoking cessation. N Engl J Med. 2014 Dec 18;371(25):2353-62. doi: 10.1056/NEJMoa1407764. PubMed PMID: 25517706.

2: Radchenko EV, Dravolina OA, Bespalov AY. Agonist and antagonist effects of cytisine in vivo. Neuropharmacology. 2015 Aug;95:206-14. doi: 10.1016/j.neuropharm.2015.03.019. Epub 2015 Mar 31. PubMed PMID: 25839895.

3: Jeong SH, Newcombe D, Sheridan J, Tingle M. Pharmacokinetics of cytisine, an α4 β2 nicotinic receptor partial agonist, in healthy smokers following a single dose. Drug Test Anal. 2015 Jun;7(6):475-82. doi: 10.1002/dta.1707. Epub 2014 Sep 17. PubMed PMID: 25231024.

4: Igari M, Alexander JC, Ji Y, Qi X, Papke RL, Bruijnzeel AW. Varenicline and cytisine diminish the dysphoric-like state associated with spontaneous nicotine withdrawal in rats. Neuropsychopharmacology. 2014 Jan;39(2):455-65. doi: 10.1038/npp.2013.216. Epub 2013 Aug 21. PubMed PMID: 23966067; PubMed Central PMCID: PMC3870769.

5: Leaviss J, Sullivan W, Ren S, Everson-Hock E, Stevenson M, Stevens JW, Strong M, Cantrell A. What is the clinical effectiveness and cost-effectiveness of cytisine compared with varenicline for smoking cessation? A systematic review and economic evaluation. Health Technol Assess. 2014 May;18(33):1-120. doi: 10.3310/hta18330. Review. PubMed PMID: 24831822; PubMed Central PMCID: PMC4780997.

6: Vakhitova YV, Farafontova EI, Zainullina LF, Vakhitov VA, Tsypysheva IP, Yunusov MS. [Search of (-)-Cytisine Derivatives as Potential Inhibitors of NF-κB and STAT1]. Bioorg Khim. 2015 May-Jun;41(3):336-45. Russian. PubMed PMID: 26502610.

7: Pieńko T, Grudzień M, Taciak PP, Mazurek AP. Cytisine basicity, solvation, logP, and logD theoretical determination as tool for bioavailability prediction. J Mol Graph Model. 2016 Jan;63:15-21. doi: 10.1016/j.jmgm.2015.11.003. Epub 2015 Nov 12. PubMed PMID: 26609940.

8: Hajek P, McRobbie H, Myers K. Efficacy of cytisine in helping smokers quit: systematic review and meta-analysis. Thorax. 2013 Nov;68(11):1037-42. doi: 10.1136/thoraxjnl-2012-203035. Epub 2013 Feb 12. Review. PubMed PMID: 23404838.

9: Zatoński W, Zatoński M. Cytisine versus nicotine for smoking cessation. N Engl J Med. 2015 Mar 12;372(11):1072. doi: 10.1056/NEJMc1500342. PubMed PMID: 25760363.

10: Grebenstein PE, Harp JL, Rowland NE. The effects of noncontingent and self-administered cytisine on body weight and meal patterns in male Sprague-Dawley rats. Pharmacol Biochem Behav. 2013 Sep;110:192-200. doi: 10.1016/j.pbb.2013.07.012. Epub 2013 Jul 20. PubMed PMID: 23876236; PubMed Central PMCID: PMC3848509.

11: Sajja RK, Rahman S. Cytisine modulates chronic voluntary ethanol consumption and ethanol-induced striatal up-regulation of ΔFosB in mice. Alcohol. 2013 Jun;47(4):299-307. doi: 10.1016/j.alcohol.2013.02.003. Epub 2013 Apr 17. PubMed PMID: 23601929.

12: Rouden J, Lasne MC, Blanchet J, Baudoux J. (-)-Cytisine and derivatives: synthesis, reactivity, and applications. Chem Rev. 2014 Jan 8;114(1):712-78. doi: 10.1021/cr400307e. Epub 2013 Oct 11. Review. PubMed PMID: 24117010.

13: Mineur YS, Einstein EB, Bentham MP, Wigestrand MB, Blakeman S, Newbold SA, Picciotto MR. Expression of the 5-HT1A serotonin receptor in the hippocampus is required for social stress resilience and the antidepressant-like effects induced by the nicotinic partial agonist cytisine. Neuropsychopharmacology. 2015 Mar;40(4):938-46. doi: 10.1038/npp.2014.269. Epub 2014 Oct 7. PubMed PMID: 25288485; PubMed Central PMCID: PMC4330507.

14: Sotomayor-Zárate R, Gysling K, Busto UE, Cassels BK, Tampier L, Quintanilla ME. Varenicline and cytisine: two nicotinic acetylcholine receptor ligands reduce ethanol intake in University of Chile bibulous rats. Psychopharmacology (Berl). 2013 May;227(2):287-98. doi: 10.1007/s00213-013-2974-3. Epub 2013 Jan 24. PubMed PMID: 23344555.

15: Stapleton JA. Cytisine is more effective than nicotine replacement for smoking cessation. Evid Based Med. 2015 Aug;20(4):130. doi: 10.1136/ebmed-2015-110188. Epub 2015 May 2. PubMed PMID: 25935656.

16: Rigotti NA. Cytisine--a tobacco treatment hiding in plain sight. N Engl J Med. 2014 Dec 18;371(25):2429-30. doi: 10.1056/NEJMe1412313. PubMed PMID: 25517710.

17: Sala M, Braida D, Pucci L, Manfredi I, Marks MJ, Wageman CR, Grady SR, Loi B, Fucile S, Fasoli F, Zoli M, Tasso B, Sparatore F, Clementi F, Gotti C. CC4, a dimer of cytisine, is a selective partial agonist at α4β2/α6β2 nAChR with improved selectivity for tobacco smoking cessation. Br J Pharmacol. 2013 Feb;168(4):835-49. doi: 10.1111/j.1476-5381.2012.02204.x. PubMed PMID: 22957729; PubMed Central PMCID: PMC3631374.

18: Pouny I, Batut M, Vendier L, David B, Yi S, Sautel F, Arimondo PB, Massiot G. Cytisine-like alkaloids from Ormosia hosiei Hemsl. & E.H. Wilson. Phytochemistry. 2014 Nov;107:97-101. doi: 10.1016/j.phytochem.2014.07.022. Epub 2014 Aug 26. PubMed PMID: 25172516.

19: Przybył AK, Kubicki M, Jastrzab R. Complexing ability of (-)-cytisine--synthesis, spectroscopy and crystal structures of the new copper and zinc complexes. J Inorg Biochem. 2014 Sep;138:47-55. doi: 10.1016/j.jinorgbio.2014.04.015. Epub 2014 May 9. PubMed PMID: 24861808.

20: Tsypysheva IP, Lobov AN, Kovalskaya AV, Petrova PR, Ivanov SP, Rameev SA, Borisevich SS, Safiullin RL, Yunusov MS. Aza-Michael reaction of 12-N-carboxamide of (-)-cytisine under high pressure conditions. Nat Prod Res. 2015;29(2):141-8. doi: 10.1080/14786419.2014.968150. Epub 2014 Oct 21. PubMed PMID: 25330752.