485-35-8 | Cytisine

Packsize	Purity	Availability	Price	Discounted Price
250mg	97%	in stock	$10.00	$7.00
1g	97%	in stock	$30.00	$21.00
5g	97%	in stock	$129.00	$90.00
10g	97%	in stock	$201.00	$141.00
25g	97%	in stock	$355.00	$248.00
100g	97%	in stock	$1,131.00	$792.00

Description

• Catalog Number: AB45828
• Chemical Name: Cytisine
• CAS Number: 485-35-8
• Molecular Formula: C11H14N2O
• Molecular Weight: 190.2417
• MDL Number: MFCD00000305
• SMILES: O=c1cccc2n1C[C@@H]1CNC[C@H]2C1
• NSC Number: 407282

Computed Properties

• Complexity: 332
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 2
• Heavy Atom Count: 14
• Hydrogen Bond Acceptor Count: 2
• Hydrogen Bond Donor Count: 1
• XLogP3: 0.2

Upstream Synthesis Route

The compound 1,5-Methano-8H-pyrido[1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)- is a versatile building block in chemical synthesis due to its unique structural characteristics. Its bicyclic ring system and stereochemistry make it a valuable intermediate for the synthesis of complex molecules in various fields of organic chemistry. In particular, this compound can serve as a key starting material for the creation of novel pharmaceuticals, agrochemicals, and materials with specific properties. Its rigid framework and chiral centers enable precise control over the stereochemistry of the resulting products, making it an essential component in the synthesis of enantiomerically pure compounds. This compound's reactivity and structural features make it a valuable tool for chemists seeking to design and produce advanced molecules with tailored properties and functionalities.

Literature

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• Selective deletion of the alpha5 subunit differentially affects somatic-dendritic versus axonally targeted nicotinic ACh receptors in mouse.

  The Journal of physiology 20050215

• Halogenated and isosteric cytisine derivatives with increased affinity and functional activity at nicotinic acetylcholine receptors.

  Bioorganic & medicinal chemistry letters 20050215

• Genetic correlation between the free-choice oral consumption of nicotine and alcohol in C57BL/6JxC3H/HeJ F2 intercross mice.

  Behavioural brain research 20050210

• Conformational mobility of immobilized alpha3beta2, alpha3beta4, alpha4beta2, and alpha4beta4 nicotinic acetylcholine receptors.

  Analytical chemistry 20050201

• Evidence for functional nicotinic receptors on pancreatic beta cells.

  Metabolism: clinical and experimental 20050201

• Syntheses of (+)-cytisine, (-)-kuraramine, (-)-isokuraramine, and (-)-jussiaeiine A.

  The Journal of organic chemistry 20050121

• Diversity of nicotinic receptors mediating Cl- current in Lymnaea neurons distinguished with specific agonists and antagonist.

  Neuroscience letters 20050120

• Subunit composition of nicotinic receptors in monkey striatum: effect of treatments with 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine or L-DOPA.

  Molecular pharmacology 20050101

• Synthesis and evaluation of nicotine alpha4beta2 receptor radioligand, 5-(3'-18F-fluoropropyl)-3-(2-(S)-pyrrolidinylmethoxy)pyridine, in rodents and PET in nonhuman primate.

  Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20050101

• Smoking during early pregnancy affects the expression pattern of both nicotinic and muscarinic acetylcholine receptors in human first trimester brainstem and cerebellum.

  Neuroscience 20050101

• Determination of quinolizidine alkaloids in Sophora tonkinensis by HPCE.

  Phytochemical analysis : PCA 20050101

• A phytochemical study of the quinolizidine alkaloids from Genista tenera by gas chromatography-mass spectrometry.

  Phytochemical analysis : PCA 20050101

• Effects on serotonin of (-)nicotine and dimethylphenylpiperazinium in the dorsal raphe and nucleus accumbens of freely behaving rats.

  Neuroscience 20050101

• Nicotine activation of alpha4* receptors: sufficient for reward, tolerance, and sensitization.

  Science (New York, N.Y.) 20041105

• Pharmacology of the neuronal nicotinic acetylcholine receptor of cultured Kenyon cells of the honeybee, Apis mellifera.

  Journal of comparative physiology. A, Neuroethology, sensory, neural, and behavioral physiology 20041001

• A-186253, a specific antagonist of the alpha 4 beta 2 nAChRs: its properties and potential to study brain nicotinic acetylcholine receptors.

  Neuropharmacology 20040901

• Ablation of primary afferent terminals reduces nicotinic receptor expression and the nociceptive responses to nicotinic agonists in the spinal cord.

  Journal of neurocytology 20040901

• Evaluation of (+)-sparteine-like diamines for asymmetric synthesis.

  The Journal of organic chemistry 20040820

• Maternal exposure to nicotine and chlorpyrifos, alone and in combination, leads to persistently elevated expression of glial fibrillary acidic protein in the cerebellum of the offspring in late puberty.

  Archives of toxicology 20040801

• A short synthesis of (+/-)-cytisine.

  Organic & biomolecular chemistry 20040707

• Binding and functional activity of nicotinic cholinergic receptors in selected rat brain regions are increased following long-term but not short-term nicotine treatment.

  Journal of neurochemistry 20040701

• Subunit composition and pharmacology of two classes of striatal presynaptic nicotinic acetylcholine receptors mediating dopamine release in mice.

  Molecular pharmacology 20040601

• Studies toward labeling cytisine with [11C]phosgene: rapid synthesis of a delta-lactam involving a new chemoselective lithiation-annulation method.

  The Journal of organic chemistry 20040528

• Prenatal nicotine exposure alters the response to nicotine administration in adolescence: effects on cholinergic systems during exposure and withdrawal.

  Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20040501

• Total enantioselective synthesis of (-)-cytisine.

  Organic letters 20040219

• Expression and function of neuronal nicotinic ACh receptors in rat microvascular endothelial cells.

  American journal of physiology. Heart and circulatory physiology 20040201

• Nicotinic acetylcholine receptors in mouse and rat optic nerves.

  Journal of neurophysiology 20040201

• Characterization of nicotinic receptors inducing noradrenaline release and absence of nicotinic autoreceptors in human neocortex.

  Brain research bulletin 20040201

• Recent developments in the synthesis of nicotinic acetylcholine receptor ligands.

  Current topics in medicinal chemistry 20040101

• ABT-089: pharmacological properties of a neuronal nicotinic acetylcholine receptor agonist for the potential treatment of cognitive disorders.

  CNS drug reviews 20040101

• [Application of bisalkaloid derivatives of dicarboxylic acids based on lupinine, anabasine and cytisine as cholinesterase inhibitors of various origin].

  Zhurnal evoliutsionnoi biokhimii i fiziologii 20040101

• Functional role of nicotinic acetylcholine receptors in apoptosis in HL-60 cell line.

  European journal of pharmacology 20031215

• Subtype-selective up-regulation by chronic nicotine of high-affinity nicotinic receptors in rat brain demonstrated by receptor autoradiography.

  The Journal of pharmacology and experimental therapeutics 20031201

• Characterization of human alpha 4 beta 2-nicotinic acetylcholine receptors stably and heterologously expressed in native nicotinic receptor-null SH-EP1 human epithelial cells.

  Molecular pharmacology 20031201

• Pharmacological characterization of dopamine, norepinephrine and serotonin release in the rat prefrontal cortex by neuronal nicotinic acetylcholine receptor agonists.

  Brain research 20031114

• The effects of beta3 subunit incorporation on the pharmacology and single channel properties of oocyte-expressed human alpha3beta4 neuronal nicotinic receptors.

  The Journal of biological chemistry 20031107

• Rigidified acetylcholine mimics: conformational requirements for binding to neuronal nicotinic receptors.

  Bioorganic & medicinal chemistry letters 20031103

• Characterization of neuronal nicotinic acetylcholine receptors in the membrane of unmyelinated human C-fiber axons by in vitro studies.

  Journal of neurophysiology 20031101

• Beta-amyloid peptide activates non-alpha7 nicotinic acetylcholine receptors in rat basal forebrain neurons.

  Journal of neurophysiology 20031101

• A structural model of agonist binding to the alpha3beta4 neuronal nicotinic receptor.

  British journal of pharmacology 20031101

• Potentiation of evoked calcitonin gene-related peptide release from oral mucosa: a potential basis for the pro-inflammatory effects of nicotine.

  The European journal of neuroscience 20031101

• Nitrogen substitution modifies the activity of cytisine on neuronal nicotinic receptor subtypes.

  European journal of pharmacology 20030620

• Localization of [3H]nicotine, [3H]cytisine, [3H]epibatidine, and [125I]alpha-bungarotoxin binding sites in the brain of Macaca mulatta.

  The Journal of comparative neurology 20030616

• Pharmacological characterization of recombinant bovine alpha3beta4 neuronal nicotinic receptors stably expressed in HEK 293 cells.

  Neuroscience letters 20030612

• 3D QSAR analyses-guided rational design of novel ligands for the (alpha4)2(beta2)3 nicotinic acetylcholine receptor.

  Journal of medicinal chemistry 20030522

• Spontaneously hypertensive rats: further evaluation of age-related memory performance and cholinergic marker expression.

  Journal of psychiatry & neuroscience : JPN 20030501

• Expression and functional characterisation of a human chimeric nicotinic receptor with alpha6beta4 properties.

  European journal of pharmacology 20030411

• Differential physiologic responses of alpha7 nicotinic acetylcholine receptors to beta-amyloid1-40 and beta-amyloid1-42.

  Journal of neurobiology 20030401

• Attenuation of cell adhesion in lymphocytes is regulated by CYTIP, a protein which mediates signal complex sequestration.

  The EMBO journal 20030303

• Deficiency of nicotinic acetylcholine receptor beta 4 subunit causes autonomic cardiac and intestinal dysfunction.

  Molecular pharmacology 20030301

• Cytisine derivatives as ligands for neuronal nicotine receptors and with various pharmacological activities.

  Farmaco (Societa chimica italiana : 1989) 20030301

• Halogenated cytisine derivatives as agonists at human neuronal nicotinic acetylcholine receptor subtypes.

  Neuropharmacology 20030301

• Cytisine binds with similar affinity to nicotinic alpha4beta2 receptors on the cell surface and in homogenates.

  Brain research 20030103

• Blockade of nicotine-induced locomotor sensitization by a novel neurotensin analog in rats.

  European journal of pharmacology 20030101

• Modulation of inhibitory synaptic activity by a non-alpha4beta2, non-alpha7 subtype of nicotinic receptors in the substantia gelatinosa of adult rat spinal cord.

  Pain 20030101

• Bisalkaloid derivatives of dicarboxylic acids on the basis of lupinine, anabasine, and cytisine as reversible cholinesterase inhibitors.

  Doklady. Biochemistry and biophysics 20030101

• Quinolizidine alkaloid profiles of two taxa of Teline maderensis.

  Zeitschrift fur Naturforschung. C, Journal of biosciences 20030101

• Nicotinic ACh receptor subtypes on gastrointestinally projecting neurones in the dorsal motor vagal nucleus of the rat.

  The Journal of physiology 20021215

• (+)-2,3-dehydro-10-oxo-alpha-isosparteine in Uresiphita reversalis larvae fed on Cytisus monspessulanus leaves.

  Phytochemistry 20021201

• Acetylcholine receptors and thresholds for convulsions from flurothyl and 1,2-dichlorohexafluorocyclobutane.

  Anesthesia and analgesia 20021201

• Influence of cytisine on catecholamine release in isolated perfused rat adrenal glands.

  Archives of pharmacal research 20021201

• Declines in different beta2* nicotinic receptor populations in monkey striatum after nigrostriatal damage.

  The Journal of pharmacology and experimental therapeutics 20021101

• Fast synaptic transmission mediated by alpha-bungarotoxin-sensitive nicotinic acetylcholine receptors in lamina X neurones of neonatal rat spinal cord.

  The Journal of physiology 20021101

• Nicotinic receptors regulate the release of glycine onto lamina X neurones of the rat spinal cord.

  Neuropharmacology 20021101

• Nicotinic receptor gene cluster on rat chromosome 8 in nociceptive and blood pressure hyperresponsiveness.

  Physiological genomics 20021029

• A readily-accessible (+)-sparteine surrogate.

  Journal of the American Chemical Society 20021009

• Differential regulation of nicotinic receptor-mediated neurotransmitter release following chronic (-)-nicotine administration.

  Neuropharmacology 20021001

• Study of the calcium dynamics of the human alpha4beta2, alpha3beta4 and alpha1beta1gammadelta nicotinic acetylcholine receptors.

  Naunyn-Schmiedeberg's archives of pharmacology 20020901

• Comparative pharmacology of rat and human alpha7 nAChR conducted with net charge analysis.

  British journal of pharmacology 20020901

• Pharmacological properties of nicotinic acetylcholine receptors expressed by guinea pig small intestinal myenteric neurons.

  The Journal of pharmacology and experimental therapeutics 20020901

• Pharmacological evaluation of a Br-76 analog of epibatidine: a potent ligand for studying brain nicotinic acetylcholine receptors.

  Synapse (New York, N.Y.) 20020801

• Characterization of epibatidine binding to medial habenula: potential role in analgesia.

  The Journal of pharmacology and experimental therapeutics 20020801

• Measuring nicotinic receptors with characteristics of alpha4beta2, alpha3beta2 and alpha3beta4 subtypes in rat tissues by autoradiography.

  Journal of neurochemistry 20020801

• Recent progress in the development of subtype selective nicotinic acetylcholine receptor ligands.

  Current drug targets. CNS and neurological disorders 20020801

• Autonomic function in mice lacking alpha5 neuronal nicotinic acetylcholine receptor subunit.

  The Journal of physiology 20020715

• Synthesis and biological evaluation at nicotinic acetylcholine receptors of N-arylalkyl- and N-aryl-7-azabicyclo[2.2.1]heptanes.

  Journal of medicinal chemistry 20020704

• FT-IR spectroscopic, AM1 and PM3 computational studies of conformation of natural products: cytisine.

  Talanta 20020610

• Chromaffin cell catecholamine secretion: bisindolylmaleimide compounds exhibit novel and potent antagonist effects at the nicotinic cholinergic receptor in pheochromocytoma cells.

  Molecular pharmacology 20020601

• First and second transmembrane segments of alpha3, alpha4, beta2, and beta4 nicotinic acetylcholine receptor subunits influence the efficacy and potency of nicotine.

  Molecular pharmacology 20020601

• Differential rate responses to nicotine in rat heart: evidence for two classes of nicotinic receptors.

  The Journal of pharmacology and experimental therapeutics 20020601

• Characterization of [(125) I]epibatidine binding and nicotinic agonist-mediated (86) Rb(+) efflux in interpeduncular nucleus and inferior colliculus of beta2 null mutant mice.

  Journal of neurochemistry 20020601

• Cytisine derivatives as high affinity nAChR ligands: synthesis and comparative molecular field analysis.

  Farmaco (Societa chimica italiana : 1989) 20020601

• A non-alpha7 nicotinic acetylcholine receptor modulates excitatory input to hippocampal CA1 interneurons.

  Journal of neurophysiology 20020301

• Distribution and pharmacology of alpha 6-containing nicotinic acetylcholine receptors analyzed with mutant mice.

  The Journal of neuroscience : the official journal of the Society for Neuroscience 20020215

• Protons enhance the gating kinetics of the alpha3/beta4 neuronal nicotinic acetylcholine receptor by increasing its apparent affinity to agonists.

  Molecular pharmacology 20020201

• [3H]Epibatidine binding to bovine adrenal medulla: evidence for alpha3beta4* nicotinic receptors.

  Neuroscience letters 20020125

• Loss of nicotinic receptors in monkey striatum after 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine treatment is due to a decline in alpha-conotoxin MII sites.

  Molecular pharmacology 20020101

• Differential nicotinic receptor expression in monkey basal ganglia: effects of nigrostriatal damage.

  Neuroscience 20020101

• 2-(2-Piperidyl)- and 2-(2-pyrrolidyl)chromans as nicotine agonists: synthesis and preliminary pharmacological characterization.

  Journal of medicinal chemistry 20011220

• Relationship between the increased cell surface alpha7 nicotinic receptor expression and neuroprotection induced by several nicotinic receptor agonists.

  Journal of neuroscience research 20011115

• [125/123I] 5-Iodo-3-pyridyl ethers. syntheses and binding to neuronal nicotinic acetylcholine receptors.

  Nuclear medicine and biology 20011101

• Chemical composition, nutritive value, and toxicology evaluation of Mexican wild lupins.

  Journal of agricultural and food chemistry 20011101

• Characterization of the functional subunit combination of nicotinic acetylcholine receptors in bovine adrenal chromaffin cells.

  Neuroscience letters 20011026

• Dorsal root ganglion neurons express multiple nicotinic acetylcholine receptor subtypes.

  Journal of neurophysiology 20011001

• Indolizidine and quinolizidine alkaloids.

  Natural product reports 20011001

• Spinal nicotinic receptor activity in a genetic model of hypertension.

  Clinical and experimental hypertension (New York, N.Y. : 1993) 20011001

• Agonist regulation of rat alpha 3 beta 4 nicotinic acetylcholine receptors stably expressed in human embryonic kidney 293 cells.

  Molecular pharmacology 20010901

• Activity of cytisine and its brominated isosteres on recombinant human alpha7, alpha4beta2 and alpha4beta4 nicotinic acetylcholine receptors.

  Journal of neurochemistry 20010901

• Differential effect of nicotinic agonists on the [3H]norepinephrine release from rat hippocampal slices.

  Neurochemical research 20010901

• Differential effects of chronic drug treatment on alpha3* and alpha7 nicotinic receptor binding sites, in hippocampal neurones and SH-SY5Y cells.

  British journal of pharmacology 20010801

• Synthesis and in vivo studies of the stereoisomers of N-[11C]methyl-homoepibatidine.

  Nuclear medicine and biology 20010801

• Characterization of human alpha4beta2 neuronal nicotinic receptors stably expressed in SH-EP1 cells.

  Neurochemical research 20010601

• In vitro effects of nicotine on mitochondrial respiration and superoxide anion generation.

  Brain research 20010504

• Syntheses and evaluation of halogenated cytisine derivatives and of bioisosteric thiocytisine as potent and selective nAChR ligands.

  European journal of medicinal chemistry 20010401

• Investigation of nicotine binding to THP-1 cells: evidence for a non-cholinergic binding site.

  Biochemical pharmacology 20010315

• Effect of nicotine on cerebellar granule neuron development.

  The European journal of neuroscience 20010101

• Nicotinic agonists stimulate acetylcholine release from mouse interpeduncular nucleus: a function mediated by a different nAChR than dopamine release from striatum.

  Journal of neurochemistry 20010101

• Alcohol preference: association with reduced striatal nicotinic receptors.

  Alcohol and alcoholism (Oxford, Oxfordshire) 20010101

• Nicotine-induced alterations in the expression of nicotinic receptors in primary cultures from human prenatal brain.

  Neuroscience 20010101

• Prenatal nicotine exposure is associated with an increase in [125I]epibatidine binding in discrete cortical regions in rats.

  Pharmacology, biochemistry, and behavior 20001001

• Chick optic lobe contains a developmentally regulated alpha2alpha5beta2 nicotinic receptor subtype.

  Molecular pharmacology 20000801

• Genetic and pharmacological strategies identify a behavioral function of neuronal nicotinic receptors.

  Behavioural brain research 20000801

• GTS-21, a mixed nicotinic receptor agonist/antagonist, does not affect the nicotine cue.

  Pharmacology, biochemistry, and behavior 19991001

• Inducible, heterologous expression of human alpha7-nicotinic acetylcholine receptors in a native nicotinic receptor-null human clonal line.

  Brain research 19990417

• Promiscuous coassembly of serotonin 5-HT3 and nicotinic alpha4 receptor subunits into Ca(2+)-permeable ion channels.

  Proceedings of the National Academy of Sciences of the United States of America 19980915

• ABT-594 [(R)-5-(2-azetidinylmethoxy)-2-chloropyridine]: a novel, orally effective analgesic acting via neuronal nicotinic acetylcholine receptors: I. In vitro characterization.

  The Journal of pharmacology and experimental therapeutics 19980501

• Characterization of human recombinant neuronal nicotinic acetylcholine receptor subunit combinations alpha2beta4, alpha3beta4 and alpha4beta4 stably expressed in HEK293 cells.

  The Journal of pharmacology and experimental therapeutics 19980201

• ABT-089 [2-methyl-3-(2-(S)-pyrrolidinylmethoxy)pyridine]: I. A potent and selective cholinergic channel modulator with neuroprotective properties.

  The Journal of pharmacology and experimental therapeutics 19971001

• Tacrine interacts with an allosteric activator site on alpha 4 beta 2 nAChRs in M10 cells.

  Neuroreport 19960902

• Pharmacology of the nicotinic acetylcholine receptor from fetal rat muscle expressed in Xenopus oocytes.

  European journal of pharmacology 19960815

• Stable expression, pharmacologic properties and regulation of the human neuronal nicotinic acetylcholine alpha 4 beta 2 receptor.

  The Journal of pharmacology and experimental therapeutics 19960101

• Regulation of alpha 4 beta 2 nicotinic acetylcholine receptors in M10 cells following treatment with nicotinic agents.

  Neuroreport 19950126

• A subtype of nicotinic cholinergic receptor in rat brain is composed of alpha 4 and beta 2 subunits and is up-regulated by chronic nicotine treatment.

  Molecular pharmacology 19920101

• Mediation of nicotine-induced convulsions by central nicotinic receptors of the 'C6' type.

  Neuropharmacology 19830301