In 1951, the Russian pharmacologist Mikhail Mashkovsky discovered that local villagers from the Urals used the wild snowdrop (Galanthus spp., most notably Galanthus woronowii Losinsk.) to stave off paralysis in children suffering from poliomyelitis. The ethnobotanical use of the snowdrop in the Urals led to the isolation of galanthamine for the first time in 1952, an alkaloid with AChE-inhibiting propertiesAlkaloid from caucasian snow-drop Galenthus woronowii, the common snowdrop Galanthus nivalis Ungernia genus, Amaryllidaceae, from Narcissus spp. Selectivity for AChE. The CAS number of Galanthamine Hydrobromide is 1953-04-4. || Nivalin Reminyl trademark approved for treatment of Alzheimer disease in Austria. || Galantamine is a specific competitive and reversible aceylcholinesterase inhibitor. It is also an allosteric modulator at nicotinic cholinergic receptor sites potentiating cholinergic nicotinic neurotransmission at the ganglionic and the neuromuscular junctions.
Type : Derivative of Galanthamine, Natural, Alkaloid, Drug, Benzazepin, Azepane, Multitarget, Nicotinic agonist
Chemical_Nomenclature : 1,2,3,4,6,7,7a,11c-octahydro-9-methoxy-2methylbenzofuro[4,3,2-efg][2]benzazocin-6-ol
Canonical SMILES : CN1CCC23C=CC(CC2OC4=C(C=CC(=C34)C1)OC)O
InChI : InChI=1S\/C17H21NO3\/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17\/h3-6,12,14,19H,7-10H2,1-2H3\/t12-,14-,17-\/m0\/s1
InChIKey : ASUTZQLVASHGKV-JDFRZJQESA-N
Other name(s) : Galantamine || Lycoremine || Jilkon || Nivalin || Reminyl || Razadyne
MW : 287.35
Formula : C17H21NO3
CAS_number : 357-70-0
PubChem : 9651
UniChem : ASUTZQLVASHGKV-JDFRZJQESA-N
IUPHAR : 6693
Wikipedia : Galanthamine
Families : Galanthamine ligand of proteins in family
ACHE
Structure :
1DX6
1QTI
1W6R
1W76
4EY6
Protein :
torca-ACHE
human-ACHE
Title : Therapeutic and medicinal effects of snowdrop (Galanthus spp.) in Alzheimer's disease: A review - Babashpour-Asl_2023_J.Educ.Health.Promot_12_128 |
Author(s) : Babashpour-Asl M , Kaboudi PS , Barez SR |
Ref : J Educ Health Promot , 12 :128 , 2023 |
Abstract : |
PubMedSearch : Babashpour-Asl_2023_J.Educ.Health.Promot_12_128 |
PubMedID: 37397105 |
Title : Galantamine improves glycemic control and diabetic nephropathy in Lepr(db\/db) mice - Meng_2023_Sci.Rep_13_15544 |
Author(s) : Meng Q , Ma J , Suo L , Pruekprasert N , Chakrapani P , Cooney RN |
Ref : Sci Rep , 13 :15544 , 2023 |
Abstract : |
PubMedSearch : Meng_2023_Sci.Rep_13_15544 |
PubMedID: 37731032 |
Title : Chemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae) - Tallini_2022_Plants.(Basel)_11_ |
Author(s) : Tallini LR , Osorio EH , Berkov S , Torras-Claveria L , Rodriguez-Escobar ML , Viladomat F , Meerow AW , Bastida J |
Ref : Plants (Basel) , 11 : , 2022 |
Abstract : |
PubMedSearch : Tallini_2022_Plants.(Basel)_11_ |
PubMedID: 36559661 |
Title : Loss of Basal Forebrain Cholinergic Neurons Following Adolescent Binge Ethanol Exposure: Recovery With the Cholinesterase Inhibitor Galantamine - Crews_2021_Front.Behav.Neurosci_15_652494 |
Author(s) : Crews FT , Fisher R , Deason C , Vetreno RP |
Ref : Front Behavioral Neuroscience , 15 :652494 , 2021 |
Abstract : |
PubMedSearch : Crews_2021_Front.Behav.Neurosci_15_652494 |
PubMedID: 33716687 |
Title : Gigantelline, gigantellinine and gigancrinine, cherylline- and crinine-type alkaloids isolated from Crinum jagus with anti-acetylcholinesterase activity - Ka_2020_Phytochemistry_175_112390 |
Author(s) : Ka S , Masi M , Merindol N , Di Lecce R , Plourde MB , Seck M , Gorecki M , Pescitelli G , Desgagne-Penix I , Evidente A |
Ref : Phytochemistry , 175 :112390 , 2020 |
Abstract : |
PubMedSearch : Ka_2020_Phytochemistry_175_112390 |
PubMedID: 32335411 |
Title : Cholinesterase-inhibitory effect and in silico analysis of alkaloids from bulbs of Hieronymiella species - Ortiz_2018_Phytomedicine_39_66 |
Author(s) : Ortiz JE , Garro A , Pigni NB , Aguero MB , Roitman G , Slanis A , Enriz RD , Feresin GE , Bastida J , Tapia A |
Ref : Phytomedicine , 39 :66 , 2018 |
Abstract : |
PubMedSearch : Ortiz_2018_Phytomedicine_39_66 |
PubMedID: 29433685 |
Title : Cooperative hydrogen bonds and mobility of the non-aromatic ring as selectivity determinants for human acetylcholinesterase to similar anti-Alzheimer's galantaminics: a computational study - Rocha_2018_J.Biomol.Struct.Dyn__1 |
Author(s) : Rocha REO , Lima LHF |
Ref : J Biomol Struct Dyn , :1 , 2018 |
Abstract : |
PubMedSearch : Rocha_2018_J.Biomol.Struct.Dyn__1 |
PubMedID: 29697300 |
Title : Post-Injury Administration of Galantamine Reduces Traumatic Brain Injury Pathology and Improves Outcome - Zhao_2018_J.Neurotrauma_35_362 |
Author(s) : Zhao J , Hylin MJ , Kobori N , Hood KN , Moore AN , Dash PK |
Ref : Journal of Neurotrauma , 35 :362 , 2018 |
Abstract : |
PubMedSearch : Zhao_2018_J.Neurotrauma_35_362 |
PubMedID: 29088998 |
Title : Alkaloids from Habranthus tubispathus and H. jamesonii, two amaryllidaceae with acetyl- and butyrylcholinesterase inhibition activity - Cavallaro_2014_Nat.Prod.Commun_9_159 |
Author(s) : Cavallaro V , Alza NP , Murray MG , Murray AP |
Ref : Nat Prod Commun , 9 :159 , 2014 |
Abstract : |
PubMedSearch : Cavallaro_2014_Nat.Prod.Commun_9_159 |
PubMedID: 24689279 |
Title : Galantamine potentiates the neuroprotective effect of memantine against NMDA-induced excitotoxicity - Lopes_2013_Brain.Behav_3_67 |
Author(s) : Lopes JP , Tarozzo G , Reggiani A , Piomelli D , Cavalli A |
Ref : Brain Behav , 3 :67 , 2013 |
Abstract : |
PubMedSearch : Lopes_2013_Brain.Behav_3_67 |
PubMedID: 23532860 |
Title : GC-MS of amaryllidaceous galanthamine-type alkaloids - Berkov_2012_J.Mass.Spectrom_47_1065 |
Author(s) : Berkov S , Viladomat F , Codina C , Suarez S , Ravelo A , Bastida J |
Ref : J Mass Spectrom , 47 :1065 , 2012 |
Abstract : |
PubMedSearch : Berkov_2012_J.Mass.Spectrom_47_1065 |
PubMedID: 22899516 |
Title : Structures of human acetylcholinesterase in complex with pharmacologically important ligands - Cheung_2012_J.Med.Chem_55_10282 |
Author(s) : Cheung J , Rudolph MJ , Burshteyn F , Cassidy MS , Gary EN , Love J , Franklin MC , Height JJ |
Ref : Journal of Medicinal Chemistry , 55 :10282 , 2012 |
Abstract : |
PubMedSearch : Cheung_2012_J.Med.Chem_55_10282 |
PubMedID: 23035744 |
Gene_locus related to this paper: human-ACHE |
Title : Rapid TLC\/GC-MS identification of acetylcholinesterase inhibitors in alkaloid extracts - Berkov_2008_Phytochem.Anal_19_411 |
Author(s) : Berkov S , Bastida J , Nikolova M , Viladomat F , Codina C |
Ref : Phytochem Anal , 19 :411 , 2008 |
Abstract : |
PubMedSearch : Berkov_2008_Phytochem.Anal_19_411 |
PubMedID: 18446766 |
Title : Galanthamine from snowdrop--the development of a modern drug against Alzheimer's disease from local Caucasian knowledge - Heinrich_2004_J.Ethnopharmacol_92_147 |
Author(s) : Heinrich M , Lee Teoh H |
Ref : J Ethnopharmacol , 92 :147 , 2004 |
Abstract : |
PubMedSearch : Heinrich_2004_J.Ethnopharmacol_92_147 |
PubMedID: 15137996 |
Title : The complex of a bivalent derivative of galanthamine with torpedo acetylcholinesterase displays drastic deformation of the active-site gorge: implications for structure-based drug design - Greenblatt_2004_J.Am.Chem.Soc_126_15405 |
Author(s) : Greenblatt HM , Guillou C , Guenard D , Argaman A , Botti SA , Badet B , Thal C , Silman I , Sussman JL |
Ref : Journal of the American Chemical Society , 126 :15405 , 2004 |
Abstract : |
PubMedSearch : Greenblatt_2004_J.Am.Chem.Soc_126_15405 |
PubMedID: 15563167 |
Gene_locus related to this paper: torca-ACHE |
Title : Acetylcholinesterase inhibitory activity of some Amaryllidaceae alkaloids and Narcissus extracts - Lopez_2002_Life.Sci_71_2521 |
Author(s) : Lopez S , Bastida J , Viladomat F , Codina C |
Ref : Life Sciences , 71 :2521 , 2002 |
Abstract : |
PubMedSearch : Lopez_2002_Life.Sci_71_2521 |
PubMedID: 12270757 |
Title : Galantamine: effect on nicotinic receptor binding, acetylcholinesterase inhibition, and learning - Woodruff-Pak_2001_Proc.Natl.Acad.Sci.U.S.A_98_2089 |
Author(s) : Woodruff-Pak DS , Vogel RW , Wenk GL |
Ref : Proceedings of the National Academy of Sciences of the United States of America , 98 :2089 , 2001 |
Abstract : |
PubMedSearch : Woodruff-Pak_2001_Proc.Natl.Acad.Sci.U.S.A_98_2089 |
PubMedID: 11172080 |
Title : Galantamine, a cholinesterase inhibitor that allosterically modulates nicotinic receptors: effects on the course of Alzheimer's disease - Coyle_2001_Biol.Psychiatry_49_289 |
Author(s) : Coyle J , Kershaw P |
Ref : Biological Psychiatry , 49 :289 , 2001 |
Abstract : |
PubMedSearch : Coyle_2001_Biol.Psychiatry_49_289 |
PubMedID: 11230880 |
Title : Three-dimensional structure of a complex of galanthamine (Nivalin) with acetylcholinesterase from Torpedo californica: implications for the design of new anti-Alzheimer drugs - Bartolucci_2001_Proteins_42_182 |
Author(s) : Bartolucci C , Perola E , Pilger C , Fels G , Lamba D |
Ref : Proteins , 42 :182 , 2001 |
Abstract : |
PubMedSearch : Bartolucci_2001_Proteins_42_182 |
PubMedID: 11119642 |
Gene_locus related to this paper: torca-ACHE |
Title : Potent acetylcholinesterase inhibitors: design, synthesis and structure-activity relationships of alkylene linked bis-galanthamine and galanthamine-galanthaminium salts - Guillou_2000_Bioorg.Med.Chem.Lett_10_637 |
Author(s) : Guillou C , Mary A , Renko DZ , Gras E , Thal C |
Ref : Bioorganic & Medicinal Chemistry Lett , 10 :637 , 2000 |
Abstract : |
PubMedSearch : Guillou_2000_Bioorg.Med.Chem.Lett_10_637 |
PubMedID: 10762042 |
Title : Galantamine: additional benefits to patients with Alzheimer's disease - Lilienfeld_2000_Dement.Geriatr.Cogn.Disord_11 Suppl 1_19 |
Author(s) : Lilienfeld S , Parys W |
Ref : Dementia & Geriatric Cognitive Disorders , 11 Suppl 1 :19 , 2000 |
Abstract : |
PubMedSearch : Lilienfeld_2000_Dement.Geriatr.Cogn.Disord_11 Suppl 1_19 |
PubMedID: 10971048 |
Title : Effect of the acetylcholinesterase inhibitor galanthamine on learning and memory in prolonged alcohol intake rat model of acetylcholine deficit - Iliev_1999_Methods.Find.Exp.Clin.Pharmacol_21_297 |
Author(s) : Iliev A , Traykov V , Prodanov D , Mantchev G , Yakimova K , Krushkov I , Boyadjieva N |
Ref : Methods Find Exp Clin Pharmacol , 21 :297 , 1999 |
Abstract : |
PubMedSearch : Iliev_1999_Methods.Find.Exp.Clin.Pharmacol_21_297 |
PubMedID: 10399139 |
Title : Capillary zone electrophoresis determination of galanthamine in biological fluids and pharmaceutical preparatives: experimental design and artificial neural network optimization - Pokorna_1999_Electrophoresis_20_1993 |
Author(s) : Pokorna L , Revilla A , Havel J , Patocka J |
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Abstract : |
PubMedSearch : Pokorna_1999_Electrophoresis_20_1993 |
PubMedID: 10451107 |
Title : The O-demethylation of the antidementia drug galanthamine is catalysed by cytochrome P450 2D6 - Bachus_1999_Pharmacogenet_9_661 |
Author(s) : Bachus R , Bickel U , Thomsen T , Roots I , Kewitz H |
Ref : Pharmacogenetics , 9 :661 , 1999 |
Abstract : |
PubMedSearch : Bachus_1999_Pharmacogenet_9_661 |
PubMedID: 10634129 |
Title : Alzheimer's disease: seeking new ways to preserve brain function. Interview by Alice V. Luddington - Davis_1999_Geriatrics_54_42 |
Author(s) : Davis KL |
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PubMedSearch : Davis_1999_Geriatrics_54_42 |
PubMedID: 10024872 |
Title : Structure of acetylcholinesterase complexed with (-)-galanthamine at 2.3 A resolution - Greenblatt_1999_FEBS.Lett_463_321 |
Author(s) : Greenblatt HM , Kryger G , Lewis T , Silman I , Sussman JL |
Ref : FEBS Letters , 463 :321 , 1999 |
Abstract : |
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PubMedID: 10606746 |
Gene_locus related to this paper: torca-ACHE |
Title : Invited review: Cholinesterase inhibitors for Alzheimer's disease therapy: from tacrine to future applications - Giacobini_1998_Neurochem.Int_32_413 |
Author(s) : Giacobini E |
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Abstract : |
PubMedSearch : Giacobini_1998_Neurochem.Int_32_413 |
PubMedID: 9676739 |
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Abstract : |
PubMedSearch : Mary_1998_Bioorg.Med.Chem_6_1835 |
PubMedID: 9839013 |
Title : Evaluation of four Narcissus cultivars as potential sources for galanthamine production [letter] - Moraes-Cerdeira_1997_Planta.Med_63_472 |
Author(s) : Moraes-Cerdeira RM , Burandt CL, Jr. , Bastos JK , Nanayakkara D , Mikell J , Thurn J , McChesney JD |
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PubMedID: 9342954 |
Title : Pharmacological basis of drug therapy of Alzheimer's disease - Sharma_1997_Indian.J.Exp.Biol_35_1146 |
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PubMedSearch : Sharma_1997_Indian.J.Exp.Biol_35_1146 |
PubMedID: 9567741 |
Title : Pharmacological evaluation of novel Alzheimer's disease therapeutics: acetylcholinesterase inhibitors related to galanthamine - Bores_1996_J.Pharmacol.Exp.Ther_277_728 |
Author(s) : Bores GM , Huger FP , Petko W , Mutlib AE , Camacho F , Rush DK , Selk DE , Wolf V , Kosley RW, Jr. , Davis L , Vargas HM |
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Abstract : |
PubMedSearch : Bores_1996_J.Pharmacol.Exp.Ther_277_728 |
PubMedID: 8627552 |
Title : Galanthamine. [Review] [23 refs] - Fulton_1996_Drugs.Aging_9_60 |
Author(s) : Fulton B , Benfield P |
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PubMedID: 8818586 |
Title : [The comparative clinico-experimental characteristics of aminostigmine and galanthamine used for treating poisonings by choline-blocking substances]. [Russian] - Prozorovskii_1996_Eksp.Klin.Farmakol_59_64 |
Author(s) : Prozorovskii VB , Velikova VD , Pshenkina NN , Vasilenko ET |
Ref : Eksperimentalnaia i Klinicheskaia Farmakologiia , 59 :64 , 1996 |
Abstract : |
PubMedSearch : Prozorovskii_1996_Eksp.Klin.Farmakol_59_64 |
PubMedID: 8704639 |
Title : Effect of the cholinesterase-inhibiting substance galanthamine on evoked visual potentials in rats - Lewandowski_1995_Acta.Neurobiol.Experiment_55_141 |
Author(s) : Lewandowski MH , Zmuda L |
Ref : Acta Neurobiologiae Experimentalis , 55 :141 , 1995 |
Abstract : |
PubMedSearch : Lewandowski_1995_Acta.Neurobiol.Experiment_55_141 |
PubMedID: 7660864 |
Title : Physostigmine, galanthamine and codeine act as 'noncompetitive nicotinic receptor agonists' on clonal rat pheochromocytoma cells - Storch_1995_Eur.J.Pharmacol_290_207 |
Author(s) : Storch A , Schrattenholz A , Cooper JC , Abdel Ghani EM , Gutbrod O , Weber KH , Reinhardt S , Lobron C , Hermsen B , Soskic V , Pereira EF , Albuquerque EX , Methfessel C , Maelicke A |
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Abstract : |
PubMedSearch : Storch_1995_Eur.J.Pharmacol_290_207 |
PubMedID: 7589215 |
Title : The pharmacology of galanthamine and its analogues - Harvey_1995_Pharmacol.Ther_68_113 |
Author(s) : Harvey AL |
Ref : Pharmacol Ther , 68 :113 , 1995 |
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PubMedSearch : Harvey_1995_Pharmacol.Ther_68_113 |
PubMedID: 8604434 |
Title : [Aminostigmine as a cholinesterase inhibitor and as an agent for treating poisonings by cholinergic blockers]. [Russian] - Prozorovskii_1994_Eksp.Klin.Farmakol_57_13 |
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Ref : Eksperimentalnaia i Klinicheskaia Farmakologiia , 57 :13 , 1994 |
Abstract : |
PubMedSearch : Prozorovskii_1994_Eksp.Klin.Farmakol_57_13 |
PubMedID: 7696893 |
Title : Inhibition of acetylcholinesterase activity in human brain tissue and erythrocytes by galanthamine, physostigmine and tacrine - Thomsen_1991_Eur.J.Clin.Chem.Clin.Biochem_29_487 |
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PubMedID: 1954303 |
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Title : Pharmacokinetics of galanthamine (a long-acting anticholinesterase drug) in anaesthetized patients - Westra_1986_Br.J.Anaesth_58_1303 |
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PubMedID: 3778794 |
Title : [Miniature currents of the endplates of the muscle fibers of the diaphragm of the rat after inhibition of acetylcholinesterase with galanthamine] - Krivoi_1985_Neirofiziologiia_17_607 |
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PubMedID: 2999623 |
Title : Homer's moly identified as Galanthus nivalis L.: physiologic antidote to stramonium poisoning - Plaitakis_1983_Clin.Neuropharmacol_6_1 |
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PubMedID: 6342763 |
Title : Reversal of central anticholinergic syndrome by galanthamine - Baraka_1977_Jama_238_2293 |
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Abstract : |
PubMedSearch : Baraka_1977_Jama_238_2293 |
PubMedID: 578850 |
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Ref : Biokhimiia , 39 :701 , 1974 |
PubMedID: 4441566 |
Title : Studies on the synthesis of heterocyclic compounds. CCCXV. Modified total synthesis of (plus or minus)-galanthamine through phenol oxidation - |
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PubMedID: |