Galanthamine

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.

General

Type : Derivative of Galanthamine, Natural, Alkaloid, Drug, Benzazepin, Azepine

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

Target

Families : Galanthamine ligand of proteins in family
ACHE

Structure :
1DX6 1QTI 1W6R 1W76 4EY6

Protein :
torca-ACHE human-ACHE

References (45)

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
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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 : 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 : 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
Ref : Electrophoresis , 20 :1993 , 1999
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
Ref : Geriatrics , 54 :42 , 1999
Abstract :
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 :
PubMedSearch : Greenblatt_1999_FEBS.Lett_463_321
PubMedID: 10606746
Gene_locus related to this paper: torca-ACHE

Title : Potent acetylcholinesterase inhibitors: design, synthesis, and structure-activity relationships of bis-interacting ligands in the galanthamine series - Mary_1998_Bioorg.Med.Chem_6_1835
Author(s) : Mary A , Renko DZ , Guillou C , Thal C
Ref : Bioorganic & Medicinal Chemistry , 6 :1835 , 1998
Abstract :
PubMedSearch : Mary_1998_Bioorg.Med.Chem_6_1835
PubMedID: 9839013

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
Ref : Neurochem Int , 32 :413 , 1998
Abstract :
PubMedSearch : Giacobini_1998_Neurochem.Int_32_413
PubMedID: 9676739

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
Ref : Planta Med , 63 :472 , 1997
Abstract :
PubMedSearch : Moraes-Cerdeira_1997_Planta.Med_63_472
PubMedID: 9342954

Title : Pharmacological basis of drug therapy of Alzheimer's disease - Sharma_1997_Indian.J.Exp.Biol_35_1146
Author(s) : Sharma A , Parikh V , Singh M
Ref : Indian J Exp Biol , 35 :1146 , 1997
Abstract :
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
Ref : Journal of Pharmacology & Experimental Therapeutics , 277 :728 , 1996
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
Ref : Drugs & Aging , 9 :60 , 1996
Abstract :
PubMedSearch : Fulton_1996_Drugs.Aging_9_60
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
Ref : European Journal of Pharmacology , 290 :207 , 1995
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
Abstract :
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
Author(s) : Prozorovskii VB , Livanov GA , Velikova VD , Afanas'ev VV , Pavlova LV
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
Author(s) : Thomsen T , Kaden B , Fischer JP , Bickel U , Barz H , Gusztony G , Cervos-Navarro J , Kewitz H
Ref : European Journal of Clinical Chemistry & Clinical Biochemistry , 29 :487 , 1991
Abstract :
PubMedSearch : Thomsen_1991_Eur.J.Clin.Chem.Clin.Biochem_29_487
PubMedID: 1954303

Title : Selective inhibition of human acetylcholinesterase by galanthamine in vitro and in vivo - Thomsen_1990_Life.Sci_46_1553
Author(s) : Thomsen T , Kewitz H
Ref : Life Sciences , 46 :1553 , 1990
Abstract :
PubMedSearch : Thomsen_1990_Life.Sci_46_1553
PubMedID: 2355800

Title : [Catalytic properties of cholinesterases immobilized in a gelatin membrane] - Kuznetsova_1990_Ukr.Biokhim.Zh_62_42
Author(s) : Kuznetsova LP , Kugusheva LI , Nikol'skaia EB
Ref : Ukr Biokhim Zh , 62 :42 , 1990
Abstract :
PubMedSearch : Kuznetsova_1990_Ukr.Biokhim.Zh_62_42
PubMedID: 2087792

Title : Pharmacokinetics of galanthamine (a long-acting anticholinesterase drug) in anaesthetized patients - Westra_1986_Br.J.Anaesth_58_1303
Author(s) : Westra P , van Thiel MJ , Vermeer GA , Soeterbroek AM , Scaf AH , Claessens HA
Ref : British Journal of Anaesthesia , 58 :1303 , 1986
Abstract :
PubMedSearch : Westra_1986_Br.J.Anaesth_58_1303
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
Author(s) : Krivoi II , Kuleshov VI , Matiushkin DP , Sanotskii VI , Sei TP
Ref : Neirofiziologiia , 17 :607 , 1985
Abstract :
PubMedSearch : Krivoi_1985_Neirofiziologiia_17_607
PubMedID: 2999623

Title : Homer's moly identified as Galanthus nivalis L.: physiologic antidote to stramonium poisoning - Plaitakis_1983_Clin.Neuropharmacol_6_1
Author(s) : Plaitakis A , Duvoisin RC
Ref : Clinical Neuropharmacology , 6 :1 , 1983
Abstract :
PubMedSearch : Plaitakis_1983_Clin.Neuropharmacol_6_1
PubMedID: 6342763

Title : Reversal of central anticholinergic syndrome by galanthamine - Baraka_1977_Jama_238_2293
Author(s) : Baraka A , Harik S
Ref : Jama , 238 :2293 , 1977
Abstract :
PubMedSearch : Baraka_1977_Jama_238_2293
PubMedID: 578850

Title : [Characteristics of galanthamine as a reversible inhibitor of cholinesterase] -
Author(s) : Vasilenko ET , Tonkopii VD
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 -
Author(s) : Kametani T , Yamaki K , Yagi H , Fukumoto K
Ref : J Chem Soc Perkin 1 , 18 :2602 , 1969
PubMedID: 5391300

Title : Galanthamine chemistry. VII. Synthesis of analogues of galanthamine -
Author(s) : Uyeo S , Shirai H , Koshiro A , Yashiro T , Kagei K
Ref : Chem Pharm Bull (Tokyo) , 14 :1033 , 1966
PubMedID: 5976510

Title : [Influence exerted by galanthamine on the acetylcholinesterase activity of various regions of the brain] -
Author(s) : Nesterenko LN
Ref : Farmakologiia i Toksikologiia , 28 :413 , 1965
PubMedID: 5868403

Title : On the pharmacology of the new alkaloid galantamine -
Author(s) : Mashkovsky MD , Kruglikova-Lvova RP
Ref : Farmakologia Toxicologia (Moskow) , 14 :27 , 1951
PubMedID: