Arecoline
An alkaloid obtained from the betel nut (Areca catechu), fruit of a palm tree. It is an agonist at both muscarinic and nicotinic acetylcholine receptors. It is used in the form of various salts as a ganglionic stimulant, a parasympathomimetic, and a vermifuge. The practice of betel nut chewing, often together with other herbs as a stimulant drug, dates back thousands of years
General
Type : Muscarinic agonist, Nicotinic agonist, Pyridine, Natural
Chemical_Nomenclature : methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate
Canonical SMILES : CN1CCC=C(C1)C(=O)OC
InChI : InChI=1S\/C8H13NO2\/c1-9-5-3-4-7(6-9)8(10)11-2\/h4H,3,5-6H2,1-2H3
InChIKey : HJJPJSXJAXAIPN-UHFFFAOYSA-N
Other name(s) : Arecolin || Arecaline || Arecholine || CHEBI:2814 || CHEMBL7303 || SCHEMBL44065 || DB04365
MW : 155.19
Formula : C8H13NO2
CAS_number : 63-75-2
PubChem : 2230
UniChem : HJJPJSXJAXAIPN-UHFFFAOYSA-N
Target
Structures : No structure
Families : Carb_B_Chordata
References (38)
| Title : Arecoline inhibits the growth of Spodoptera litura by inducing intestinal metabolic dysfunction - Zhou_2024_Pestic.Biochem.Physiol_204_106044 |
| Author(s) : Zhou Y , Huang Q , Li HG , Liang S , He B , Bao M |
| Ref : Pestic Biochem Physiol , 204 :106044 , 2024 |
| Abstract : |
| PubMedSearch : Zhou_2024_Pestic.Biochem.Physiol_204_106044 |
| PubMedID: 39277371 |
| Title : In vitro hydrolysis of areca nut xenobiotics in human liver - Paolillo_2024_Drug.Metab.Pharmacokinet_60_101039 |
| Author(s) : Paolillo V , Jayakumar M , Sheperd C , Tran A , Hoang S , Dao N , Jain P , Myers AL |
| Ref : Drug Metab Pharmacokinet , 60 :101039 , 2024 |
| Abstract : |
| PubMedSearch : Paolillo_2024_Drug.Metab.Pharmacokinet_60_101039 |
| PubMedID: 39667079 |
| Title : Metabolism of the areca alkaloids - toxic and psychoactive constituents of the areca (betel) nut - Myers_2022_Drug.Metab.Rev__1 |
| Author(s) : Myers AL |
| Ref : Drug Metabolism Reviews , :1 , 2022 |
| Abstract : |
| PubMedSearch : Myers_2022_Drug.Metab.Rev__1 |
| PubMedID: 35543097 |
| Title : Enhanced arecoline derivatives as muscarinic acetylcholine receptor M1 ligands for potential application as PET radiotracers - Ozenil_2020_Eur.J.Med.Chem_204_112623 |
| Author(s) : Ozenil M , Pacher K , Balber T , Vraka C , Roller A , Holzer W , Spreitzer H , Mitterhauser M , Wadsak W , Hacker M , Pichler V |
| Ref : Eur Journal of Medicinal Chemistry , 204 :112623 , 2020 |
| Abstract : |
| PubMedSearch : Ozenil_2020_Eur.J.Med.Chem_204_112623 |
| PubMedID: 32717485 |
| Title : Evaluation of the toxic potential of arecoline toward the third instar larvae of transgenic Drosophila melanogaster (hsp70-lacZ) Bg(9) - Shakya_2018_Toxicol.Res.(Camb)_7_432 |
| Author(s) : Shakya B , Siddique YH |
| Ref : Toxicol Res (Camb) , 7 :432 , 2018 |
| Abstract : |
| PubMedSearch : Shakya_2018_Toxicol.Res.(Camb)_7_432 |
| PubMedID: 30090593 |
| Title : Effect of novel arecoline thiazolidinones as muscarinic receptor 1 agonist in Alzheimer's dementia models - Chandra_2008_Neurochem.Int_52_376 |
| Author(s) : Chandra JN , Malviya M , Sadashiva CT , Subhash MN , Rangappa KS |
| Ref : Neurochem Int , 52 :376 , 2008 |
| Abstract : |
| PubMedSearch : Chandra_2008_Neurochem.Int_52_376 |
| PubMedID: 17719699 |
| Title : Involvement of ionotropic glutamate receptors in the appearance of arecoline tremor in mice - Lukomskaya_2008_Neurosci.Behav.Physiol_38_421 |
| Author(s) : Lukomskaya NY , Lavrent'eva VV , Starshinova LA , Zhabko EP , Gmiro VE , Magazanik LG |
| Ref : Neurosci Behav Physiol , 38 :421 , 2008 |
| Abstract : |
| PubMedSearch : Lukomskaya_2008_Neurosci.Behav.Physiol_38_421 |
| PubMedID: 18401736 |
| Title : Effect of novel N-aryl sulfonamide substituted 3-morpholino arecoline derivatives as muscarinic receptor 1 agonists in Alzheimer's dementia models - Kumar_2008_Bioorg.Med.Chem_16_5157 |
| Author(s) : Kumar YC , Malviya M , Chandra JN , Sadashiva CT , Kumar CS , Prasad SB , Prasanna DS , Subhash MN , Rangappa KS |
| Ref : Bioorganic & Medicinal Chemistry , 16 :5157 , 2008 |
| Abstract : |
| PubMedSearch : Kumar_2008_Bioorg.Med.Chem_16_5157 |
| PubMedID: 18359231 |
| Title : Developmental toxicity of arecoline, the major alkaloid in betel nuts, in zebrafish embryos - Chang_2004_Birth.Defects.Res.A.Clin.Mol.Teratol_70_28 |
| Author(s) : Chang BE , Liao MH , Kuo MY , Chen CH |
| Ref : Birth Defects Res A Clin Mol Teratol , 70 :28 , 2004 |
| Abstract : |
| PubMedSearch : Chang_2004_Birth.Defects.Res.A.Clin.Mol.Teratol_70_28 |
| PubMedID: 14745892 |
| Title : Mechanism of vascular relaxation by cholinomimetic drugs with special reference to pilocarpine and arecoline - Patil_2002_J.Ocul.Pharmacol.Ther_18_25 |
| Author(s) : Patil PN , Stearns R |
| Ref : J Ocul Pharmacol Ther , 18 :25 , 2002 |
| Abstract : |
| PubMedSearch : Patil_2002_J.Ocul.Pharmacol.Ther_18_25 |
| PubMedID: 11858612 |
| Title : Synthesis and muscarinic receptor pharmacology of a series of 4,5,6,7-tetrahydroisothiazolo[4,5-c]pyridine bioisosteres of arecoline - Pedersen_1999_Bioorg.Med.Chem_7_795 |
| Author(s) : Pedersen H , Brauner-Osborne H , Ball RG , Frydenvang K , Meier E , Bogeso KP , Krogsgaard-Larsen P |
| Ref : Bioorganic & Medicinal Chemistry , 7 :795 , 1999 |
| Abstract : |
| PubMedSearch : Pedersen_1999_Bioorg.Med.Chem_7_795 |
| PubMedID: 10400332 |
| Title : Arecoline via miniosmotic pump improves AF64A-impaired radial maze performance in rats: a possible model of Alzheimer's disease - Bartolomeo_1997_Neurobiol.Learn.Mem_68_333 |
| Author(s) : Bartolomeo AC , Morris H , Boast CA |
| Ref : Neurobiol Learn Mem , 68 :333 , 1997 |
| Abstract : |
| PubMedSearch : Bartolomeo_1997_Neurobiol.Learn.Mem_68_333 |
| PubMedID: 9398593 |
| Title : 1,2,5-Thiadiazole derivatives of arecoline stimulate M1 receptors coupled to phosphoinositide turnover - Periyasamy_1995_Brain.Res_693_118 |
| Author(s) : Periyasamy S , Messer WS, Jr. , Roknich S , Sauerberg P , Hoss WP |
| Ref : Brain Research , 693 :118 , 1995 |
| Abstract : |
| PubMedSearch : Periyasamy_1995_Brain.Res_693_118 |
| PubMedID: 8653399 |
| Title : Annulated heterocyclic bioisosteres of norarecoline. Synthesis and molecular pharmacology at five recombinant human muscarinic acetylcholine receptors - Brauner-Osborne_1995_J.Med.Chem_38_2188 |
| Author(s) : Brauner-Osborne H , Ebert B , Brann MR , Falch E , Krogsgaard-Larsen P |
| Ref : Journal of Medicinal Chemistry , 38 :2188 , 1995 |
| Abstract : |
| PubMedSearch : Brauner-Osborne_1995_J.Med.Chem_38_2188 |
| PubMedID: 7783150 |
| Title : Bioisosteres of arecoline: 1,2,3,6-tetrahydro-5-pyridyl-substituted and 3-piperidyl-substituted derivatives of tetrazoles and 1,2,3-triazoles. Synthesis and muscarinic activity - Moltzen_1994_J.Med.Chem_37_4085 |
| Author(s) : Moltzen EK , Pedersen H , Bogeso KP , Meier E , Frederiksen K , Sanchez C , Love Lembol H |
| Ref : Journal of Medicinal Chemistry , 37 :4085 , 1994 |
| Abstract : |
| PubMedSearch : Moltzen_1994_J.Med.Chem_37_4085 |
| PubMedID: 7990109 |
| Title : Conformational aspects of the muscarinic receptor interactions of bicyclic isoxazole ester bioisosteres of arecoline - Lagersted_1993_Drug.Des.Discov_9_237 |
| Author(s) : Lagersted A , Falch E , Ebert B , Krogsgaard-Larsen P |
| Ref : Drug Des Discov , 9 :237 , 1993 |
| Abstract : |
| PubMedSearch : Lagersted_1993_Drug.Des.Discov_9_237 |
| PubMedID: 8400005 |
| Title : Poster: Electronic requirements in a series of arecoline derivatives for muscarinic receptor-stimulated phosphoinositide metabolism in the rat brain - |
| Author(s) : Hoss WP , Ngur DO , Roknich S , Mitch CH , Quimby SJ , Ward JS , Merritt L , Sauerberg P , Messer WS, Jr. |
| Ref : Life Sciences , 52(5-6) :552 , 1993 |
| PubMedID: |
| Title : Cholinergic agents: effect of methyl substitution in a series of arecoline derivatives on binding to muscarinic acetylcholine receptors - Moos_1992_J.Pharm.Sci_81_1015 |
| Author(s) : Moos WH , Bergmeier SC , Coughenour LL , Davis RE , Hershenson FM , Kester JA , McKee JS , Marriott JG , Schwarz RD , Tecle H , Thomas AJ |
| Ref : J Pharm Sci , 81 :1015 , 1992 |
| Abstract : |
| PubMedSearch : Moos_1992_J.Pharm.Sci_81_1015 |
| PubMedID: 1432612 |
| Title : Steric and electronic requirements for muscarinic receptor-stimulated phosphoinositide turnover in the CNS in a series of arecoline bioisosteres - Ngur_1992_Biochem.Biophys.Res.Commun_187_1389 |
| Author(s) : Ngur D , Roknich S , Mitch CH , Quimby SJ , Ward JS , Merritt L , Sauerberg P , Messer WS, Jr. , Hoss WP |
| Ref : Biochemical & Biophysical Research Communications , 187 :1389 , 1992 |
| Abstract : |
| PubMedSearch : Ngur_1992_Biochem.Biophys.Res.Commun_187_1389 |
| PubMedID: 1329735 |
| Title : Impairment of radial-arm maze performance in rats following lesions involving the cholinergic medial pathway: reversal by arecoline and differential effects of muscarinic and nicotinic antagonists - McGurk_1991_Neurosci_44_137 |
| Author(s) : McGurk SR , Levin ED , Butcher LL |
| Ref : Neuroscience , 44 :137 , 1991 |
| Abstract : |
| PubMedSearch : McGurk_1991_Neurosci_44_137 |
| PubMedID: 1770993 |
| Title : The cholinergic rapid eye movement induction test with arecoline in depression - Gillin_1991_Arch.Gen.Psychiatry_48_264 |
| Author(s) : Gillin JC , Sutton L , Ruiz C , Kelsoe J , Dupont RM , Darko D , Risch SC , Golshan S , Janowsky D |
| Ref : Arch Gen Psychiatry , 48 :264 , 1991 |
| Abstract : |
| PubMedSearch : Gillin_1991_Arch.Gen.Psychiatry_48_264 |
| PubMedID: 1996921 |
| Title : Poster: CI-969: An orally active muscarinic receptor agonist related to arecoline - |
| Author(s) : Pavia MR , Schwarz AD , Coughenour LL , Davis RE , Dudley DT , Moos WH , Pugsley TA , Tecle H , Clark CA |
| Ref : Trends in Pharmacological Sciences , Suppl :100 , 1989 |
| PubMedID: |
| Title : Synthesis and muscarinic activity of a series of tertiary and quaternary N-substituted guvacine esters structurally related to arecoline and arecaidine propargyl ester - Wolf-Pflugmann_1989_Arzneimittelforschung_39_539 |
| Author(s) : Wolf-Pflugmann M , Lambrecht G , Wess J , Mutschler E |
| Ref : Arzneimittelforschung , 39 :539 , 1989 |
| Abstract : |
| PubMedSearch : Wolf-Pflugmann_1989_Arzneimittelforschung_39_539 |
| PubMedID: 2757669 |
| Title : Tacrine or arecoline mediates reversal of anoxia- or AF64A-induced behavioural disorders in the developing rat - Speiser_1989_Neuropharmacol_28_1325 |
| Author(s) : Speiser Z , Reicher S , Gitter S , Cohen S |
| Ref : Neuropharmacology , 28 :1325 , 1989 |
| Abstract : |
| PubMedSearch : Speiser_1989_Neuropharmacol_28_1325 |
| PubMedID: 2615915 |
| Title : Effect of acute arecoline, tacrine, and arecoline + tacrine post-training administration on retention in late middle-aged mice - Flood_1988_J.Gerontol_43_B54 |
| Author(s) : Flood JF |
| Ref : J Gerontol , 43 :B54 , 1988 |
| Abstract : |
| PubMedSearch : Flood_1988_J.Gerontol_43_B54 |
| PubMedID: 3346520 |
| Title : Effect of acute arecoline, tacrine and arecoline + tacrine post-training administration on retention in old mice - Flood_1988_Neurobiol.Aging_9_5 |
| Author(s) : Flood JF , Cherkin A |
| Ref : Neurobiology of Aging , 9 :5 , 1988 |
| Abstract : |
| PubMedSearch : Flood_1988_Neurobiol.Aging_9_5 |
| PubMedID: 3380255 |
| Title : Heterocyclic muscarinic agonists. Synthesis and biological activity of some bicyclic sulfonium arecoline bioisosteres - Sauerberg_1988_J.Med.Chem_31_1312 |
| Author(s) : Sauerberg P , Falch E , Meier E , Lembol HL , Krogsgaard-Larsen P |
| Ref : Journal of Medicinal Chemistry , 31 :1312 , 1988 |
| Abstract : |
| PubMedSearch : Sauerberg_1988_J.Med.Chem_31_1312 |
| PubMedID: 3385727 |
| Title : Bioisosteres of arecoline as novel CNS-active muscarinic agonists - |
| Author(s) : Krogsgaard-Larsen P , Falch E , Sauerberg P , Freedman SB , Lembol HL , Meier E |
| Ref : Trends in Pharmacological Sciences , Suppl :69 , 1988 |
| PubMedID: 3074541 |
| Title : Enhanced elevation of corticosterone following arecoline administration to rats selectively bred for increased cholinergic function - Overstreet_1986_Psychopharmacology.(Berl)_88_129 |
| Author(s) : Overstreet DH , Booth RA , Dana R , Risch SC , Janowsky DS |
| Ref : Psychopharmacology (Berl) , 88 :129 , 1986 |
| Abstract : |
| PubMedSearch : Overstreet_1986_Psychopharmacology.(Berl)_88_129 |
| PubMedID: 3080772 |
| Title : The central action of various arecaidine esters (arecoline derivatives) on blood pressure and heart rate in the cat. Comparison with the peripheral effects - Porsius_1978_Arzneimittelforschung_28_1373 |
| Author(s) : Porsius AJ , Mutschler E , van Zwieten PA |
| Ref : Arzneimittelforschung , 28 :1373 , 1978 |
| Abstract : |
| PubMedSearch : Porsius_1978_Arzneimittelforschung_28_1373 |
| PubMedID: 582403 |
| Title : Human serial learning: enhancement with arecholine and choline impairment with scopolamine - Sitaram_1978_Science_201_274 |
| Author(s) : Sitaram N , Weingartner H , Gillin JC |
| Ref : Science , 201 :274 , 1978 |
| Abstract : |
| PubMedSearch : Sitaram_1978_Science_201_274 |
| PubMedID: 351808 |
| Title : Interaction between cellular metabolism and acetylcholine turnover of rat brain cortex slices in the presence of arecoline - von Schwarzenfeld_1975_Acta.Biol.Med.Ger_34_1525 |
| Author(s) : von Schwarzenfeld I , Fischer HD , Oelszner W |
| Ref : Acta Biologica et Medica Germanica , 34 :1525 , 1975 |
| Abstract : |
| PubMedSearch : von Schwarzenfeld_1975_Acta.Biol.Med.Ger_34_1525 |
| PubMedID: 1221740 |
| Title : Quaternary isoarecoline: a potent muscarine-like and nicotine-like acting agonist - |
| Author(s) : Lambrecht G , Mutschler E |
| Ref : Experientia , 31 :1317 , 1975 |
| PubMedID: 1204788 |
| Title : [Influence of arecoline on GSSG-inhibition of Na+-K+-ATPase incubated striatum slices of the rat] - |
| Author(s) : von Schwarzenfeld I , Fischer HD , Oelszner W |
| Ref : Acta Biologica et Medica Germanica , 33 :521 , 1974 |
| PubMedID: 4282817 |
| Title : Effects of pilocarpine or arecoline administration on acetylcholine levels and serotonin turnover in rat brain - |
| Author(s) : Haubrich DR , Reid WD |
| Ref : Journal of Pharmacology & Experimental Therapeutics , 181 :19 , 1972 |
| PubMedID: 4335170 |
| Title : Synthesis of aldoxime analogs of arecoline as reactivators of organophosphorus inhibited cholinesterase - |
| Author(s) : Wells JN , Davisson JN , Boime I , Haubrick DR , Yim GKW |
| Ref : Journal of Pharmacological Sciences , 56 :1190 , 1967 |
| PubMedID: |
| Title : [On the chemistry and pharmacology of the alkaloids damascenine and arecoline. 5. On structure-effect relations in cyclical acetylcholine derivatives of the arecoline and damascenine series] - |
| Author(s) : Mutschler E |
| Ref : Arzneimittelforschung , 16 :73 , 1966 |
| PubMedID: 6013760 |