Arecoline

Arecoline
	149px
	149px
Systematic (IUPAC) name
	methyl methyl-1,2,5,6-tetrahydropyridine-3-carboxylate
Identifiers
CAS Number	63-75-2
ATC code	none
PubChem	CID 2230
IUPHAR/BPS	296
DrugBank	EXPT03296
ChemSpider	13872064
Chemical data
Formula	C8H13NO2
Molar mass	155.194 g/mol[[Script error: No such module "String".]]
	Script error: No such module "collapsible list".
Physical data
Density	1.0495 g/cm3
Boiling point	209 °C (408 °F)
(verify)

Script error: No such module "TemplatePar".Expression error: Unexpected < operator.

Arecoline is an alkaloid natural product found in the areca nut, the fruit of the areca palm (Areca catechu).^[1] It is an odourless oily liquid volatile in steam, miscible with most organic solvents and water, but extractable from the latter by ether in presence of dissolved salts. The salts are crystalline, but usually deliquescent; the hydrobromide, B•HBr, forms slender prisms, mp. 177-9 °C from hot alcohol; the aurichloride, B•HAuCl₄, is an oil, but the platinichloride, B₂•H₂PtCl₆, mp. 176 °C, crystallises from water in orange-red rhombs. The methiodide forms glancing prisms, mp. 173-4 °C.

Mechanism

In many Asian cultures, the areca nut is chewed along with betel leaf to obtain a stimulating effect.^[2] Arecoline is the primary active ingredient responsible for the central nervous system effects which are roughly comparable to those of nicotine, which has a similar chemical structure. Arecoline is known to be a partial agonist of muscarinic acetylcholine M₁, M₂ and M₃ receptors,^[1]^[3]^[4] which is believed to be the primary cause of its parasympathetic effects (such as pupillary constriction, bronchial constriction, etc.).

Uses

Owing to its muscarinic and nicotinic agonist properties, arecoline has shown improvement in the learning ability of healthy volunteers. Since one of the hallmarks of Alzheimer's disease is a cognitive decline, arecoline was suggested as a treatment to slow down this process and arecoline administered via i.v. route did indeed show modest verbal and spatial memory improvement in Alzheimer's patients, though due to arecoline's possible carcinogenic properties, ^[5] it is not the first drug of choice for this degenerative disease. ^[6]

Arecoline has also been used medicinally as an antihelmintic (a drug against parasitic worms).^[7]

References

Cite error: Invalid <references> tag; parameter "group" is allowed only.

Use <references />, or <references group="..." />

This pharmacology-related article is a stub. You can help ssf by expanding it.

de:Arecolin

it:Arecolina ja:アレコリン pl:Arekolina

sv:Arekolin

↑ ^1.0 ^1.1 Ghelardini C, Galeotti N, Lelli C, Bartolini A. (2001). "Arecoline M1 receptor activation is a requirement for arecoline analgesia". Farmaco. 56 (5–7): 383–5. doi:10.1016/S0014-827X(01)01091-6. PMID 11482763.
↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
↑ Yang YR, Chang KC, Chen CL, Chiu TH. (2000). "Arecoline excites rat locus coeruleus neurons by activating the M2-muscarinic receptor". Chin J Physiol. 43 (1): 23–8. PMID 10857465.
↑ Xie DP, Chen LB, Liu CY, Zhang CL, Liu KJ, Wang PS. (2004). "Arecoline excites the colonic smooth muscle motility via M3 receptor in rabbits". Chin J Physiol. 47 (2): 89–94. PMID 15481791.
↑ Saikia JR, Schneeweiss FH, Sharan RN. (1999). "Arecoline-induced changes of poly-ADP-ribosylation of cellular proteins and its influence on chromatin organization". Cancer Letters. 139 (1): 59–65. doi:10.1016/S0304-3835(99)00008-7. PMID 10408909.
↑ Christie JE, Shering A, Ferguson J (1981). "Physostigmine and arecoline: effects of intravenous infusions in Alzheimer's presenile dementia". British Journal of Psychiatry. 138: 46–50. doi:10.1192/bjp.138.1.46. PMID 7023592.
↑ Yusuf H, Yong SL (2002). "Oral submucous fibrosis in a 12-year-old Bangladeshi boy: a case report and review of literature". International journal of paediatric dentistry / the British Paedodontic Society [and] the International Association of Dentistry for Children. 12 (4): 271–6. PMID 12121538.

[ArecolineM1-Ghelardini-1] 1.0 ^1.1 Ghelardini C, Galeotti N, Lelli C, Bartolini A. (2001). "Arecoline M1 receptor activation is a requirement for arecoline analgesia". Farmaco. 56 (5–7): 383–5. doi:10.1016/S0014-827X(01)01091-6. PMID 11482763.

[2] Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.

[ArecolineM2-Yang-3] Yang YR, Chang KC, Chen CL, Chiu TH. (2000). "Arecoline excites rat locus coeruleus neurons by activating the M2-muscarinic receptor". Chin J Physiol. 43 (1): 23–8. PMID 10857465.

[ArecolineM3-Xie-4] Xie DP, Chen LB, Liu CY, Zhang CL, Liu KJ, Wang PS. (2004). "Arecoline excites the colonic smooth muscle motility via M3 receptor in rabbits". Chin J Physiol. 47 (2): 89–94. PMID 15481791.

[carcinogen-Saikia-5] Saikia JR, Schneeweiss FH, Sharan RN. (1999). "Arecoline-induced changes of poly-ADP-ribosylation of cellular proteins and its influence on chromatin organization". Cancer Letters. 139 (1): 59–65. doi:10.1016/S0304-3835(99)00008-7. PMID 10408909.

[Alzheimer.27s-6] Christie JE, Shering A, Ferguson J (1981). "Physostigmine and arecoline: effects of intravenous infusions in Alzheimer's presenile dementia". British Journal of Psychiatry. 138: 46–50. doi:10.1192/bjp.138.1.46. PMID 7023592.

[pmid12121538-7] Yusuf H, Yong SL (2002). "Oral submucous fibrosis in a 12-year-old Bangladeshi boy: a case report and review of literature". International journal of paediatric dentistry / the British Paedodontic Society [and] the International Association of Dentistry for Children. 12 (4): 271–6. PMID 12121538.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

v t e Stimulants
Adamantanes	Adaphenoxate • Adapromine • Amantadine • Bromantane • Chlodantane • Gludantane • Memantine • Midantane
Arylcyclohexylamines	Benocyclidine • Dieticyclidine • Esketamine • Eticyclidine • Gacyclidine • Ketamine • Phencyclamine • Phencyclidine • Rolicyclidine • Tenocyclidine • Tiletamine
Benzazepines	6-Br-APB • SKF-77434 • SKF-81297 • SKF-82958
Cholinergics	A-84543 • A-366,833 • ABT-202 • ABT-418 • AR-R17779 • Altinicline • Anabasine • Arecoline • Cotinine • Cytisine • Dianicline • Epibatidine • Epiboxidine • GTS-21 • Ispronicline • Nicotine • PHA-543,613 • PNU-120,596 • PNU-282,987 • Pozanicline • Rivanicline • Sazetidine A • SIB-1553A • SSR-180,711 • TC-1698 • TC-1827 • TC-2216 • TC-5619 • Tebanicline • UB-165 • Varenicline • WAY-317,538
Convulsants	Anatoxin-a • Bicuculline • DMCM • Flurothyl • Gabazine • Pentetrazol • Picrotoxin • Strychnine • Thujone
Eugeroics	Adrafinil • Armodafinil • CRL-40941 • Modafinil
Oxazolines	4-Methylaminorex • Aminorex • Clominorex • Cyclazodone • Fenozolone • Fluminorex • Pemoline • Thozalinone
Phenethylamines	1-(4-Methylphenyl)-2-aminobutane • 2-Fluoroamphetamine • 2-Fluoromethamphetamine • 2-OH-PEA • 2-Phenyl-3-aminobutane • 2-Phenyl-3-methylaminobutane • 2,3-MDA • 3-Fluoroamphetamine • 3-Fluoroethamphetamine • 3-Fluoromethcathinone • 3-Methoxyamphetamine • 3-Methylamphetamine • 4-BMC • 4-Ethylamphetamine • 4-FA • 4-FMA • 4-MA • 4-MMA • 4-MTA • 6-FNE • Alfetamine • α-Ethylphenethylamine • Amfecloral • Amfepentorex • Amfepramone • Amidephrine • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Arbutamine • Atomoxetine (Tomoxetine) • β-Methylphenethylamine • β-Phenylmethamphetamine • Benfluorex • Benzphetamine • BDB (J) • BOH (Hydroxy-J) • BPAP • Buphedrone • Bupropion (Amfebutamone) • Butylone • Cathine • Cathinone • Chlorphentermine • Clenbuterol • Clobenzorex • Cloforex • Clortermine • D-Deprenyl • Denopamine • Dimethoxyamphetamine • Dimethylamphetamine • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Dobutamine • DOPA (Dextrodopa, Levodopa) • Dopamine • Dopexamine • Droxidopa • EBDB (Ethyl-J) • Ephedrine • Epinephrine (Adrenaline) • Epinine (Deoxyepinephrine) • Etafedrine • Ethcathinone (Ethylpropion) • Ethylamphetamine (Etilamfetamine) • Ethylnorepinephrine (Butanefrine) • Ethylone • Etilefrine • Famprofazone • Fenbutrazate • Fencamine • Fencamfamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenmetramide • Fenproporex • Flephedrone • Fludorex • Furfenorex • Gepefrine • HMMA • Hordenine • Ibopamine • IMP • Indanylamphetamine • Isoetarine • Isoprenaline (Isoproterenol) • L-Deprenyl (Selegiline) • Lefetamine • Lisdexamfetamine • Lophophine (Homomyristicylamine) • Manifaxine • MBDB (Methyl-J; "Eden") • MDA (Tenamfetamine) • MDBU • MDEA ("Eve") • MDMA ("Ecstasy", "Adam") • MDMPEA (Homarylamine) • MDOH • MDPR • MDPEA (Homopiperonylamine) • Mefenorex • Mephedrone • Mephentermine • Metanephrine • Metaraminol • Methamphetamine (Desoxyephedrine, Methedrine; Dextromethamphetamine, Levomethamphetamine) • Methoxamine • Methoxyphenamine • MMA • Methcathinone (Methylpropion) • Methedrone • Methoxyphenamine • Methylone • MMDA • MMDMA • MMMA • Morazone • Naphthylamphetamine • Nisoxetine • Norepinephrine (Noradrenaline) • Norfenefrine • Norfenfluramine • Normetanephrine • Octopamine • Orciprenaline • Ortetamine • Oxilofrine • Paredrine (Norpholedrine, Oxamphetamine, Mycadrine) • PBA • PCA • PHA • Pargyline • Pentorex (Phenpentermine) • Pentylone • Phendimetrazine • Phenmetrazine • Phenpromethamine • Phentermine • Phenylalanine • Phenylephrine (Neosynephrine) • Phenylpropanolamine • Pholedrine • PIA • PMA • PMEA • PMMA • PPAP • Prenylamine • Propylamphetamine • Pseudoephedrine • Radafaxine • Ropinirole • Salbutamol (Albuterol; Levosalbutamol) • Sibutramine • Synephrine (Oxedrine) • Theodrenaline • Tiflorex (Flutiorex) • Tranylcypromine • Tyramine • Tyrosine • Xamoterol • Xylopropamine • Zylofuramine
Piperazines	2C-B-BZP • BZP • CM156 • DBL-583 • GBR-12783 • GBR-12935 • GBR-13069 • GBR-13098 • GBR-13119 • MeOPP • MBZP • Vanoxerine
Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine • 2-Benzylpiperidine • 3,4-Dichloromethylphenidate • 4-Benzylpiperidine • 4-Methylmethylphenidate • Desoxypipradrol • Difemetorex • Diphenylpyraline • Ethylphenidate • Methylnaphthidate • Methylphenidate (Dexmethylphenidate) • Nocaine • Phacetoperane • Pipradrol • SCH-5472
Pyrrolidines	α-PPP • α-PBP • α-PVP • MDPPP • MDPBP • MDPV • MPBP • MPHP • MPPP • MOPPP • Naphyrone • PEP • Prolintane • Pyrovalerone
Tropanes	3-CPMT • 3-Pseudotropyl-4-fluorobenzoate • 4'-Fluorococaine • AHN-1055 • Altropane (IACFT) • Brasofensine • CFT (WIN 35,428) • β-CIT (RTI-55) • Cocaethylene • Cocaine • Dichloropane (RTI-111) • Difluoropine • FE-β-CPPIT • FP-β-CPPIT • Ioflupane (¹²³I) • Norcocaine • PIT • PTT • RTI-31 • RTI-32 • RTI-51 • RTI-105 • RTI-112 • RTI-113 • RTI-117 • RTI-121 (IPCIT) • RTI-126 • RTI-150 • RTI-154 • RTI-171 • RTI-177 • RTI-183 • RTI-194 • RTI-202 • RTI-229 • RTI-241 • RTI-336 • RTI-354 • RTI-371 • RTI-386 • Salicylmethylecgonine • Tesofensine • Troparil (β-CPT, WIN 35,065-2) • Tropoxane • WF-23 • WF-33 • WF-60
Xanthines	Aminophylline • Caffeine • Dimethazan • Paraxanthine • Theobromine • Theophylline
Others	1-(Thiophen-2-yl)-2-aminopropane • 2-Amino-1,2-dihydronaphthalene • 2-Aminoindane • 2-Aminotetralin • 2-Diphenylmethylpyrrolidine • 2-MDP • 3,3-Diphenylcyclobutanamine • 5-(2-Aminopropyl)indole • 5-Iodo-2-aminoindane • AL-1095 • Amfonelic acid • Amineptine • Amiphenazole • Atipamezole • Bemegride • Benzydamine • BTQ • BTS 74,398 • Carphedon • Ciclazindol • Cilobamine • Clofenciclan • Cropropamide • Crotetamide • Diclofensine • Dimethocaine • Diphenylprolinol • Efaroxan • Etamivan • EXP-561 • Fenpentadiol • Feprosidnine • Gamfexine • Gilutensin • GYKI-52895 • Hexacyclonate • Idazoxan • Indanorex • Indatraline • JNJ-7925476 • JZ-IV-10 • Lazabemide • Leptacline • Levopropylhexedrine • LR-5182 • Mazindol • Meclofenoxate • Medifoxamine • Mefexamide • Mesocarb • Nefopam • Nikethamide • Nomifensine • O-2172 • Oxaprotiline • Phthalimidopropiophenone • PNU-99,194 • Propylhexedrine • PRC200-SS • Rasagiline • Rauwolscine • Rubidium chloride • Setazindol • Tametraline • Tandamine • Trazium • UH-232 • Yohimbine
See also Sympathomimetic amines

Arecoline

Mechanism

Uses

References

Navigation menu

Views

Personal tools

Navigation

Search

Tools

adverts