Arecoline

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Arecoline
Arekolina.svg
Arecoline3d.png
Systematic (IUPAC) name
Methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate
Clinical data
Legal status
  • Uncontrolled
Identifiers
CAS number 63-75-2 YesY
ATC code None
PubChem CID 2230
IUPHAR ligand 296
DrugBank DB04365
ChemSpider 13872064 YesY
UNII 4ALN5933BH YesY
KEGG C10129 YesY
ChEBI CHEBI:2814 N
ChEMBL CHEMBL7303 YesY
Chemical data
Formula C8H13NO2 
Mol. mass 155.194 g/mol
Physical data
Density 1.0495 g/cm³
Boiling point 209 °C (408 °F)
 N (what is this?)  (verify)

Arecoline (/əˈrɛkəln/) is a nicotinic acids-based alkaloid found in the areca nut, the fruit of the areca palm (Areca catechu).[1] It is an odourless oily liquid.

Chemistry[edit]

Arecoline is a strong base, with pKa ~ 6.8.[2] Arecoline is volatile in steam, miscible with most organic solvents and water, but extractable from the latter by ether in presence of dissolved salts. Being basic, arecoline forms salts with acids. The salts are crystalline, but usually deliquescent: the hydrochloride, arecoline•HCl, forms needles, m.p. 158°C;[2] the hydrobromide, arecoline•HBr, forms slender prisms, mp. 177-179 °C from hot alcohol; the aurichloride, arecoline•HAuCl4, is an oil, but the platinichloride, arecoline2•H2PtCl6, mp. 176 °C, crystallizes from water in orange-red rhombohedrons. The methiodide forms glancing prisms, mp. 173-174 °C.

Biological Action[edit]

In many Asian cultures, the areca nut is chewed along with betel leaf to obtain a stimulating effect.[3] Arecoline is the primary active ingredient responsible for the central nervous system effects of the areca nut. Arecoline has been compared to nicotine; however, nicotine acts primarily on the nicotinic acetylcholine receptor. Arecoline is known to be a partial agonist of muscarinic acetylcholine M1, M2, M3 receptors and M4,[1][4][5] which is believed to be the primary cause of its parasympathetic effects (such as pupillary constriction, bronchial constriction, etc.).

LD50: 100 mg/kg, administered subcutaneously in mouse.[2]

Uses[edit]

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 intravenously did indeed show modest verbal and spatial memory improvement in Alzheimer's patients, though due to arecoline's possible carcinogenic properties,[6] it is not the first drug of choice for this degenerative disease.[7]

Arecoline has also been used medicinally as an antihelmintic (a drug against parasitic worms).[8]

References[edit]

  1. ^ a b 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. ^ a b c The Merck Index, 10th Ed. (1983) p.113, Rahway: Merck & Co.
  3. ^ Gupta Prakash Chandra, Ray Cecily S (July 2004). "Epidemiology of betel quid usage". Ann. Acad. Med. Singap. 33 (4 Suppl): 31–6. PMID 15389304. 
  4. ^ 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. 
  5. ^ 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. 
  6. ^ 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. 
  7. ^ Christie JE, Shering A, Ferguson J (1981). "Physostigmine and arecoline: effects of intravenous infusions in Alzheimer’s presenile dementia". British Journal of Psychiatry 138 (1): 46–50. doi:10.1192/bjp.138.1.46. PMID 7023592. 
  8. ^ 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.