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Encyclopedia > Arecoline
Arecoline
Systematic (IUPAC) name
methyl1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate
Identifiers
CAS number 63-75-2
ATC code  ?
PubChem 2230
DrugBank EXPT03296
Chemical data
Formula C8H13NO2 
Mol. mass 155.194 g/mol
SMILES search in eMolecules, PubChem
Physical data
Density 1.0495 g/cm³
Boiling point 209 °C (408 °F)
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

? Image File history File links Arekolina. ... Image File history File links No higher resolution available. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... For other uses, see Density (disambiguation). ... Italic text This article is about the boiling point of liquids. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... The kidneys are important excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status
Routes  ?

Arecoline is an alkaloid-type natural product found in betel nuts from the betel palm (Areca catechu).[1] It is an oily liquid that is soluble in water, alcohols, and ether. The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... Chemical structure of ephedrine, a phenethylamine alkaloid An alkaloid is, strictly speaking, a naturally occurring amine produced by a plant,[1] but amines produced by animals and fungi are also called alkaloids. ... Binomial name Areca catechu Linnaeus Areca nut, or pinang, more commonly known as betel nut, is the seed of the betel palm or Areca catechu, a species of palm tree which grows throughout the Pacific, Asia, and parts of east Africa. ...


Mechanism

In many Asian cultures, the betel nut is chewed to obtain a stimulating effect. Arecoline is the primary active ingredient responsible for the central nervous system affects which are roughly comparable to those of nicotine, which has a similar chemical structure. Arecoline is known to be an agonist of muscarinic acetylcholine M1, M2 and M3 receptors,[1][2][3] which is believed to be the primary cause of its parasympathetic effects (such as pupillary constriction, bronchial constriction, etc.). This article is about the chemical compound. ... Amanita muscaria from which muscarine was isolated Acetylcholine - natural agonist of muscarinic and nicotinic receptors. ... The chemical compound acetylcholine, often abbreviated as ACh, was the first neurotransmitter to be identified. ... Anatomy and Physiology of the A.N.S. In contrast to the voluntary nervous system, the involuntary or autonomic nervous system is responsible for homeostasis, maintaining a relatively constant internal environment by controlling such involuntary functions as digestion, respiration, and metabolism, and by modulating blood pressure. ...


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, [4] it is not the first drug of choice for this degenerative disease. [5]


Arecoline has also been used medicinally as an antihelmintic (a drug against parasitic worms).[6] Anthelmintics (in the U.S., antihelminthics) are drugs that expel parasitic worms (helminthes) from the body or kill them. ...


References

  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. PMID 11482763. 
  2. ^ 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. 
  3. ^ 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. 
  4. ^ 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. PMID 10408909. 
  5. ^ 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. PMID 7023592. 
  6. ^ 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. 

  Results from FactBites:
 
Arecoline - Health Encyclopedia (143 words)
Arecoline is a stimulant which acts on the parasympathetic nervous system to induce a range of different effects including a heightened sense of awareness as well as increased salivation, heart rate, blood pressure, body temperature and intestinal function.
Regional brain metabolic responsivity to the muscarinic cholinergic agonist arecoline is similar in young and aged Fischer-344 rats.
Arecoline is a parasympathetic agent and increases the tonus and the mobility of smooth muscle resulting in the purgation of E. Retrieved from "http://www.steadyhealth.com/encyclopedia/Arecoline"
Betel Nut : by Ray Sahelian, M.D., Benefits of Betel Nut (1564 words)
The plant extract was subjected to activity-directed fractionation and all resultant fractions showed atropine-sensitive spasmogenicity in rabbit jejunum and also AChE inhibitory effect at doses similar to that for the parent crude extract, the ethyl acetate fraction being slightly less potent.
Some of the known constituents of betel nut, including arecoline, were tested for the possible inhibitory effect on AChE, none were found active.
In study 2, 15 Indian men received gels delivering 0 or 10 mg arecoline after consuming a 2.5 MJ meal, and the same protocol was then applied as in study 1.
  More results at FactBites »

 
 

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