You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:36:18 UTC
Update Date2017-12-07 03:03:52 UTC
HMDB IDHMDB0030353
Secondary Accession Numbers
  • HMDB30353
Metabolite Identification
Common NameArecoline
DescriptionArecoline is found in nuts. Arecoline is isolated from betel nuts Arecoline is an alkaloid natural product found in the areca nut, the fruit of the areca palm (Areca catechu). It is an oily liquid that is soluble in water, alcohols, and ether. 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, it is not the first drug of choice for this degenerative disease
Structure
Thumb
Synonyms
ValueSource
Arecaidine methyl esterChEBI
ArecalineChEBI
ArecholineChEBI
ArekolinChEBI
MethylarecaidenChEBI
MethylarecaidinChEBI
1,2,5,6-tetrahydro-1-Methylnicotinic acid, methyl esterHMDB
ArecholinHMDB
ArecolinHMDB
Arecoline baseHMDB
Arecoline hydrobromideHMDB
Methyl 1,2,5, 6-tetrahydro-1-methylnicotinateHMDB
Methyl 1,2,5,6-tetrahydro-1-methylnicotinateHMDB
Methyl 1-methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylateHMDB
Methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylateHMDB
Methyl 1-methyl-5,6-dihydro-2H-pyridine-3-carboxylateHMDB
Methyl N-methyl-1,2,5, 6-tetrahydronicotinateHMDB
Methyl N-methyl-1,2,5,6-tetrahydronicotinateHMDB
Methyl N-methyltetrahydronicotinateHMDB
N-Methyl-beta -carboxylic acid methyl esterHMDB
N-Methyltetrahydronicotinic acid, methyl esterHMDB
Nicotinic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl esterHMDB
Chemical FormulaC8H13NO2
Average Molecular Weight155.1943
Monoisotopic Molecular Weight155.094628665
IUPAC Namemethyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate
Traditional Namearecoline
CAS Registry Number63-75-2
SMILES
COC(=O)C1=CCCN(C)C1
InChI Identifier
InChI=1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3
InChI KeyHJJPJSXJAXAIPN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Alkaloid or derivatives
  • Hydropyridine
  • Methyl ester
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary amine
  • Tertiary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility446 g/LALOGPS
logP0.55ALOGPS
logP0.65ChemAxon
logS0.46ALOGPS
pKa (Strongest Basic)8.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.86 m³·mol⁻¹ChemAxon
Polarizability17.1 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006w-9400000000-98b26a9d2867d710059eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-13bcb3825f7244e9bfd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-5900000000-4c54ca467a6647c61870View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rw-9000000000-ff7785df405dc6c7b136View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-1de11420c61028c65308View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-ff4ff3298d65bc8e1a2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9300000000-f368ae9f151a5d63114cView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9400000000-c2ac70d939302e3f979bView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04365
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002198
KNApSAcK IDC00002020
Chemspider ID13872064
KEGG Compound IDC10129
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkArecoline
METLIN IDNot Available
PubChem Compound2230
PDB IDNot Available
ChEBI ID2814
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shih YT, Chen PS, Wu CH, Tseng YT, Wu YC, Lo YC: Arecoline, a major alkaloid of the areca nut, causes neurotoxicity through enhancement of oxidative stress and suppression of the antioxidant protective system. Free Radic Biol Med. 2010 Nov 30;49(10):1471-9. doi: 10.1016/j.freeradbiomed.2010.07.017. Epub 2010 Aug 4. [PubMed:20691257 ]
  2. Yang YR, Chang KC, Chen CL, Chiu TH: Arecoline excites rat locus coeruleus neurons by activating the M2-muscarinic receptor. Chin J Physiol. 2000 Mar 31;43(1):23-8. [PubMed:10857465 ]
  3. Wang SW, Hwang GS, Chen TJ, Wang PS: Effects of arecoline on testosterone release in rats. Am J Physiol Endocrinol Metab. 2008 Aug;295(2):E497-504. doi: 10.1152/ajpendo.00045.2008. Epub 2008 Jun 17. [PubMed:18559981 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular weight:
51420.4
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]