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Identification
NameArecoline
Accession NumberDB04365  (EXPT03296)
TypeSmall Molecule
GroupsExperimental
DescriptionAn 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, especially in veterinary practice. It has been used as a euphoriant in the Pacific Islands. [PubChem]
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII4ALN5933BH
CAS number63-75-2
WeightAverage: 155.1943
Monoisotopic: 155.094628665
Chemical FormulaC8H13NO2
InChI KeyInChIKey=HJJPJSXJAXAIPN-UHFFFAOYSA-N
InChI
InChI=1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3
IUPAC Name
methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate
SMILES
COC(=O)C1=CCCN(C)C1
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
  • Guvacine
  • Tetrahydropyridine
  • Hydropyridine
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9713
Blood Brain Barrier+0.9613
Caco-2 permeable+0.6557
P-glycoprotein substrateSubstrate0.6628
P-glycoprotein inhibitor INon-inhibitor0.6202
P-glycoprotein inhibitor IINon-inhibitor0.9697
Renal organic cation transporterInhibitor0.6075
CYP450 2C9 substrateNon-substrate0.8958
CYP450 2D6 substrateSubstrate0.5321
CYP450 3A4 substrateSubstrate0.5051
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9061
CYP450 3A4 inhibitorNon-inhibitor0.982
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9564
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.8927
BiodegradationReady biodegradable0.9234
Rat acute toxicity1.8241 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5396
hERG inhibition (predictor II)Non-inhibitor0.8535
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point< 25 °CPhysProp
boiling point209 °CPhysProp
water solubility1E+006 mg/L (at 25 °C)MERCK INDEX (1996)
logP0.35HANSCH,C ET AL. (1995)
logS0.81ADME Research, USCD
pKa7.16MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility446.0 mg/mLALOGPS
logP0.55ALOGPS
logP0.65ChemAxon
logS0.46ALOGPS
pKa (Strongest Basic)8.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.86 m3·mol-1ChemAxon
Polarizability17.1 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0006-9400000000-c2ac70d939302e3f979bView in MoNA
References
Synthesis Reference

K. S. Keshave Murthy, Allan W. Rey, Dan S. Matu, “Preparation of 1,2,5,6-tetra-hydro-3-carboalkoxypridines such as arecoline and salts of 1,2,5,6-tetrahydro-3-carboalkoxypridines and arecoline hydrobromide.” U.S. Patent US6132286, issued October 17, 2000.

US6132286
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when 1,10-Phenanthroline is combined with Arecoline.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Arecoline.
AlprenololThe risk or severity of adverse effects can be increased when Alprenolol is combined with Arecoline.
AmbenoniumThe risk or severity of adverse effects can be increased when Ambenonium is combined with Arecoline.
ArotinololThe risk or severity of adverse effects can be increased when Arotinolol is combined with Arecoline.
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Arecoline.
BefunololThe risk or severity of adverse effects can be increased when Befunolol is combined with Arecoline.
BetaxololThe risk or severity of adverse effects can be increased when Betaxolol is combined with Arecoline.
BevantololThe risk or severity of adverse effects can be increased when Bevantolol is combined with Arecoline.
BisoprololThe risk or severity of adverse effects can be increased when Bisoprolol is combined with Arecoline.
BopindololThe risk or severity of adverse effects can be increased when Bopindolol is combined with Arecoline.
BufuralolThe risk or severity of adverse effects can be increased when Bufuralol is combined with Arecoline.
BupranololThe risk or severity of adverse effects can be increased when Bupranolol is combined with Arecoline.
CarteololThe risk or severity of adverse effects can be increased when Carteolol is combined with Arecoline.
CarvedilolThe risk or severity of adverse effects can be increased when Carvedilol is combined with Arecoline.
CeliprololThe risk or severity of adverse effects can be increased when Celiprolol is combined with Arecoline.
CimetropiumArecoline may decrease the anticholinergic activities of Cimetropium.
CoumaphosThe risk or severity of adverse effects can be increased when Coumaphos is combined with Arecoline.
DecamethoniumThe risk or severity of adverse effects can be increased when Decamethonium is combined with Arecoline.
DemecariumThe risk or severity of adverse effects can be increased when Demecarium is combined with Arecoline.
DichlorvosThe risk or severity of adverse effects can be increased when Dichlorvos is combined with Arecoline.
DonepezilThe risk or severity of adverse effects can be increased when Donepezil is combined with Arecoline.
EchothiophateThe risk or severity of adverse effects can be increased when Echothiophate is combined with Arecoline.
EdrophoniumThe risk or severity of adverse effects can be increased when Edrophonium is combined with Arecoline.
EsmololThe risk or severity of adverse effects can be increased when Esmolol is combined with Arecoline.
FenthionThe risk or severity of adverse effects can be increased when Fenthion is combined with Arecoline.
GalantamineThe risk or severity of adverse effects can be increased when Galantamine is combined with Arecoline.
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Gallamine Triethiodide is combined with Arecoline.
Ginkgo bilobaThe risk or severity of adverse effects can be increased when Ginkgo biloba is combined with Arecoline.
Huperzine AThe risk or severity of adverse effects can be increased when Huperzine A is combined with Arecoline.
IndenololThe risk or severity of adverse effects can be increased when Indenolol is combined with Arecoline.
IsoflurophateThe risk or severity of adverse effects can be increased when Isoflurophate is combined with Arecoline.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Arecoline.
LevobunololThe risk or severity of adverse effects can be increased when Levobunolol is combined with Arecoline.
MalathionThe risk or severity of adverse effects can be increased when Malathion is combined with Arecoline.
MefloquineThe risk or severity of adverse effects can be increased when Mefloquine is combined with Arecoline.
MemantineThe risk or severity of adverse effects can be increased when Memantine is combined with Arecoline.
MetipranololThe risk or severity of adverse effects can be increased when Metipranolol is combined with Arecoline.
MetoprololThe risk or severity of adverse effects can be increased when Metoprolol is combined with Arecoline.
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Arecoline.
NadololThe risk or severity of adverse effects can be increased when Nadolol is combined with Arecoline.
NeostigmineThe risk or severity of adverse effects can be increased when Neostigmine is combined with Arecoline.
OxprenololThe risk or severity of adverse effects can be increased when Oxprenolol is combined with Arecoline.
PenbutololThe risk or severity of adverse effects can be increased when Penbutolol is combined with Arecoline.
PhysostigmineThe risk or severity of adverse effects can be increased when Physostigmine is combined with Arecoline.
PindololThe risk or severity of adverse effects can be increased when Pindolol is combined with Arecoline.
PractololThe risk or severity of adverse effects can be increased when Practolol is combined with Arecoline.
PropranololThe risk or severity of adverse effects can be increased when Propranolol is combined with Arecoline.
PyridostigmineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Arecoline.
RivastigmineThe risk or severity of adverse effects can be increased when Rivastigmine is combined with Arecoline.
SotalolThe risk or severity of adverse effects can be increased when Sotalol is combined with Arecoline.
TacrineThe risk or severity of adverse effects can be increased when Tacrine is combined with Arecoline.
TimololThe risk or severity of adverse effects can be increased when Timolol is combined with Arecoline.
TrichlorfonThe risk or severity of adverse effects can be increased when Trichlorfon is combined with Arecoline.
TubocurarineThe risk or severity of adverse effects can be increased when Tubocurarine is combined with Arecoline.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Phosphatidylinositol phospholipase c activity
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:
51420.375 Da
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:24