Arecoline

Identification

Name
Arecoline
Accession Number
DB04365  (EXPT03296)
Type
Small Molecule
Groups
Experimental
Description

An 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.

Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Arecoline hydrobromide24S79B9CX7300-08-3AXOJRQLKMVSHHZ-UHFFFAOYSA-N
Categories
UNII
4ALN5933BH
CAS number
63-75-2
Weight
Average: 155.1943
Monoisotopic: 155.094628665
Chemical Formula
C8H13NO2
InChI Key
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UMuscarinic acetylcholine receptor M1Not AvailableHuman
UMuscarinic acetylcholine receptor M3Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
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.
AmikacinThe therapeutic efficacy of Arecoline can be decreased when used in combination with Amikacin.
AnisodamineThe risk or severity of adverse effects can be increased when Anisodamine is combined with Arecoline.
ApramycinThe therapeutic efficacy of Arecoline can be decreased when used in combination with Apramycin.
ArbekacinThe therapeutic efficacy of Arecoline can be decreased when used in combination with Arbekacin.
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.
Food Interactions
Not Available

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 References
Not Available
External Links
Human Metabolome Database
HMDB0030353
KEGG Compound
C10129
PubChem Compound
2230
PubChem Substance
46507231
ChemSpider
13872064
BindingDB
46858
ChEBI
2814
ChEMBL
CHEMBL7303
IUPHAR
296
Guide to Pharmacology
GtP Drug Page
Wikipedia
Arecoline

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)< 25 °CPhysProp
boiling point (°C)209 °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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0006-9400000000-c2ac70d939302e3f979b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Not Available
Sub Class
Not Available
Direct Parent
Alkaloids and derivatives
Alternative Parents
Hydropyridines / Methyl esters / Enoate esters / Trialkylamines / Amino acids and derivatives / Monocarboxylic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
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
show 13 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
methyl ester, enoate ester, tetrahydropyridine, pyridine alkaloid (CHEBI:2814) / Pyridine alkaloids (C10129)

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...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Receptor 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...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 Da
References
  1. Jakubik J, Bacakova L, El-Fakahany EE, Tucek S: Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors. Mol Pharmacol. 1997 Jul;52(1):172-9. [PubMed:9224827]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 09:14