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Substance Name: Arecoline
RN: 63-75-2
UNII: 4ALN5933BH
InChIKey: HJJPJSXJAXAIPN-UHFFFAOYSA-N

Note

  • 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.

Molecular Formula

  • C8-H13-N-O2

Molecular Weight

  • 155.196
 

Classification Codes

  • Cholinergic Agents
  • Cholinergic Agonists
  • Mutation Data
  • Neurotransmitter Agents
  • Tumor Data
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Names and Synonyms

Name of Substance

  • Arecoline

MeSH Heading

  • Arecoline

Synonyms

  • 1,2,5,6-Tetrahydro-1-methyl-3-pyridinecarboxylic acid methyl ester
  • 1,2,5,6-Tetrahydro-1-methylnicotinic acid, methyl ester
  • 1-Methyl-delta(sup 3,4)tetrahydro-3-pyridinecarboxylate
  • 5-22-01-00322 (Beilstein Handbook Reference)
  • Arecaidine methyl ester
  • Arecaline
  • Arecholine
  • Arecolin
  • Arecoline
  • Arecoline base
  • Arekolin
  • BRN 0123045
  • CCRIS 7688
  • EINECS 200-565-5
  • Methyl 1,2,5,6-tetrahydro-1-methylnicotinate
  • Methyl N-methyl-1,2,5,6-tetrahydronicotinate
  • Methyl N-methyltetrahydronicotinate
  • Methylarecaiden
  • N-Methyltetrahydronicotinic acid, methyl ester
  • N-Methyltetrahydropyridine-beta-carboxylic acid methyl ester
  • NSC 56321
  • UNII-4ALN5933BH

Systematic Names

  • 3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester
  • Arecoline
  • Nicotinic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester

Registry Numbers

CAS Registry Number

  • 63-75-2

FDA UNII

  • 4ALN5933BH

System Generated Number

  • 0000063752

Structure Descriptors

InChI

1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3

InChIKey

HJJPJSXJAXAIPN-UHFFFAOYSA-N

Smiles

C1[N@@](CC(=CC1)C(OC)=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 subcutaneous 5mg/kg (5mg/kg)   Fortschritte der Arzneimittelforschung. Progress in Drug Research. Vol. 17, Pg. 108, 1973.
dog LDLo unreported 5mg/kg (5mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
mouse LD50 intraperitoneal 190mg/kg (190mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 192, Pg. 88, 1971.
mouse LD50 intravenous 36mg/kg (36mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT
Farmakologiya i Toksikologiya Vol. 28, Pg. 33, 1965.
mouse LD50 oral 550mg/kg (550mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 26, Pg. 853, 1991.
mouse LDLo unreported 100mg/kg (100mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rat LD50 intraperitoneal 40mg/kg (40mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

VASCULAR: CONTRACTION (ISOLATED TISSUES)
Biochemical Journal. Vol. 113, Pg. 123, 1969.
rat LD50 oral 2500mg/kg (2500mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 26, Pg. 853, 1991.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point < 25 deg C   EXP
Boiling Point 209 deg C   EXP
pKa Dissociation Constant 7.16 (none)   EXP
log P (octanol-water) 0.35 (none)   EXP
Water Solubility 1.00E+06 mg/L 25 EXP
Henry's Law Constant 4.96E-08 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.18E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.