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Arecoline

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Name

Arecoline

EINECS 200-565-5
CAS No. 63-75-2 Density 1.059g/cm3
PSA N/A LogP N/A
Solubility (161 g/L) (25 oC) Melting Point <25 oC
Formula C8H13 N O2 Boiling Point 209°Cat760mmHg
Molecular Weight 155.197 Flash Point 81.1°C
Transport Information N/A Appearance Yellow Oil
Safety Poison by subcutaneous and intraperitoneal routes. Moderately toxic by ingestion. Questionable carcinogen with experimental neoplastigenic data. It mimics the action of acetylcholine, a neuro-transmitter, and is a parasympathetic nervous system stimulant. Its action on the central nervous system can cause tremors. Human mutation data reported. It is easily nitrosated to several nitrosamines. See also ESTERS and NITROSAMINES. It is the major alkaloid found in betel quid. Combustible, can react with oxidizing materials. When heated to decomposition it emits highly toxic fumes of NOx. Risk Codes N/A
Molecular Structure Molecular Structure of 63-75-2 (arecoline) Hazard Symbols N/A
Synonyms

Arecoline(6CI);Nicotinic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester (8CI);1-Methyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester;3-Methoxycarbonyl-1-methyl-1,2,5,6-tetrahydropyridine;Arecaidine methyl ester;Arecolin;Arecoline base;Methyl 1,2,5,6-tetrahydro-1-methylnicotinate;MethylN-methyl-1,2,5,6-tetrahydronicotinate;Methyl arecaidin;Methylarecaidine;NSC56321;

Article Data 23

Arecoline Chemical Properties

IUPAC name: Methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate
Molecular Formula: C8H13NO2
Molecular Weight: 155.194320 g/mol
EINECS: 200-565-5
Appearance: Oily Liquid
Index of Refraction: 1.483
Surface Tension: 35.1 dyne/cm
Density: 1.059 g/cm3
Flash Point: 81.1 °C
Enthalpy of Vaporization: 44.53 kJ/mol
Boiling Point: 209 °C at 760 mmHg
Vapour Pressure: 0.208 mmHg at 25 °C
Product Categories: Heterocyclic Compounds;Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals 
Following is the structure of Arecoline (CAS NO.63-75-2):
   

Arecoline Uses

Owing to its muscarinic and nicotinic agonist properties, Arecoline (CAS NO.63-75-2) 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. Arecoline has also been used medicinally as an antihelmintic (a drug against parasitic worms). It is used in the form of various salts as a ganglionic stimulant, a parasympathomimetic, and a vermifuge, especially in veterinary practice. It has also been used as a euphoriant in the Pacific Islands. 

Arecoline Toxicity Data With Reference

1.    

dnd-hmn:Cells-uns 20 µg/tube

    MUREAV    Mutation Research. 278 (1992),271.
2.    

dni-hmn:Cells-uns 339 µmol/L

    IJCNAW    International Journal of Cancer. 47 (1991),396.
3.    

orl-rat LD50:2500 mg/kg

    EJMCA5    European Journal of Medicinal Chemistry. Chimie Therapeutique. 26 (1991),853.
4.    

ipr-rat LD50:40 mg/kg

    BIJOAK    Biochemical Journal. 113 (1969),123.
5.    

orl-mus LD50:550 mg/kg

    EJMCA5    European Journal of Medicinal Chemistry. Chimie Therapeutique. 26 (1991),853.
6.    

ipr-mus LD50:190 mg/kg

    AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 192 (1971),88.
7.    

ivn-mus LD50:36 mg/kg

    FATOAO    Farmakologiya i Toksikologiya (Moscow). 28 (1965),33.
8.    

unk-mus LDLo:100 mg/kg

    HBAMAK    “Abdernalden’s Handbuch der Biologischen Arbeitsmethoden.“ 4 (1935),1289.
9.    

scu-dog LD50:5 mg/kg

    FAZMAE    Fortschritte der Arzneimittelforschung. 17 (1973),108.
10.    

unk-dog LDLo:5 mg/kg

    HBAMAK    “Abdernalden’s Handbuch der Biologischen Ar

Arecoline Consensus Reports

IARC Cancer Review: Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 37 (1985),p. 141.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) .

Arecoline Safety Profile

Poison by subcutaneous and intraperitoneal routes. Moderately toxic by ingestion. Questionable carcinogen with experimental neoplastigenic data. It mimics the action of acetylcholine, a neuro-transmitter, and is a parasympathetic nervous system stimulant. Its action on the central nervous system can cause tremors. Human mutation data reported. It is easily nitrosated to several nitrosamines. See also ESTERS and NITROSAMINES. It is the major alkaloid found in betel quid. Combustible, can react with oxidizing materials. When heated to decomposition it emits highly toxic fumes of NOx.

Arecoline Specification

 Arecoline, its cas register number is 63-75-2. It also can be called 1,2,5,6-Tetrahydro-1-methyl-3-pyridinecarboxylic acid
methyl ester ; Methyl 1,2,5,6-tetrahydro-1-methylnicotinate ; and Methyl N-methyl-1,2,5,6-tetrahydronicotinate . And its classification code are Cholinergic Agents;Cholinergic Agonists;Mutation data;Neurotransmitter Agents;Tumor data. 
 Arecoline (CAS NO.63-75-2) is an alkaloid natural product found in the areca nut, the fruit of the areca palm (Areca catechu). It is an odourless oily liquid volatile in steam, miscible with most organic solvents and water, but extractable from the latter by ether in presence of dissolved salts. The salts are crystalline, but usually deliquescent. 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.

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