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| CAS No.: | 63-75-2 |
|---|---|
| Name: | arecoline |
| Molecular Structure: | |
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| Formula: | C8H13 N O2 |
| Molecular Weight: | 155.197 |
| 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; |
| EINECS: | 200-565-5 |
| Density: | 1.059g/cm3 |
| Melting Point: | <25 oC |
| Boiling Point: | 209°Cat760mmHg |
| Flash Point: | 81.1°C |
| Solubility: | (161 g/L) (25 oC) |
| 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. |
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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):
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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.
| 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 |
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) .
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, 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.
