Arecolin
Methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate · Arecolin · NSC 56321 · ARECOLINE · Arecaidin · Methyl arecaidin · Methylarecaidine · Ephedrine alkaloid
Identifikatoren & physikalische Daten
| CAS No. | 63-75-2 |
|---|---|
| Summenformel | C8H13NO2 |
| Durchschnittliche Molmasse | 155,19 g/mol |
| Monoisotopische Masse | 155,09462866 g/mol |
| SMILES | COC(=O)C1=CCCN(C)C1 |
| InChIKey | HJJPJSXJAXAIPN-UHFFFAOYSA-N |
| PubChem CID | 2230 |
| ChEMBL | CHEMBL7303 |
| ChEBI | CHEBI:2814 |
| EC No. | 200-565-5 |
| DTXSID | DTXSID3022617 |
| Lokaler Name | Arecolin |
Chemische & physikalische Eigenschaften
| XLogP | 0,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 29,5 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 187 |
| LogP (Verteilungskoeffizient) | 0.350.350 |
| LogS | 0.81 |
| Löslichkeit | 10000001.00E+06 mg/L @ 25 °C (exp)Chloroform (Sparingly), Methanol (Slightly) |
| Siedepunkt | 209209.00 °C. @ 760.00 mm Hg209℃ |
| Schmelzpunkt | < 25 °C<25℃ |
| Dissociation Constants | 7.647.16 |
| Kovats Retention Index | 11951236.1 |
| Dichte | 1.0504 g/cm3 (20 ºC) |
| Brechungsindex | 1.4860 (589.3 nm 20℃) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Aggregatzustand | Oil |
| pKa (Säurekonstante) | 6.84(at 25℃) |
| Farbe | Oily liquid |
| InChI | 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 | C1N(C)CCC=C1C(OC)=O |
| LogP (Verteilungskoeffizient) | 0.350 |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.DangerH315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H340 (50%): May cause genetic defects [Danger Germ cell mutagenicity]H351 (50%): Suspected of causing cancer [Warning Carcinogenicity]P203, P264, P264+P265, P280, P302+P352, P305+P351+P338, P318, P321, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 1 of 2 reports by companies.There is 1 notification provided by 1 of 2 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Hazard Traits - CarcinogenicityAuthoritative List - IARC Carcinogens - 2BReport - regardless of intended function of ingredient in the product |
| Hazard Classes and Categories | Skin Irrit. 2 (50%)Eye Irrit. 2 (50%)Muta. 1A (50%)Carc. 2 (50%) |
| Gesundheitliche Auswirkungen | Pupillary constriction, bronchial constriction. |
| Expositionspfade | Ingestion |
| Toxizitätsübersicht | Arecoline is the primary active ingredient responsible for the central nervous system effects of the areca nut. Arecoline has been compared to nicotinehowever, nicotine acts primarily on the nicotinic acetylcholine receptor. Arecoline is known to be a partial agonist of muscarinic acetylcholine M1, M2, M3 receptors and M4, which is believed to be the primary cause of its parasympathetic effects (such as pupillary constriction, bronchial constriction, etc.). (Wikipedia) Arecoline is cytotoxic to human gingival fibroblasts at a concentration higher than 50 μg/ml by depleting intracellular thiols and inhibiting mitochondrial activity (P<0.05). In addition, the cells displayed a marked arrest at G2/M phase in a dose-dependent manner. (A15351) |
| Carcinogen Classification | ArecolineGroup 2B: Possibly carcinogenic to humansVolume 128: (2021) Acrolein, Crotonaldehyde, and Arecoline2021 online2020Not listed by IARC. |
| Toxicity Data | LD50: 100 mg/kg, administered subcutaneously in mouse (Wikipedia) |
| Toxizität | LD50 in mice, dogs (mg/kg): 100, 5 s.c. (Burrows) |
Anwendungen & Verwendung
Beschreibung
Areca catechu L. (Bin Lang), a palm plant native to Malaysia, is mainly distributed in tropical regions of Asia and the Americas. Arecoline is extracted from dry mature seeds of areca. The mature seeds of areca are 3–5 cm in diameter, with fibrous peel and a seed, namely, areca nut. The endosperm of areca nut is hard, with grayish-brown spots. Areca nut is harvested from August to November every year before the fruit is fully mature. The seeds are peeled, boiled, and cut into thin slices. The dried slices are brown or black, and it is an important medicine in traditional Chinese medicine. Areca nut is the raw materials of catechu. Areca nut was used as anthelmintics with arecoline as the main alkaloid in it.
History
Arecoline, an alkaloid extracted from Areca catechu L., is first reported by Jahns in 1888. Mujumdar found that there were at least six kinds of alkaloids in areca, including arecoline, arecaidine, guavacoline, and guavacine. The content of arecoline in the fresh fruit of areca was 0.3–0.63% as determined with HPLC .It has been found first that arecoline has the effect of antiparasite and is promoting the motility of the gastrointestinal smooth muscle. It activates the M and N cholinergic receptors, excites the nervous system, promotes the body excitability, and improves the ability of learning and memory .
Verwenden
Arecoline is a cholinergic alkaloid from seeds of the betel nut palm Areca catechu. 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.