Arecoline Hydrobromide

HCID 9301CAS 300-08-3

Grundinformationen

Standard-SMILES
Br.COC(=O)C1=CCCN(C)C1
InChIKey
AXOJRQLKMVSHHZ-UHFFFAOYSA-N
Summenformel
C8H14BrNO2
Durchschnittliche Molmasse
236,11 g/mol
Monoisotopische Masse
235,02079079

Überblick

Arecoline hydrobromide is an organic molecular entity. It has a role as a toxin and a carcinogenic agent.

Namen und Bezeichner

Bevorzugter Name
Arecoline Hydrobromide
IUPAC
methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate;hydrobromide

Namen und Synonyme

Arecoline hydrobromide300-08-3ARECOLINE HBrNSC-3175024S79B9CX7DTXSID90753793-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester, hydrobromidemethyl 1-methyl-1,2,3,6-tetrahydropyridin-1-ium-5-carboxylate;bromideRefChem:113811DTXCID6038112206-087-3Arecoline bromide
Weitere Namen anzeigen
Methyl 1-Methyl-1,2,5,6-tetrahydropyridine-3-carboxylate hydrobromideMFCD00039041Esterase3-Pyridinecarboxylicacid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester, hydrobromideArecoline (hydrobromide)methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate,hydrobromideMLS000028840Arekolinhydrobromid

Datenbank-Bezeichner

CAS
300-08-3
PubChem CID
9301
DTXSID
DTXSID9075379
ChEMBL
CHEMBL449209
ChEBI
CHEBI:233150
UNII
24S79B9CX7
EC Number
206-087-3

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
29,5 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
2
Schwere Atome
12

Experimentelle und physikochemische Eigenschaften

Solubility>35.4 [ug/mL] (The mean of the results at pH 7.4)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H301 (95.8%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 72 reports by companies from 3 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory InformationARECOLINIUM BROMIDE: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 3 (95.8%)

Toxikologische Informationen

Health EffectsPupillary constriction, bronchial constriction.
Exposure RoutesIngestion
Toxicity Summary · 1 Eintrag

Arecoline is the primary active ingredient responsible for the central nervous system effects of the areca nut. Arecoline has been compared to nicotine; however, 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 ClassificationNot listed by IARC.
Toxicity DataLD50: 100 mg/kg, administered subcutaneously in mouse (Wikipedia)

Chemie und Industrie

Verwendung und Herstellung

Uses · 1 Eintrag

Arecoline is found in nuts. Arecoline is isolated from betel nuts Arecoline is an alkaloid natural product found in the areca nut, the fruit of the areca palm (Areca catechu). 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. Arecoline has also been used medicinally as an antihelmintic (a drug against parasitic worms).

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