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Basic information
- CAS
300-08-3- Standard SMILES
Br.COC(=O)C1=CCCN(C)C1- InChIKey
AXOJRQLKMVSHHZ-UHFFFAOYSA-N- Molecular formula
- C8H14BrNO2
- Average molar mass
- 236.11 g/mol
- Monoisotopic mass
- 235.02079079
Overview
Arecoline hydrobromide is an organic molecular entity. It has a role as a toxin and a carcinogenic agent.
Names & identifiers
- Preferred name
- Arecoline Hydrobromide
- IUPAC
- methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate;hydrobromide
Names & synonyms
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
Show more names
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
Database identifiers
- CAS
300-08-3- PubChem CID
- 9301
- DTXSID
DTXSID9075379- ChEMBL
CHEMBL449209- ChEBI
CHEBI:233150- UNII
- 24S79B9CX7
- EC Number
- 206-087-3
Properties
Computed structural propertiesFilling in
- Topological polar surface area
- 29.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 187
Experimental & physicochemical properties
Solubility>35.4 [ug/mL] (The mean of the results at pH 7.4)
Safety & regulation
GHS classification
GHS Classification
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.
Hazard information
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%)
Toxicology
Health EffectsPupillary constriction, bronchial constriction.
Exposure RoutesIngestion
Toxicity Summary
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)
Chemistry & industry
Uses & manufacturing
Uses
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).
Related reactions
5 records
Compound notes
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