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Arecoline

Arecoline structure

CAS No:
63-75-2
Formula:
C8H13NO2
Chemical Name:
Arecoline
Synonyms:
3-Pyridinecarboxylic acid,1,2,5,6-tetrahydro-1-methyl-,methyl ester;Nicotinic acid,1,2,5,6-tetrahydro-1-methyl-,methyl ester;Arecoline;Arecaidine methyl ester;Arecoline base;Methyl 1,2,5,6-tetrahydro-1-methylnicotinate;3-Methoxycarbonyl-1-methyl-1,2,5,6-tetrahydropyridine;Methyl N-methyl-1,2,5,6-tetrahydronicotinate;Arecolin;Methyl arecaidin;NSC 56321;Methylarecaidine;1-Methyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester;1398-01-2
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Oily Liquid

Arecoline is a tetrahydropyridine that is 1,2,5,6-tetrahydropyridine with a methyl group at position 1, and a methoxycarbonyl group at position 3. An alkaloid found in the areca nut, it acts as an agonist of muscarinic acetylcholine. It has a role as a muscarinic agonist and a metabolite. It is a tetrahydropyridine, an enoate ester, a pyridine alkaloid and a methyl ester.|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. 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.

Arecoline Basic Attributes

Molecular Weight：

155.196

Exact Mass：

155.19

EC Number：

200-565-5

UNII：

4ALN5933BH

NSC Number：

56321

DSSTox ID：

DTXSID3022617

HScode：

2933399090

Characteristics

PSA：

29.5

XLogP3：

0.35

Density：

1.0495 g/cm³ @ Temp: 20 °C

Melting Point：

<25 °C

Boiling Point：

209 °C

Flash Point：

81.1ºC

Refractive Index：

1.483

Water Solubility：

1000000 mg/L (at 25 °C)

Vapor Pressure：

0.08 mmHg

Toxicity：

Oral-rat LD50: 40 mg/kg; Oral-Mouse LD50: 550 mg/kg

Flammability characteristics：

Flammable; burning produces toxic nitrogen oxide fumes

PKA：

7.16None

Dissociation Constants：

7.16

Safety Information

Storage features：

Treasury is ventilated, low temperature and dry; stored separately from oxidant

Explosive characteristics：

Reacts with oxidants

Toxicity

Toxicity class：

moderately toxic

Drug Information

MeSH：

Drugs that bind to and activate cholinergic receptors. (See all compounds classified as Cholinergic Agonists.)

MeSH Entry Terms：

Arecaline

Arecoline Use and Manufacturing

Uses

A cholinergic alkaloid from seeds of the betel nut palm Areca catechu. Anthelmintic (Cestodes); cathartic

Use Classification：

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Computed Properties

Molecular Weight:155.19
XLogP3:0.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:155.094628657
Monoisotopic Mass:155.094628657
Topological Polar Surface Area:29.5
Heavy Atom Count:11
Complexity:187
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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