63-75-2 Usage
Chemical Description
Arecoline is a natural alkaloid found in the areca nut and is used as a substrate in the reaction.
Description
Arecoline, also known as Areca catechu L. (Bin Lang), is a cholinergic alkaloid derived from the seeds of the betel nut palm Areca catechu. It is an oily liquid with a boiling point of 209°C and a density of 1.059 g/cm3. Arecoline is soluble in water, ethanol, ether, and chloroform, and can be synthesized into salts with organic acids such as arecoline hydrobromide, arecoline acetarsol, and arecoline p-antimony carboxybenzoic acid. It acts as an agonist of muscarinic acetylcholine and has been used in traditional Chinese medicine.
Uses
Used in Pharmaceutical Industry:
Arecoline is used as an anthelmintic agent, particularly effective against cestodes. It is also used as a cathartic, aiding in the treatment of constipation.
Used in Medical Research:
Arecoline has shown regulatory properties in controlling plasminogen activator inhibitor-1 expression in human buccal mucosa fibroblasts, which can be beneficial in various medical applications.
Used in Traditional Chinese Medicine:
Areca nut, the source of arecoline, has been used as an important medicine in traditional Chinese medicine, particularly for its anthelminthic properties with arecoline as the main alkaloid.
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 .
Indications
This product has no source standard.
Tablets: anthelmintics, less used now. Eye drops: cholinergic drugs for glaucoma
treatment.
Pharmacology
Paralysis was the main mechanism of the antiparasite effect of arecoline.
The effect of arecoline on cholinergic receptors is similar to that of pilocarpine.
It can agonize M-cholinergic receptors (M1, M2, M3, M4) and increase the
secretion of glands, especially the salivary. It can also agonize N-cholinergic
receptors and activate the muscles of skeletal, ganglia, carotid body, etc. The central
nervous system is also influenced by the cholinergic effect of arecoline. Intravenous
injection of small dosage of arecoline can cause wake-up reaction of the cortex in
cats, which is inhibited or blocked by atropine. Arecoline can cause salivation, vomiting, diuretic, lethargy, and convulsion when overdosed.In addition, arecoline can enhance intestinal peristalsis, contract bronchus, lower
heart rate, dilate blood vessels, and decrease blood pressure. While in rabbit, it
induces coronary artery contraction.Eye drops can reduce the pupil.Pharmacokinetic parameters for arecoline after oral administration of arecoline
(3? mg/kg): Tmax, 120.07? min; Cmax, 60.61? ng/mL; t1/2, 69.32? min; AUC0? – t,
15116.86? min/ng/mL; AUC0-∞, 15771.37? min/ng/mL; plasma clearance, 0.19? L/
min/kg .
Clinical Use
Arecoline is of historical interest, because its structure, like those of many other early medicinal agents, was determined and confirmed by a
19th-century German pharmacist, E. Jahns. Xanomeline may be viewed as a nonclassical bio-isostere of the ester moiety of arecoline. It is a
muscarinic M1/M4 agonist that is showing promise in clinical trials for the treatment of Alzheimer's disease. Although it is not tolerated at
orally effective doses, transdermal delivery systems are showing promise.
Safety Profile
Poison by
subcutaneous and intraperitoneal routes.
Moderately toxic by ingestion. Questionable
carcinogen with experimental neoplastigenic
data. It mimics the action of acetylcholine, a
neurotransmitter, 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 oxidzing
materials. When heated to decomposition it
emits hghly toxic fumes of NOx.
Check Digit Verification of cas no
The CAS Registry Mumber 63-75-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 3 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 63-75:
(4*6)+(3*3)+(2*7)+(1*5)=52
52 % 10 = 2
So 63-75-2 is a valid CAS Registry Number.
63-75-2Relevant articles and documents
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Kozello et al.
, (1979)
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Preparation method of arecoline
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Paragraph 0021, (2016/10/31)
The invention provides a preparation method of arecoline. On the presence of organic base, reaction raw materials such as nicotinic acid and the like have esterification and alkylation reactions with a compound capable of providing alkyl in the organic solvent, and arecoline can be prepared through a reduction reaction and aftertreatment. Two procedures including esterification and N-methylation are combined, and the process route of preparation of arecoline is shortened. According to the method, the operation conditions are simple, and the intermediate treatment is more convenient; expensive alkyl halide (such as methyl iodide) cannot be used as a reaction raw material, cheaper sulfolipid or phosphate ester compounds are selected, a good implementation effect is also obtained, and the product has a cost advantage.
CYCLIC AMINE AZAHETEROCYCLIC CARBOXAMIDES
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Page/Page column 50, (2012/02/13)
The invention provides novel cyclic amine azaheterocyclic carboxamide according to Formula (I), Formula (II) and Formula (III) their manufacture and use for the treatment of hyperproliferative diseases, such as cancer.
