Arecaidine methyl ester

SYNS ARECAIDINE METHYL ESTER ARECOLINE BASE METHYL-1,2,5,6-TETRA-HYDRO-l-METHYL-NICOTINATE N-METHYL-A-TETRAHYDRONICOTIN-IC ACID METHYL ESTER N-METHYLTETRAHYDRO-PYRIDINE-P-CARBO-XYLIC ACID METHYL ESTER 1,2,5,6-TETRA-HYDRO-l-METHYLNICOTINIC ACID, METHYL ESTER... 

Beilstein Handbook Reference) Arecaidine methyl ester Arecaline Arecholine Arecolin Arecoline Arekolin BRN 0123045 CCRIS 7688 EINECS 200-565-5 Methyl N-methyl-... 

Arecoline arecaidine methyl ester, found in betel nut derived from the palm Areca catechu, is widely used in many countries as a masticant. Areca also contains about 15% tannins. 

Seeds of Areca catechu (betel nut) (Palmae) contain the simple jV-methyltetrahydropyridine 3-carboxylic acid (jV-methyl-A -tetrahydronicotinic acid) arecaidine and arecoline (arecai-dine methyl ester) (Section 1, Appendix) that are mACh-R agonists and accordingly parasympathetic stimulants. Betel nut also yields guvacine (A -tetrahydronicotinic acid) that is an anti-epileptic GABA transport inhibitor. Conversely the jV-methyl dihydropyridone derivative ricinine from seeds of Ricinus communis (castor seed) (Euphorbiaceae) is a stimulatory agonist acting at the benzodiazepine site of the GABA(A) receptor. 

Since naturally occurring arecaidine is optically inactive and since neither synthetic arecaidine nor its methyl ester (arecoline) can be resolved, it was concluded that the double bond in arecaidine could not occupy the A -position because such a molecule (IX) includes an asymmetric C-atom (84). Structures with the double bond in either the A -position (X) or the A -position (XI) are the only two which do not involve a center of asymmetry. Structure XI (A -position) was shown to be correct by an... 

Arecoline (N - Methyl - A - tetrahydronicotinic acid meOiyl ester, methyl ester of arecaidine)... 

Arecoline, 1,2,5,6-tetrahydro-l-metkyl-3-pyridl-necarboxylic acid methyl ester the main areca alkaloid (A/, 155.19, b.p. 209 C) and the methyl ester of the alkaloid arecaidine (Af, 141.9, m.p. 232°C). A. is... 

Merck and Maeder have patented the manufacture of arecaidine by loss of water from l-methyl-4-hydroxypiperidine-3-carboxylic acid. A method of producing the latter has been describd by Mannich and Veit and has been developed by Ugriumov for the production of arecaidine and arecoline. With the same objective, Dankova, Sidorova and Preobrachenski use what is substantially McElvain s process,but start by converting ethylene oxide, via the chlorohydrin and the cyanohydrin, into -chloropropionic acid. The ethyl ester of this with methylamine in benzene at 140° furnishes methylbis(2-carbethoxyethyl) amine (I) which on refluxing with sodium or sodium Moamyloxide in xylene yields l-methyl-3-carbethoxy-4-piperidone (II). The latter is reduced by sodium amalgam in dilute hydrochloric acid at 0° to l-methyl-3-carbethoxy-4-hydroxypiperidine (III) which on dehydration, and hydrolysis, yields arecaidine (IV R = H), convertible by methylation into arecoline (IV R = CH3). 

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