Guvacine

Arecoline is usually stated to be present to the extent of 0-1 per cent., but Chemnitius gives the yield of hydrobromide as 0-35 to 0-4 per cent. Arecaidine and guvacine occur in smaller quantities, whilst guvacoline and arecolidine are found only in minute amounts. Alkaloidal assay processes for areca nuts have been published by Bourcet, and the National Formulary Committee, and Bond has described a method of estimation for arecoline hydrobromide. A microchemical test for the identification of arecoline has been devised by Gornyi. ... 

Guvacoline, CjHjjOjN. K. Hess assigned this name to an alkaloid, obtained by E. Merck from areca nut, which yields a hydrobromide, short prisms, m.p. 144-5°, that he identified with guvacine methyl ester hydrobromide see above). The base is a colourless oil, b.p. 114°/13 mm., which yields a hydrochloride, m.p. 121-2°, a platinichloride, m.p. 211°, and on methylation furnishes a mixture of arecoline methiodide and hydriodide (p. 12). 

During the last two decades, a large number of GABA analogs based on A-substitutions of the GABA mimetics nipecotic acid, guvacine, THPO, THAO, and exo-THPO... 

Larsson, O. M., Falch, E., Krogsgaard-Larsen, P, and Schousboe, A. (1988) Kinetic characterization of inhibition of y-aminobutyric acid uptake into cultured neurons and astrocytes by 4,4-diphenyl-3-butenyl derivatives of nipecotic acid and guvacine. J. Neurochem. 50, 818-823. 

Knutsen, L. J., Andersen, K. E., Lau, J., et al. (1999) Synthesis of novel GABA uptake inhibitors. 3. Diaryloxime and diarylvinyl ether derivatives of nipecotic acid and guvacine as anticonvulsant agents. J. Med. Chem. 42, 3447-3462. 

Lobelia cathechu guvacoline guvacine Lobelia inflata Lobeline Nicotinic ACh agonist... 

Acetylcholine All four alkaloids derived from areca (arecoline, arecaidine, guvacoline, and guvacine) act as full agonists at muscarinic acetylcholine receptors (Wolf-Pflugmann et al. 1989). Peripherally administered arecoline (10 mg/kg) subtly reduces cortical and subcortical acetylcholine levels (Molinengo et al. 1986). 

Areca (Areca catechu) is a tall palm tree that yields a nut, commonly chewed in Asia for its stimulant effects. It is discussed at greater length in chapter 4, but is mentioned here briefly for its cognitive effects. Areca s psychoactive constituents (arecoline, arecaidine, guvacoline, and guvacine) are agonists at muscarinic acetylcholine receptors. They also directly inhibit reuptake of GABA. 

Lodge D, Johnston GA, Curtis DR, Brand SJ. (1977). Effects of the Areca nut constituents arecaidine and guvacine on the action of GABA in the cat central nervous system. Brain Res. 136(3) 513-22. 

Wolf-Pflugmann M, Lambrecht G, Wess J, Mutschler E. (1989). Synthesis and muscarinic activity of a series of tertiary and quaternary N-substituted guvacine esters structurally related to arecoline and arecaidine propargyl ester. Arzneimittelforschung. 39(5) 539-44. 

The other alkaloids derived from nicotinic acid, with pyridine nucleus such as arecoline, arecaidine and guvacoline, are tetrahydronicotinic acid (guvacine) derivatives. 

Areca catechu L. A. hortonsis Lour. Bing Lang (Betel nut palm) (nut) Arecholine, arecholidine, guvacoline, guvacine.33 Treat taeniasis. 

Areca catechu L. China Arecholine, arecholidine, guvacoline, guvacine.33 Treat taeniasis. 

N.A. Arecoline, arecaine, arecaidine, arecolidine, isoguvacine, guvacine, givacoline, tannins, palmitic acid, stearic acid, myristic acid, lauric acid, margaric acid, nonadecanoid, heneicosanic acid.100 A breath sweetening masticatory, treat abdominal tumor, an astringent, stomachic, stimulant, and anthelmintic. 

---