Arecaidine

Arecaidine
Clinical data
Other names	Methylguvacine; Arecaine; N-Methylguvacine
Drug class	GABA reuptake inhibitor
Identifiers
	IUPAC name 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylic acid;
CAS Number	499-04-7;
PubChem CID	10355;
IUPHAR/BPS	9487;
ChemSpider	9928;
UNII	0S8YEV0D4O;
KEGG	C10128;
ChEBI	CHEBI:2813;
ChEMBL	ChEMBL432561;
CompTox Dashboard (EPA)	DTXSID60198139 ;
Chemical and physical data
Formula	C7H11NO2
Molar mass	141.170 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CCC=C(C1)C(=O)O;
	InChI InChI=1S/C7H11NO2/c1-8-4-2-3-6(5-8)7(9)10/h3H,2,4-5H2,1H3,(H,9,10); Key:DNJFTXKSFAMXQF-UHFFFAOYSA-N;

Arecaidine, also known as N-methylguvacine, is an alkaloid in areca nuts and a GABA reuptake inhibitor.^[1]^[2]^[3] It is structurally similar to the GABA reuptake inhibitors guvacine and nipecotic acid.^[1] Arecaidine has been found to produce sedative effects in mice and to protect against the lethality of the GABA_A receptor antagonists bicuculline and pentylenetetrazol.^[3] On the other hand, it did not produce anticonvulsant effects.^[3] Lime is said to hydrolyse arecoline to arecaidine.^[2]

References

^ ^a ^b Volgin AD, Bashirzade A, Amstislavskaya TG, Yakovlev OA, Demin KA, Ho YJ, Wang D, Shevyrin VA, Yan D, Tang Z, Wang J, Wang M, Alpyshov ET, Serikuly N, Wappler-Guzzetta EA, Lakstygal AM, Kalueff AV (May 2019). "DARK Classics in Chemical Neuroscience: Arecoline". ACS Chem Neurosci. 10 (5): 2176–2185. doi:10.1021/acschemneuro.8b00711. PMID 30664352.
^ ^a ^b Johnston GA, Krogsgaard-Larsen P, Stephanson A (December 1975). "Betel nut constituents as inhibitors of gamma-aminobutyric acid uptake". Nature. 258 (5536): 627–628. Bibcode:1975Natur.258..627J. doi:10.1038/258627a0. PMID 1207742. S2CID 4147760.
^ ^a ^b ^c Lodge D, Johnston GA, Curtis DR, Brand SJ (November 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): 513–522. doi:10.1016/0006-8993(77)90075-0. PMID 922499.

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