Guvacine

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Guvacine
1,2,5,6-tetrahydropyridine-3-carboxylic acid.svg
Names
Preferred IUPAC name
1,2,5,6-Tetrahydropyridine-3-carboxylic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C6H9NO2/c8-6(9)5-2-1-3-7-4-5/h2,7H,1,3-4H2,(H,8,9)
    Key: QTDZOWFRBNTPQR-UHFFFAOYSA-N
  • InChI=1/C6H9NO2/c8-6(9)5-2-1-3-7-4-5/h2,7H,1,3-4H2,(H,8,9)
    Key: QTDZOWFRBNTPQR-UHFFFAOYAX
  • C1CNCC(=C1)C(=O)O
Properties
C6H9NO2
Molar mass 127.143 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Guvacine is an hydrogenated pyridine alkaloid found in areca nuts. [1] It is the N-demethylated derivative of arecaidine and the product of ester hydrolysis of guvacoline, both of which are also found in areca nuts as well. It is also an inhibitor of gamma-aminobutyric acid uptake. Lime is said to hydrolyse guvacoline to guvacine. [2]

Related Research Articles

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<span class="mw-page-title-main">Betel</span> Species of plant

The betel, Piper betle, is a species of flowering plant in the pepper family Piperaceae, native to Southeast Asia. It is an evergreen, dioecious vine, with glossy heart-shaped leaves and white catkins. Betel plants are cultivated for their leaves which are most commonly used as flavoring in chewing areca nut.

<span class="mw-page-title-main">Betel nut chewing</span> Preparation of betel leaf and areca nut

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<i>Areca catechu</i> Species of palm

Areca catechu is a species of palm which grows in much of the tropical Pacific, Asia, and parts of east Africa. The palm is native to the Philippines, but is widespread in cultivation and is considered naturalized in Malaysia, Indonesia, New Guinea, Taiwan, Madagascar, Cambodia, Laos, Myanmar, Thailand, Vietnam, southern China, India, Nepal, Bangladesh, the Maldives, Sri Lanka, parts of the Pacific Islands, and also in the West Indies.

<span class="mw-page-title-main">Arecoline</span> Mild stimulant

Arecoline is a nicotinic acid-based mild parasympathomimetic stimulant alkaloid found in the areca nut, the fruit of the areca palm. It is an odourless oily liquid. It can bring a sense of enhanced alertness and energy along with mild feelings of euphoria and relaxation. The psychoactive effects are comparable to that of nicotine.

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<span class="mw-page-title-main">Reuptake inhibitor</span> Type of drug

Reuptake inhibitors (RIs) are a type of reuptake modulators. It is a drug that inhibits the plasmalemmal transporter-mediated reuptake of a neurotransmitter from the synapse into the pre-synaptic neuron. This leads to an increase in extracellular concentrations of the neurotransmitter and an increase in neurotransmission. Various drugs exert their psychological and physiological effects through reuptake inhibition, including many antidepressants and psychostimulants.

<span class="mw-page-title-main">Gabaculine</span> Chemical compound

Gabaculine is a naturally occurring neurotoxin first isolated from the bacteria Streptomyces toyacaensis, which acts as a potent and irreversible GABA transaminase inhibitor, and also a GABA reuptake inhibitor. Gabaculine is also known as 3-amino-2,3-dihydrobenzoic acid hydrochloride and 5-amino cyclohexa-1,3 dienyl carboxylic acid. Gabaculine increased GABA levels in the brain and had an effect on convulsivity in mice.

<span class="mw-page-title-main">Nipecotic acid</span> Chemical compound

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<span class="mw-page-title-main">GABA reuptake inhibitor</span> Drug class

A GABA reuptake inhibitor (GRI) is a type of drug which acts as a reuptake inhibitor for the neurotransmitter gamma-Aminobutyric acid (GABA) by blocking the action of the gamma-Aminobutyric acid transporters (GATs). This in turn leads to increased extracellular concentrations of GABA and therefore an increase in GABAergic neurotransmission.

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Isoguvacine is a GABAA receptor agonist used in scientific research.

<span class="mw-page-title-main">Arecaidine</span> Chemical compound

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<span class="mw-page-title-main">GABA analogue</span> Class of drugs

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<span class="mw-page-title-main">Areca nut production in India</span>

Areca nut production in India is dominant in the coastal region within 400 kilometres (250 mi) from the coast line, and also in some other non-coastal states of India. Areca nut, a tropical crop, is popularly known as betel nut, as its common usage in the country is for mastication with betel leaves. It is a palm tree species under the family of Arecaceae. It has commercial and economic importance not only in India but also in China and Southeast Asia.

<span class="mw-page-title-main">Guvacoline</span> Chemical compound

Guvacoline is a compound with the chemical formula C7H11NO2. It is a component of Areca nut and a precursor of guvacine. It agonizes musacarinic receptors just like arecoline but unlike arecoline it lacks nicotinic activity.

<span class="mw-page-title-main">Areca alkaloids</span>

Areca alkaloids are a group of piperidine alkaloids found in the areca nut, the seeds of the areca palm.

References

  1. Voigt, V; Laug, L; Zebisch, K; Thondorf, I; Markwardt, F; Brandsch, M (2013). "Transport of the areca nut alkaloid arecaidine by the human proton-coupled amino acid transporter 1 (hPAT1)". The Journal of Pharmacy and Pharmacology. 65 (4): 582–90. doi: 10.1111/jphp.12006 . PMID   23488788. S2CID   27577546.
  2. Johnston, G. A. R.; Krogsgaard-Larsen, P.; Stephanson, A. (1975). "Betel nut constituents as inhibitors of γ-aminobutyric acid uptake". Nature. 258 (5536): 627–628. Bibcode:1975Natur.258..627J. doi:10.1038/258627a0. ISSN   0028-0836. PMID   1207742. S2CID   4147760.