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Preferred IUPAC name 1,2,5,6-Tetrahydropyridine-3-carboxylic acid | |
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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 a tetrahydropyridine 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 hydrolyzes guvacoline to guvacine. [2]
The areca nut or betel nut is the fruit of the areca palm. The palm is originally native to the Philippines, but was carried widely through the tropics by the Austronesian migrations and trade since at least 1500 BCE due to its use in betel nut chewing. It is widespread in cultivation and is considered naturalized in much of the tropical Pacific, South Asia, Southeast Asia, and parts of east Africa. It is not to be confused with betel leaves that are often used to wrap it. The practice of betel nut chewing, often together with other herbs as a stimulant drug, dates back thousands of years, and continues to the present day in many countries.
GABA is the chief inhibitory neurotransmitter in the developmentally mature mammalian central nervous system. Its principal role is reducing neuronal excitability throughout the nervous system.
Betel 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 for chewing areca nut in so-called betel quid, which is toxic and is associated with a wide range of serious health conditions.
Betel nut chewing, also called betel quid chewing or areca nut chewing, is a practice in which areca nuts are chewed together with slaked lime and betel leaves for their stimulant and narcotic effects, the primary psychoactive compound being arecoline. The practice is widespread in Southeast Asia, Micronesia, Island Melanesia, and South Asia. It is also found among both Han Chinese immigrants and indigenous peoples of Taiwan, Madagascar, and parts of southern China. It was introduced to the Caribbean in colonial times.
Tiagabine is an anticonvulsant medication produced by Cephalon that is used in the treatment of epilepsy. The drug is also used off-label in the treatment of anxiety disorders and panic disorder.
Areca catechu is a species of palm native to the Philippines cultivated for areca nuts. It was carried widely through the tropics by the Austronesian migrations and trade since at least 1500 BCE due to its use in betel nut chewing. It 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.
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.
Pinolenic acid is a fatty acid contained in Siberian Pine nuts, Korean Pine nuts and the seeds and xylem of other pine (Pinus) species. The highest percentage of pinolenic acid is found in Siberian pine nuts and the oil produced from them.
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.
Nipecotic acid is a GABA uptake inhibitor used in scientific research.
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. Gamma-aminobutyric acid (GABA) is an amino acid that functions as the predominant inhibitory neurotransmitter within the central nervous system, playing a crucial role in modulating neuronal activity in both the brain and spinal cord. While GABA predominantly exerts inhibitory actions in the adult brain, it has an excitatory role during developmental stages. When the neuron receives the action potential, GABA is released from the pre-synaptic cell to the synaptic cleft. After the action potential transmission, GABA is detected on the dendritic side, where specific receptors collectively contribute to the inhibitory outcome by facilitating GABA transmitter uptake. Facilitated by specific enzymes, GABA binds to post-synaptic receptors, with GABAergic neurons playing a key role in system regulation. The inhibitory effects of GABA diminish when presynaptic neurons reabsorb it from the synaptic cleft for recycling by GABA transporters (GATs). The reuptake mechanism is crucial for maintaining neurotransmitter levels and synaptic functioning. Gamma-aminobutyric acid Reuptake Inhibitors (GRIs) hinder the functioning of GATs, preventing GABA reabsorption in the pre-synaptic cell. This results in increased GABA levels in the extracellular environment, leading to elevated GABA-mediated synaptic activity in the brain.
Isoguvacine is a GABAA receptor agonist used in scientific research.
Arecaidine is a bio-active alkaloid in areca nuts. It is a competitive GABA reuptake inhibitor. Lime is said to hydrolyse arecoline to arecaidine
CI-966 (developmental code name) is a central nervous system depressant acting as a GABA reuptake inhibitor, specifically a highly potent and selective blocker of the GABA transporter 1 (GAT-1) (IC50 = 0.26 μM), and hence indirect and non-selective GABA receptor full agonist. It was investigated as a potential anticonvulsant, anxiolytic, and neuroprotective therapeutic but was discontinued during clinical development due to the incidence of severe adverse effects at higher doses and hence was never marketed.
A GABA analogue is a compound which is an analogue or derivative of the neurotransmitter gamma-Aminobutyric acid (GABA).
Tolibut, also known as 3-(p-tolyl)-4-aminobutyric acid (or β-(4-methylphenyl)-GABA), is drug that was developed in Russia. It is an analogue of γ-aminobutyric acid (GABA) and is the 4-methyl analogue of phenibut, and is also an analogue of baclofen where the 4-chloro substitution has been replaced with a 4-methyl substitution. Tolibut has been described as possessing analgesic, tranquilizing, and neuroprotective properties. It is not fully clear as to whether the drug was ever approved or used medically in Russia.
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.
Guvacoline is a compound with the chemical formula C7H11NO2. It is a component of Areca nut and a precursor of guvacine. It agonizes muscarinic receptors just like arecoline but unlike arecoline it lacks nicotinic activity.
Areca alkaloids are a group of piperidine alkaloids found in the areca nut, the seeds of the areca palm.