Guvacoline

Last updated
Guvacoline
Guvacoline.png
Names
Preferred IUPAC name
Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C7H11NO2/c1-10-7(9)6-3-2-4-8-5-6/h3,8H,2,4-5H2,1H3
    Key: DYPLDWLIOGXSSE-UHFFFAOYSA-N
  • COC(=O)C1=CCCNC1
Properties
C7H11NO2
Molar mass 141.170 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Guvacoline is a compound with the chemical formula C7H11NO2. [1] 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. [2]

See also

Related Research Articles

<span class="mw-page-title-main">Areca nut</span> Fruit of the areca palm chewed as a stimulant

The areca nut is the fruit of the areca palm, which grows in much of the tropical Pacific, South Asia, Southeast Asia, and parts of east Africa. It is commonly referred to as betel nut, not to be confused with betel leaves that are often used to wrap it. Consumption has many harmful effects on health and is carcinogenic to humans. Various compounds present in the nut, including arecoline, contribute to histologic changes in the oral mucosa. It is known to be a major risk factor for cancers of the mouth and esophagus. As with chewing tobacco, use is discouraged by preventive efforts. Consumption by hundreds of millions of people worldwide – mainly of South Asian or Southeast Asian origins – has been described as a "neglected global public health emergency".

<i>Areca</i> Genus of palms

Areca is a genus of 51 species of palms in the family Arecaceae, found in humid tropical forests from the islands of the Philippines, Malaysia and India, across Southeast Asia to Melanesia. The generic name Areca is derived from a name used locally on the Malabar Coast of India.

<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

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 practice is widespread in Southeast Asia, Micronesia, Island Melanesia, and South Asia. It is also found among the indigenous peoples of Taiwan, Madagascar, and parts of southern China. It has also been introduced to the Caribbean in colonial times.

A parasympathomimetic drug, sometimes called a cholinomimetic drug or cholinergic receptor stimulating agent, is a substance that stimulates the parasympathetic nervous system (PSNS). These chemicals are also called cholinergic drugs because acetylcholine (ACh) is the neurotransmitter used by the PSNS. Chemicals in this family can act either directly by stimulating the nicotinic or muscarinic receptors, or indirectly by inhibiting cholinesterase, promoting acetylcholine release, or other mechanisms. Common uses of parasympathomimetics include glaucoma, Sjögren syndrome and underactive bladder.

<span class="mw-page-title-main">Muscarinic acetylcholine receptor</span> Acetylcholine receptors named for their selective binding of muscarine

Muscarinic acetylcholine receptors, or mAChRs, are acetylcholine receptors that form G protein-coupled receptor complexes in the cell membranes of certain neurons and other cells. They play several roles, including acting as the main end-receptor stimulated by acetylcholine released from postganglionic fibers in the parasympathetic nervous system.

An active ingredient is any ingredient that provides biologically active or other direct effect in the diagnosis, cure, mitigation, treatment, or prevention of disease or to affect the structure or any function of the body of humans or animals.

<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, 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, euphoria and relaxation. The psychoactive effects are comparable to that of nicotine.

<span class="mw-page-title-main">Muscarinic agonist</span> Activating agent of the muscarinic acetylcholine receptor

A muscarinic agonist is an agent that activates the activity of the muscarinic acetylcholine receptor. The muscarinic receptor has different subtypes, labelled M1-M5, allowing for further differentiation.

<span class="mw-page-title-main">Smokeless tobacco</span> Tobacco product used by means other than smoking.

Smokeless tobacco is a tobacco product that is used by means other than smoking. Their use involves chewing, sniffing, or placing the product between gum and the cheek or lip. Smokeless tobacco products are produced in various forms, such as chewing tobacco, snuff, snus, and dissolvable tobacco products. Smokeless tobacco products typically contain over 3000 constituents. All smokeless tobacco products contain nicotine and are therefore highly addictive. Quitting smokeless tobacco use is as challenging as smoking cessation.

<span class="mw-page-title-main">Euphoria</span> Intense feelings of well-being

Euphoria is the experience of pleasure or excitement and intense feelings of well-being and happiness. Certain natural rewards and social activities, such as aerobic exercise, laughter, listening to or making music and dancing, can induce a state of euphoria. Euphoria is also a symptom of certain neurological or neuropsychiatric disorders, such as mania. Romantic love and components of the human sexual response cycle are also associated with the induction of euphoria. Certain drugs, many of which are addictive, can cause euphoria, which at least partially motivates their recreational use.

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

Epiboxidine is a chemical compound which acts as a partial agonist at neural nicotinic acetylcholine receptors, binding to both the α3β4 and the α4β2 subtypes. It was developed as a less toxic analogue of the potent frog-derived alkaloid epibatidine, which is around 200 times stronger than morphine as an analgesic but produces extremely dangerous toxic nicotinic side effects.

Oral submucous fibrosis is a chronic, complex, premalignant condition of the oral cavity, characterized by juxta-epithelial inflammatory reaction and progressive fibrosis of the submucosal tissues. As the disease progresses, the oral mucosa becomes fibrotic to the point that the person is unable to open the mouth. The condition is remotely linked to oral cancers and is associated with areca nut and / or its by-products chewing, majorly practiced in South and South-East Asian countries. The incidence of OSMF has also increased in the western countries due to the changing habits and constant migrating population.

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

Leucocyanidin is a colorless chemical compound that is a member of the class of natural products known as leucoanthocyanidins.

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

Coronaridine, also known as 18-carbomethoxyibogamine, is an alkaloid found in Tabernanthe iboga and related species, including Tabernaemontana divaricata for which it was named.

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

Arecaidine is a bio-active alkaloid in areca nuts. It is a competitive GABA uptake inhibitor. Lime is said to hydrolyse arecoline to arecaidine

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

Guvacine is an hydrogenated pyridine alkaloid found in areca nuts. 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.

<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.

References

  1. PubChem. "Guvacoline". pubchem.ncbi.nlm.nih.gov. Retrieved 2020-06-14.
  2. Horenstein NA, Quadri M, Stokes C, Shoaib M, Papke RL (May 2019). "Cracking the Betel Nut: Cholinergic Activity of Areca Alkaloids and Related Compounds". Nicotine & Tobacco Research . 21 (6): 805–812. doi:10.1093/ntr/ntx187. PMC   6528145 . PMID   29059390.