Myosmine

Last updated
Myosmine
Myosmine.svg
Myosmine 3D ball.png
Names
Preferred IUPAC name
3-(3,4-Dihydro-2H-pyrrol-5-yl)pyridine
Other names
3-(1-Pyrrolin-2-yl)pyridine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.165.015 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 637-297-7
KEGG
PubChem CID
UNII
  • InChI=1S/C9H10N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7H,2,4,6H2
    Key: DPNGWXJMIILTBS-UHFFFAOYSA-N
  • n1cccc(c1)/C2=N/CCC2
Properties
C9H10N2
Molar mass 146.193 g·mol−1
Hazards
GHS labelling: [1]
GHS-pictogram-exclam.svg
Warning
H302, H315, H319, H335
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Related compounds
Related compounds
Isomyosamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Myosmine is an alkaloid found in tobacco [2] and other plants. [3] Chemically, it is closely related to nicotine. It inhibits aromatase sevenfold more potently than nicotine. [4] It also releases dopamine in adult but not adolescent rats. [5]

See also

Related Research Articles

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<span class="mw-page-title-main">Tobacco smoking</span> Practice of burning tobacco and breathing the resulting smoke

Tobacco smoking is the practice of burning tobacco and ingesting the resulting smoke. The smoke may be inhaled, as is done with cigarettes, or simply released from the mouth, as is generally done with pipes and cigars. The practice is believed to have begun as early as 5000–3000 BC in Mesoamerica and South America. Tobacco was introduced to Eurasia in the late 17th century by European colonists, where it followed common trade routes. The practice encountered criticism from its first import into the Western world onwards but embedded itself in certain strata of a number of societies before becoming widespread upon the introduction of automated cigarette-rolling apparatus.

<span class="mw-page-title-main">Cotinine</span> Alkaloid found in tobacco. used as a biomarker for exposure to tobacco smoke.

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<span class="mw-page-title-main">Aromatase</span> Enzyme involved in estrogen production

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<span class="mw-page-title-main">Nicotine poisoning</span> Medical condition

Nicotine poisoning describes the symptoms of the toxic effects of nicotine following ingestion, inhalation, or skin contact. Nicotine poisoning can potentially be deadly, though serious or fatal overdoses are rare. Historically, most cases of nicotine poisoning have been the result of use of nicotine as an insecticide. More recent cases of poisoning typically appear to be in the form of Green Tobacco Sickness, or due to unintended ingestion of tobacco or tobacco products or consumption of nicotine-containing plants.

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<i>Nicotiana tabacum</i> Species of plant

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<span class="mw-page-title-main">Electronic cigarette</span> Device that vaporizes a liquid nicotine solution for inhalation

An electronic cigarette is a device that simulates tobacco smoking. It consists of an atomizer, a power source such as a battery, and a container such as a cartridge or tank filled with liquid. Instead of smoke, the user inhales "vapor". As such, using an e-cigarette is often called "vaping". The atomizer is a heating element that vaporizes a liquid solution called e-liquid, which quickly cools into an aerosol of tiny droplets, vapor and air. E-cigarettes are activated by taking a puff or pressing a button. Some look like traditional cigarettes, and most kinds are reusable. The vapor mainly comprises propylene glycol and/or glycerin, usually with nicotine and flavoring. Its exact composition varies, and depends on several things including user behavior.

<span class="mw-page-title-main">SB-277,011-A</span> Chemical compound

SB-277,011A is a drug which acts as a potent and selective dopamine D3 receptor antagonist, which is around 80-100x selective for D3 over D2, and lacks any partial agonist activity.

<span class="mw-page-title-main">Flavored tobacco</span> Tobacco product with added flavorings

Flavored tobacco products — tobacco products with added flavorings — include types of cigarettes, cigarillos and cigars, hookahs and hookah tobacco, various types of smokeless tobacco, and more recently electronic cigarettes. Flavored tobacco products are especially popular with youth and have therefore become targets of regulation in several countries.

<span class="mw-page-title-main">Ibogamine</span> Anti-convulsant, anti-addictive CNS stimulant alkaloid

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<span class="mw-page-title-main">BP-897</span> Chemical compound

BP-897 is a drug used in scientific research which acts as a potent selective dopamine D3 receptor partial agonist with an in vitro intrinsic activity of ~0.6 and ~70x greater affinity for D3 over D2 receptors and is suspected to have partial agonist or antagonist activity in vivo. It has mainly been used in the study of treatments for cocaine addiction. A study comparing BP-897 with the potent, antagonistic, and highly D3 selective SB-277,011-A found, "SB 277011-A (1–10 mg/kg) was able to block cue-induced reinstatement of nicotine-seeking, indicating that DRD3 selective antagonism may be an effective approach to prevent relapse for nicotine. In contrast, BP 897 did not block the cue-induced reinstatement of nicotine-seeking or nicotine-taking under the FR5 schedule."

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

Nornicotine is an alkaloid found in various plants including Nicotiana, the tobacco plant. It is chemically similar to nicotine, but does not contain a methyl group.

Iboga-type alkaloids are a set of monoterpene indole alkaloids comprising naturally-occurring compounds found in Tabernanthe and Tabernaemontana, as well as synthetic structural analogs. Naturally-occuring iboga-type alkaloids include ibogamine, ibogaine, tabernanthine, and other substituted ibogamines (see below). Many iboga-type alkaloids display biological activities such as cardiac toxicity and psychoactive effects, and some have been studied as potential treatments for drug addiction.

<span class="mw-page-title-main">Usage of electronic cigarettes</span> Overview about the usage of electronic cigarettes

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Exposure to nicotine, from conventional or electronic cigarettes during adolescence can impair the developing human brain. E-cigarette use is recognized as a substantial threat to adolescent behavioral health. The use of tobacco products, no matter what type, is almost always started and established during adolescence when the developing brain is most vulnerable to nicotine addiction. Young people's brains build synapses faster than adult brains. Because addiction is a form of learning, adolescents can get addicted more easily than adults. The nicotine in e-cigarettes can also prime the adolescent brain for addiction to other drugs such as cocaine. Exposure to nicotine and its great risk of developing an addiction, are areas of significant concern.

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

Nicotryine is lesser known and minor tobacco alkaloid. It inhibits metabolism of nicotine through CYP2A6 enzyme inhibition. It also inhibits CYP2A13 which might play role in nicotine metabolism. Nicotyrine is formed by gradual oxidation of nicotine in e-liquids and causes delayed nicotine clearance and attenuated withdrawal symptoms.

References

  1. "Myosmine". pubchem.ncbi.nlm.nih.gov. Retrieved 14 August 2023.
  2. C. Laszlo, K. Kaminski, H. Guan, M. Fatarova, J. Wei, A. Bergounioux, W. K. Schlage, S. Schorderet-Weber, P. A. Guy, N. V. Ivanov, K. Lamottke and J. Hoeng (Nov 2022). "Fractionation and Extraction Optimization of Potentially Valuable Compounds and Their Profiling in Six Varieties of Two Nicotiana Species", Molecules 2022, 27(22), 8105.
  3. Tyroller, Stefan; Zwickenpflug, Wolfgang; Richter, Elmar (2002). "New Sources of Dietary Myosmine Uptake from Cereals, Fruits, Vegetables, and Milk". Journal of Agricultural and Food Chemistry. 50 (17): 4909–15. doi:10.1021/jf020281p. PMID   12166981.
  4. Doering IL, Richter E (April 2009). "Inhibition of human aromatase by myosmine". Drug Metabolism Letters . 3 (2): 83–6. doi:10.2174/187231209788654045. PMID   19601869.
  5. Marusich JA, Darna M, Wilson AG, Denehy ED, Ebben A, Deaciuc AG, Dwoskin LP, Bardo MT, Lefever TW, Wiley JL, Reissig CJ, Jackson KJ (November 2017). "Tobacco's minor alkaloids: Effects on place conditioning and nucleus accumbens dopamine release in adult and adolescent rats". European Journal of Pharmacology . 814: 196–206. doi:10.1016/j.ejphar.2017.08.029. PMC   6563910 . PMID   28844873.