Pinoline

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Pinoline
Pinoline (small).svg
Identifiers
CAS number 20315-68-8 N
PubChem 1868
ChemSpider 1797 N
Jmol-3D images Image 1
Properties
Molecular formula C12H14N2O
Molar mass 202.25 g mol−1
Melting point 216 to 224 °C (421 to 435 °F; 489 to 497 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Pinoline is a methoxylated tryptoline (5-methoxytryptoline) that is produced in the pineal gland during the metabolism of melatonin. Its IUPAC name is 6-methoxy-1,2,3,4-tetrahydro-β-carboline, usually abbreviated as 6-MeO-THBC, and its more common name is a combination of "pineal beta-carboline".[1] The biological activity of this molecule is of interest as a potential free radical scavenger, also known as an antioxidant,[2] and as a monoamine oxidase A inhibitor.[3]

Bausch & Lomb filed a patent for this molecule as a potential drug delivery device to treat various ophthalmic disorders in 2006.[4]

Protection of cellular membranes[edit]

Aluminium toxicity causes an increase in lipid peroxidation, with most damage occurring in the brain. A recent review of studies shows pinoline and melatonin to be effective at reducing the lipid peroxidation. Studies included both human and animal subjects. The studies’ results support that pinoline has antioxidant properties.[5]

Lipopolysaccharide is produced by Gram-negative bacteria and stimulates the production of free radicals which in turn cause lipid peroxidation. A recent study compared the effectiveness of melatonin and other similar compounds on the lipopolysaccharide induced lipid peroxidation. The results showed support for pinoline’s ability to reduce damage from lipid peroxidation. Pinoline was also shown to be more effective than vitamin E at reducing lipopolysaccharide activity in the retina.[6]

Another recent study compared the antioxidant properties of compounds from the tryptophan metabolic pathway in the pineal gland against oxidative damage to the lipids and proteins of synaptosomes. Synaptosomes isolated from rat brains were used in an experiment assessing damage by measuring malondialdehyde, 4-hydroxyalkenal, and carbonyl content in the proteins. Pinoline was shown to be the most powerful antioxidant. These results support the evidence for pinoline’s antioxidant abilities and the potential to protect against oxidative damage.[7]

References[edit]

  1. ^ Callaway, James C.; Gyntber, Jukka; Poso, Antti; Airaksinen, Mauno M.; Vepsäläinen, Jouko (1994). "The pictet-spengler reaction and biogenic tryptamines: Formation of tetrahydro-β-carbolines at physiologicalpH". Journal of Heterocyclic Chemistry 31 (2): 431. doi:10.1002/jhet.5570310231. 
  2. ^ Schiller, Erich; Bartsch, H. (2003). Free Radicals and Inhalation Pathology: Respiratory System, Mononuclear Phagocyte System, Hypoxia and Reoxygenation, Pneumoconioses, and Other Granulomatoses, Cancer (Google Books, page view). Springer. p. 107. ISBN 978-3-540-00201-7. Retrieved 2009-02-14. 
  3. ^ Airaksinen, M. M., Huang, J. T., Ho, B. T., Taylor, D., and Walker, K. (1978). "The Uptake of 6-Methoxy-1,2,3,4-Tetrahydro-β-carboline and its Effect on 5-Hydroxytryptamine Uptake and Release in Blood Platelets". Acta Pharmacol Toxicol 43 (5): 375–380. doi:10.1111/j.1600-0773.1978.tb02281.x. 
  4. ^ Bartels, S. P. (2006) U.S. Patent No. 20,060,292,202 Washington, DC: U.S.
  5. ^ Mohammadir, Azadeh; Abdollahi, Mohammad (2011). "A Systematic Review on Oxidant/Antioxidant Imbalance in Aluminium Toxicity". International Journal of Pharmacology 7: 12. doi:10.3923/ijp.2011.12.21. 
  6. ^ Sewerynek, E; Wiktorska, JA; Stuss, M (2011). "6-methoxytryptophol reduces lipopolysaccharide-induced lipid peroxidation in vitro more effectively than melatonin". Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 62 (6): 677–83. PMID 22314571. 
  7. ^ Millán-Plano, Sergio; Piedrafita, Eduardo; Miana-Mena, Francisco J.; Fuentes-Broto, Lorena; Martínez-Ballarín, Enrique; López-Pingarrón, Laura; Sáenz, María A.; García, Joaquín J. (2010). "Melatonin and Structurally-Related Compounds Protect Synaptosomal Membranes from Free Radical Damage". International Journal of Molecular Sciences 11 (1): 312–28. doi:10.3390/ijms11010312. PMC 2821006. PMID 20162018.