# Pinoline > Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Pinoline > Markdown URL: https://mediated.wiki/source/Pinoline.md > Source: https://en.wikipedia.org/wiki/Pinoline > Source revision: 1347509039 > License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/) {{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424794361 | ImageFile = Pinoline-2D.svg | ImageClass = skin-invert-image | ImageSize = 220px | ImageFile2 = Pinoline 3D BS.png | ImageClass2 = bg-transparent | ImageSize2 = 220px | PIN = 6-Methoxy-2,3,4,9-tetrahydro-1''H''-pyrido[3,4-''b'']indole | OtherNames = 6-MeO-THBC; 5-MeO-TLN; Pinoline; 6-Methoxy-2,3,4,9-tetrahydro-1''H''-β-carboline; 6-Methoxy-1,2,3,4-tetrahydro-β-carboline; 6-Methoxy-tetrahydronorharman; 6-Methoxy-2,3,4,9-tetrahydro-1''H''-β-carboline |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|changed|??}} | CASNo = 20315-68-8 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = BR3W85U4GS | PubChem = 1868 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 1797 | SMILES = COC1=CC2=C(C=C1)NC3=C2CCNC3 | InChI = 1/C12H14N2O/c1-15-8-2-3-11-10(6-8)9-4-5-13-7-12(9)14-11/h2-3,6,13-14H,4-5,7H2,1H3 | InChIKey = QYMDEOQLJUUNOF-UHFFFAOYAW | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C12H14N2O/c1-15-8-2-3-11-10(6-8)9-4-5-13-7-12(9)14-11/h2-3,6,13-14H,4-5,7H2,1H3 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = QYMDEOQLJUUNOF-UHFFFAOYSA-N }} |Section2={{Chembox Properties | C=12|H=14|N=2|O=1 | Appearance = | Density = | MeltingPtC = 216 to 224 | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} '''Pinoline''' is a [β-carboline](/source/substituted_%CE%B2-carboline) and [methoxyl](/source/methoxyl)ated [tryptoline](/source/tryptoline) (5-methoxytryptoline) long claimed to be produced in the [pineal gland](/source/pineal_gland) during the metabolism of [melatonin](/source/melatonin), however its pineal occurrence remains controversial.{{cite journal|doi=10.1002/bmc.2981 | pmid=23881860 | volume=27 | issue=12 | title=LC/MS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate | journal=Biomedical Chromatography | pages=1690–1700 | last1 = Barker | first1 = Steven A.| url=https://deepblue.lib.umich.edu/bitstream/2027.42/101767/1/bmc2981.pdf | year=2013 | hdl=2027.42/101767 | hdl-access=free }} 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 contraction of "'''pineal β-carboline'''".{{cite journal | doi = 10.1002/jhet.5570310231 | title = The pictet-spengler reaction and biogenic tryptamines: Formation of tetrahydro-β-carbolines at physiologicalpH | year = 1994 | last1 = Callaway | first1 = James C. | last2 = Gyntber | first2 = Jukka | last3 = Poso | first3 = Antti | last4 = Airaksinen | first4 = Mauno M. | last5 = Vepsäläinen | first5 = Jouko | journal = Journal of Heterocyclic Chemistry | volume = 31 | issue = 2 | pages = 431}} The [biological activity](/source/biological_activity) of this molecule is of interest as a potential [free radical](/source/free_radical) scavenger, also known as an [antioxidant](/source/antioxidant),{{cite book |last= Schiller |first= Erich |author2=Bartsch, H. |title=Free Radicals and Inhalation Pathology: Respiratory System, Mononuclear Phagocyte System, Hypoxia and Reoxygenation, Pneumoconioses, and Other Granulomatoses, Cancer |url= https://books.google.com/books?id=y5aQMpT6tC0C |format= Google Books, page view |access-date= 2009-02-14 |year= 2003 |publisher= Springer |isbn= 978-3-540-00201-7 |pages= 107 }} and as a [monoamine oxidase A](/source/monoamine_oxidase_A) inhibitor.{{cite journal | author = Airaksinen, M. M., Huang, J. T., Ho, B. T., Taylor, D., and Walker, K. | year = 1978 | journal = Acta Pharmacologica et Toxicologica | volume = 43 | pages = 375–380 | doi = 10.1111/j.1600-0773.1978.tb02281.x | title = The Uptake of 6-Methoxy-1,2,3,4-Tetrahydro-β-carboline and its Effect on 5-Hydroxytryptamine Uptake and Release in Blood Platelets | issue = 5| pmid = 726902 }} [Bausch & Lomb](/source/Bausch_%26_Lomb) filed a patent for a drug delivery device utilizing this molecule, designed to treat various ophthalmic disorders in 2006.Bartels, S. P. (2006) ''U.S. Patent No. 20,060,292,202'' Washington, DC: U.S. == Pharmacology == One of pinoline's pharmacological properties is its ability to promote [neurogenesis](/source/neurogenesis) in vitro; even at trace concentrations.Mario de la Fuente et al. 2015 "Neurogenic Potential Assessment and Pharmacological Characterization of 6-Methoxy-1,2,3,4-tetrahydro-β-carboline (Pinoline) and Melatonin–Pinoline Hybrids" {{doi|10.1021/acschemneuro.5b00041}} [Aluminium toxicity](/source/Aluminium) causes an increase in [lipid peroxidation](/source/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.{{Citation needed|date=December 2019|reason=removed citation to predatory publisher content}} [Lipopolysaccharide](/source/Lipopolysaccharide) is produced by [Gram-negative bacteria](/source/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](/source/lipid_peroxidation){{Citation needed|date=May 2020|reason=No reference for claim provided}}. Pinoline was also shown to be more effective than [vitamin E](/source/vitamin_E) at reducing lipopolysaccharide activity in the retina.{{cite journal | pmid = 22314571 | year = 2011 | last1 = Sewerynek | first1 = E | last2 = Wiktorska | first2 = JA | last3 = Stuss | first3 = M | title = 6-methoxytryptophol reduces lipopolysaccharide-induced lipid peroxidation in vitro more effectively than melatonin | volume = 62 | issue = 6 | pages = 677–83 | journal = Journal of Physiology and Pharmacology }} 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](/source/synaptosomes). Synaptosomes isolated from rat brains were used in an experiment assessing damage by measuring malondialdehyde, 4-hydroxyalkenal, and [carbonyl](/source/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.{{cite journal | doi = 10.3390/ijms11010312 | title = Melatonin and Structurally-Related Compounds Protect Synaptosomal Membranes from Free Radical Damage | year = 2010 | last1 = Millán-Plano | first1 = Sergio | last2 = Piedrafita | first2 = Eduardo | last3 = Miana-Mena | first3 = Francisco J. | last4 = Fuentes-Broto | first4 = Lorena | last5 = Martínez-Ballarín | first5 = Enrique | last6 = López-Pingarrón | first6 = Laura | last7 = Sáenz | first7 = María A. | last8 = García | first8 = Joaquín J. | journal = International Journal of Molecular Sciences | volume = 11 | pages = 312–28 | pmid = 20162018 | issue = 1 | pmc = 2821006| doi-access = free }} ==See also== * [Substituted β-carboline](/source/Substituted_%CE%B2-carboline) * [6-Methoxyharmalan](/source/6-Methoxyharmalan) * [Norharmane](/source/Norharmane) * [Harmane](/source/Harmane) * [Harmala alkaloid](/source/Harmala_alkaloid) == References == {{Reflist}} {{Tryptamines}} Category:5-Methoxytryptamines Category:N-Monoalkyltryptamines Category:Tryptolines --- Adapted from the Wikipedia article [Pinoline](https://en.wikipedia.org/wiki/Pinoline) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Pinoline?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.