Pinoline

Pinoline
Names
Preferred IUPAC name
6-Methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
Other names
6-MeO-THBC; 5-MeO-TLN; Pinoline; 6-Methoxy-2,3,4,9-tetrahydro-1H-β-carboline; 6-Methoxy-1,2,3,4-tetrahydro-β-carboline; 6-Methoxy-tetrahydronorharman; 6-Methoxy-2,3,4,9-tetrahydro-1H-β-carboline
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.161.873 Edit this at Wikidata
UNII
  • InChI=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 ☒N
    Key: QYMDEOQLJUUNOF-UHFFFAOYSA-N ☒N
  • 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
    Key: QYMDEOQLJUUNOF-UHFFFAOYAW
  • COC1=CC2=C(C=C1)NC3=C2CCNC3
Properties
C12H14N2O
Molar mass 202.257 g·mol−1
Melting point 216 to 224 °C (421 to 435 °F; 489 to 497 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pinoline is a methoxylated tryptoline (5-methoxytryptoline) long claimed to be produced in the pineal gland during the metabolism of melatonin, however its pineal occurrence remains controversial.[1] 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".[2] The biological activity of this molecule is of interest as a potential free radical scavenger, also known as an antioxidant,[3] and as a monoamine oxidase A inhibitor.[4]

Bausch & Lomb filed a patent for a drug delivery device utilizing this molecule, designed to treat various ophthalmic disorders in 2006.[5]

  1. ^ Barker, Steven A. (2013). "LC/MS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate" (PDF). Biomedical Chromatography. 27 (12): 1690–1700. doi:10.1002/bmc.2981. hdl:2027.42/101767. PMID 23881860.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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 Pharmacologica et Toxicologica. 43 (5): 375–380. doi:10.1111/j.1600-0773.1978.tb02281.x. PMID 726902.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ^ Bartels, S. P. (2006) U.S. Patent No. 20,060,292,202 Washington, DC: U.S.