Pinoline

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 424794361

| ImageFile = Pinoline.svg

| ImageSize = 220px

| ImageFile2 = Pinoline 3D BS.png

| ImageSize2 = 220px

| PIN = 6-Methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

| OtherNames = 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

|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 and methoxylated tryptoline (5-methoxytryptoline) long claimed to be produced in the pineal gland during the metabolism of 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 of this molecule is of interest as a potential free radical scavenger, also known as an 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 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 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.