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| 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 |
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| ECHA InfoCard | 100.161.873 |
| UNII | |
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| 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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Pinoline is aβ-carboline andmethoxylatedtryptoline (5-methoxytryptoline) long claimed to be produced in thepineal gland during the metabolism ofmelatonin, however its pineal occurrence remains controversial.[1] Its IUPAC name is6-methoxy-1,2,3,4-tetrahydro-β-carboline, usually abbreviated as6-MeO-THBC, and its more common name is a contraction of "pineal β-carboline".[2] Thebiological activity of this molecule is of interest as a potentialfree radical scavenger, also known as anantioxidant,[3] and as amonoamine 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]
One of pinoline's pharmacological properties is its ability to promoteneurogenesis in vitro; even at trace concentrations.[6]
Aluminium toxicity causes an increase inlipid 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]
Lipopolysaccharide is produced byGram-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 fromlipid peroxidation[citation needed]. Pinoline was also shown to be more effective thanvitamin E at reducing lipopolysaccharide activity in the retina.[7]
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 ofsynaptosomes. Synaptosomes isolated from rat brains were used in an experiment assessing damage by measuring malondialdehyde, 4-hydroxyalkenal, andcarbonyl 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.[8]
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