Pinoline

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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).
☒N verify (what is checkY☒N ?)

Pinoline is a methoxylated

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]

Pharmacology

One of pinoline's pharmacological properties is its ability to promote neurogenesis in vitro; even at trace concentrations.[6]

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.[citation needed]

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[citation needed]. Pinoline was also shown to be more effective than vitamin 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 of

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.[8]

See also

References

  1. PMID 23881860
    .
  2. doi:10.1002/jhet.5570310231
    .
  3. ISBN 978-3-540-00201-7
    . Retrieved 2009-02-14.
  4. 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.
  6. ^ { 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" http://pubs.acs.org/doi/abs/10.1021/acschemneuro.5b00041}
  7. PMID 22314571
    .
  8. PMID 20162018
    .
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