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Pinoline
Sign in to savePinoline 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. 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". The biological activity of this molecule is of interest as a potential free radical scavenger, also known as an antioxidant, and as a monoamine oxidase A inhibitor.
Chemical data
- Formula
- C12H14N2O
- Molecular weight
- 202.25 g/mol
- IUPAC name
- 6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
- SMILES
- COC1=CC2=C(C=C1)NC3=C2CCNC3
- InChIKey
- QYMDEOQLJUUNOF-UHFFFAOYSA-N
- XLogP
- 1.5
- Polar surface area
- 37.1 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
79 papers- Pinoline may be used as a probe for CYP2D6 activity.Drug metabolism and disposition: the biological fate of chemicals · 2009
- Neurogenic Potential Assessment and Pharmacological Characterization of 6-Methoxy-1,2,3,4-tetrahydro-β-carboline (Pinoline) and Melatonin-Pinoline Hybrids.ACS chemical neuroscience · 2015
- Role of pinoline and melatonin in stabilizing hepatic microsomal membranes against oxidative stress.Journal of bioenergetics and biomembranes · 1999
- Melatonin and pinoline prevent aluminium-induced lipid peroxidation in rat synaptosomes.Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS) · 2003
- Behavioural effects of pinoline in the rat forced swimming, open field and elevated plus-maze tests.Pharmacological research · 1996
via PubMed
Wikidata facts
- Mass
- 202.110613
Show 5 more facts
- chemical formula
- C₁₂H₁₄N₂O
- canonical SMILES
- COC1=CC2=C(C=C1)NC3=C2CCNC3
- found in taxon
- Phyllodium pulchellum
- subject has role
- anticonvulsant agent
- Commons category
- Pinoline
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- Pharmacology
- See also
- References
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. 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". The biological activity of this molecule is of interest as a potential free radical scavenger, also known as an antioxidant, and as a monoamine oxidase A inhibitor.
Bausch & Lomb filed a patent for a drug delivery device utilizing this molecule, designed to treat various ophthalmic disorders in 2006.
Excerpted from Wikipedia’s “Pinoline” article, available under the CC BY-SA 4.0 licence.