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Indole-3-carboxylate esters: Any compound containing a 1H-indole-3-carboxylate ester structure with the ester oxygen bearing a napthyl, quinolinyl, isoquinolinyl, or adamantyl group and substitution at the one position of the indole ring by an alkyl, haloalkyl, alkenyl, cycloalkylmethyl, cycloalkylethyl, benzyl, N-methyl-2-piperidinylmethyl, or ...
6-MeO-THH, or 6-methoxy-1,2,3,4-tetrahydroharman, is a β-carboline (or more specifically a pinoline) derivative and a structural isomer of tetrahydroharmine (7-MeO-THH). 6-MeO-THH is mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved), stating that 6-MeO-THH is very similar to the other carbolines. [1]
Indole can also be metabolized by the liver into indoxyl sulfate, a compound that is toxic in high concentrations and associated with vascular disease and renal dysfunction. [2] AST-120 ( activated charcoal ), an intestinal sorbent that is taken by mouth , adsorbs indole, in turn decreasing the concentration of indoxyl sulfate in blood plasma.
β-Carbolines belong to the group of indole alkaloids and consist of a pyridine ring that is fused to an indole skeleton. [27] The structure of β-carboline is similar to that of tryptamine , with the ethylamine chain re-connected to the indole ring via an extra carbon atom, to produce a three-ringed structure.
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.
The carbanion (2) formed by reacting diethyl malonate (1) with a suitable base can be alkylated with a suitable electrophile. This alkylated 1,3-dicarbonyl compound ( 3 ) readily undergoes decarboxylation with loss of carbon dioxide, to give a substituted acetic acid ( 4 ):
That gives new opportunities to make water-soluble derivatives [5]. These hexacyclic CPT become more active when electron-withdrawing groups are put in position 11 and methyl or amino groups at 10. Exatecan is an example of hexacyclic CPT that has a 6 membered ring over position 7 and 9, and is 10-methyl, 11-fluoro substituted [4].
Indole-3-carboxylate decarboxylase (EC 4.1.1.92) is an enzyme with systematic name indole-3-carboxylate carboxy-lyase. [1] This enzyme catalyses the following chemical reaction indole-3-carboxylate ⇌ {\displaystyle \rightleftharpoons } indole + CO 2