Decahydroisoquinoline is a nitrogen-containing

heterocycle A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...

with the chemical formula . It is the saturated form of

isoquinoline Isoquinoline is an individual chemical specimen - a heterocyclic aromatic organic compound - as well as the name of a family of many thousands of natural plant alkaloids, any one of which might be referred to as "an isoquinoline". It is a struc ...

. Decahydroisoquinoline can be formed by the

hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...

of isoquinoline or

tetrahydroisoquinoline Tetrahydroisoquinoline (TIQ or THIQ), also known as AMPH-CR, is an organic compound with the chemical formula C9H11N. Classified as a secondary amine, it is derived from isoquinoline by hydrogenation. It is a colorless viscous liquid that is mis ...

Isomers

There are four

stereoisomer In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...

s of decahydroisoquinoline which differ by the configuration of the two carbon atoms at the ring fusion:

Occurrence

The decahydroisoquinoline occurs naturally in some

alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ...

s, including

gephyrotoxin Gephyrotoxin is a naturally occurring product that stems from the Colombian tropical frog '' Dendrobates histrionicus''. It is a member of the class of compounds known as histrionicotoxins. This alkaloid skin secretion was first isolated from th ...

s and pumiliotoxin C which are found in amphibian skins. A variety of pharmaceutical drugs include a decahydroisoquinoline ring system within their structure, including ciprefadol, dasolampanel,

nelfinavir Nelfinavir, sold under the brand name Viracept, is an antiretroviral medication used in the treatment of HIV/AIDS. Nelfinavir belongs to the class of drugs known as protease inhibitor (pharmacology), protease inhibitors (PIs) and like other PIs ...

saquinavir Saquinavir, sold under the brand name Invirase among others, is an antiretroviral medication used together with other medications to treat or prevent HIV/AIDS. Typically it is used with ritonavir or lopinavir/ritonavir to increase its effect. I ...

, and

tezampanel Tezampanel (, ) (developmental code names LY-293,558, LY-326,325, NGX-424) is a drug originally developed by Eli Lilly which acts as a competitive antagonist of the AMPA and kainate subtypes of the ionotropic glutamate receptor family, with sel ...

References

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