Decahydroisoquinoline is a nitrogen-containing
heterocycle with the chemical formula . It is the
saturated
Saturation, saturated, unsaturation or unsaturated may refer to:
Chemistry
* Saturation, a property of organic compounds referring to carbon-carbon bonds
** Saturated and unsaturated compounds
**Degree of unsaturation
** Saturated fat or fatty ac ...
form of
isoquinoline.
Decahydroisoquinoline can be formed by the
hydrogenation of isoquinoline or
tetrahydroisoquinoline.
Isomers
There are four
stereoisomers of decahydroisoquinoline which differ by the configuration of the two carbon atoms at the ring fusion:
Occurrence
The decahydroisoquinoline occurs naturally in some
alkaloids, 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 t ...
s and
pumiliotoxin C
Pumiliotoxins (PTXs), are one of several toxins found in the skin of poison dart frogs. The frog species, Bibron's toadlet, P. bibronii also produces PTXs to deter predators. Closely related, though more toxic, are allopumiliotoxins, (aPTXs). Other ...
which are found in amphibian skins.
A variety of pharmaceutical drugs include a decahydroisoquinoline ring system within their structure, including
ciprefadol
Ciprefadol is an opioid analgesic that is an isoquinoline derivative most closely related to cyclazocine and picenadol, with a number of other related compounds known. Ciprefadol is a mixed agonist–antagonist at μ-opioid receptors and can p ...
,
dasolampanel
Dasolampanel (INN, USAN, code name NGX-426) is an orally bioavailable analog of tezampanel and thereby competitive antagonist of the AMPA and kainate receptors which was under development by Raptor Pharmaceuticals/ Torrey Pines Therapeutics f ...
,
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 inhibitors (PIs) and like other PIs is almost always used in combination ...
,
saquinavir, and
tezampanel
Tezampanel (INN, USAN) (code names LY-293,558, 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 selectivity for the G ...
.
References
{{reflist