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Decahydroisoquinoline is a nitrogen-containing heterocycle with the chemical formula C9H17N.[1] It is the saturated form of isoquinoline.
Decahydroisoquinoline can be formed by the hydrogenation of isoquinoline or tetrahydroisoquinoline.[2]
Isomers
There are four stereoisomers of decahydroisoquinoline which differ by the configuration of the two carbon atoms at the ring fusion:
(4aR,8aR)‐cis-decahydroisoquinoline
(4aS,8aS)‐cis-decahydroisoquinoline
(4aR,8aS)‐trans-decahydroisoquinoline
(4aS,8aR)‐trans-decahydroisoquinoline
Occurrence
The decahydroisoquinoline occurs naturally in some alkaloids, including gephyrotoxins and pumiliotoxin C which are found in amphibian skins.[3]
A variety of pharmaceutical drugs include a decahydroisoquinoline ring system within their structure, including ciprefadol,[4] dasolampanel,[5] nelfinavir,[6] saquinavir,[7] and tezampanel.[8]
References
- ^ CID 97812 from PubChem
- ^ Okazaki, Hiroshi; Soeda, Mahito; Ikefuji, Yoshio; Tamura, Ryuji (1988). "Selective hydrogenation of neat isoquinoline". Applied Catalysis. 43: 71–84. doi:10.1016/S0166-9834(00)80901-X.
- ^ Daly, John W.; Martin Garraffo, H.; Spande, Thomas F. (1999). Alkaloids from Amphibian Skins. Alkaloids: Chemical and Biological Perspectives. Vol. 13. pp. 1–161. doi:10.1016/S0735-8210(99)80024-7. ISBN 9780080434032.
- ^ "Ciprefadol". Pubchem.
- ^ "Dasolampanel". Pubchem.
- ^ "Nelfinavir". Pubchem.
- ^ "Saquinavir". Pubchem.
- ^ "Tezampanel". Pubchem.
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