Decahydroisoquinoline is a nitrogen-containing heterocycle with the chemical formula C9H17N.[1] It is the saturated form of isoquinoline.
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| Names | |
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| IUPAC name
1,2,3,4,4a,5,6,7,8,8a-Decahydroisoquinoline
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| Other names
Perhydroisoquinoline
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.026.093 |
| EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C9H17N | |
| Molar mass | 139.242 g·mol−1 |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Decahydroisoquinoline can be formed by the hydrogenation of isoquinoline or tetrahydroisoquinoline.[2]
Isomers
editThere are four stereoisomers of decahydroisoquinoline which differ by the configuration of the two carbon atoms at the ring fusion:
%E2%80%90cis-decahydroisoquinoline.svg)
(4aR,8aR)‐cis-decahydroisoquinoline
%E2%80%90cis-decahydroisoquinoline.svg)
(4aS,8aS)‐cis-decahydroisoquinoline
%E2%80%90trans-decahydroisoquinoline.svg){kind=spacer}
(4aR,8aS)‐trans-decahydroisoquinoline
%E2%80%90trans-decahydroisoquinoline.svg){kind=spacer}
(4aS,8aR)‐trans-decahydroisoquinoline
Occurrence
editThe 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
edit- ^ 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.