Decahydroisoquinoline
Chemical compound
From Wikipedia, the free encyclopedia
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 | |
| Other names
Perhydroisoquinoline | |
| 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
There are four stereoisomers of decahydroisoquinoline which differ by the configuration of the two carbon atoms at the ring fusion:
‐cis-decahydroisoquinoline.svg)
‐cis-decahydroisoquinoline.svg)
‐trans-decahydroisoquinoline.svg){kind=spacer}
‐trans-decahydroisoquinoline.svg){kind=spacer}
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]