Decahydroisoquinoline is a nitrogen-containing heterocycle with the chemical formula C9H17N.[1] It is the saturated form of isoquinoline.

Decahydroisoquinoline
Names
IUPAC name
1,2,3,4,4a,5,6,7,8,8a-Decahydroisoquinoline
Other names
Perhydroisoquinoline
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.026.093 Edit this at Wikidata
EC Number
  • 228-702-4
  • InChI=1S/C9H17N/c1-2-4-9-7-10-6-5-8(9)3-1/h8-10H,1-7H2
    Key: NENLYAQPNATJSU-UHFFFAOYSA-N
  • C1CCC2CNCCC2C1
Properties
C9H17N
Molar mass 139.242 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
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).

Decahydroisoquinoline can be formed by the hydrogenation of isoquinoline or tetrahydroisoquinoline.[2]

Isomers

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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

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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

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  1. ^ CID 97812 from PubChem
  2. ^ 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.
  3. ^ 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.
  4. ^ "Ciprefadol". Pubchem.
  5. ^ "Dasolampanel". Pubchem.
  6. ^ "Nelfinavir". Pubchem.
  7. ^ "Saquinavir". Pubchem.
  8. ^ "Tezampanel". Pubchem.