Decahydroisoquinoline

Decahydroisoquinoline
Names
	IUPAC name 1,2,3,4,4a,5,6,7,8,8a-Decahydroisoquinoline
	Other names Perhydroisoquinoline
Identifiers
CAS Number	6329-61-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	88287;
ECHA InfoCard	100.026.093
EC Number	228-702-4;
PubChem CID	97812;
	InChI InChI=1S/C9H17N/c1-2-4-9-7-10-6-5-8(9)3-1/h8-10H,1-7H2 Key: NENLYAQPNATJSU-UHFFFAOYSA-N;
	SMILES C1CCC2CNCCC2C1;
Properties
Chemical formula	C9H17N
Molar mass	139.242 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). Infobox references

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

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]

^ 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.