Leelamine

Leelamine (dehydroabietylamine) is a diterpene amine that has weak affinity for the cannabinoid receptors CB₁ and CB₂, as well as being an inhibitor of pyruvate dehydrogenase kinase.[1] Optically active leelamine is also used as a chiral resolving agent for carboxylic acids.[2][3] Leelamine has been shown to be effective against certain cancer cells, independent from its activity on CB receptors or PDK1 - it accumulates inside the acidic lysosomes leading to disruption of intracellular cholesterol transport, autophagy and endocytosis followed by cell death.[4]

Leelamine

Names
IUPAC name [(1R,4aS,10aR)-1,4a-Dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine
Systematic IUPAC name Abieta-8,11,13-trien-18-amine
Other names (+)-Dehydroabietylamine; Amine D
Identifiers
CAS Number	1446-61-3
3D model (JSmol)	Interactive image
ChemSpider	55878
ECHA InfoCard	100.014.454
PubChem CID	62034
UNII	33289O147P
CompTox Dashboard (EPA)	DTXSID2041834
InChI InChI=1S/C20H31N/c1-14(2)15-6-8-17-16(12-15)7-9-18-19(3,13-21)10-5-11-20(17,18)4/h6,8,12,14,18H,5,7,9-11,13,21H2,1-4H3/t18-,19-,20+/m0/s1 Key: JVVXZOOGOGPDRZ-SLFFLAALSA-N InChI=1/C20H31N/c1-14(2)15-6-8-17-16(12-15)7-9-18-19(3,13-21)10-5-11-20(17,18)4/h6,8,12,14,18H,5,7,9-11,13,21H2,1-4H3/t18-,19-,20+/m0/s1 Key: JVVXZOOGOGPDRZ-SLFFLAALBG
SMILES CC(C)c1ccc2c(c1)CC[C@@H]3[C@@]2(CCC[C@@]3(C)CN)C
Properties
Chemical formula	C20H31N
Molar mass	285.475 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

Abietic acid

References

1. "Leelamine - Dehydroabietylamine - Cayman Chemical". Retrieved May 20, 2013.
2. US patent 3454626
3. US patent 4559178
4. Kuzu, O. F.; Gowda, R.; Sharma, A.; Robertson, G. P. (2014). "Leelamine Mediates Cancer Cell Death through Inhibition of Intracellular Cholesterol Transport". Molecular Cancer Therapeutics. 13 (7): 1690–703. doi:10.1158/1535-7163.MCT-13-0868. PMC 4373557. PMID 24688051.