Leelamine

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Leelamine
Dehydroabietylamine.svg
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
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.014.454
Properties
C20H31N
Molar mass 285.48 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

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 Cannabinoids or PDK1. Due to its lysosomotropic property, it accumulates inside the acidic organelles leading to distruption of intracellular cholesterol transport, autophagy and endocytosis followed by cell death.[4]

See also[edit]

References[edit]

  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 4373557Freely accessible. PMID 24688051.