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Leelamine

Leelamine
Names
IUPAC name
Abieta-8,11,13-trien-18-amine
Systematic IUPAC name
1-[(1R,4aS,10aR)-1,4a-Dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl]methanamine
Other names
(+)-Dehydroabietylamine; Amine D
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.454 Edit this at Wikidata
UNII
  • 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
  • CC(C)c1ccc2c(c1)CC[C@@H]3[C@@]2(CCC[C@@]3(C)CN)C
Properties
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).

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]

See also

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.
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