Leelamine
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| 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 (JSmol) |
|
| ChemSpider | |
| ECHA InfoCard | 100.014.454 |
PubChem CID |
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| |
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| 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 disruption of intracellular cholesterol transport, autophagy and endocytosis followed by cell death.[4]
See also
References
- ↑ "Leelamine - Dehydroabietylamine - Cayman Chemical". Retrieved May 20, 2013.
- ↑ US patent 3454626
- ↑ US patent 4559178
- ↑ 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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