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| ImageFile = Dehydroabietylamine.svg
| ImageFile = Dehydroabietylamine.svg
| ImageSize = 200px
| ImageSize = 200px
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| IUPACName = Abieta-8,11,13-trien-18-amine
| IUPACName = [(1''R'',4a''S'',10a''R'')-1,4a-Dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine
| SystematicName = 1-[(1''R'',4a''S'',10a''R'')-1,4a-Dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl]methanamine
⚫
| SystematicName = Abieta-8,11,13-trien-18-amine
| OtherNames = (+)-Dehydroabietylamine; Amine D
| OtherNames = (+)-Dehydroabietylamine; Amine D
|Section1={{Chembox Identifiers
|Section1 = {{Chembox Identifiers
| CASNo = 1446-61-3
| CASNo = 1446-61-3
| CASNo_Ref = {{cascite|correct|CAS}}
⚫
| PubChem = 62034
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 33289O147P
⚫
| PubChem = 62034
| ChemSpiderID = 55878
| ChemSpiderID = 55878
| SMILES = CC(C)c1ccc2c(c1)CC[C@@H]3[C@@]2(CCC[C@@]3(C)CN)C
| SMILES = CC(C)c1ccc2c(c1)CC[C@@H]3[C@@]2(CCC[C@@]3(C)CN)C
| 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
| 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
| InChIKey = JVVXZOOGOGPDRZ-SLFFLAALBG
| InChIKey = JVVXZOOGOGPDRZ-SLFFLAALBG
| StdInChI = 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
| StdInChI = 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
| StdInChIKey = JVVXZOOGOGPDRZ-SLFFLAALSA-N
| StdInChIKey = JVVXZOOGOGPDRZ-SLFFLAALSA-N
}}
}}
|Section2={{Chembox Properties
|Section2 ={{Chembox Properties
| C=20 | H=31 | N=1
| C=20 | H=31 | N=1
| Appearance =
| Appearance =
| Density =
| Density =
| MeltingPt =
| MeltingPt =
| BoilingPt =
| BoilingPt =
| Solubility =
| Solubility =
}}
}}
|Section3={{Chembox Hazards
|Section3 ={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| AutoignitionPt =
| AutoignitionPt =
}}
}}
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| title = Leelamine - Dehydroabietylamine - Cayman Chemical
| title = Leelamine - Dehydroabietylamine - Cayman Chemical
| url = https://www.caymanchem.com/app/template/Product.vm/catalog/10006148
| url = https://www.caymanchem.com/app/template/Product.vm/catalog/10006148
| accessdate = May 20, 2013 }}
| access-date = May 20, 2013 }}
</ref> [[Optical rotation|Optically active]] leelamine is also used as a [[Chiral derivatizing agent|chiral resolving agent]] for carboxylic acids.<ref>{{US patent reference | number = 3454626}}</ref><ref>{{US patent reference | number = 4559178}}</ref> 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.<ref>{{cite journal |doi=10.1158/1535-7163.MCT-13-0868 |pmid=24688051 |title=Leelamine Mediates Cancer Cell Death through Inhibition of Intracellular Cholesterol Transport |journal=Molecular Cancer Therapeutics |volume=13 |issue=7 |year=2014 |last1=Kuzu |first1=O. F. |last2=Gowda |first2=R. |last3=Sharma |first3=A. |last4=Robertson |first4=G. P. }}</ref>
</ref> [[Optical rotation|Optically active]] leelamine is also used as a [[Chiral derivatizing agent|chiral resolving agent]] for carboxylic acids.<ref>{{US patent reference | number = 3454626}}</ref><ref>{{US patent reference | number = 4559178}}</ref> 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.<ref>{{cite journal |doi=10.1158/1535-7163.MCT-13-0868 |pmid=24688051 |pmc=4373557 |title=Leelamine Mediates Cancer Cell Death through Inhibition of Intracellular Cholesterol Transport |journal=Molecular Cancer Therapeutics |volume=13 |issue=7 |pages=1690–703 |year=2014 |last1=Kuzu |first1=O. F. |last2=Gowda |first2=R. |last3=Sharma |first3=A. |last4=Robertson |first4=G. P. }}</ref>


==See also==
==See also==
* [[THC]]
* [[Abietic acid]]
* [[Resin acid]]


== References ==
==References==
<references />
<references />

==External links==
*[https://simpleleaf.com/ Simple Leaf CBD]


{{Cannabinoids}}
{{Cannabinoids}}
{{Cannabinoidergics}}
{{Cannabinoidergics}}


⚫
[[Category:Cannabinoids]]
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[[Category:Diterpenes]]
[[Category:Amines]]
[[Category:Amines]]
⚫
[[Category:Cannabinoids]]

[[Category:Diterpene alkaloids]]
[[Category:Isopropyl compounds]]
⚫
[[Category:Phenanthrenes]]


{{cannabinoid-stub}}
{{cannabinoid-stub}}

Latest revision as of 14:33, 3 May 2023

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

[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 4373557. PMID 24688051.
[edit]
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