Misplaced Pages

Leelamine

Article snapshot taken from[REDACTED] with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Leelamine
Names
IUPAC name Abieta-8,11,13-trien-18-amine
Systematic IUPAC name 1-methanamine
Other names (+)-Dehydroabietylamine; Amine D
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.454 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: 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/s1Key: JVVXZOOGOGPDRZ-SLFFLAALBG
SMILES
  • CC(C)c1ccc2c(c1)CC32(CCC3(C)CN)C
Properties
Chemical formula C20H31N
Molar mass 285.475 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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. Optically active leelamine is also used as a chiral resolving agent for carboxylic acids. 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.

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.

External links

Cannabinoids
Phytocannabinoids
(comparison)
Cannabibutols
Cannabichromenes
Cannabicyclols
Cannabidiols
Cannabielsoins
Cannabigerols
Cannabiphorols
Cannabinols
Cannabitriols
Cannabivarins
Delta-8-tetrahydrocannabinols
Delta-9-tetrahydrocannabinols
Delta-10-Tetrahydrocannabinols
Miscellaneous cannabinoids
Active metabolites
Endocannabinoids
Synthetic
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids
(dibenzopyrans)
Non-classical
cannabinoids
Adamantoylindoles
Benzimidazoles
Benzoylindoles
Cyclohexylphenols
Eicosanoids
Indazole-3-
carboxamides
Indole-3-carboxamides
Indole-3-carboxylates
Naphthoylindazoles
Naphthoylindoles
Naphthoylpyrroles
Naphthylmethylindenes
Naphthylmethylindoles
Phenylacetylindoles
Pyrazolecarboxamides
Tetramethylcyclo-
propanoylindazoles
Tetramethylcyclo-
propanoylindoles
Others
Allosteric CBRTooltip Cannabinoid receptor ligands
Endocannabinoid
enhancers
(inactivation inhibitors)
Anticannabinoids
(antagonists/inverse
agonists/antibodies)
Cannabinoid receptor modulators
Receptor
(ligands)
CB1Tooltip Cannabinoid receptor type 1
Agonists
(abridged,
full list)
Inverse agonists
Antagonists
CB2Tooltip Cannabinoid receptor type 2
Agonists
Antagonists
NAGly
(GPR18)
Agonists
Antagonists
GPR55
Agonists
Antagonists
GPR119
Agonists
Transporter
(modulators)
eCBTsTooltip Endocannabinoid transporter
Enzyme
(modulators)
FAAHTooltip Fatty acid amide hydrolase
MAGL
ABHD6
ABHD12
Others
  • Others: 2-PG (directly potentiates activity of 2-AG at CB1 receptor)
  • ARN-272 (FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)
Stub icon

This cannabinoid related article is a stub. You can help Misplaced Pages by expanding it.

Categories:
Leelamine Add topic