LY-2183240

LY-2183240 is a drug which acts both as a potent inhibitor of the reuptake of the endocannabinoid anandamide and as an inhibitor of fatty acid amide hydrolase (FAAH), the primary enzyme responsible for degrading anandamide. This leads to markedly elevated anandamide levels in the brain, and LY-2183240 has been shown to produce both analgesic and anxiolytic effects in animal models.[1][2][3] While LY-2183240 is a potent inhibitor of FAAH, it has relatively poor selectivity and also inhibits several other enzyme side targets.[4] Consequently, it was never developed for clinical use, though it remains widely used in research, and has also been sold as a designer drug.[5]

LY-2183240
Names
IUPAC name
N,N-dimethyl-5-[(4-biphenyl)methyl]tetrazole-1-carboxamide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.189.657
PubChem CID
UNII
InChI
  • InChI=1S/C17H17N5O/c1-21(2)17(23)22-16(18-19-20-22)12-13-8-10-15(11-9-13)14-6-4-3-5-7-14/h3-11H,12H2,1-2H3
    Key: GZNIYOXWFCDBBJ-UHFFFAOYSA-N
  • InChI=1/C17H17N5O/c1-21(2)17(23)22-16(18-19-20-22)12-13-8-10-15(11-9-13)14-6-4-3-5-7-14/h3-11H,12H2,1-2H3
    Key: GZNIYOXWFCDBBJ-UHFFFAOYAF
SMILES
  • CN(C)C(=O)n1nnnc1Cc2ccc(cc2)-c3ccccc3
Properties
Chemical formula
 C17H17N5O
Molar mass 307.349
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. Dickason-Chesterfield AK, Kidd SR, Moore SA, Schaus JM, Liu B, Nomikos GG, Felder CC (2006). "Pharmacological characterization of endocannabinoid transport and fatty acid amide hydrolase inhibitors". Cellular and Molecular Neurobiology. 26 (4–6): 407–23. doi:10.1007/s10571-006-9072-6. PMID 16736384. S2CID 24361518.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. Maione S, Morera E, Marabese I, Ligresti A, Luongo L, Ortar G, Di Marzo V (Nov 2008). "Antinociceptive effects of tetrazole inhibitors of endocannabinoid inactivation: cannabinoid and non-cannabinoid receptor-mediated mechanisms". British Journal of Pharmacology. 155 (5): 775–82. doi:10.1038/bjp.2008.308. PMC 2584918. PMID 18660824.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. Powers MS, Barrenha GD, Mlinac NS, Barker EL, Chester JA (Dec 2010). "Effects of the novel endocannabinoid uptake inhibitor, LY2183240, on fear-potentiated startle and alcohol-seeking behaviors in mice selectively bred for high alcohol preference". Psychopharmacology. 212 (4): 571–83. doi:10.1007/s00213-010-1997-2. PMC 2982902. PMID 20838777.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. Alexander JP, Cravatt BF (Aug 2006). "The putative endocannabinoid transport blocker LY2183240 is a potent inhibitor of FAAH and several other brain serine hydrolases". Journal of the American Chemical Society. 128 (30): 9699–704. doi:10.1021/ja062999h. PMID 16866524.
  5. Uchiyama N, Matsuda S, Kawamura M, Shimokawa Y, Kikura-Hanajiri R, Aritake K, Urade Y, Goda Y (2014). "Characterization of four new designer drugs, 5-chloro-NNEI, NNEI indazole analog, α-PHPP and α-POP, with 11 newly distributed designer drugs in illegal products". Forensic Sci Int. 243: 1–13. doi:10.1016/j.forsciint.2014.03.013. PMID 24769262.{{cite journal}}: CS1 maint: multiple names: authors list (link)

Further reading

Moore, S. A.; Nomikos, G. G.; Dickason-Chesterfield, A. K.; Schober, D. A.; Schaus, J. M.; Ying, B. P.; Xu, Y. C.; Phebus, L; Simmons, R. M.; Li, D; Iyengar, S; Felder, C. C. (2005). "Identification of a high-affinity binding site involved in the transport of endocannabinoids". Proceedings of the National Academy of Sciences. 102 (49): 17852–7. doi:10.1073/pnas.0507470102. PMC 1295594. PMID 16314570.

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