LY-2183240

{{Chembox

| ImageFile = LY-2183240 Structure.svg

| ImageSize =

| IUPACName = N,N-dimethyl-5-[(4-biphenyl)methyl]tetrazole-1-carboxamide

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo = 874902-19-9

| PubChem = 11507802

| ChemSpiderID = 9682599

| ChEBI = 92670

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 2WBU91OKM7

| 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

| InChIKey = GZNIYOXWFCDBBJ-UHFFFAOYAF

| StdInChI = 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

| StdInChIKey = GZNIYOXWFCDBBJ-UHFFFAOYSA-N

| SMILES = CN(C)C(=O)n1nnnc1Cc2ccc(cc2)-c3ccccc3

}}

|Section2={{Chembox Properties

| Formula = C₁₇H₁₇N₅O

| MolarMass = 307.349

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

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|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

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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.{{cite journal | author = Dickason-Chesterfield AK, Kidd SR, Moore SA, Schaus JM, Liu B, Nomikos GG, Felder CC | year = 2006 | title = Pharmacological characterization of endocannabinoid transport and fatty acid amide hydrolase inhibitors | journal = Cellular and Molecular Neurobiology | volume = 26 | issue = 4–6| pages = 407–23 | pmid = 16736384 | doi = 10.1007/s10571-006-9072-6 | s2cid = 24361518 | pmc = 11881822 }}{{cite journal | author = Maione S, Morera E, Marabese I, Ligresti A, Luongo L, Ortar G, Di Marzo V | date = Nov 2008 | title = Antinociceptive effects of tetrazole inhibitors of endocannabinoid inactivation: cannabinoid and non-cannabinoid receptor-mediated mechanisms | journal = British Journal of Pharmacology | volume = 155 | issue = 5| pages = 775–82 | pmid = 18660824 | doi = 10.1038/bjp.2008.308 | pmc = 2584918 }}{{cite journal | author = Powers MS, Barrenha GD, Mlinac NS, Barker EL, Chester JA | date = Dec 2010 | title = Effects of the novel endocannabinoid uptake inhibitor, LY2183240, on fear-potentiated startle and alcohol-seeking behaviors in mice selectively bred for high alcohol preference | journal = Psychopharmacology | volume = 212 | issue = 4| pages = 571–83 | pmid = 20838777 | doi = 10.1007/s00213-010-1997-2 | pmc = 2982902 }} While LY-2183240 is a potent inhibitor of FAAH, it has relatively poor selectivity and also inhibits several other enzyme side targets.{{cite journal | author = Alexander JP, Cravatt BF | date = Aug 2006 | title = The putative endocannabinoid transport blocker LY2183240 is a potent inhibitor of FAAH and several other brain serine hydrolases | journal = Journal of the American Chemical Society | volume = 128 | issue = 30| pages = 9699–704 | pmid = 16866524 | doi = 10.1021/ja062999h }} Consequently, it was never developed for clinical use, though it remains widely used in research, and has also been sold as a designer drug.{{cite journal | author = Uchiyama N, Matsuda S, Kawamura M, Shimokawa Y, Kikura-Hanajiri R, Aritake K, Urade Y, Goda Y | year = 2014 | title = 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 | journal = Forensic Sci Int | volume = 243 | pages = 1–13 | pmid = 24769262 | doi = 10.1016/j.forsciint.2014.03.013 }}