From Wikipedia, the free encyclopedia
LY-2183240
Names
IUPAC name
N,N-dimethyl-5-[(4-biphenyl)methyl]tetrazole-1-carboxamide
Identifiers
ChemSpider
ECHA InfoCard
100.189.657
UNII
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
CN(C)C(=O)n1nnnc1Cc2ccc(cc2)-c3ccccc3
Properties
C17 H17 N5 O
Molar mass
307.349
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
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]
See also
References
^ 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 )
^ 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 )
^ 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 )
^ 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 .
^ 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 .
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
Hydrocarbons Indazole carboxamides Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles
Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles Tetramethylcyclo- propylindoles Others
Allosteric
CBR Tooltip Cannabinoid receptor
ligands
Endocannabinoid enhancers (inactivation inhibitors)
Anticannabinoids (antagonists/inverse agonists/antibodies)
Receptor (
ligands )
CB1 Tooltip Cannabinoid receptor type 1
Agonists(abridged,
full list ) Inverse agonists Antagonists
CB2 Tooltip Cannabinoid receptor type 2
Agonists
2-AG
2-AGE (noladin ether)
3,3'-Diindolylmethane
4-O-Methylhonokiol
α-Amyrin · β-Amyrin
A-796,260
A-834,735
A-836,339
AM-1172
AM-1221
AM-1235
AM-1241
AM-2232
Anandamide
AZ-11713908
Cannabinol
Caryophyllene
CB-13
CBS-0550
CP 55,940
GW-405,833 (L-768,242)
GW-842,166X
HU-308
JTE 7-31
JWH-007
JWH-015
JWH-018
JWH-73
JWH-133
L-759,633
L-759,656
Lenabasum (anabasum)
Magnolol
MDA-19
Nabitan
NADA
Olorinab (APD-371)
PF-03550096
S-444,823
SER-601
Serinolamide A
UR-144
Tedalinab
THC (dronabinol)
THCV
Tetrahydromagnolol
Virodhamine
Antagonists
NAGly (
GPR18 )
GPR55
GPR119
Transporter (
modulators )
eCBTs Tooltip Endocannabinoid transporter
Enzyme (
modulators )
Others
Others:
2-PG (directly potentiates activity of 2-AG at CB1 receptor)
ARN-272 (FAAH-like anandamide transporter inhibitor)