LY2183240 | LY 2183240 | CAS#874902-19-9 | FAAH inhibitor

MedKoo Cat#: 526738 | Name: LY-2183240

Description:

WARNING: This product is for research use only, not for human or veterinary use.

LY2183240 is a potent inhibitor of FAAH 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. LY-2183240 has been shown to produce both analgesic and anxiolytic effects in animal models. LY-2183240 has relatively poor selectivity and also inhibits several other enzyme side targets. Consequently, it was never developed for clinical use, though it remains widely used in research, and has also been sold as a designer drug.

Chemical Structure

LY-2183240

CAS#874902-19-9

Theoretical Analysis

MedKoo Cat#: 526738

Name: LY-2183240

CAS#: 874902-19-9

Chemical Formula: C17H17N5O

Exact Mass: 307.1433

Molecular Weight: 307.36

Elemental Analysis: C, 66.43; H, 5.58; N, 22.79; O, 5.21

Price and Availability

Size	Price	Availability
25mg	USD 250.00	2 Weeks
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,650.00	2 Weeks
1g	USD 3,850.00	2 Weeks
2g	USD 6,450.00	2 Weeks

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Related CAS #

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Synonym

LY2183240; LY-2183240; LY 2183240.

IUPAC/Chemical Name

5-([1,1'-biphenyl]-4-ylmethyl)-N,N-dimethyl-1H-tetrazole-1-carboxamide

InChi Key

CUCQDDZYZNBQFE-KUNNFNOCSA-N

InChi Code

InChI=1S/C12H10ClN5O5S2/c13-3-1-24-10-6(9(20)18(10)7(3)11(21)22)16-8(19)5(17-23)4-2-25-12(14)15-4/h2,6,10,23H,1H2,(H2,14,15)(H,16,19)(H,21,22)/b17-5-/t6-,10-/m1/s1

SMILES Code

O=C(N1N=NN=C1CC2=CC=C(C3=CC=CC=C3)C=C2)N(C)C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

LY2183240 is a highly potent blocker of anandamide uptake (IC50= 270 pM; Ki=540 nM).

In vitro activity:

LY2183240 is a potent, covalent inhibitor of the EC-degrading enzyme fatty acid amide hydrolase (FAAH). LY2183240 inactivates FAAH by carbamylation of the enzyme's serine nucleophile. Reference: J Am Chem Soc. 2006 Aug 2;128(30):9699-704. https://pubmed.ncbi.nlm.nih.gov/16866524/

In vivo activity:

Repeated administration of LY2183240 (30 mg/kg) reduced the expression of FPS (fear-potentiated startle) in HAP (high alcohol preference) but not LAP (low alcohol preference) mice when given prior to a second FPS test 48 h after fear conditioning. Both the 10 and 30 mg/kg doses of LY2183240 enhanced the expression of alcohol-induced CPP and this effect persisted in the absence of the drug. Reference: Psychopharmacology (Berl). 2010 Dec;212(4):571-83. https://pubmed.ncbi.nlm.nih.gov/20838777/

	Solvent	mg/mL	mM
Solubility
	DMF	3.0	9.76
	DMSO	37.7	122.55
	Ethanol	35.5	115.50
	Ethanol:PBS (pH 7.2) (1:5)	0.1	0.33

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 307.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Alexander JP, Cravatt BF. The putative endocannabinoid transport blocker LY2183240 is a potent inhibitor of FAAH and several other brain serine hydrolases. J Am Chem Soc. 2006 Aug 2;128(30):9699-704. doi: 10.1021/ja062999h. PMID: 16866524. 2. Powers MS, Barrenha GD, Mlinac NS, Barker EL, Chester JA. 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 (Berl). 2010 Dec;212(4):571-83. doi: 10.1007/s00213-010-1997-2. Epub 2010 Sep 14. PMID: 20838777; PMCID: PMC2982902.

In vitro protocol:

Alexander JP, Cravatt BF. The putative endocannabinoid transport blocker LY2183240 is a potent inhibitor of FAAH and several other brain serine hydrolases. J Am Chem Soc. 2006 Aug 2;128(30):9699-704. doi: 10.1021/ja062999h. PMID: 16866524.

In vivo protocol:

Powers MS, Barrenha GD, Mlinac NS, Barker EL, Chester JA. 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 (Berl). 2010 Dec;212(4):571-83. doi: 10.1007/s00213-010-1997-2. Epub 2010 Sep 14. PMID: 20838777; PMCID: PMC2982902.

1: Köfalvi A, Lemos C, Martín-Moreno AM, Pinheiro BS, García-García L, Pozo MA, Valério-Fernandes Â, Beleza RO, Agostinho P, Rodrigues RJ, Pasquaré SJ, Cunha RA, de Ceballos ML. Stimulation of brain glucose uptake by cannabinoid CB(2) receptors and its therapeutic potential in Alzheimer's disease. Neuropharmacology. 2016 Mar 11. pii: S0028-3908(16)30087-9. doi: 10.1016/j.neuropharm.2016.03.015. [Epub ahead of print] PubMed PMID: 26976670. 2: Nicolussi S, Chicca A, Rau M, Rihs S, Soeberdt M, Abels C, Gertsch J. Correlating FAAH and anandamide cellular uptake inhibition using N-alkylcarbamate inhibitors: from ultrapotent to hyperpotent. Biochem Pharmacol. 2014 Dec 15;92(4):669-89. doi: 10.1016/j.bcp.2014.09.020. Epub 2014 Nov 4. PubMed PMID: 25283614. 3: Uchiyama N, Matsuda S, Kawamura M, Shimokawa Y, Kikura-Hanajiri R, Aritake K, Urade Y, Goda Y. 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. 2014 Oct;243:1-13. doi: 10.1016/j.forsciint.2014.03.013. Epub 2014 Mar 27. PubMed PMID: 24769262. 4: Gonzalez-Islas C, Garcia-Bereguiain MA, Wenner P. Tonic and transient endocannabinoid regulation of AMPAergic miniature postsynaptic currents and homeostatic plasticity in embryonic motor networks. J Neurosci. 2012 Sep 26;32(39):13597-607. PubMed PMID: 23015449; PubMed Central PMCID: PMC3470113. 5: Powers MS, Barrenha GD, Mlinac NS, Barker EL, Chester JA. 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 (Berl). 2010 Dec;212(4):571-83. doi: 10.1007/s00213-010-1997-2. Epub 2010 Sep 14. PubMed PMID: 20838777; PubMed Central PMCID: PMC2982902. 6: Pelorosso FG, Gago JE, Del Rey G, Menéndez SD, Errasti AE, Rothlin RP. The endocannabinoid anandamide inhibits kinin B1 receptor sensitization through cannabinoid CB1 receptor stimulation in human umbilical vein. Eur J Pharmacol. 2009 Jan 5;602(1):176-9. doi: 10.1016/j.ejphar.2008.10.058. Epub 2008 Nov 11. PubMed PMID: 19022239. 7: Maione S, Morera E, Marabese I, Ligresti A, Luongo L, Ortar G, Di Marzo V. Antinociceptive effects of tetrazole inhibitors of endocannabinoid inactivation: cannabinoid and non-cannabinoid receptor-mediated mechanisms. Br J Pharmacol. 2008 Nov;155(5):775-82. doi: 10.1038/bjp.2008.308. Epub 2008 Jul 28. PubMed PMID: 18660824; PubMed Central PMCID: PMC2584918. 8: Njie YF, He F, Qiao Z, Song ZH. Aqueous humor outflow effects of 2-arachidonylglycerol. Exp Eye Res. 2008 Aug;87(2):106-14. doi: 10.1016/j.exer.2008.05.003. Epub 2008 May 14. PubMed PMID: 18597752. 9: Ortar G, Cascio MG, Moriello AS, Camalli M, Morera E, Nalli M, Di Marzo V. Carbamoyl tetrazoles as inhibitors of endocannabinoid inactivation: a critical revisitation. Eur J Med Chem. 2008 Jan;43(1):62-72. Epub 2007 Mar 19. PubMed PMID: 17452063. 10: Alexander JP, Cravatt BF. The putative endocannabinoid transport blocker LY2183240 is a potent inhibitor of FAAH and several other brain serine hydrolases. J Am Chem Soc. 2006 Aug 2;128(30):9699-704. PubMed PMID: 16866524. 11: Dickason-Chesterfield AK, Kidd SR, Moore SA, Schaus JM, Liu B, Nomikos GG, Felder CC. Pharmacological characterization of endocannabinoid transport and fatty acid amide hydrolase inhibitors. Cell Mol Neurobiol. 2006 Jul-Aug;26(4-6):407-23. Epub 2006 May 31. PubMed PMID: 16736384.