LY255582 | CAS#119193-09-8

MedKoo Cat#: 530678 | Name: LY255582

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Description:

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

LY255582 is a phenylpiperidine non-selective opioid antagonist. It has been shown to reduce ethanol consumption in experiments carried out on rats. It has also been shown to reduce food and water consumption in rats. LY255582 inhibits the diet-associated increases in mesolimbic dopamine levels and reduces the consumption of highly-palatable food intake.

Chemical Structure

LY255582

CAS#119193-09-8

Theoretical Analysis

MedKoo Cat#: 530678

Name: LY255582

CAS#: 119193-09-8

Chemical Formula: C22H35NO2

Exact Mass: 345.2668

Molecular Weight: 345.53

Elemental Analysis: C, 76.48; H, 10.21; N, 4.05; O, 9.26

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 weeks

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Synonym

LY255582; LY-255582; LY 255582.

IUPAC/Chemical Name

(3R,4R)-3,4-Dimethyl-1-[(3S)-3-hydroxy-3-cyclohexyl-propyl]-4-(3-hydroxyphenyl)piperidine

InChi Key

LVVHEFJXPXAUDD-BULFRSBZSA-N

InChi Code

InChI=1S/C22H35NO2/c1-17-16-23(13-11-21(25)18-7-4-3-5-8-18)14-12-22(17,2)19-9-6-10-20(24)15-19/h6,9-10,15,17-18,21,24-25H,3-5,7-8,11-14,16H2,1-2H3/t17-,21-,22+/m0/s1

SMILES Code

OC1=CC([C@@]2(C)[C@@H](C)CN(CC[C@H](O)C3CCCCC3)CC2)=CC=C1

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:

LY255582 is a phenylpiperidine non-selective opioid antagonist.

In vitro activity:

Comparison of the relative in vivo biological activity with in vitro receptor binding assays of LY255582 and its stereoisomers shows that the order of the affinity of the mu and kappa opioid receptors correlates well with biological activity. LY255582 is the most biologically effective and has the highest affinity for both receptors. Reference: Int J Obes. 1991 Jun;15(6):387-95. https://pubmed.ncbi.nlm.nih.gov/1653188/

In vivo activity:

Opioid antagonist LY255582 administration with HFD decreased food intake, body weight and BMI, in addition to the improvement of HFD related metabolic abnormalities (dyslipidemia and insulin resistance) during the dynamic phase of obesity development than in animals with already developed dietary obesity. Reference: Endocr Regul. 2015 Oct;49(4):198-205. https://pubmed.ncbi.nlm.nih.gov/26494038/

Preparing Stock Solutions

The following data is based on the product molecular weight 345.53 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. Shaw WN, Mitch CH, Leander JD, Mendelsohn LG, Zimmerman DM. The effect of the opioid antagonist LY255582 on body weight of the obese Zucker rat. Int J Obes. 1991 Jun;15(6):387-95. PMID: 1653188. 2. Ibrahim IY, Ibrahim HM, Aziz NM, Rahman DM. The protective role of the opioid antagonist LY255582 in the management of high fat diet-induced obesity in adult male albino rats. Endocr Regul. 2015 Oct;49(4):198-205. doi: 10.4149/endo_2015_04_198. PMID: 26494038. 3. Dhaher R, Toalston JE, Hauser SR, Bell RL, McKinzie DL, McBride WJ, Rodd ZA. Effects of naltrexone and LY255582 on ethanol maintenance, seeking, and relapse responding by alcohol-preferring (P) rats. Alcohol. 2012 Feb;46(1):17-27. doi: 10.1016/j.alcohol.2011.08.011. Epub 2011 Oct 1. PMID: 21962974; PMCID: PMC4581853.

In vitro protocol:

1. Shaw WN, Mitch CH, Leander JD, Mendelsohn LG, Zimmerman DM. The effect of the opioid antagonist LY255582 on body weight of the obese Zucker rat. Int J Obes. 1991 Jun;15(6):387-95. PMID: 1653188.

In vivo protocol:

1. Ibrahim IY, Ibrahim HM, Aziz NM, Rahman DM. The protective role of the opioid antagonist LY255582 in the management of high fat diet-induced obesity in adult male albino rats. Endocr Regul. 2015 Oct;49(4):198-205. doi: 10.4149/endo_2015_04_198. PMID: 26494038. 2. Dhaher R, Toalston JE, Hauser SR, Bell RL, McKinzie DL, McBride WJ, Rodd ZA. Effects of naltrexone and LY255582 on ethanol maintenance, seeking, and relapse responding by alcohol-preferring (P) rats. Alcohol. 2012 Feb;46(1):17-27. doi: 10.1016/j.alcohol.2011.08.011. Epub 2011 Oct 1. PMID: 21962974; PMCID: PMC4581853.

1: Ibrahim IY, Ibrahim HM, Aziz NM, Rahman DM. The protective role of the opioid antagonist LY255582 in the management of high fat diet-induced obesity in adult male albino rats. Endocr Regul. 2015 Oct;49(4):198-205. PubMed PMID: 26494038. 2: Dhaher R, Toalston JE, Hauser SR, Bell RL, McKinzie DL, McBride WJ, Rodd ZA. Effects of naltrexone and LY255582 on ethanol maintenance, seeking, and relapse responding by alcohol-preferring (P) rats. Alcohol. 2012 Feb;46(1):17-27. doi: 10.1016/j.alcohol.2011.08.011. Epub 2011 Oct 1. PubMed PMID: 21962974; PubMed Central PMCID: PMC4581853. 3: Shaw WN. Long-term treatment of obese Zucker rats with LY255582 and other appetite suppressants. Pharmacol Biochem Behav. 1993 Nov;46(3):653-9. PubMed PMID: 8278442. 4: Shaw WN, Mitch CH, Leander JD, Mendelsohn LG, Zimmerman DM. The effect of the opioid antagonist LY255582 on body weight of the obese Zucker rat. Int J Obes. 1991 Jun;15(6):387-95. PubMed PMID: 1653188. 5: Swanson SP, Catlow J, Pohland RC, Chay SH, Johnson T. Disposition of the opioid antagonist, LY255582, in rats and dogs. Drug Metab Dispos. 1995 Sep;23(9):916-21. PubMed PMID: 8565781. 6: Levine AS, Grace M, Billington CJ, Zimmerman DM. Central administration of the opioid antagonist, LY255582, decreases short- and long-term food intake in rats. Brain Res. 1991 Dec 6;566(1-2):193-7. PubMed PMID: 1667609. 7: Sahr AE, Sindelar DK, Alexander-Chacko JT, Eastwood BJ, Mitch CH, Statnick MA. Activation of mesolimbic dopamine neurons during novel and daily limited access to palatable food is blocked by the opioid antagonist LY255582. Am J Physiol Regul Integr Comp Physiol. 2008 Aug;295(2):R463-71. doi: 10.1152/ajpregu.00390.2007. Epub 2008 Jun 4. PubMed PMID: 18525013. 8: Need AB, McKinzie JH, Mitch CH, Statnick MA, Phebus LA. In vivo rat brain opioid receptor binding of LY255582 assessed with a novel method using LC/MS/MS and the administration of three tracers simultaneously. Life Sci. 2007 Oct 13;81(17-18):1389-96. Epub 2007 Sep 19. PubMed PMID: 17935738. 9: Statnick MA, Tinsley FC, Eastwood BJ, Suter TM, Mitch CH, Heiman ML. Peptides that regulate food intake: antagonism of opioid receptors reduces body fat in obese rats by decreasing food intake and stimulating lipid utilization. Am J Physiol Regul Integr Comp Physiol. 2003 Jun;284(6):R1399-408. PubMed PMID: 12736177. 10: Gackenheimer SL, Suter TM, Pintar JE, Quimby SJ, Wheeler WJ, Mitch CH, Gehlert DR, Statnick MA. Localization of opioid receptor antagonist [3H]-LY255582 binding sites in mouse brain: comparison with the distribution of mu, delta and kappa binding sites. Neuropeptides. 2005 Dec;39(6):559-67. Epub 2005 Nov 9. PubMed PMID: 16289278. 11: Rothman RB, Xu H, Char GU, Kim A, De Costa BR, Rice KC, Zimmerman DM. Phenylpiperidine opioid antagonists that promote weight loss in rats have high affinity for the kappa 2B (enkephalin-sensitive) binding site. Peptides. 1993 Jan-Feb;14(1):17-20. PubMed PMID: 8382809. 12: Emmerson PJ, McKinzie JH, Surface PL, Suter TM, Mitch CH, Statnick MA. Na+ modulation, inverse agonism, and anorectic potency of 4-phenylpiperidine opioid antagonists. Eur J Pharmacol. 2004 Jun 28;494(2-3):121-30. PubMed PMID: 15212965. 13: Díaz N, Benvenga M, Emmerson P, Favors R, Mangold M, McKinzie J, Patel N, Peters S, Quimby S, Shannon H, Siegel M, Statnick M, Thomas E, Woodland J, Surface P, Mitch C. SAR and biological evaluation of novel trans-3,4-dimethyl-4-arylpiperidine derivatives as opioid antagonists. Bioorg Med Chem Lett. 2005 Sep 1;15(17):3844-8. PubMed PMID: 15993591. 14: Carroll FI, Dolle RE. The discovery and development of the N-substituted trans-3,4-dimethyl-4-(3'-hydroxyphenyl)piperidine class of pure opioid receptor antagonists. ChemMedChem. 2014 Aug;9(8):1638-54. doi: 10.1002/cmdc.201402142. Epub 2014 Jun 30. Review. PubMed PMID: 24981721. 15: Mitch CH, Leander JD, Mendelsohn LG, Shaw WN, Wong DT, Cantrell BE, Johnson BG, Reel JK, Snoddy JD, Takemori AE, et al. 3,4-Dimethyl-4-(3-hydroxyphenyl)piperidines: opioid antagonists with potent anorectant activity. J Med Chem. 1993 Oct 1;36(20):2842-50. PubMed PMID: 8410999. 16: Werner JA, Cerbone LR, Frank SA, Ward JA, Labib P, Tharp-Taylor RW, Ryan CW. Synthesis of trans-3,4-Dimethyl-4-(3-hydroxyphenyl)piperidine Opioid Antagonists: Application of the Cis-Thermal Elimination of Carbonates to Alkaloid Synthesis. J Org Chem. 1996 Jan 26;61(2):587-597. PubMed PMID: 11666979.