BW 373U86 | CAS# 150428-54-9 | selective agonist for the δ-opioid receptor

MedKoo Cat#: 412169 | Name: BW 373U86

Description:

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

BW 373U86 is an opioid analgesic drug used in scientific research.[1][2] BW373U86 is a selective agonist for the δ-opioid receptor, with approximately 15x stronger affinity for the δ-opioid than the μ-opioid receptor. It has potent analgesic and antidepressant effects in animal studies. In studies on rats, BW373U86 appears to protect heart muscle cells from apoptosis in conditions of ischemia (oxygen deprivation, such as in heart attack). The mechanism for this is complex and may be separate from its delta agonist effects.

Chemical Structure

BW 373U86

CAS#150428-54-9

Theoretical Analysis

MedKoo Cat#: 412169

Name: BW 373U86

CAS#: 150428-54-9

Chemical Formula: C27H37N3O2

Exact Mass: 435.2886

Molecular Weight: 435.61

Elemental Analysis: C, 74.45; H, 8.56; N, 9.65; O, 7.35

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

BW 373U86; BW-373U86; BW373U86

IUPAC/Chemical Name

4-((R)-((2S,5R)-4-allyl-2,5-dimethylpiperazin-1-yl)(3-hydroxyphenyl)methyl)-N,N-diethylbenzamide

InChi Key

LBLDMHBSVIVJPM-YZIHRLCOSA-N

InChi Code

InChI=1S/C27H37N3O2/c1-6-16-29-18-21(5)30(19-20(29)4)26(24-10-9-11-25(31)17-24)22-12-14-23(15-13-22)27(32)28(7-2)8-3/h6,9-15,17,20-21,26,31H,1,7-8,16,18-19H2,2-5H3/t20-,21+,26-/m1/s1

SMILES Code

CCN(C(c1ccc([C@H](c2cc(O)ccc2)N3C[C@H](N(C[C@@H]3C)CC=C)C)cc1)=O)CC

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

>3 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 435.61 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

1: Yang L, Zhao X, Sun M, Sun X, Yao L, Yu D, Ding Q, Gao C, Chai W. Delta opioid receptor agonist BW373U86 attenuates post-resuscitation brain injury in a rat model of asphyxial cardiac arrest. Resuscitation. 2014 Feb;85(2):299-305. doi: 10.1016/j.resuscitation.2013.10.022. Epub 2013 Nov 5. PMID: 24200890. 2: Donner D, Headrick JP, Peart JN, du Toit EF. Obesity improves myocardial ischaemic tolerance and RISK signalling in insulin-insensitive rats. Dis Model Mech. 2013 Mar;6(2):457-66. doi: 10.1242/dmm.010959. Epub 2012 Nov 16. PMID: 23161371; PMCID: PMC3597027. 3: Bradbury FA, Zelnik JC, Traynor JR. G protein independent phosphorylation and internalization of the delta-opioid receptor. J Neurochem. 2009 Jun;109(5):1526-35. doi: 10.1111/j.1471-4159.2009.06082.x. Epub 2009 Apr 1. PMID: 19344370; PMCID: PMC4372060. 4: White DA, Ballard ME, Harmon AC, Holtzman SG. Acute delta- and kappa-opioid agonist pretreatment potentiates opioid antagonist-induced suppression of water consumption. Brain Res Bull. 2008 Aug 15;76(6):597-604. doi: 10.1016/j.brainresbull.2008.04.002. Epub 2008 May 9. PMID: 18598850; PMCID: PMC2504860. 5: Kao TK, Ou YC, Liao SL, Chen WY, Wang CC, Chen SY, Chiang AN, Chen CJ. Opioids modulate post-ischemic progression in a rat model of stroke. Neurochem Int. 2008 May;52(6):1256-65. doi: 10.1016/j.neuint.2008.01.007. Epub 2008 Jan 20. PMID: 18294735. 6: Gross ER, Hsu AK, Gross GJ. GSK3beta inhibition and K(ATP) channel opening mediate acute opioid-induced cardioprotection at reperfusion. Basic Res Cardiol. 2007 Jul;102(4):341-9. doi: 10.1007/s00395-007-0651-6. Epub 2007 Apr 23. PMID: 17450314. 7: Jutkiewicz EM, Baladi MG, Folk JE, Rice KC, Woods JH. The convulsive and electroencephalographic changes produced by nonpeptidic delta-opioid agonists in rats: comparison with pentylenetetrazol. J Pharmacol Exp Ther. 2006 Jun;317(3):1337-48. doi: 10.1124/jpet.105.095810. Epub 2006 Mar 14. PMID: 16537798. 8: Zhang H, Torregrossa MM, Jutkiewicz EM, Shi YG, Rice KC, Woods JH, Watson SJ, Ko MC. Endogenous opioids upregulate brain-derived neurotrophic factor mRNA through delta- and micro-opioid receptors independent of antidepressant-like effects. Eur J Neurosci. 2006 Feb;23(4):984-94. doi: 10.1111/j.1460-9568.2006.04621.x. PMID: 16519663; PMCID: PMC1462954. 9: Torregrossa MM, Folk JE, Rice KC, Watson SJ, Woods JH. Chronic administration of the delta opioid receptor agonist (+)BW373U86 and antidepressants on behavior in the forced swim test and BDNF mRNA expression in rats. Psychopharmacology (Berl). 2005 Nov;183(1):31-40. doi: 10.1007/s00213-005-0113-5. Epub 2005 Oct 22. PMID: 16220339; PMCID: PMC1315298. 10: Jutkiewicz EM, Kaminsky ST, Rice KC, Traynor JR, Woods JH. Differential behavioral tolerance to the delta-opioid agonist SNC80 ([(+)-4-[(alphaR)-alpha-[ (2S,5R)-2,5-dimethyl-4-(2-propenyl)-1-piperazinyl]-(3-methoxyphenyl)methyl]-N,N- diethylbenzamide) in Sprague-Dawley rats. J Pharmacol Exp Ther. 2005 Oct;315(1):414-22. doi: 10.1124/jpet.105.088831. Epub 2005 Jul 13. PMID: 16014751; PMCID: PMC1307500. 11: Jutkiewicz EM, Walker NP, Folk JE, Rice KC, Portoghese PS, Woods JH, Traynor JR. Comparison of peptidic and nonpeptidic delta-opioid agonists on guanosine 5'-O-(3-[35S]thio)triphosphate ([35S]GTPgammaS) binding in brain slices from Sprague-Dawley rats. J Pharmacol Exp Ther. 2005 Mar;312(3):1314-20. doi: 10.1124/jpet.104.078741. Epub 2004 Dec 1. PMID: 15574687; PMCID: PMC1780166. 12: Patel HH, Hsu AK, Gross GJ. COX-2 and iNOS in opioid-induced delayed cardioprotection in the intact rat. Life Sci. 2004 May 28;75(2):129-40. doi: 10.1016/j.lfs.2003.10.036. PMID: 15120566. 13: Calderon SN, Coop A. SNC 80 and related delta opioid agonists. Curr Pharm Des. 2004;10(7):733-42. doi: 10.2174/1381612043453054. PMID: 15032699. 14: Gross ER, Hsu AK, Gross GJ. Opioid-induced cardioprotection occurs via glycogen synthase kinase beta inhibition during reperfusion in intact rat hearts. Circ Res. 2004 Apr 16;94(7):960-6. doi: 10.1161/01.RES.0000122392.33172.09. Epub 2004 Feb 19. PMID: 14976126. 15: Shinmura K, Nagai M, Tamaki K, Bolli R. Gender and aging do not impair opioid-induced late preconditioning in rats. Basic Res Cardiol. 2004 Jan;99(1):46-55. doi: 10.1007/s00395-003-0436-5. Epub 2003 Sep 9. PMID: 14685705. 16: Torregrossa MM, Isgor C, Folk JE, Rice KC, Watson SJ, Woods JH. The delta- opioid receptor agonist (+)BW373U86 regulates BDNF mRNA expression in rats. Neuropsychopharmacology. 2004 Apr;29(4):649-59. doi: 10.1038/sj.npp.1300345. PMID: 14647482. 17: Peart JN, Patel HH, Gross GJ. Delta-opioid receptor activation mimics ischemic preconditioning in the canine heart. J Cardiovasc Pharmacol. 2003 Jul;42(1):78-81. doi: 10.1097/00005344-200307000-00012. PMID: 12827030. 18: Broom DC, Jutkiewicz EM, Rice KC, Traynor JR, Woods JH. Behavioral effects of delta-opioid receptor agonists: potential antidepressants? Jpn J Pharmacol. 2002 Sep;90(1):1-6. doi: 10.1254/jjp.90.1. PMID: 12396021. 19: Broom DC, Nitsche JF, Pintar JE, Rice KC, Woods JH, Traynor JR. Comparison of receptor mechanisms and efficacy requirements for delta-agonist-induced convulsive activity and antinociception in mice. J Pharmacol Exp Ther. 2002 Nov;303(2):723-9. doi: 10.1124/jpet.102.036525. PMID: 12388657. 20: Shinmura K, Nagai M, Tamaki K, Tani M, Bolli R. COX-2-derived prostacyclin mediates opioid-induced late phase of preconditioning in isolated rat hearts. Am J Physiol Heart Circ Physiol. 2002 Dec;283(6):H2534-43. doi: 10.1152/ajpheart.00209.2002. Epub 2002 Aug 8. PMID: 12388283.