CYM51010
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MedKoo CAT#: 555940

CAS#: 1069498-96-9

Description: CYM51010, also known as CID23723457 and ML335, is a biased ligand of μ-opioid receptor – δ-opioid receptor heterodimers. CYM51010 exhibits anti-nociceptive activity similar to morphine, but with a decreased levels of tolerance development and withdrawal symptoms. ML335 showed an EC50 of 403 nM, and selectivities vs. OPRM1, OPRD1, and HTR5A of 37, 2.7, and >99, respectively.


Chemical Structure

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CYM51010
CAS# 1069498-96-9

Theoretical Analysis

MedKoo Cat#: 555940
Name: CYM51010
CAS#: 1069498-96-9
Chemical Formula: C25H32N2O3
Exact Mass: 408.24
Molecular Weight: 408.542
Elemental Analysis: C, 73.50; H, 7.90; N, 6.86; O, 11.75

Price and Availability

Size Price Availability Quantity
100mg USD 950 2 Weeks
200mg USD 1450 2 Weeks
500mg USD 2850 2 Weeks
1g USD 3450 2 Weeks
2g USD 5950 2 Weeks
Bulk inquiry

Synonym: CID23723457; CID-23723457; CID 23723457; ML335; ML-335; ML 335; CYM51010; CYM-51010; CYM 51010;

IUPAC/Chemical Name: 1-[[4-(Acetylamino)phenyl]methyl]-4-(2-phenylethyl)-4-Piperidinecarboxylic acid ethyl ester

InChi Key: VUXRYYSKTWDPLO-UHFFFAOYSA-N

InChi Code: InChI=1S/C25H32N2O3/c1-3-30-24(29)25(14-13-21-7-5-4-6-8-21)15-17-27(18-16-25)19-22-9-11-23(12-10-22)26-20(2)28/h4-12H,3,13-19H2,1-2H3,(H,26,28)

SMILES Code: O=C(C1(CCC2=CC=CC=C2)CCN(CC3=CC=C(NC(C)=O)C=C3)CC1)OCC

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:
Biological target: CYM51010 is a biased ligand of μ-opioid receptor – δ-opioid receptor heterodimers with an EC50 of 403 nM.
In vitro activity: This study reports the identification of compounds targeting μOR-δOR heteromers through high-throughput screening of a small-molecule library. Among them, CYM51010 was found to be a μOR-δOR-biased ligand, because its activity is blocked by the μOR-δOR heteromer antibody. Notably, systemic administration of CYM51010 induced antinociceptive activity similar to morphine, and chronic administration of CYM51010 resulted in lesser antinociceptive tolerance compared with morphine. Taken together, these results suggest that CYM51010, a μOR-δOR-biased ligand, could serve as a scaffold for the development of a unique type (heteromer-biased) of drug that is more potent and without the severe side effects associated with conventional clinical opioids. Reference: Proc Natl Acad Sci U S A. 2013 Jul 16;110(29):12072-7. https://pubmed.ncbi.nlm.nih.gov/23818586/
In vivo activity: This study examined the effects of spinal nerve injury on µ-δ heteromer expression in dorsal root ganglion (DRG) neurons and the effects of a µ-δ heteromer-targeting agonist, CYM51010, on neuropathic pain behavior in rats and mice. Importantly, in SNL rats, subcutaneous injection of CYM51010 inhibited mechanical hypersensitivity in a dose-related manner (EC50: 1.09 mg/kg) and also reversed heat hyperalgesia and attenuated ongoing pain (2 mg/kg, subcutaneously). Electrophysiologic studies showed that CYM51010 inhibited the C-component and windup phenomenon in spinal wide dynamic range neurons of SNL rats. The pain inhibitory effects of CYM51010 persisted in morphine-tolerant rats but was markedly attenuated in µ-OR knockout mice. Reference: Pain. 2020 Apr;161(4):842-855. https://pubmed.ncbi.nlm.nih.gov/31815916/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 5.0 12.24

Preparing Stock Solutions

The following data is based on the product molecular weight 408.54 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.

Recalculate based on batch purity %
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. Gomes I, Fujita W, Gupta A, Saldanha SA, Negri A, Pinello CE, Eberhart C, Roberts E, Filizola M, Hodder P, Devi LA. Identification of a μ-δ opioid receptor heteromer-biased agonist with antinociceptive activity. Proc Natl Acad Sci U S A. 2013 Jul 16;110(29):12072-7. doi: 10.1073/pnas.1222044110. Epub 2013 Jul 1. Erratum in: Proc Natl Acad Sci U S A. 2013 Oct 15;110(42):1760. Saldanha, Adrian S [corrected to Saldanha, S Adrian]; Eberhart, Christina [added]. PMID: 23818586; PMCID: PMC3718106. 2. Tiwari V, He SQ, Huang Q, Liang L, Yang F, Chen Z, Tiwari V, Fujita W, Devi LA, Dong X, Guan Y, Raja SN. Activation of µ-δ opioid receptor heteromers inhibits neuropathic pain behavior in rodents. Pain. 2020 Apr;161(4):842-855. doi: 10.1097/j.pain.0000000000001768. PMID: 31815916; PMCID: PMC7085422.
In vitro protocol: Gomes I, Fujita W, Gupta A, Saldanha SA, Negri A, Pinello CE, Eberhart C, Roberts E, Filizola M, Hodder P, Devi LA. Identification of a μ-δ opioid receptor heteromer-biased agonist with antinociceptive activity. Proc Natl Acad Sci U S A. 2013 Jul 16;110(29):12072-7. doi: 10.1073/pnas.1222044110. Epub 2013 Jul 1. Erratum in: Proc Natl Acad Sci U S A. 2013 Oct 15;110(42):1760. Saldanha, Adrian S [corrected to Saldanha, S Adrian]; Eberhart, Christina [added]. PMID: 23818586; PMCID: PMC3718106.
In vivo protocol: Tiwari V, He SQ, Huang Q, Liang L, Yang F, Chen Z, Tiwari V, Fujita W, Devi LA, Dong X, Guan Y, Raja SN. Activation of µ-δ opioid receptor heteromers inhibits neuropathic pain behavior in rodents. Pain. 2020 Apr;161(4):842-855. doi: 10.1097/j.pain.0000000000001768. PMID: 31815916; PMCID: PMC7085422.

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1: Zyrianova T, Lopez B, Olcese R, Belperio J, Waters CM, Wong L, Nguyen V, Talapaneni S, Schwingshackl A. K2P2.1 (TREK-1) potassium channel activation protects against hyperoxia-induced lung injury. Sci Rep. 2020 Dec 15;10(1):22011. doi: 10.1038/s41598-020-78886-y. PMID: 33319831; PMCID: PMC7738539.


2: Lolicato M, Natale AM, Abderemane-Ali F, Crottès D, Capponi S, Duman R, Wagner A, Rosenberg JM, Grabe M, Minor DL Jr. K2P channel C-type gating involves asymmetric selectivity filter order-disorder transitions. Sci Adv. 2020 Oct 30;6(44):eabc9174. doi: 10.1126/sciadv.abc9174. PMID: 33127683; PMCID: PMC7608817.


3: Lolicato M, Arrigoni C, Mori T, Sekioka Y, Bryant C, Clark KA, Minor DL Jr. K2P2.1 (TREK-1)-activator complexes reveal a cryptic selectivity filter binding site. Nature. 2017 Jul 20;547(7663):364-368. doi: 10.1038/nature22988. Epub 2017 Jul 10. PMID: 28693035; PMCID: PMC5778891.


4: Pinello C, Guerrero M, Eberhart C, Volmar CH, Saldanha SA, Cayanan C, Urbano M, Brown SJ, Ferguson J, Gomes I, Devi LA, Roberts E, Hodder P, Rosen H. Characterization of an agonist probe for opioid receptor mu 1 (OPRM1)-opioid receptor delta 1 (OPRD1) heterodimerization. 2012 Dec 17 [updated 2013 Apr 5]. In: Probe Reports from the NIH Molecular Libraries Program [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2010–. PMID: 23833799.