Oliceridine HCl

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

MedKoo CAT#: 510256

CAS#: 1401031-39-7 (HCl)

Description: Oliceridine, also known as TRV130, is a µ- opioid receptor agonist, that is currently under evaluation in human clinical trials for the treatment of acute severe pain. It is a functionally selective μ-opioid receptor agonist developed by Trevena Inc. TRV130 elicits robust G protein signaling, with potency and efficacy similar to morphine, but with far less β-arrestin 2 recruitment and receptor internalization, it displays less adverse effects than morphine. (http://en.wikipedia.org/wiki/TRV130). Oliceridine is now discontinued since it was recently listed as a controlled substance.


Chemical Structure

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Oliceridine HCl
CAS# 1401031-39-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 510256
Name: Oliceridine HCl
CAS#: 1401031-39-7 (HCl)
Chemical Formula: C22H30N2O2S
Exact Mass: 386.2028
Molecular Weight: 386.5508
Elemental Analysis: C, 68.36; H, 7.82; N, 7.25; O, 8.28; S, 8.30

Size Price Shipping out time Quantity
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Pricing updated 2021-03-03. Prices are subject to change without notice.

Oliceridine is now discontinued since it was recently listed as a controlled substance.

Related CAS #: 1401031-39-7 (HCl)   1401028-24-7 (free base)    

Synonym: TRV130; TRV 130; TRV130; Oliceridine; Oliceridine HCl; Oliceridine hydrochloride

IUPAC/Chemical Name: (R)-N-((3-methoxythiophen-2-yl)methyl)-2-(9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl)ethanamine hydrochloride

InChi Key: YIIWXYLJZRISQP-ZMBIFBSDSA-N

InChi Code: InChI=1S/C22H30N2O2S.ClH/c1-25-18-7-15-27-19(18)16-23-13-10-21(20-6-2-5-12-24-20)11-14-26-22(17-21)8-3-4-9-22;/h2,5-7,12,15,23H,3-4,8-11,13-14,16-17H2,1H3;1H/t21-;/m1./s1

SMILES Code: COC1=C(CNCC[C@@](C2)(C3=NC=CC=C3)CCOC42CCCC4)SC=C1.[H]Cl

Appearance:
White solid powder, highly hygroscopic!

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, soluble in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO or aqueous buffer (preferably in acidic pH)

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

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO, soluble in water 100.0

Preparing Stock Solutions

The following data is based on the product molecular weight 386.5508 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.

Select a batch to recalculate based on the batch molecular weight:
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

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1: Soergel DG, Subach RA, Burnham N, Lark MW, James IE, Sadler BM, Skobieranda F, Violin JD, Webster LR. Biased agonism of the μ-opioid receptor by TRV130 increases analgesia and reduces on-target adverse effects versus morphine: A randomized, double-blind, placebo-controlled, crossover study in healthy volunteers. Pain. 2014 Sep;155(9):1829-35. doi: 10.1016/j.pain.2014.06.011. Epub 2014 Jun 19. PubMed PMID: 24954166.

2: Violin JD, Crombie AL, Soergel DG, Lark MW. Biased ligands at G-protein-coupled receptors: promise and progress. Trends Pharmacol Sci. 2014 Jul;35(7):308-16. doi: 10.1016/j.tips.2014.04.007. Epub 2014 May 28. Review. PubMed PMID: 24878326.

3: Soergel DG, Subach RA, Sadler B, Connell J, Marion AS, Cowan CL, Violin JD, Lark MW. First clinical experience with TRV130: pharmacokinetics and pharmacodynamics in healthy volunteers. J Clin Pharmacol. 2014 Mar;54(3):351-7. doi: 10.1002/jcph.207. Epub 2014 Jan 28. PubMed PMID: 24122908.

4: Chen XT, Pitis P, Liu G, Yuan C, Gotchev D, Cowan CL, Rominger DH, Koblish M, Dewire SM, Crombie AL, Violin JD, Yamashita DS. Structure-activity relationships and discovery of a G protein biased μ opioid receptor ligand, [(3-methoxythiophen-2-yl)methyl]({2-[(9R)-9-(pyridin-2-yl)-6-oxaspiro-[4.5]decan- 9-yl]ethyl})amine (TRV130), for the treatment of acute severe pain. J Med Chem. 2013 Oct 24;56(20):8019-31. doi: 10.1021/jm4010829. Epub 2013 Oct 14. PubMed PMID: 24063433.

5: DeWire SM, Yamashita DS, Rominger DH, Liu G, Cowan CL, Graczyk TM, Chen XT, Pitis PM, Gotchev D, Yuan C, Koblish M, Lark MW, Violin JD. A G protein-biased ligand at the μ-opioid receptor is potently analgesic with reduced gastrointestinal and respiratory dysfunction compared with morphine. J Pharmacol Exp Ther. 2013 Mar;344(3):708-17. doi: 10.1124/jpet.112.201616. Epub 2013 Jan 8. PubMed PMID: 23300227.



Additional Information

TRV130 is an opioid drug that is under evaluation in human clinical trials for the treatment of acute severe pain. It is a functionally selective μ-opioid receptor agonist developed by Trevena Inc. TRV130 elicits robust G protein signaling, with potency and efficacy similar to morphine, but with far less β-arrestin 2 recruitment and receptor internalization, it displays less adverse effects than morphine. (https://en.wikipedia.org/wiki/TRV130).