Oxymorphindole

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

MedKoo CAT#: 466029

CAS#: 111469-88-6

Description: Oxymorphindole is a δ-Opioid receptor agonist.


Chemical Structure

img
Oxymorphindole
CAS# 111469-88-6

Theoretical Analysis

MedKoo Cat#: 466029
Name: Oxymorphindole
CAS#: 111469-88-6
Chemical Formula: C23H22N2O3
Exact Mass: 374.163
Molecular Weight: 374.44
Elemental Analysis: C, 73.78; H, 5.92; N, 7.48; O, 12.82

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Oxymorphindole; OMI;

IUPAC/Chemical Name: (4bS,8R,8aS,14bR)-7-methyl-5,6,7,8,14,14b-hexahydro-4,8-methanobenzofuro[2,3-a]pyrido[4,3-b]carbazole-1,8a(9H)-diol

InChi Key: YQNZUKAKYJMEFE-LMDOGRNLSA-N

InChi Code: InChI=1S/C23H22N2O3/c1-25-9-8-22-18-12-6-7-16(26)20(18)28-21(22)19-14(11-23(22,27)17(25)10-12)13-4-2-3-5-15(13)24-19/h2-7,17,21,24,26-27H,8-11H2,1H3/t17-,21+,22+,23-/m1/s1

SMILES Code: O[C@@]1(CC2=C([C@]3([H])O4)NC5=CC=CC=C25)[C@@]63CCN(C)[C@]1([H])CC7=C6C4=C(O)C=C7

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

Preparing Stock Solutions

The following data is based on the product molecular weight 374.44 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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Griffith JI, Kim M, Bruce DJ, Peterson CD, Kitto KF, Mohammad AS, Rathi S, Fairbanks CA, Wilcox GL, Elmquist WF. Central Nervous System Distribution of an Opioid Agonist Combination with Synergistic Activity. J Pharmacol Exp Ther. 2022 Jan;380(1):34-46. doi: 10.1124/jpet.121.000821. Epub 2021 Oct 18. PMID: 34663676.

2: Uhelski ML, Bruce D, Speltz R, Wilcox GL, Simone DA. Topical Application of Loperamide/Oxymorphindole, Mu and Delta Opioid Receptor Agonists, Reduces Sensitization of C-fiber Nociceptors that Possess NaV1.8. Neuroscience. 2020 Oct 15;446:102-112. doi: 10.1016/j.neuroscience.2020.08.022. Epub 2020 Aug 25. PMID: 32858141; PMCID: PMC7532699.

3: Bruce DJ, Peterson CD, Kitto KF, Akgün E, Lazzaroni S, Portoghese PS, Fairbanks CA, Wilcox GL. Combination of a δ-opioid Receptor Agonist and Loperamide Produces Peripherally-mediated Analgesic Synergy in Mice. Anesthesiology. 2019 Sep;131(3):649-663. doi: 10.1097/ALN.0000000000002840. PMID: 31343460; PMCID: PMC6693899.

4: Schuster DJ, Metcalf MD, Kitto KF, Messing RO, Fairbanks CA, Wilcox GL. Ligand requirements for involvement of PKCε in synergistic analgesic interactions between spinal μ and δ opioid receptors. Br J Pharmacol. 2015 Jan;172(2):642-53. doi: 10.1111/bph.12774. Epub 2014 Nov 24. PMID: 24827408; PMCID: PMC4292975.

5: 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.

6: Jutkiewicz EM, Baladi MG, Folk JE, Rice KC, Woods JH. The delta-opioid receptor agonist SNC80 [(+)-4-[alpha(R)-alpha-[(2S,5R)-4-allyl-2,5-dimethyl-1-pi perazinyl]-(3-methoxybenzyl)-N,N-diethylbenzamide] synergistically enhances the locomotor-activating effects of some psychomotor stimulants, but not direct dopamine agonists, in rats. J Pharmacol Exp Ther. 2008 Feb;324(2):714-24. doi: 10.1124/jpet.107.123844. Epub 2007 Nov 6. PMID: 17986650.

7: Metcalf MD, Coop A. 5'-halogenated analogs of oxymorphindole. Bioorg Med Chem Lett. 2007 Nov 1;17(21):5916-7. doi: 10.1016/j.bmcl.2007.07.098. Epub 2007 Aug 23. PMID: 17826993; PMCID: PMC2062523.

8: Wu HE, Sun HS, Darpolar M, Dunn W 3rd, Tseng LF. Antinociceptive properties of oxymorphazole in the mouse. Eur J Pharmacol. 2003 Jul 25;473(2-3):143-8. doi: 10.1016/s0014-2999(03)01912-5. PMID: 12892831.

9: Grundt P, Jales AR, Traynor JR, Lewis JW, Husbands SM. 14-amino, 14-alkylamino, and 14-acylamino analogs of oxymorphindole. Differential effects on opioid receptor binding and functional profiles. J Med Chem. 2003 Apr 10;46(8):1563-6. doi: 10.1021/jm021073r. PMID: 12672258.

10: Hosohata Y, Varga EV, Stropova D, Li X, Knapp RJ, Hruby VJ, Rice KC, Nagase H, Roeske WR, Yamamura HI. Mutation W284L of the human delta opioid receptor reveals agonist specific receptor conformations for G protein activation. Life Sci. 2001 Apr 6;68(19-20):2233-42. doi: 10.1016/s0024-3205(01)01011-6. PMID: 11358332.

11: Shenderovich MD, Liao S, Qian X, Hruby VJ. A three-dimensional model of the delta-opioid pharmacophore: comparative molecular modeling of peptide and nonpeptide ligands. Biopolymers. 2000 Jun;53(7):565-80. doi: 10.1002/(SICI)1097-0282(200006)53:7<565::AID-BIP4>3.0.CO;2-5. PMID: 10766952.

12: Coop A, Jacobson AE. The LMC delta opioid recognition pharmacophore: comparison of SNC80 and oxymorphindole. Bioorg Med Chem Lett. 1999 Feb 8;9(3):357-62. doi: 10.1016/s0960-894x(98)00745-8. PMID: 10091684.

13: Clark MJ, Emmerson PJ, Mansour A, Akil H, Woods JH, Portoghese PS, Remmers AE, Medzihradsky F. Opioid efficacy in a C6 glioma cell line stably expressing the delta opioid receptor. J Pharmacol Exp Ther. 1997 Nov;283(2):501-10. PMID: 9353363.

14: Lomize AL, Pogozheva ID, Mosberg HI. Development of a model for the delta- opioid receptor pharmacophore: 3. Comparison of the cyclic tetrapeptide, Tyr-c[D-Cys-Phe-D-Pen]OH with other conformationally constrained delta-receptor selective ligands. Biopolymers. 1996 Feb;38(2):221-34. doi: 10.1002/(SICI)1097-0282(199602)38:2%3C221::AID-BIP8%3E3.0.CO;2-X. PMID: 8589255.

15: Lai J, Ma SW, Zhu RH, Rothman RB, Lentes KU, Porreca F. Pharmacological characterization of the cloned kappa opioid receptor as a kappa 1b subtype. Neuroreport. 1994 Oct 27;5(16):2161-4. doi: 10.1097/00001756-199410270-00043. PMID: 7865767.

16: Xu H, Partilla JS, de Costa BR, Rice KC, Rothman RB. Interaction of opioid peptides and other drugs with multiple delta ncx binding sites in rat brain: further evidence for heterogeneity. Peptides. 1992 Nov-Dec;13(6):1207-13. doi: 10.1016/0196-9781(92)90030-7. PMID: 1337380.

17: Carr DJ, Radulescu RT, DeCosta BR, Rice KC, Blalock JE. Opioid modulation of immunoglobulin production by lymphocytes isolated from Peyer's patches and spleen. Ann N Y Acad Sci. 1992 Apr 15;650:125-7. doi: 10.1111/j.1749-6632.1992.tb49108.x. PMID: 1605469.

18: Takemori AE, Sultana M, Nagase H, Portoghese PS. Agonist and antagonist activities of ligands derived from naltrexone and oxymorphone. Life Sci. 1992;50(20):1491-5. doi: 10.1016/0024-3205(92)90138-f. PMID: 1315896.

19: Remmers AE, Medzihradsky F. Resolution of biphasic binding of the opioid antagonist naltrexone in brain membranes. J Neurochem. 1991 Oct;57(4):1265-9. doi: 10.1111/j.1471-4159.1991.tb08288.x. PMID: 1654389.

20: Jiang Q, Rice KC, deCosta B, Porreca F. Effects of oxymorphindole on morphine induced-antinociception in mice and rats. NIDA Res Monogr. 1990;105:384-5. PMID: 1652080.