WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 574781
CAS#: 616884-63-0
Description: OMDM-2 is an endocannabinoid analog specifically designed to be a potent and selective inhibitor of the cellular uptake of AEA.
MedKoo Cat#: 574781
Name: OMDM-2
CAS#: 616884-63-0
Chemical Formula: C26H43NO3
Exact Mass: 417.3243
Molecular Weight: 417.634
Elemental Analysis: C, 74.78; H, 10.38; N, 3.35; O, 11.49
Synonym: (R)-N-oleoyl Tyrosinol; OMDM-2
IUPAC/Chemical Name: (R)-N-(1-(4-hydroxyphenyl)-2-hydroxyethyl)oleamide
InChi Key: ICDMLAQPOAVWNH-HAAQQRBASA-N
InChi Code: InChI=1S/C27H45NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-27(31)28-25(23-29)22-24-18-20-26(30)21-19-24/h9-10,18-21,25,29-30H,2-8,11-17,22-23H2,1H3,(H,28,31)/b10-9-/t25-/m1/s1
SMILES Code: CCCCCCCC/C=C\CCCCCCCC(N[C@H](C1=CC=C(O)C=C1)CO)=O
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
| Biological target: | OMDM-2 is a potent, selective and metabolically stable inhibitor of anandamide cellular uptake (ACU), with a Ki of 3.0 μM. |
| In vitro activity: | Application of the AMT inhibitors OMDM-2 or VDM-11 significantly reduced the potency and efficacy of AEA-, NADA- and capsaicin-evoked CGRP release. Moreover OMDM-2 (IC50 values ranging from 6.4-9.6 microM) and VDM-11 (IC50 values ranging from 5.3-11 microM) inhibited CGRP release evoked by EC80 concentrations of AEA, NADA and CAP and these values were consistent with IC50s obtained for inhibition of uptake. Reference: Neuropharmacology. 2005 Jul;49(1):25-39. https://pubmed.ncbi.nlm.nih.gov/15992578/ |
| In vivo activity: | OMDM-2 and, to a lesser extent, VDM-11 (5 mg/kg, i.p.) enhanced the motor-inhibitory effects of a noneffective dose (2 mg/kg, i.p.) of anandamide, while OMDM-1 did not. In a typical test of acute analgesia, OMDM-2 and VDM-11 (1-10 mg/kg, i.p.), but not OMDM-1, significantly enhanced the time spent by rats on a "hot plate." Thus, this study determined if, like other previously developed anandamide reuptake inhibitors, OMDM-1 and OMDM-2 inhibit spasticity in an animal model of multiple sclerosis-the chronic relapsing experimental allergic encephalomyelitis in mice. As previously shown with a higher dose of VDM-11, both novel compounds (5 mg/kg, i.v.) significantly reduced spasticity of the hindlimb in mice with chronic relapsing experimental allergic encephalomyelitis. Reference: Eur J Pharmacol. 2004 Jan 26;484(2-3):249-57. https://pubmed.ncbi.nlm.nih.gov/14744610/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMF | 30.0 | 71.83 | |
| DMSO:PBS (pH 7.2) (1:1) | 0.5 | 1.2 | |
| Ethanol | 30.0 | 71.83 |
The following data is based on the product molecular weight 417.634 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. Price TJ, Patwardhan AM, Flores CM, Hargreaves KM. A role for the anandamide membrane transporter in TRPV1-mediated neurosecretion from trigeminal sensory neurons. Neuropharmacology. 2005 Jul;49(1):25-39. doi: 10.1016/j.neuropharm.2005.01.031. Epub 2005 Apr 1. PMID: 15992578; PMCID: PMC1892309. 2. Seillier A, Giuffrida A. The cannabinoid transporter inhibitor OMDM-2 reduces social interaction: Further evidence for transporter-mediated endocannabinoid release. Neuropharmacology. 2018 Mar 1;130:1-9. doi: 10.1016/j.neuropharm.2017.11.032. Epub 2017 Nov 21. PMID: 29169961. 3. de Lago E, Ligresti A, Ortar G, Morera E, Cabranes A, Pryce G, Bifulco M, Baker D, Fernandez-Ruiz J, Di Marzo V. In vivo pharmacological actions of two novel inhibitors of anandamide cellular uptake. Eur J Pharmacol. 2004 Jan 26;484(2-3):249-57. doi: 10.1016/j.ejphar.2003.11.027. PMID: 14744610. |
| In vitro protocol: | 1. Price TJ, Patwardhan AM, Flores CM, Hargreaves KM. A role for the anandamide membrane transporter in TRPV1-mediated neurosecretion from trigeminal sensory neurons. Neuropharmacology. 2005 Jul;49(1):25-39. doi: 10.1016/j.neuropharm.2005.01.031. Epub 2005 Apr 1. PMID: 15992578; PMCID: PMC1892309. |
| In vivo protocol: | 1. Seillier A, Giuffrida A. The cannabinoid transporter inhibitor OMDM-2 reduces social interaction: Further evidence for transporter-mediated endocannabinoid release. Neuropharmacology. 2018 Mar 1;130:1-9. doi: 10.1016/j.neuropharm.2017.11.032. Epub 2017 Nov 21. PMID: 29169961. 2. de Lago E, Ligresti A, Ortar G, Morera E, Cabranes A, Pryce G, Bifulco M, Baker D, Fernandez-Ruiz J, Di Marzo V. In vivo pharmacological actions of two novel inhibitors of anandamide cellular uptake. Eur J Pharmacol. 2004 Jan 26;484(2-3):249-57. doi: 10.1016/j.ejphar.2003.11.027. PMID: 14744610. |
1. Khanolkar, A.D., and Makriyannis, A. Structure-activity relationships of anandamide, an endogenous cannabinoid ligand. Life Sciences 65, 607-616 (1999).
2. Deutsch, D.G., Glaser, S.T., Howell, J.M., et al. The cellular uptake of anandamide is coupled to its breakdown by fatty-acid amide hydrolase. The Journal of Biological Chemisty 276(10), 6967-6973 (2001).
3. Ortar, G., Ligresti, A., De Petrocellis, L., et al. Novel selective and metabolically stable inhibitors of anandamide cellular uptake. Biochemical Pharmacology 65, 1473-1481 (2003).
