MedKoo Biosciences

OMDM-2
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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.

Chemical Structure

OMDM-2

CAS# 616884-63-0

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 574781
Name: OMDM-2
CAS#: 616884-63-0
Chemical Formula: C26H43NO3
Exact Mass: 417.32
Molecular Weight: 417.634
Elemental Analysis: C, 74.78; H, 10.38; N, 3.35; O, 11.49

Price and Availability

Size	Price	Availability
1mg	USD 195	2 Weeks
5mg	USD 355	2 Weeks
10mg	USD 565	2 Weeks
50mg	USD 1095	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

More Info:

Product Data:

Product Data

Instruction:

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	30.0	71.83
	DMSO:PBS (pH 7.2) (1:1)	0.5	1.20
	Ethanol	30.0	71.83

Preparing Stock Solutions

The following data is based on the product molecular weight 417.63 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.

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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).

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