OMDM-2 | CAS# 616884-63-0 | AEA inhibitor

MedKoo Cat#: 574781 | Name: OMDM-2

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Description:

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

OMDM-2 is an endocannabinoid analog specifically designed to be a potent and selective inhibitor of the cellular uptake of AEA. OMDM-2 inhibits CGRP release evoked by EC80 concentrations of AEA, NADA and CAP and these values are consistent with IC50s obtained for inhibition of uptake.

Chemical Structure

OMDM-2

CAS#616884-63-0

Theoretical Analysis

MedKoo Cat#: 574781

Name: OMDM-2

CAS#: 616884-63-0

Chemical Formula: C26H43NO3

Exact Mass: 417.3243

Molecular Weight: 417.63

Elemental Analysis: C, 74.78; H, 10.38; N, 3.35; O, 11.49

Price and Availability

Size	Price	Availability
1mg	USD 195.00	2 Weeks
5mg	USD 355.00	2 Weeks
10mg	USD 565.00	2 Weeks
50mg	USD 1,095.00	2 Weeks

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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

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Product Data

Product Data

Instruction

View handling instruction

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

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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:

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: 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: Hajdu Z, Nicolussi S, Rau M, Lorántfy L, Forgo P, Hohmann J, Csupor D, Gertsch J. Identification of endocannabinoid system-modulating N-alkylamides from Heliopsis helianthoides var. scabra and Lepidium meyenii. J Nat Prod. 2014 Jul 25;77(7):1663-9. doi: 10.1021/np500292g. Epub 2014 Jun 27. PMID: 24972328. 3: Nicolussi S, Viveros-Paredes JM, Gachet MS, Rau M, Flores-Soto ME, Blunder M, Gertsch J. Guineensine is a novel inhibitor of endocannabinoid uptake showing cannabimimetic behavioral effects in BALB/c mice. Pharmacol Res. 2014 Feb;80:52-65. doi: 10.1016/j.phrs.2013.12.010. Epub 2014 Jan 8. PMID: 24412246. 4: Murillo-Rodríguez E, Palomero-Rivero M, Millán-Aldaco D, Di Marzo V. The administration of endocannabinoid uptake inhibitors OMDM-2 or VDM-11 promotes sleep and decreases extracellular levels of dopamine in rats. Physiol Behav. 2013 Jan 17;109:88-95. doi: 10.1016/j.physbeh.2012.11.007. Epub 2012 Dec 11. PMID: 23238438. 5: Chicca A, Marazzi J, Nicolussi S, Gertsch J. Evidence for bidirectional endocannabinoid transport across cell membranes. J Biol Chem. 2012 Oct 5;287(41):34660-82. doi: 10.1074/jbc.M112.373241. Epub 2012 Aug 9. PMID: 22879589; PMCID: PMC3464571. 6: Lewis DY, Brett RR. Activity-based anorexia in C57/BL6 mice: effects of the phytocannabinoid, Delta9-tetrahydrocannabinol (THC) and the anandamide analogue, OMDM-2. Eur Neuropsychopharmacol. 2010 Sep;20(9):622-31. doi: 10.1016/j.euroneuro.2010.04.002. Epub 2010 May 14. PMID: 20471226. 7: López-Gallardo M, Llorente R, Llorente-Berzal A, Marco EM, Prada C, Di Marzo V, Viveros MP. Neuronal and glial alterations in the cerebellar cortex of maternally deprived rats: gender differences and modulatory effects of two inhibitors of endocannabinoid inactivation. Dev Neurobiol. 2008 Oct;68(12):1429-40. doi: 10.1002/dneu.20672. PMID: 18726913. 8: Llorente R, Llorente-Berzal A, Petrosino S, Marco EM, Guaza C, Prada C, López-Gallardo M, Di Marzo V, Viveros MP. Gender-dependent cellular and biochemical effects of maternal deprivation on the hippocampus of neonatal rats: a possible role for the endocannabinoid system. Dev Neurobiol. 2008 Sep 15;68(11):1334-47. doi: 10.1002/dneu.20666. PMID: 18666205. 9: Di Marzo V, Capasso R, Matias I, Aviello G, Petrosino S, Borrelli F, Romano B, Orlando P, Capasso F, Izzo AA. The role of endocannabinoids in the regulation of gastric emptying: alterations in mice fed a high-fat diet. Br J Pharmacol. 2008 Mar;153(6):1272-80. doi: 10.1038/sj.bjp.0707682. Epub 2008 Jan 28. PMID: 18223666; PMCID: PMC2275439. 10: Hillard CJ, Shi L, Tuniki VR, Falck JR, Campbell WB. Studies of anandamide accumulation inhibitors in cerebellar granule neurons: comparison to inhibition of fatty acid amide hydrolase. J Mol Neurosci. 2007 Sep;33(1):18-24. doi: 10.1007/s12031-007-0045-0. PMID: 17901541; PMCID: PMC2248273. 11: Vlachou S, Nomikos GG, Panagis G. Effects of endocannabinoid neurotransmission modulators on brain stimulation reward. Psychopharmacology (Berl). 2006 Oct;188(3):293-305. doi: 10.1007/s00213-006-0506-0. Epub 2006 Sep 5. PMID: 16953388. 12: De Lago E, Gustafsson SB, Fernández-Ruiz J, Nilsson J, Jacobsson SO, Fowler CJ. Acyl-based anandamide uptake inhibitors cause rapid toxicity to C6 glioma cells at pharmacologically relevant concentrations. J Neurochem. 2006 Oct;99(2):677-88. doi: 10.1111/j.1471-4159.2006.04104.x. Epub 2006 Aug 8. PMID: 16899063. 13: Lee J, Di Marzo V, Brotchie JM. A role for vanilloid receptor 1 (TRPV1) and endocannabinnoid signalling in the regulation of spontaneous and L-DOPA induced locomotion in normal and reserpine-treated rats. Neuropharmacology. 2006 Sep;51(3):557-65. doi: 10.1016/j.neuropharm.2006.04.016. Epub 2006 Jun 30. PMID: 16806299. 14: Schiano Moriello A, Balas L, Ligresti A, Cascio MG, Durand T, Morera E, Ortar G, Di Marzo V. Development of the first potential covalent inhibitors of anandamide cellular uptake. J Med Chem. 2006 Apr 6;49(7):2320-32. doi: 10.1021/jm051226l. PMID: 16570928. 15: Di S, Boudaba C, Popescu IR, Weng FJ, Harris C, Marcheselli VL, Bazan NG, Tasker JG. Activity-dependent release and actions of endocannabinoids in the rat hypothalamic supraoptic nucleus. J Physiol. 2005 Dec 15;569(Pt 3):751-60. doi: 10.1113/jphysiol.2005.097477. Epub 2005 Oct 20. PMID: 16239276; PMCID: PMC1464259. 16: 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. 17: Glaser ST, Kaczocha M, Deutsch DG. Anandamide transport: a critical review. Life Sci. 2005 Aug 19;77(14):1584-604. doi: 10.1016/j.lfs.2005.05.007. PMID: 15979096. 18: de Lago E, Petrosino S, Valenti M, Morera E, Ortega-Gutierrez S, Fernandez- Ruiz J, Di Marzo V. Effect of repeated systemic administration of selective inhibitors of endocannabinoid inactivation on rat brain endocannabinoid levels. Biochem Pharmacol. 2005 Aug 1;70(3):446-52. doi: 10.1016/j.bcp.2005.05.011. PMID: 15963472. 19: Mestre L, Correa F, Arévalo-Martín A, Molina-Holgado E, Valenti M, Ortar G, Di Marzo V, Guaza C. Pharmacological modulation of the endocannabinoid system in a viral model of multiple sclerosis. J Neurochem. 2005 Mar;92(6):1327-39. doi: 10.1111/j.1471-4159.2004.02979.x. PMID: 15748152. 20: Bátkai S, Pacher P, Osei-Hyiaman D, Radaeva S, Liu J, Harvey-White J, Offertáler L, Mackie K, Rudd MA, Bukoski RD, Kunos G. Endocannabinoids acting at cannabinoid-1 receptors regulate cardiovascular function in hypertension. Circulation. 2004 Oct 5;110(14):1996-2002. doi: 10.1161/01.CIR.0000143230.23252.D2. Epub 2004 Sep 27. PMID: 15451779; PMCID: PMC2756479.