Oleoyl-D-lysine sodium
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MedKoo CAT#: 574134

CAS#: NONE

Description: Oleoyl-D-lysine sodium is an inhibitor of glycine transporter 2a (GlyT2a). It selectively inhibits GlyT2a over GlyT1b and reduces allodynia in a nerve ligation rat model of neuropathic pain.

Chemical Structure

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Oleoyl-D-lysine sodium
CAS# NONE
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 574134
Name: Oleoyl-D-lysine sodium
CAS#: NONE
Chemical Formula: C24H45N2NaO3
Exact Mass: 432.33
Molecular Weight: 432.625
Elemental Analysis: C, 66.63; H, 10.48; N, 6.48; Na, 5.31; O, 11.09

Price and Availability

Size Price Availability Quantity
1mg USD 210
5mg USD 425
10mg USD 685
25mg USD 1200
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Synonym: Oleoyl-D-lysine sodium

IUPAC/Chemical Name: N2-[(9Z)-1-oxo-9-octadecen-1-yl]-D-lysine, monosodium salt

InChi Key: OWBHGNNUDAIRSI-KVVVOXFISA-N

InChi Code: InChI=1S/C24H46N2O3.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20-23(27)26-22(24(28)29)19-17-18-21-25;/h9-10,22H,2-8,11-21,25H2,1H3,(H,26,27)(H,28,29);/b10-9-;

SMILES Code: O=C(N[C@H](CCCCN)C(O)=O)CCCCCCC/C=C\CCCCCCCC.[Na]

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: Oleoyl-D-lysine sodium is an inhibitor of glycine transporter 2a (GlyT2a).
In vitro activity: For 33 (oleoyl-D-lysine), GlyT2 was potently inhibited (IC50 48.3 nM), while little inhibition of GlyT1 was seen at maximal concentrations (3 μM). This study also tested 33 at Nav, Cav channels, and α7 nicotinic acetylcholine receptors (Table 3S) which are known pain target to rule out analgesia through this mechanism, and no significant inhibition was observed. The cannabinoid receptors, CB1 and CB2, as well as the sphingosine-1-phosphate receptor are targeted by similar lipid based ligands, such as anandamide, and so these receptors were also screened for 33 activity (Table 4S), but no activity as either an agonist or antagonist was observed for all three receptors. Reference: J Med Chem. 2019 Mar 14;62(5):2466-2484. https://pubmed.ncbi.nlm.nih.gov/30714733/
In vivo activity: Here, intraperitoneally administered oleoyl-D-lysine, a lipid-based GlyT2 inhibitor, was characterized in mouse models of acute (hot plate), inflammatory (complete Freund's adjuvant), and chronic neuropathic (chronic constriction injury) pain. Oleoyl-D-lysine produced near complete antiallodynia for chronic neuropathic pain, but no antiallodynia/analgesia in inflammatory or acute pain. Oleoyl-D-lysine (30 mg/kg) did not cause any respiratory depression, a problematic side effect of opiates. These results show the safe and effective reversal of neuropathic pain in mice by oleoyl-D-lysine and provide evidence for a distinct role of glycine in chronic pain over acute or short-term pain conditions. Reference: J Pharmacol Exp Ther. 2022 Sep;382(3):246-255. https://pubmed.ncbi.nlm.nih.gov/35779948/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 10.0 23.11
DMSO 30.0 69.34
Ethanol 50.0 115.57
PBS (pH 7.2) 0.3 0.58

Preparing Stock Solutions

The following data is based on the product molecular weight 432.62 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
Formulation protocol: 1. Mostyn SN, Rawling T, Mohammadi S, Shimmon S, Frangos ZJ, Sarker S, Yousuf A, Vetter I, Ryan RM, Christie MJ, Vandenberg RJ. Development of an N-Acyl Amino Acid That Selectively Inhibits the Glycine Transporter 2 To Produce Analgesia in a Rat Model of Chronic Pain. J Med Chem. 2019 Mar 14;62(5):2466-2484. doi: 10.1021/acs.jmedchem.8b01775. Epub 2019 Feb 20. PMID: 30714733; PMCID: PMC6420064. 2. Wilson BS, Peiser-Oliver J, Gillis A, Evans S, Alamein C, Mostyn SN, Shimmon S, Rawling T, Christie MJ, Vandenberg RJ, Mohammadi SA. Peripheral Administration of Selective Glycine Transporter-2 Inhibitor, Oleoyl-D-Lysine, Reverses Chronic Neuropathic Pain but Not Acute or Inflammatory Pain in Male Mice. J Pharmacol Exp Ther. 2022 Sep;382(3):246-255. doi: 10.1124/jpet.122.001265. Epub 2022 Jul 2. PMID: 35779948.
In vitro protocol: 1. Mostyn SN, Rawling T, Mohammadi S, Shimmon S, Frangos ZJ, Sarker S, Yousuf A, Vetter I, Ryan RM, Christie MJ, Vandenberg RJ. Development of an N-Acyl Amino Acid That Selectively Inhibits the Glycine Transporter 2 To Produce Analgesia in a Rat Model of Chronic Pain. J Med Chem. 2019 Mar 14;62(5):2466-2484. doi: 10.1021/acs.jmedchem.8b01775. Epub 2019 Feb 20. PMID: 30714733; PMCID: PMC6420064.
In vivo protocol: 1. Wilson BS, Peiser-Oliver J, Gillis A, Evans S, Alamein C, Mostyn SN, Shimmon S, Rawling T, Christie MJ, Vandenberg RJ, Mohammadi SA. Peripheral Administration of Selective Glycine Transporter-2 Inhibitor, Oleoyl-D-Lysine, Reverses Chronic Neuropathic Pain but Not Acute or Inflammatory Pain in Male Mice. J Pharmacol Exp Ther. 2022 Sep;382(3):246-255. doi: 10.1124/jpet.122.001265. Epub 2022 Jul 2. PMID: 35779948.

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1. Mostyn, S.N., Rawling, T., Mohammadi, S., et al. Development of an N-acyl amino acid that selectively inhibits the glycine transporter 2 to produce analgesia in a rat model of chronic pain. J. Med. Chem. 62(5), 2466-2484 (2019).