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MedKoo Cat#: 531268 | Name: PRE-084 HCl
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Description:

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

PRE 084 is a high affinity selective sigma 1 agonist.

Chemical Structure

PRE-084 HCl
CAS#75136-54-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 531268

Name: PRE-084 HCl

CAS#: 75136-54-8 (HCl)

Chemical Formula: C19H28ClNO3

Exact Mass: 0.0000

Molecular Weight: 353.89

Elemental Analysis: C, 64.49; H, 7.98; Cl, 10.02; N, 3.96; O, 13.56

Price and Availability

Size Price Availability Quantity
10mg USD 110.00 Ready to ship
25mg USD 235.00 Ready to ship
50mg USD 385.00 Ready to ship
100mg USD 650.00 Ready to ship
200mg USD 1,150.00 Ready to ship
500mg USD 2,450.00 Ready to ship
1g USD 3,950.00 Ready to ship
2g USD 6,650.00 Ready to ship
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Related CAS #
75136-54-8 (HCl) 138847-85-5 (free base)
Synonym
PRE 084; PRE-084; PRE084. PRE-084 HCl; PRE-084 hydrochloride
IUPAC/Chemical Name
Cyclohexanecarboxylic acid, 1-phenyl-, 2-(4-morpholinyl)ethyl ester hydrochloride
InChi Key
QUJWFJNHTBKCLU-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H27NO3.ClH/c21-18(23-16-13-20-11-14-22-15-12-20)19(9-5-2-6-10-19)17-7-3-1-4-8-17;/h1,3-4,7-8H,2,5-6,9-16H2;1H
SMILES Code
O=C(C1(C2=CC=CC=C2)CCCCC1)OCCN3CCOCC3.[H]Cl
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
>2 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
Biological target:
PRE-084 is a high affinity sigma receptor 1 (σ1) agonist.
In vitro activity:
The aim of this study was to assess the selective sigma-1 receptor agonist 2-(4-morpholinethyl)1-phenylcyclohexanecarboxylate (PRE-084) in models of inflammation-sensitized hyperoxia-induced developing brain injury. For in vitro studies, oligodendroglial cells were subjected to hyperoxic conditions in the presence or absence of proinflammatory cytokines and PRE-084. Cell membrane integrity and cell viability were assessed by means of lactate dehydrogenase and 2,3-bis-(2-methoxy-4-nitro-5-sulfophenyl)-2H-tetrazolium-5-carboxanilide (XTT) assays. Inflammatory presensitization significantly increased hyperoxia-induced injury both in vivo and in vitro. PRE-084 administration did not attenuate damage. Sigma-1 receptor agonists have been described as a promising therapeutic strategy for brain injury. We were not able to confirm this in the present model. The exact mechanisms of action of sigma-1 receptor agonists as well as the pathophysiologic pathways involved in hyperoxia-induced injury in the developing brain remain to be elucidated. Reference: Posod A, Krepp Y, Urbanek M, Stock K, Kiechl-Kohlendorfer U, Griesmaier E. In vivo and in vitro evaluation of the effect of 2-(4-morpholinethyl)1-phenylcyclohexanecarboxylate on inflammation-sensitized hyperoxia-induced developing brain injury. J Neurosci Res. 2013 Nov;91(11):1463-72. doi: 10.1002/jnr.23271. Epub 2013 Aug 23. PMID: 24038156.
In vivo activity:
In this study, rats were assigned randomly to three groups with computer (n = 14 for each group): a sham group, an I/R group, and a PRE-084 group. In the PRE-084 group, rats were administered PRE-084 1 h before operation. In the myocardial I/R model, the left anterior descending branch of rats was ligated and opened half an hour later. Cardiac function was assessed, and the apoptosis index was evaluated. The mechanisms of the cardioprotective effects of PRE-084 were explored. PRE-084 pretreatment preserved cardiac function and reduced myocardial apoptosis (F = 86.0, P < 0.01) with Western blotting analysis, showing significantly reduced expression of Bax (F = 75.7, P < 0.01) and cleaved-caspase 3 (F = 44.7, P < 0.01), along with increased expression of the Bcl-2 protein (P < 0.01) and phosphorylated protein kinase B (p-Akt) (P < 0.01) and phosphorylated-endothelial nitric oxide synthase (p-eNOS; P < 0.01). Reference: Gao QJ, Yang B, Chen J, Shi SB, Yang HJ, Liu X. Sigma-1 Receptor Stimulation with PRE-084 Ameliorates Myocardial Ischemia-Reperfusion Injury in Rats. Chin Med J (Engl). 2018 Mar 5;131(5):539-543. doi: 10.4103/0366-6999.226076. PMID: 29483387; PMCID: PMC5850669.
Solvent mg/mL mM comments
Solubility
DMSO 50.0 141.28
Ethanol 15.0 42.39
Water 15.0 42.39
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 353.89 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:
Posod A, Krepp Y, Urbanek M, Stock K, Kiechl-Kohlendorfer U, Griesmaier E. In vivo and in vitro evaluation of the effect of 2-(4-morpholinethyl)1-phenylcyclohexanecarboxylate on inflammation-sensitized hyperoxia-induced developing brain injury. J Neurosci Res. 2013 Nov;91(11):1463-72. doi: 10.1002/jnr.23271. Epub 2013 Aug 23. PMID: 24038156.
In vitro protocol:
Posod A, Krepp Y, Urbanek M, Stock K, Kiechl-Kohlendorfer U, Griesmaier E. In vivo and in vitro evaluation of the effect of 2-(4-morpholinethyl)1-phenylcyclohexanecarboxylate on inflammation-sensitized hyperoxia-induced developing brain injury. J Neurosci Res. 2013 Nov;91(11):1463-72. doi: 10.1002/jnr.23271. Epub 2013 Aug 23. PMID: 24038156.
In vivo protocol:
Gao QJ, Yang B, Chen J, Shi SB, Yang HJ, Liu X. Sigma-1 Receptor Stimulation with PRE-084 Ameliorates Myocardial Ischemia-Reperfusion Injury in Rats. Chin Med J (Engl). 2018 Mar 5;131(5):539-543. doi: 10.4103/0366-6999.226076. PMID: 29483387; PMCID: PMC5850669.
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Antinociceptive effect of LMH-2, a new sigma-1 receptor antagonist analog of haloperidol, on the neuropathic pain of diabetic mice. Biomed Pharmacother. 2024 May;174:116524. doi: 10.1016/j.biopha.2024.116524. Epub 2024 Apr 3. PMID: 38574622. 5: Nakahara H, Hiranita T, Shibata O. A Sigma1 Receptor Agonist Alters Fluidity and Stability of Lipid Monolayers. Langmuir. 2024 Mar 26;40(12):6484-6492. doi: 10.1021/acs.langmuir.4c00053. Epub 2024 Mar 12. PMID: 38470245. 6: Izumi Y, Reiersen AM, Lenze EJ, Mennerick SJ, Zorumski CF. Sertraline modulates hippocampal plasticity and learning via sigma 1 receptors, cellular stress and neurosteroids. bioRxiv [Preprint]. 2024 Jan 24:2024.01.23.576911. doi: 10.1101/2024.01.23.576911. PMID: 38328198; PMCID: PMC10849579. 7: Mahamed Z, Shadab M, Najar RA, Millar MW, Bal J, Pressley T, Fazal F. The Protective Role of Mitochondria-Associated Endoplasmic Reticulum Membrane (MAM) Protein Sigma-1 Receptor in Regulating Endothelial Inflammation and Permeability Associated with Acute Lung Injury. Cells. 2023 Dec 19;13(1):5. doi: 10.3390/cells13010005. PMID: 38201208; PMCID: PMC10778450. 8: Crouzier L, Meunier J, Carles A, Morilleau A, Vrigneau C, Schmitt M, Bourguignon JJ, Delprat B, Maurice T. Convolamine, a tropane alkaloid extracted from Convolvulus plauricalis, is a potent sigma-1 receptor-positive modulator with cognitive and neuroprotective properties. Phytother Res. 2024 Feb;38(2):694-712. doi: 10.1002/ptr.8068. Epub 2023 Nov 27. PMID: 38011416. 9: Mogilski S, Kubacka M, Świerczek A, Wyska E, Szczepańska K, Sapa J, Kieć- Kononowicz K, Łażewska D. Efficacy of the Multi-Target Compound E153 in Relieving Pain and Pruritus of Different Origins. Pharmaceuticals (Basel). 2023 Oct 17;16(10):1481. doi: 10.3390/ph16101481. 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