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MedKoo Cat#: 413387 | Name: Cutamesine
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Description:

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

Cutamesine is a synthetic sigma receptor agonist which is selective for the σ1 receptor, a chaperone protein mainly found in the endoplasmic reticulum of cells in the central nervous system. These σ1 receptors play a key role in the modulation of Ca²⁺ release and apoptosis.

Chemical Structure

Cutamesine
Cutamesine
CAS#165377-43-5 (free base)

Theoretical Analysis

MedKoo Cat#: 413387

Name: Cutamesine

CAS#: 165377-43-5 (free base)

Chemical Formula: C23H32N2O2

Exact Mass: 368.2464

Molecular Weight: 368.52

Elemental Analysis: C, 74.96; H, 8.75; N, 7.60; O, 8.68

Price and Availability

Size Price Availability Quantity
25mg USD 250.00 2 Weeks
50mg USD 425.00 2 Weeks
100mg USD 750.00 2 Weeks
250mg USD 1,250.00 2 Weeks
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Related CAS #
165377-44-6 (HCl) 165377-43-5 (free base)
Synonym
Cutamesine; UNII-9J7A4144BX
IUPAC/Chemical Name
1-(3,4-dimethoxyphenethyl)-4-(3-phenylpropyl)piperazine
InChi Key
UVSWWUWQVAQPJR-UHFFFAOYSA-N
InChi Code
InChI=1S/C23H32N2O2/c1-26-22-11-10-21(19-23(22)27-2)12-14-25-17-15-24(16-18-25)13-6-9-20-7-4-3-5-8-20/h3-5,7-8,10-11,19H,6,9,12-18H2,1-2H3
SMILES Code
COc1c(OC)cc(CCN2CCN(CC2)CCCc3ccccc3)cc1
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
Solvent mg/mL mM
Solubility
Soluble in DMSO 0.0 100.00
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 368.52 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
1: Ramakrishnan NK, Schepers M, Luurtsema G, Nyakas CJ, Elsinga PH, Ishiwata K, Dierckx RA, van Waarde A. Cutamesine Overcomes REM Sleep Deprivation-Induced Memory Loss: Relationship to Sigma-1 Receptor Occupancy. Mol Imaging Biol. 2015 Jun;17(3):364-72. doi: 10.1007/s11307-014-0808-2. PMID: 25449772. 2: Qin J, Wang P, Li Y, Yao L, Liu Y, Yu T, Lin J, Fang X, Huang Z. Activation of Sigma-1 Receptor by Cutamesine Attenuates Neuronal Apoptosis by Inhibiting Endoplasmic Reticulum Stress and Mitochondrial Dysfunction in a Rat Model of Asphyxia Cardiac Arrest. Shock. 2019 Jan;51(1):105-113. doi: 10.1097/SHK.0000000000001119. PMID: 29424796. 3: Yamashita D, Sun GW, Cui Y, Mita S, Otsuki N, Kanzaki S, Nibu K, Ogawa K, Matsunaga T. Neuroprotective effects of cutamesine, a ligand of the sigma-1 receptor chaperone, against noise-induced hearing loss. J Neurosci Res. 2015 May;93(5):788-95. doi: 10.1002/jnr.23543. Epub 2015 Jan 22. PMID: 25612541. 4: Shimazawa M, Sugitani S, Inoue Y, Tsuruma K, Hara H. Effect of a sigma-1 receptor agonist, cutamesine dihydrochloride (SA4503), on photoreceptor cell death against light-induced damage. Exp Eye Res. 2015 Mar;132:64-72. doi: 10.1016/j.exer.2015.01.017. Epub 2015 Jan 20. PMID: 25616094. 5: Maher CM, Thomas JD, Haas DA, Longen CG, Oyer HM, Tong JY, Kim FJ. Small- Molecule Sigma1 Modulator Induces Autophagic Degradation of PD-L1. Mol Cancer Res. 2018 Feb;16(2):243-255. doi: 10.1158/1541-7786.MCR-17-0166. Epub 2017 Nov 8. PMID: 29117944. 6: Urfer R, Moebius HJ, Skoloudik D, Santamarina E, Sato W, Mita S, Muir KW; Cutamesine Stroke Recovery Study Group. Phase II trial of the Sigma-1 receptor agonist cutamesine (SA4503) for recovery enhancement after acute ischemic stroke. Stroke. 2014 Nov;45(11):3304-10. doi: 10.1161/STROKEAHA.114.005835. Epub 2014 Sep 30. PMID: 25270629. 7: Hashimoto K. Repurposing of CNS drugs to treat COVID-19 infection: targeting the sigma-1 receptor. Eur Arch Psychiatry Clin Neurosci. 2021 Jan 5:1–10. doi: 10.1007/s00406-020-01231-x. Epub ahead of print. PMID: 33403480; PMCID: PMC7785036. 8: Niitsu T, Iyo M, Hashimoto K. Sigma-1 receptor agonists as therapeutic drugs for cognitive impairment in neuropsychiatric diseases. Curr Pharm Des. 2012;18(7):875-83. doi: 10.2174/138161212799436476. PMID: 22288409. 9: Fujimoto M, Hayashi T, Urfer R, Mita S, Su TP. Sigma-1 receptor chaperones regulate the secretion of brain-derived neurotrophic factor. Synapse. 2012 Jul;66(7):630-9. doi: 10.1002/syn.21549. Epub 2012 Mar 16. PMID: 22337473; PMCID: PMC3824965. 10: Wilson H, Pagano G, de Natale ER, Mansur A, Caminiti SP, Polychronis S, Middleton LT, Price G, Schmidt KF, Gunn RN, Rabiner EA, Politis M. Mitochondrial Complex 1, Sigma 1, and Synaptic Vesicle 2A in Early Drug-Naive Parkinson's Disease. Mov Disord. 2020 Aug;35(8):1416-1427. doi: 10.1002/mds.28064. Epub 2020 Apr 29. PMID: 32347983.