Cutamesine

Cutamesine
Names
	Preferred IUPAC name 1-[2-(3,4-Dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine
Identifiers
CAS Number	165377-43-5 ; dihydrochloride: 165377-44-6 ;
3D model (JSmol)	Interactive image; dihydrochloride: Interactive image;
ChEMBL	ChEMBL408867; dihydrochloride: ChEMBL3216524;
ChemSpider	8082975; dihydrochloride: 8130551;
DrugBank	DB06618;
PubChem CID	9907323; dihydrochloride: 9954941;
UNII	9J7A4144BX ; dihydrochloride: B66RO93FXQ ;
CompTox Dashboard (EPA)	DTXSID50167935 ;
	InChI 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 Key: UVSWWUWQVAQPJR-UHFFFAOYSA-N; dihydrochloride: InChI=1S/C23H32N2O2.2ClH/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;2*1H Key: XWOXAKBQEMQMFH-UHFFFAOYSA-N;
	SMILES COC1=C(OC)C=C(CCN2CCN(CCCC3=CC=CC=C3)CC2)C=C1; dihydrochloride: COC1=C(C=C(C=C1)CCN2CCN(CC2)CCCC3=CC=CC=C3)OC.Cl.Cl;
Properties
Chemical formula	C23H32N2O2
Molar mass	368.521 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Cutamesine (SA 4503) 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.^[1]^[2]^[3]^[4] These σ1 receptors play a key role in the modulation of Ca²⁺ release and apoptosis.^[3] Cutamesine's activation of the σ1 receptor is tied to a variety of physiological phenomena in the CNS, including activation of dopamine-releasing neurons and repression of the MAPK/ERK pathway.^[5]^[6]

^ Skuza, Grazyna (November 2003). "Potential antidepressant activity of sigma ligands". Polish Journal of Pharmacology. 55 (6): 923–934. ISSN 1230-6002. PMID 14730086.
^ "cutamesine | C23H32N2O2 | ChemSpider". www.chemspider.com. Retrieved 2019-06-12.
^ ^a ^b Hayashi, Teruo; Su, Tsung-Ping (November 2007). "Sigma-1 Receptor Chaperones at the ER- Mitochondrion Interface Regulate Ca2+ Signaling and Cell Survival". Cell. 131 (3): 596–610. doi:10.1016/j.cell.2007.08.036. PMID 17981125. S2CID 18885068.
^ Weissman, A. D.; Su, T. P.; Hedreen, J. C.; London, E. D. (October 1988). "Sigma receptors in post-mortem human brains". The Journal of Pharmacology and Experimental Therapeutics. 247 (1): 29–33. ISSN 0022-3565. PMID 2845055.
^ Skuza, G.; Wedzony, K. (November 2004). "Behavioral Pharmacology of σ-Ligands". Pharmacopsychiatry. 37 (S 3): 183–188. doi:10.1055/s-2004-832676. ISSN 0176-3679. PMID 15547784. S2CID 87032896.
^ Tuerxun, Tuerhong; Numakawa, Tadahiro; Adachi, Naoki; Kumamaru, Emi; Kitazawa, Hiromi; Kudo, Motoshige; Kunugi, Hiroshi (January 2010). "SA4503, a sigma-1 receptor agonist, prevents cultured cortical neurons from oxidative stress-induced cell death via suppression of MAPK pathway activation and glutamate receptor expression". Neuroscience Letters. 469 (3): 303–308. doi:10.1016/j.neulet.2009.12.013. PMID 20025928. S2CID 20552121.

[:0-1] Skuza, Grazyna (November 2003). "Potential antidepressant activity of sigma ligands". Polish Journal of Pharmacology. 55 (6): 923–934. ISSN 1230-6002. PMID 14730086.

[:1-2] "cutamesine | C23H32N2O2 | ChemSpider". www.chemspider.com. Retrieved 2019-06-12.

[:2-3] Hayashi, Teruo; Su, Tsung-Ping (November 2007). "Sigma-1 Receptor Chaperones at the ER- Mitochondrion Interface Regulate Ca2+ Signaling and Cell Survival". Cell. 131 (3): 596–610. doi:10.1016/j.cell.2007.08.036. PMID 17981125. S2CID 18885068.

[:3-4] Weissman, A. D.; Su, T. P.; Hedreen, J. C.; London, E. D. (October 1988). "Sigma receptors in post-mortem human brains". The Journal of Pharmacology and Experimental Therapeutics. 247 (1): 29–33. ISSN 0022-3565. PMID 2845055.

[:4-5] Skuza, G.; Wedzony, K. (November 2004). "Behavioral Pharmacology of σ-Ligands". Pharmacopsychiatry. 37 (S 3): 183–188. doi:10.1055/s-2004-832676. ISSN 0176-3679. PMID 15547784. S2CID 87032896.

[:5-6] Tuerxun, Tuerhong; Numakawa, Tadahiro; Adachi, Naoki; Kumamaru, Emi; Kitazawa, Hiromi; Kudo, Motoshige; Kunugi, Hiroshi (January 2010). "SA4503, a sigma-1 receptor agonist, prevents cultured cortical neurons from oxidative stress-induced cell death via suppression of MAPK pathway activation and glutamate receptor expression". Neuroscience Letters. 469 (3): 303–308. doi:10.1016/j.neulet.2009.12.013. PMID 20025928. S2CID 20552121.

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Cutamesine

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