BRL-52537

BRL-52537
Identifiers
	IUPAC name 2-(3,4-dichlorophenyl)-1-[(2S)-2-(pyrrolidin-1-ylmethyl)piperidin-1-yl]ethanone;
CAS Number	130497-33-5 ;
PubChem CID	6603740;
ChemSpider	5036053 ;
CompTox Dashboard (EPA)	DTXSID501137900 DTXSID00462129, DTXSID501137900 ;
Chemical and physical data
Formula	C18H24Cl2N2O
Molar mass	355.30 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CCN([C@@H](C1)CN2CCCC2)C(=O)CC3=CC(=C(C=C3)Cl)Cl;
	InChI InChI=1S/C18H24Cl2N2O/c19-16-7-6-14(11-17(16)20)12-18(23)22-10-2-1-5-15(22)13-21-8-3-4-9-21/h6-7,11,15H,1-5,8-10,12-13H2/t15-/m0/s1 ; Key:GHCCBWMZKJQGLS-HNNXBMFYSA-N ;
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BRL-52537 is a drug which acts as a potent and highly selective κ-opioid agonist.^[1] It has neuroprotective effects in animal studies,^[2]^[3] and is used for research into potential treatments for stroke and heart attack as well as more general brain research.^[4]^[5]^[6]

References

^ Vecchietti V, Giordani A, Giardina G, Colle R, Clarke GD (January 1991). "(2S)-1-(arylacetyl)-2-(aminomethyl)piperidine derivatives: novel, highly selective kappa opioid analgesics". Journal of Medicinal Chemistry. 34 (1): 397–403. doi:10.1021/jm00105a061. PMID 1846921.
^ Goyagi T, Toung TJ, Kirsch JR, Traystman RJ, Koehler RC, Hurn PD, Bhardwaj A (June 2003). "Neuroprotective kappa-opioid receptor agonist BRL 52537 attenuates ischemia-evoked nitric oxide production in vivo in rats". Stroke: A Journal of Cerebral Circulation. 34 (6): 1533–8. doi:10.1161/01.STR.0000072512.30658.E7. PMID 12738895.
^ Zhang Z, Chen TY, Kirsch JR, Toung TJ, Traystman RJ, Koehler RC, Hurn PD, Bhardwaj A (December 2003). "Kappa-opioid receptor selectivity for ischemic neuroprotection with BRL 52537 in rats". Anesthesia and Analgesia. 97 (6): 1776–83. doi:10.1213/01.ane.0000087800.56290.2e. PMID 14633559.
^ Chen TY, Goyagi T, Toung TJ, Kirsch JR, Hurn PD, Koehler RC, Bhardwaj A (May 2004). "Prolonged opportunity for ischemic neuroprotection with selective kappa-opioid receptor agonist in rats". Stroke: A Journal of Cerebral Circulation. 35 (5): 1180–5. doi:10.1161/01.STR.0000125011.93188.c6. PMID 15031456.
^ Peart JN, Gross ER, Gross GJ (March 2004). "Effect of exogenous kappa-opioid receptor activation in rat model of myocardial infarction". Journal of Cardiovascular Pharmacology. 43 (3): 410–5. doi:10.1097/00005344-200403000-00012. PMID 15076225.
^ Britt JP, McGehee DS (February 2008). "Presynaptic opioid and nicotinic receptor modulation of dopamine overflow in the nucleus accumbens". Journal of Neuroscience. 28 (7): 1672–81. doi:10.1523/JNEUROSCI.4275-07.2008. PMC 6671549. PMID 18272687.

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[pmid1846921-1] Vecchietti V, Giordani A, Giardina G, Colle R, Clarke GD (January 1991). "(2S)-1-(arylacetyl)-2-(aminomethyl)piperidine derivatives: novel, highly selective kappa opioid analgesics". Journal of Medicinal Chemistry. 34 (1): 397–403. doi:10.1021/jm00105a061. PMID 1846921.

[pmid12738895-2] Goyagi T, Toung TJ, Kirsch JR, Traystman RJ, Koehler RC, Hurn PD, Bhardwaj A (June 2003). "Neuroprotective kappa-opioid receptor agonist BRL 52537 attenuates ischemia-evoked nitric oxide production in vivo in rats". Stroke: A Journal of Cerebral Circulation. 34 (6): 1533–8. doi:10.1161/01.STR.0000072512.30658.E7. PMID 12738895.

[pmid14633559-3] Zhang Z, Chen TY, Kirsch JR, Toung TJ, Traystman RJ, Koehler RC, Hurn PD, Bhardwaj A (December 2003). "Kappa-opioid receptor selectivity for ischemic neuroprotection with BRL 52537 in rats". Anesthesia and Analgesia. 97 (6): 1776–83. doi:10.1213/01.ane.0000087800.56290.2e. PMID 14633559.

[pmid15031456-4] Chen TY, Goyagi T, Toung TJ, Kirsch JR, Hurn PD, Koehler RC, Bhardwaj A (May 2004). "Prolonged opportunity for ischemic neuroprotection with selective kappa-opioid receptor agonist in rats". Stroke: A Journal of Cerebral Circulation. 35 (5): 1180–5. doi:10.1161/01.STR.0000125011.93188.c6. PMID 15031456.

[pmid15076225-5] Peart JN, Gross ER, Gross GJ (March 2004). "Effect of exogenous kappa-opioid receptor activation in rat model of myocardial infarction". Journal of Cardiovascular Pharmacology. 43 (3): 410–5. doi:10.1097/00005344-200403000-00012. PMID 15076225.

[pmid18272687-6] Britt JP, McGehee DS (February 2008). "Presynaptic opioid and nicotinic receptor modulation of dopamine overflow in the nucleus accumbens". Journal of Neuroscience. 28 (7): 1672–81. doi:10.1523/JNEUROSCI.4275-07.2008. PMC 6671549. PMID 18272687.

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Identifiers

IUPAC name 2-(3,4-dichlorophenyl)-1-[(2S)-2-(pyrrolidin-1-ylmethyl)piperidin-1-yl]ethanone
CAS Number	130497-33-5^Y
PubChem CID	6603740
ChemSpider	5036053^N
CompTox Dashboard (EPA)	DTXSID501137900 DTXSID00462129, DTXSID501137900
Chemical and physical data
Formula	C₁₈H₂₄Cl₂N₂O
Molar mass	355.30 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1CCN([C@@H](C1)CN2CCCC2)C(=O)CC3=CC(=C(C=C3)Cl)Cl
InChI InChI=1S/C18H24Cl2N2O/c19-16-7-6-14(11-17(16)20)12-18(23)22-10-2-1-5-15(22)13-21-8-3-4-9-21/h6-7,11,15H,1-5,8-10,12-13H2/t15-/m0/s1^N Key:GHCCBWMZKJQGLS-HNNXBMFYSA-N^N
^NY (what is this?) (verify)