Niravoline

Niravoline
Names
	Preferred IUPAC name N-Methyl-2-(3-nitrophenyl)-N-[(1S,2S)-2-(pyrrolidin-1-yl)-2,3-dihydro-1H-inden-1-yl]acetamide
Identifiers
CAS Number	130610-93-4 ;
3D model (JSmol)	Interactive image ;
ChEMBL	ChEMBL2105162 ;
ChemSpider	7996923 ;
PubChem CID	9821174 ;
UNII	R8T17Q4LXC ;
CompTox Dashboard (EPA)	DTXSID601123055 ;
	InChI InChI=1S/C22H25N3O3/c1-23(21(26)14-16-7-6-9-18(13-16)25(27)28)22-19-10-3-2-8-17(19)15-20(22)24-11-4-5-12-24/h2-3,6-10,13,20,22H,4-5,11-12,14-15H2,1H3/t20-,22-/m0/s1 Key: ZSDAQBWGAOKTSI-UNMCSNQZSA-N;
	SMILES CN([C@@H]1[C@H](CC2=CC=CC=C12)N3CCCC3)C(=O)CC4=CC(=CC=C4)[N+](=O)[O-];
Properties
Chemical formula	C22H25N3O3
Molar mass	379.460 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Last updated November 20, 2025

Niravoline is a chemical compound with the formula C^₂₂H^₂₅N^₃O^₃.^[1] It has diuretic and aquaretic effects and has been studied for its potential use for cerebral edema ^[2] and cirrhosis.^[3]

It exerts its pharmacological effect as a kappa opioid receptor agonist.^[4]

References

↑ CID 9821174 from PubChem
↑ Guéniau, C.; Oberlander, C. (1997). "The kappa opioid agonist niravoline decreases brain edema in the mouse middle cerebral artery occlusion model of stroke". The Journal of Pharmacology and Experimental Therapeutics. 282 (1): 1–6. PMID 9223533.
↑ Gadano, A.; Moreau, R.; Pessione, F.; Trombino, C.; Giuily, N.; Sinnassamy, P.; Valla, D.; Lebrec, D. (2000). "Aquaretic effects of niravoline, a kappa-opioid agonist, in patients with cirrhosis". Journal of Hepatology. 32 (1): 38–42. doi:10.1016/S0168-8278(00)80187-7. PMID 10673065.
↑ "Niravoline". NCI Thesaurus. National Cancer Institute.

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[1] CID 9821174 from PubChem

[2] Guéniau, C.; Oberlander, C. (1997). "The kappa opioid agonist niravoline decreases brain edema in the mouse middle cerebral artery occlusion model of stroke". The Journal of Pharmacology and Experimental Therapeutics. 282 (1): 1–6. PMID 9223533.

[3] Gadano, A.; Moreau, R.; Pessione, F.; Trombino, C.; Giuily, N.; Sinnassamy, P.; Valla, D.; Lebrec, D. (2000). "Aquaretic effects of niravoline, a kappa-opioid agonist, in patients with cirrhosis". Journal of Hepatology. 32 (1): 38–42. doi:10.1016/S0168-8278(00)80187-7. PMID 10673065.

[4] "Niravoline". NCI Thesaurus. National Cancer Institute.

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Names

Preferred IUPAC name N-Methyl-2-(3-nitrophenyl)-N-[(1S,2S)-2-(pyrrolidin-1-yl)-2,3-dihydro-1H-inden-1-yl]acetamide
Identifiers
CAS Number	130610-93-4 ^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2105162
ChemSpider	7996923
PubChem CID	9821174
UNII	R8T17Q4LXC
CompTox Dashboard (EPA)	DTXSID601123055
InChI InChI=1S/C22H25N3O3/c1-23(21(26)14-16-7-6-9-18(13-16)25(27)28)22-19-10-3-2-8-17(19)15-20(22)24-11-4-5-12-24/h2-3,6-10,13,20,22H,4-5,11-12,14-15H2,1H3/t20-,22-/m0/s1 Key: ZSDAQBWGAOKTSI-UNMCSNQZSA-N
SMILES CN([C@@H]1[C@H](CC2=CC=CC=C12)N3CCCC3)C(=O)CC4=CC(=CC=C4)[N+](=O)[O-]
Properties
Chemical formula	C₂₂H₂₅N₃O₃
Molar mass	379.460 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references