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
IdentifiersCategory:Articles without KEGG source
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • 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
  • CN([C@@H]1[C@H](CC2=CC=CC=C12)N3CCCC3)C(=O)CC4=CC(=CC=C4)[N+](=O)[O-]
Properties
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).
Category:Articles containing unverified chemical infoboxesCategory:Chembox image size set

Niravoline, also known as RU-51599, 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 κ-opioid receptor agonist.[4] The drug produces hallucinogenic effects at high doses in humans.[5][6]

References

  1. ↑ CID 9821174 from PubChemCategory:PubChem ID (CID) same as Wikidata
  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.
  5. ↑ Farahbakhsh ZZ, Siciliano CA (January 2026). "Kappa opioid receptor control of motivated behavior revisited". Neuropsychopharmacology. 51 (2): 383–398. doi:10.1038/s41386-025-02226-9. PMC 12708679. PMID 41083597.
  6. ↑ Gadano A, Moreau R, Pessione F, Trombino C, Giuily N, Sinnassamy P, Valla D, Lebrec D (January 2000). "Aquaretic effects of niravoline, a kappa-opioid agonist, in patients with cirrhosis". J Hepatol. 32 (1): 38–42. doi:10.1016/s0168-8278(00)80187-7. PMID 10673065.
Category:Abandoned drugs Category:Diuretics Category:Hallucinogenic kappa-opioid receptor agonists Category:3-Nitrophenyl compounds Category:1-Pyrrolidinyl compounds
Category:1-Pyrrolidinyl compounds Category:3-Nitrophenyl compounds Category:Abandoned drugs Category:All stub articles Category:Articles containing unverified chemical infoboxes Category:Articles with short description Category:Articles without KEGG source Category:Chembox image size set Category:Diuretics Category:Hallucinogen stubs Category:Hallucinogenic kappa-opioid receptor agonists Category:PubChem ID (CID) same as Wikidata Category:Short description matches Wikidata