Niravoline

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]

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
3D model (JSmol)
PubChem CID
UNII
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

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

References
  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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