Fedotozine

Title: Fedotozine
CAS Registry Number: 123618-00-8
CAS Name: (aR)-a-Ethyl-N,N-dimethyl-a-[[(3,4,5-trimethoxyphenyl)methoxy]methyl]benzenemethanamine
Additional Names: (+)-(R)-a-ethyl-N,N-dimethyl-a-[[(3,4,5-trimethoxybenzyl)oxy]methyl]benzylamine; (+)-(1R)-1-phenyl-1-[(3,4,5-trimethoxy)benzyloxymethyl]-N,N-dimethyl-n-propylamine
Molecular Formula: C22H31NO4
Molecular Weight: 373.49
Percent Composition: C 70.75%, H 8.37%, N 3.75%, O 17.14%
Literature References: Peripheral kappa opioid receptor agonist. Prepn of racemate: NL 80 03601; D. R. Torossian et al., US 4301163 (both 1981 to Soc. Ind. Prod. Synth.); of isomers: G. G. Aubard et al., EP 384088; eidem, US 5245080 (1990, 1993 both to Jouveinal). Mechanism of action and pharmacokinetics in dogs: N. Pascaud et al., J. Pharm. Pharmacol. 42, 546 (1990). Clinical trial in nonulcer dyspepsia: B. Fraitag et al., Dig. Dis. Sci. 39, 1072 (1994).
Properties: Pale yellow, viscous oil. [a]D +16.5° (c = 6 in ethanol).
Optical Rotation: [a]D +16.5° (c = 6 in ethanol)
Derivative Type: D(-)-Tartrate
CAS Registry Number: 133267-27-3
Manufacturers' Codes: JO-1196
Molecular Formula: C22H31NO4.C4H6O6
Molecular Weight: 523.57
Percent Composition: C 59.64%, H 7.12%, N 2.68%, O 30.56%
Properties: Crystals from ethanol, mp 147°. [a]D25 +14.5° (c = 5 in HCl).
Melting point: mp 147°
Optical Rotation: [a]D25 +14.5° (c = 5 in HCl)
Therap-Cat: Gastroprokinetic.
Keywords: Gastroprokinetic.
Felbamate Felbinac Felinine Felodipine Fenadiazole

Fedotozine
Fedotozine structure.svg
Systematic (IUPAC) name
(2R)-N,N-dimethyl-2-phenyl-1-[(3,4,5-trimethoxybenzyl)oxy]-2-butanamine
Clinical data
Legal status Non-regulated
Routes Oral
Identifiers
CAS number 123618-00-8
133267-27-3 (tartrate)
ATC code None
PubChem CID 6918160
ChemSpider 5293373
ChEMBL CHEMBL2106275
Chemical data
Formula C22H31NO4 
Mol. mass 373.486 g/mol

Fedotozine (INN; Jo-1196) is an opioid drug of the arylacetamide series which acts as a peripherally-specific, selective κ1-opioid receptor agonist with preference for the κ1A subtype.[1] It was under investigation for the treatment of gastrointestinal conditions like irritable bowel syndrome and functional dyspepsia and made it to phase III clinical trials,[1][2][3] but ultimately development was discontinued and it was never marketed.