Feprosidnine

Last updated
Feprosidnine
Feprosidnine chemical structure.png
Clinical data
ATC code
  • none
Identifiers
  • 5-Imino-3-(1-phenylpropan-2-yl)-5H-1,2,3-oxadiazol-3-ium-2-ide
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
Formula C11H13N3O
Molar mass 203.245 g·mol−1
3D model (JSmol)
  • n1oc([NH-])c[n+]1C(Cc2ccccc2)C
  • InChI=1S/C11H13N3O/c1-9(14-8-11(12)15-13-14)7-10-5-3-2-4-6-10/h2-6,8-9,12H,7H2,1H3 Yes check.svgY
  • Key:HFLCEELTJROKMJ-UHFFFAOYSA-N Yes check.svgY
   (verify)

Feprosidnine (Sydnophen) is a stimulant drug which was developed in the USSR in the 1970s. [1] [2] It is structurally related to another Russian drug mesocarb but unlike mesocarb, was withdrawn earlier from production. In comparison with mesocarb it has own antidepressant activity, which makes it useful in treating depressions. Indications of feprosidnine included apathic, asthenic depressions, fatigue, apathic syndrome, narcolepsy and other similar conditions. Therapeutic range of doses: 10-50mg a day. Sydnophen has multiple mechanisms of action, the relative importance of which has not been clearly established. Effects on the body include reversible monoamine oxidase inhibition, cholinergic, [3] adrenergic, [4] opioid [5] and nitric oxide donating [6] actions, all of which may contribute to its pharmacological effects to some extent.

Contents

Chemistry

Feprosidnine is a mesoionic sydnone imine.

A similar agent is described in the Amfetaminil article.

Synthesis

Patent: Feprosidnine synthesis.svg
Patent:

Base catalyzed reaction between acetone cyanohydrin and 40% formaldehyde solution gives glycolonitrile (1) & some acetone by-product. The amphetamine [300-62-9] (2) is then added and this is allowed to react overnight to give N-(1-phenyl-2-propylamine)-acetonitrile (3). Nitrosylation of the amino group by in situ creation of nitrous acid from hydrochloric acid and sodium nitrite results in a 51.5% yield of feprosidnine based on the initial weight of the amine (4).

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References

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  2. Koniaeva EI, Beketov AI (1987). "[Effect of caffeine and sidnofen on the blood supply of the brain, kidneys and hindlimbs during antiorthostatism]". Farmakologiia I Toksikologiia (in Russian). 50 (3): 39–42. PMID   3609274.
  3. Samonina GE, Mandriko EV (April 1989). "[Peripheral cholinolytic action--one of the effects of sidnofen]". Biulleten' Eksperimental'noi Biologii I Meditsiny (in Russian). 107 (4): 449–51. PMID   2720163.
  4. Babskaia NE (1992). "[Sidnofen-dependent pre- and postsynaptic activation of peripheral adrenergic transmission]". Eksperimental'naia i Klinicheskaia Farmakologiia (in Russian). 55 (5): 21–5. PMID   1339046.
  5. D'iakonova TL, Samonina GE (1994). "[The naloxone-dependent effects of the psychostimulant sidnofen: a study on identified neurons of the snail]". Zhurnal Vysshei Nervnoi Deiatelnosti Imeni I P Pavlova (in Russian). 44 (4–5): 786–95. PMID   7810220.
  6. Arzamastsev AP, Severina IS, Grigor'ev NB, Granik VG (2003). "[Exogenous donors of nitric oxide and inhibitors of NO-synthase (chemical aspects)]". Vestnik Rossiiskoi Akademii Meditsinskikh Nauk (in Russian) (12): 88–95. PMID   14724985.
  7. Mashkovsky Mikhail Davydovich & Yashunsky Vladimir Genrikhovic; GB1242743 (1971 to Vni Khim Farmatsevtichesky I I [RU]).