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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| verifiedrevid = 443446592
| verifiedrevid = 447997208
| IUPAC_name = 5-Imino-3-(1-phenylpropan-2-yl)-5''H''-1,2,3-oxadiazol-3-ium-2-ide
| IUPAC_name = 5-Imino-3-(1-phenylpropan-2-yl)-5''H''-1,2,3-oxadiazol-3-ium-2-ide
| image = Feprosidnine_chemical_structure.png
| image = Feprosidnine_chemical_structure.png
Line 8: Line 9:
| tradename =
| tradename =
| legal_status =
| legal_status =
| routes_of_administration =
| routes_of_administration =


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 3441-64-3
| CAS_number = 22293-47-6
| ATC_prefix = none
| ATC_prefix = none
| PubChem = 72088
| PubChem = 72088
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 65073
| ChemSpiderID = 65073
| ChEMBL = 2104320
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1G4W8NR1PT
| UNII = 1G4W8NR1PT
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<!--Chemical data-->
<!--Chemical data-->
| C=11 | H=13 | N=3 | O=1
| C=11 | H=13 | N=3 | O=1
| molecular_weight = 203.24 g/mol
| smiles = n1oc([NH-])c[n+]1C(Cc2ccccc2)C
| smiles = n1oc([NH-])c[n+]1C(Cc2ccccc2)C
| InChI = 1/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
| InChIKey = HFLCEELTJROKMJ-UHFFFAOYAT
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChI = 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
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}}
}}


'''Feprosidnine''' ('''Sydnophen''') is a [[stimulant]] drug which was developed in the [[USSR]] in the 1970s.<ref>Veksler IG, Riabukha VN, Balitskiĭ KP, Al'tshuler RA, Mashkovskiĭ MD. Immunostimulating and antitumor action of psychotropic preparations of the sydnonimine series. (Russian) ''Farmakologiia i Toksikologiia''. 1980 May-Jun;43(3):349-52.</ref><ref>Koniaeva EI, Beketov AI. Effect of caffeine and sidnofen on the blood supply of the brain, kidneys and hindlimbs during antiorthostatism. (Russian) ''Farmakologiia i Toksikologiia'' 1987 May-Jun;50(3):39-42.</ref> It is structurally related to another Russian drug [[mesocarb]] but unlike mesocarb it has not been developed for medical use in humans.
'''Feprosidnine''', sold under the brand name '''Sydnophen''', is a [[stimulant]] drug which was developed in the [[USSR]] in the 1970s.<ref name="pmid7449977">{{cite journal | vauthors = Veksler IG, Riabukha VN, Balitskiĭ KP, Al'tshuler RA, Mashkovskiĭ MD | title = [Immunostimulating and antitumor action of psychotropic preparations of the sydnonimine series] | language = ru | journal = Farmakologiia I Toksikologiia | volume = 43 | issue = 3 | pages = 349–52 | date = 1980 | pmid = 7449977 }}</ref><ref name="pmid3609274">{{cite journal | vauthors = Koniaeva EI, Beketov AI | title = [Effect of caffeine and sidnofen on the blood supply of the brain, kidneys and hindlimbs during antiorthostatism] | language = ru | journal = Farmakologiia I Toksikologiia | volume = 50 | issue = 3 | pages = 39–42 | date = 1987 | pmid = 3609274 }}</ref> 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, [[acetylcholine|cholinergic]],<ref name="pmid2720163">{{cite journal | vauthors = Samonina GE, Mandriko EV | title = [Peripheral cholinolytic action--one of the effects of sidnofen] | language = ru | journal = Biulleten' Eksperimental'noi Biologii I Meditsiny | volume = 107 | issue = 4 | pages = 449–51 | date = April 1989 | pmid = 2720163 }}</ref> [[adrenaline|adrenergic]],<ref name="pmid1339046">{{cite journal | vauthors = Babskaia NE | title = [Sidnofen-dependent pre- and postsynaptic activation of peripheral adrenergic transmission] | language = ru | journal = Eksperimental'naia i Klinicheskaia Farmakologiia | volume = 55 | issue = 5 | pages = 21–5 | date = 1992 | pmid = 1339046 }}</ref> [[opioid]]<ref name="pmid7810220">{{cite journal | vauthors = D'iakonova TL, Samonina GE | title = [The naloxone-dependent effects of the psychostimulant sidnofen: a study on identified neurons of the snail] | language = ru | journal = Zhurnal Vysshei Nervnoi Deiatelnosti Imeni I P Pavlova | volume = 44 | issue = 4–5 | pages = 786–95 | date = 1994 | pmid = 7810220 }}</ref> and [[Endothelium-derived relaxing factor|nitric oxide donating]]<ref name="pmid14724985">{{cite journal | vauthors = Arzamastsev AP, Severina IS, Grigor'ev NB, Granik VG | title = [Exogenous donors of nitric oxide and inhibitors of NO-synthase (chemical aspects)] | language = ru | journal = Vestnik Rossiiskoi Akademii Meditsinskikh Nauk | issue = 12 | pages = 88–95 | date = 2003 | pmid = 14724985 }}</ref> actions, all of which may contribute to its pharmacological effects to some extent.

⚫
Sydnophen has multiple mechanisms of action, the relative importance of which has not been clearly established. Effects on the body include [[acetylcholine|cholinergic]],<ref>Samonina GE, Mandriko EV. Peripheral cholinolytic action--one of the effects of sidnofen. (Russian) ''Biulleten Eksperimental'noi Biologii i Meditsiny''. 1989 Apr;107(4):449-51.</ref> [[adrenaline|adrenergic]],<ref>Babskaia NE. Sidnofen-dependent pre- and postsynaptic activation of peripheral adrenergic transmission. (Russian) ''Eksperimental'naia i Klinicheskaia Farmakologiia''. 1992 Sep-Oct;55(5):21-5.</ref> [[opioid]]<ref>D'iakonova TL, Samonina GE. The naloxone-dependent effects of the psychostimulant sidnofen: a study on identified neurons of the snail. (Russian) ''Zhurnal Vysshei Nervnoi Deiatelnosti Imeni I P Pavlova''. 1994 Jul-Oct;44(4-5):786-95.</ref> and [[Endothelium-derived relaxing factor|nitric oxide donating]]<ref>Arzamastsev AP, Severina IS, Grigor'ev NB, Granik VG. Exogenous donors of nitric oxide and inhibitors of NO-synthase (chemical aspects). (Russian). ''Vestnik Rossiiskoi Akademii Meditsinskikh Nauk''. 2003;(12):88-95.</ref> actions, all of which may contribute to its pharmacological effects to some extent.


== Chemistry ==
== Chemistry ==

Feprosidnine is a [[mesoionic]] [[sydnone imine]].
Feprosidnine is a [[mesoionic]] [[sydnone imine]].

A similar agent is described in the [[Amfetaminil]] article.

==Synthesis==
[[File:Feprosidnine synthesis.svg|thumb|center|500px|Patent:<ref>Mashkovsky Mikhail Davydovich & Yashunsky Vladimir Genrikhovic; GB1242743 (1971 to Vni Khim Farmatsevtichesky I I [RU]).</ref>]]

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''').

==See also==
* [[List of Russian drugs]]


== References ==
== References ==
{{Reflist}}
<div class="references-small">
<references/>
</div>


{{stimulants}}


[[Category:Stimulants]]
{{Stimulants}}
{{Monoamine releasing agents}}
⚫
[[Category:Oxadiazoles]]
{{Nitric oxide signaling modulators}}


[[Category:Drugs in the Soviet Union]]
[[ru:Фепрозиднин]]
⚫
[[Category:Oxadiazoles]]
[[Category:Monoamine releasing agents]]
[[Category:Russian drugs]]
[[Category:Stimulants]]
[[Category:Wakefulness-promoting agents]]

Latest revision as of 01:59, 8 October 2024

Feprosidnine
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
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H13N3O
Molar mass203.245 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 checkY
  • Key:HFLCEELTJROKMJ-UHFFFAOYSA-N checkY
  (verify)

Feprosidnine, sold under the brand name 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.

Chemistry

[edit]

Feprosidnine is a mesoionic sydnone imine.

A similar agent is described in the Amfetaminil article.

Synthesis

[edit]
Patent:[7]

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).

See also

[edit]

References

[edit]
  1. ^ Veksler IG, Riabukha VN, Balitskiĭ KP, Al'tshuler RA, Mashkovskiĭ MD (1980). "[Immunostimulating and antitumor action of psychotropic preparations of the sydnonimine series]". Farmakologiia I Toksikologiia (in Russian). 43 (3): 349–52. PMID 7449977.
  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]).


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