Feprosidnine - Misplaced Pages

Chemical compound Pharmaceutical compound

Feprosidnine
Clinical data

ATC code	none
Identifiers
IUPAC name 5-Imino-3-(1-phenylpropan-2-yl)-5H-1,2,3-oxadiazol-3-ium-2-ide
CAS Number	22293-47-6
PubChem CID	72088
ChemSpider	65073
UNII	1G4W8NR1PT
ChEMBL	ChEMBL2104320
CompTox Dashboard (EPA)	DTXSID801027235
Chemical and physical data
Formula	C₁₁H₁₃N₃O
Molar mass	203.245 g·mol
3D model (JSmol)	Interactive image
SMILES n1oc()c1C(Cc2ccccc2)C
InChI 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 Key:HFLCEELTJROKMJ-UHFFFAOYSA-N
(verify)

Feprosidnine, sold under the brand name Sydnophen, is a stimulant drug which was developed in the USSR in the 1970s. It is structurally related to another Russian drug mesocarb but unlike mesocarb, was withdrawn earlier from production.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, adrenergic, opioid and nitric oxide donating actions, all of which may contribute to its pharmacological effects to some extent.

Chemistry

Feprosidnine is a mesoionic sydnone imine.

A similar agent is described in the Amfetaminil article.

Synthesis

Base catalyzed reaction between acetone cyanohydrin and 40% formaldehyde solution gives glycolonitrile (1) & some acetone by-product. The amphetamine (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).

References

Veksler IG, Riabukha VN, Balitskiĭ KP, Al'tshuler RA, Mashkovskiĭ MD (1980). "". Farmakologiia I Toksikologiia (in Russian). 43 (3): 349–52. PMID 7449977.
Koniaeva EI, Beketov AI (1987). "". Farmakologiia I Toksikologiia (in Russian). 50 (3): 39–42. PMID 3609274.
Samonina GE, Mandriko EV (April 1989). "". Biulleten' Eksperimental'noi Biologii I Meditsiny (in Russian). 107 (4): 449–51. PMID 2720163.
Babskaia NE (1992). "". Eksperimental'naia i Klinicheskaia Farmakologiia (in Russian). 55 (5): 21–5. PMID 1339046.
D'iakonova TL, Samonina GE (1994). "". Zhurnal Vysshei Nervnoi Deiatelnosti Imeni I P Pavlova (in Russian). 44 (4–5): 786–95. PMID 7810220.
Arzamastsev AP, Severina IS, Grigor'ev NB, Granik VG (2003). "". Vestnik Rossiiskoi Akademii Meditsinskikh Nauk (in Russian) (12): 88–95. PMID 14724985.
Mashkovsky Mikhail Davydovich & Yashunsky Vladimir Genrikhovic; GB1242743 (1971 to Vni Khim Farmatsevtichesky I I ).

v t e Stimulants
Adamantanes	Adapromine Amantadine Bromantane Memantine Rimantadine
Adenosine antagonists	8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Istradefylline Paraxanthine SCH-58261 Theobromine Theophylline
Alkylamines	Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane
Ampakines	CX-516 CX-546 CX-614 CX-691 CX-717 IDRA-21 LY-404,187 LY-503,430 Nooglutyl Org 26576 PEPA S-18986 Sunifiram Unifiram
Arylcyclohexylamines	Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine
Benzazepines	6-Br-APB SKF-77434 SKF-81297 SKF-82958
Cathinones	3-FMC 3-MMC 3,4-DMMC 4-BMC 4-CMC 4-Methylbuphedrone 4-Methylcathinone 4-MEAP 4-Methylpentedrone Amfepramone Benzedrone Buphedrone Bupropion Butylone Cathinone Dimethylcathinone Ethcathinone Ethylone Flephedrone Hexedrone Isoethcathinone Mephedrone Methcathinone Methedrone Methylenedioxycathinone Methylone Mexedrone N-Ethylbuphedrone N-Ethylhexedrone Pentedrone Pentylone Phthalimidopropiophenone
Cholinergics	A-84,543 A-366,833 ABT-202 ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A SIB-1553A SSR-180,711 TC-1698 TC-1827 TC-2216 Tebanicline UB-165 Varenicline WAY-317,538
Convulsants	Anatoxin-a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine Thujone
Eugeroics	Adrafinil Armodafinil CRL-40,940 CRL-40,941 Fluorenol Modafinil
Oxazolines	4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines	1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fluoroamphetamine 2-Fluoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fluoroamphetamine 3-Fluoroethamphetamine 3-Methoxyamphetamine 3-Methylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-MMA 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Camfetamine Cathine Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethylnorepinephrine Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Feprosidnine Fludorex Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methoxyphenamine MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Prenylamine Propylamphetamine Pseudoephedrine Ropinirole Salbutamol (Levosalbutamol) Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine
Phenylmorpholines	3-Fluorophenmetrazine Fenbutrazate Fenmetramide G-130 Manifaxine Morazone Morforex Oxaflozane PD-128,907 Phendimetrazine Phenmetrazine 2-Phenyl-3,6-dimethylmorpholine Pseudophenmetrazine Radafaxine
Piperazines	2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 JJC8-088 MeOPP MBZP oMPP Vanoxerine
Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate JZ-IV-10 Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate Serdexmethylphenidate SCH-5472
Pyrrolidines	2-Diphenylmethylpyrrolidine 4-Cl-PVP 5-DBFPV α-PPP α-PBP α-PCYP α-PHiP α-PHP α-PHPP α-PVP α-PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone
Racetams	Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide
Tropanes	4-fluorotropacocaine 4'-Fluorococaine Altropane (IACFT) Brasofensine CFT (WIN 35,428) β-CIT (RTI-55) Cocaethylene Cocaine Dichloropane (RTI-111) Difluoropine FE-β-CPPIT FP-β-CPPIT Ioflupane (I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-120 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (β-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33
Tryptamines	4-HO-αMT 4-Methyl-αET 4-Methyl-αMT 5-Chloro-αMT 5-Fluoro-αMT 5-MeO-αET 5-MeO-αMT 5-MeO-DIPT 6-Fluoro-αMT 7-Methyl-αET αET αMT
Others	2-MDP 3,3-Diphenylcyclobutanamine Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Centanafadine Ciclazindol Clofenciclan Cropropamide Crotetamide D-161 Desipramine Diclofensine Dimethocaine Efaroxan Etamivan Fenisorex Fenpentadiol Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 Lazabemide Leptacline Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Methamnetamine Methastyridone Methiopropamine Naphthylaminopropane Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline PNU-99,194 PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Thiopropamine Thiothinone Trazium UH-232 Yohimbine
ATC code: N06B

Monoamine releasing agents

DRAsTooltip Dopamine releasing agents

Morpholines: Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine
Oxazolines: 4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines: 2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine (Dextroamphetamine Levoamphetamine) Amphetaminil β-Me-PEA BDB BOH Benzphetamine Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine D-Deprenyl DMA DMMA Dimethylamphetamine Ephedrine Ethcathinone EBDB Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4-Hydroxyamphetamine Iofetamine (123I) Lisdexamfetamine Lophophine Mefenorex Mephedrone Metamfepramone Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone MMDA MMDMA MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) MDMPEA MDOH MDPEA Methylone Morforex Ortetamine pBA pCA pIA Pholedrine Phenethylamine Pholedrine Phenpromethamine Prenylamine Propylamphetamine Pseudoephedrine Tiflorex Tyramine Xylopropamine Zylofuramine
Piperazines: 2C-B-BZP BZP MBZP MDBZP MeOPP oMPP
Others: 2-ADN 2-AI 2-AT 4-BP 5-APDI 5-IAI Amineptine Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Naphthylaminopropane Octodrine Phthalimidopropiophenone Phenylbiguanide Propylhexedrine

NRAsTooltip Norepinephrine releasing agents

Morpholines: Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine
Oxazolines: 4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines: 2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine Dextroamphetamine Levoamphetamine Amphetaminil β-Me-PEA BDB Benzphetamine BOH Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine Dimethylamphetamine DMA DMMA EBDB Ephedrine Ethcathinone Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4-Hydroxyamphetamine 5-APDI (IAP) Iofetamine (123I) Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) Metamfepramone MDMPEA MDOH MDPEA Mefenorex Mephedrone Mephentermine Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone Methylone Morforex Naphthylaminopropane Ortetamine pBA pCA Pentorex Phenethylamine Pholedrine Phenpromethamine Phentermine Phenylpropanolamine pIA Prenylamine Propylamphetamine Pseudoephedrine Selegiline (also D-Deprenyl) Tiflorex Tyramine Xylopropamine Zylofuramine
Piperazines: 2C-B-BZP BZP MBZP mCPP MDBZP MeOPP oMPP pFPP
Others: 2-ADN 2-AI 2-AT 2-BP 4-BP 5-IAI Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Octodrine Phthalimidopropiophenone Propylhexedrine Tuaminoheptane

SRAsTooltip Serotonin releasing agents

Aminoindanes: 5-IAI AMMI ETAI MDAI MDMAI MMAI TAI
Aminotetralins: 6-CAT 8-OH-DPAT MDAT MDMAT
Oxazolines: 4-Methylaminorex Aminorex Clominorex Fluminorex
Phenethylamines: 2-Methyl-MDA 4-CAB 4-FA 4-FMA 4-HA 4-MTA 5-APDB 5-Methyl-MDA 6-APDB 6-Methyl-MDA AEMMA Amiflamine BDB BOH Brephedrone Butylone Chlorphentermine Cloforex Amfepramone Metamfepramone DCA Dexfenfluramine DFMDA DMA DMMA EBDB EDMA Ethylone Etolorex Fenfluramine Flephedrone Flucetorex IAP Iofetamine Levofenfluramine Lophophine MBDB MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDMPEA MDOH MDPEA Mephedrone Methedrone Methylone MMA MMDA MMDMA MMMA NAP Norfenfluramine 4-TFMA pBA pCA pIA PMA PMEA PMMA TAP
Piperazines: 2C-B-BZP 3-MeOPP BZP DCPP MBZP mCPP MDBZP MeOPP Mepiprazole oMPP pCPP pFPP pTFMPP TFMPP
Tryptamines: 4-Methyl-αET 4-Methyl-αMT 5-CT 5-MeO-αET 5-MeO-αMT 5-MT αET αMT DMT Tryptamine
Others: Indeloxazine Viqualine

Others

DAT modulators: Agonist-like: SoRI-9804
SoRI-20040; Antagonist-like: SoRI-20041

Adrenergic release blockers: Bethanidine
Bretylium
Guanadrel
Guanazodine
Guanethidine
Guanoxan

See also: Receptor/signaling modulators • Monoamine reuptake inhibitors • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins

Nitric oxide signaling modulators

Forms

Targets

sGC	Activators/stimulators: Ataciguat BAY 41-2272 BAY 41-8543 BAY 60-4552 BI-703704 Cinaciguat (BAY 58-2667) GSK-2181236A Praliciguat Riociguat Vericiguat Inhibitors: ODQ

NO donors
(prodrugs)

Nitroso compounds/nitrites: Nitrite (NO
₂); O-Nitroso compounds (alkyl nitrites): Amyl nitrite (isoamyl nitrite, isopentyl nitrite)
Cyclohexyl nitrite
Ethyl nitrite
Hexyl nitrite
Isobutyl nitrite (2-methylpropyl nitrite)
Isopropyl nitrite
Methyl nitrite
n-Butyl nitrite
Pentyl nitrite
tert-Butyl nitrite; S-Nitroso compounds (thionitrites): LA810
S-Nitrosoalbumin (SNALB)
S-Nitrosated AR545C
S-Nitroso-N-acetylcysteine (SNAC)
S-Nitroso-N-acetylpenicillamine (SNAP)
S-Nitroso-N-valerylpenicillamine (SNVP)
S-Nitrosocaptopril (SNO-Cap)
S-Nitrosocysteine (SNC, CysNO, SNO-Cys)
S-Nitrosodiclofenac
S-Nitrosoglutathione (GSNO, SNOG)
SNO-t-PA
SNO-vWF; N-Nitroso compounds (e.g., nitrosamines): SIN-1A

Nitrosyl compounds: Metal nitrosyl complexes: Roussin's black salt
Roussin's red salt
Sodium nitroprusside (SNP)

NONOates (diazeniumdiolates): Diethylamine/NO (DEA/NO)
Diethylenetriamine/NO (DETA/NO)
GLO/NO
JS-K
Methylamine hexamethylene methylamine/NO (MAHMA/NO)
PROLI/NO
Spermine/NO (SPER/NO)
V-PYRRO/NO

Heterocyclic compounds: Furoxans: Furoxan
REC15/2739; Sydnonimines: Feprosidnine
Linsidomine (SIN-1)
Molsidomine (SIN-10)
Sydnonimine

Unsorted: Cimlanod
FK-409
FR144220
FR146881
N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide

Enzyme
(inhibitors)

NOS

nNOS	3-Bromo-7-nitroindazole 3-Chloroindazole 3-Chloro-5-nitroindazole 5-Nitroindazole 6-Nitroindazole 7-Nitroindazole A-84643 Aminoguanidine (pimagedine) ARL-17477 Indazole N-(1-Iminoethyl)-L-ornithine (L-NIO) N-Methyl-L-arginine (L-NMA) N-Propyl-L-arginine (L-NPA) Nitroarginine (NNA, NOARG) Pentamidine isethionate TRIM
iNOS	1-Amino-2-hydroxyguanidine 2-Ethylaminoguanidine 2-Iminopiperidine 1400W AEITU Aminoguanidine (pimagedine) AMT AR-C 102222 BYK-191023 Canavanine Cindunistat (SD-6010) EITU IPTU MITU N-(1-Iminoethyl)-L-ornithine (L-NIO) N-(1-Iminoethyl)-L-lysine (L-NIL) N-Methyl-L-arginine (L-NMA) Ronopterin (VAS-203) TRIM
eNOS	Aminoguanidine (pimagedine) N-(1-Iminoethyl)-L-ornithine (L-NIO) N-Methyl-L-arginine (L-NMA) Nitroarginine (NNA, NOARG)
Unsorted	Asymmetric dimethylarginine (ADMA) CKD-712 Guanidinoethyldisulfide (GED) GW-273629 Indospicine KD-7040 Nitroarginine methyl ester (NAME) NCX-456 NXN-462 ONO-1714 VAS-2381

Arginase

CAMK

Others

Precursors: L-Arginine
N-Hydroxy-L-arginine (NOHA)

Cofactors: NADPH
FAD
FMN
Heme
BH₄
CaM
O₂
Ca

Indirect/downstream NO modulators: ACE inhibitors/AT-II receptor antagonists (e.g., captopril, losartan)
ET_B receptor antagonists (e.g., bosentan)
L-Type calcium channel blockers (e.g., dihydropyridines: nifedipine)
Nebivolol (beta blocker)
PDE5 inhibitors (e.g., sildenafil)
non-selective PDE inhibitors (e.g., caffeine)
PDE9 inhibitors (e.g., paraxanthine)
cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil)
Statins (e.g., simvastatin)

See also: Receptor/signaling modulators

Categories: