Ipidacrine

Ipidacrine (Neiromidin) is a drug first synthesized by the National Research Center for Biologically Active Compounds in the Russian Federation. This compound is a ring-constricted derivative of tacrine (Cognex).[1]

Ipidacrine
Clinical data

Trade names	Neiromidin
Other names	Amiridine; NIK-247
ATC code	N06DA05 (WHO)
Legal status
Legal status	US: Unscheduled Not FDA approved
Identifiers
IUPAC name 2,3,5,6,7,8-Hexahydro-1H-cyclopenta[b]quinolin-9-amine
PubChem CID	604519
ChemSpider	525510
ChEMBL	ChEMBL130880
CompTox Dashboard (EPA)	DTXSID7048299
ECHA InfoCard	100.201.385
Chemical and physical data
Formula	C₁₂H₁₆N₂
Molar mass	188.27 g/mol g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1CCc2c(c(c3c(n2)CCC3)N)C1
InChI InChI=1S/C12H16N2/c13-12-8-4-1-2-6-10(8)14-11-7-3-5-9(11)12/h1-7H2,(H2,13,14) Key:YLUSMKAJIQOXPV-UHFFFAOYSA-N

Ipidacrine is a reversible acetylcholinesterase inhibitor used in memory disorders of different origins.[2][3][4]

Ipidacrine directly stimulates impulse transmission in the central nervous system and neuromuscular synapses by blocking membrane potassium channels. Ipidacrine enhances not only choline, but also adrenaline, serotonin, histamine, and oxytocin effects on smooth muscle.[5]

References

Kojima, Jun; Onodera, Kenji; Ozeki, Mitsuo; Nakayama, Kunio (1998). "Ipidacrine (NIK-247): A Review of Multiple Mechanisms as an Antidementia Agent". CNS Drug Reviews. 4 (3): 247. doi:10.1111/j.1527-3458.1998.tb00067.x.
Damulin, IV; Stepkina, DA; Lokshina, AB (2011). "Neuromidin in mixed vascular and Alzheimer's dementia". Zhurnal Nevrologii i Psikhiatrii Imeni S.S. Korsakova. 111 (2): 40–3. PMID 21350422.
Pustokhanova, LV; Morozova, EM (2011). "Cognitive disorders in the early rehabilitation period of ischemic stroke and possibilities of their treatment with neuromidin". Zhurnal Nevrologii i Psikhiatrii Imeni S.S. Korsakova. 111 (4 Pt 2): 23–7. PMID 23120773.
Onodera, K; Kojima, J; Wachi, M (1998). "Ipidacrine (NIK-247), a novel antidementia, rapidly enters the brain and improves scopolamine-induced amnesia in rats during the Morris water maze task". Nihon shinkei seishin yakurigaku zasshi = Japanese journal of psychopharmacology. 18 (2): 33–7. PMID 9656230.
Neiromidin Product Information

Psychoanaleptics: Anti-dementia agents (ATC code N06D and others)
AChE inhibitor medications	Donepezil Galantamine Ipidacrine Rivastigmine Tacrine
Other medications	Bifemelane Ginkgo folium Meclofenoxate (centrophenoxine) Memantine Nicergoline
Experimental BACE inhibitors	Lanabecestat Verubecestat

Acetylcholine metabolism and transport modulators

Enzyme
(modulators)

ChAT	Inhibitors: 1-(-Benzoylethyl)pyridinium 2-(α-Naphthoyl)ethyltrimethylammonium 3-Chloro-4-stillbazole 4-(1-Naphthylvinyl)pyridine Acetylseco hemicholinium-3 Acryloylcholine AF64A B115 BETA CM-54,903 N,N-Dimethylaminoethylacrylate N,N-Dimethylaminoethylchloroacetate
AChE	Inhibitors: Reversible: Carbamates: Aldicarb Aminocarb Bendiocarb Bufencarb Carbaryl Carbendazim Carbetamide Carbofuran Carbosulfan Chlorbufam Chloropropham Dimetilan Ethienocarb Ethiofencarb Fenobucarb Formetanate Formparanate Methiocarb Methomyl Metolcarb Miotine Oxamyl Phenmedipham Pinmicarb Pirimicarb Propamocarb Propham Propoxur Thiofanox; Stigmines: Distigmine Eptastigmine Ganstigmine Neostigmine Phenserine Physostigmine Pyridostigmine Quilostigmine Rivastigmine Terestigmine; Others: Acotiamide Ambenonium Caffeine Donepezil EA-3990 EA-4056 Edrophonium Galantamine Huperzine A Ipidacrine Itopride Ladostigil Minaprine Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) T-1123 TL-599 TL-1238 Tacrine Zanapezil Irreversible: Organophosphates: 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Acephate Anatoxin-a(S) Armine Azinphos-ethyl Azinphos-methyl BAY-29952 Bensulide Cadusafos Carbophenothion Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Crotylsarin Cyanophos Cyclosarin (GF) Demephion Demeton Demeton-S-methyl Dialifor Diazinon Dichlorvos Dicrotophos Diisopropyl fluorophosphate Diisopropylphosphate Dimefox Dimethoate Dimethyl 4-(methylthio)phenyl phosphate Dioxathion Disulfoton EA-2012 EA-2054 EA-2098 EA-2192 EA-2613 EA-3148 EA-4352 Echothiophate Ethylsarin (GE) Endothion Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fluorotabun Fonofos Formothion Fosthiazate GD-42 GH GT-45 GV Hexaethyl tetraphosphate Isofluorophate Isoxathion Leptophos Malaoxon Malathion Methamidophos Methidathion Methyl phenkapton Methylfluorophosphonylcholine (MFPCh) Metrifonate Mevinphos Mipafox Monocrotophos Naled Novichok agent Omethoate Oxydemeton-methyl Paraoxon Parathion Parathion-methyl Phorate Phosalone Phosfolan Phosmet Phosphamidon Phoxim Pirimiphos-methyl Profenofos Prothoate Ro 3-0340 Ro 3-0346 Ro 3-0347 Ro 3-0351 Ro 3-0352 Ro 3-0397 Ro 3-0411 Ro 3-0412 Ro 3-0417 Ro 3-0419 Ro 3-0422 Ro 3-0433 Sarin (GB) Schradan Soman (GD) Tabun (GA) Tebupirimfos Temefos Terbufos Tetrachlorvinphos Tetraethyl pyrophosphate Triazofos Tribufos Trichlorfon Trichloronate Tricresyl phosphate VE VG VM VP VS VR VX; Others: Demecarium Fasciculins (green mamba toxins) (1, 2, 3, 4) Onchidal (Onchidella binneyi) Methanesulfonyl fluoride Unsorted: α-Pinene α-Viniferin Affinine Affinisine Arisugacin A Bulbocapnine Conodurine Coronaridine Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol Ungeremine Ungiminorine Dimethylcarbamoyl fluoride BW284C51 Reactivators: Asoxime chloride Methoxime Obidoxime Pralidoxime Trimedoxime bromide
BChE	Inhibitors: Affinine Affinisine Conodurine Cymserine Ladostigil Profenamine (ethopropazine) Rivastigmine Tacrine ZINC-12613047 Many of the other AChE inhibitors listed above

Transporter
(modulators)

CHT	Inhibitors: Hemicholinium-3 (hemicholine) Triethylcholine Enhancers: Coluracetam
VAChT	Inhibitors: Vesamicol

Release
(modulators)

Inhibitors	SNAP-25 inactivators: Botulinum toxin (A, C, E) VAMP inactivators: Botulinum toxin (B, D, F, G) Others: Bungarotoxins (β-bungarotoxin, γ-bungarotoxin)
Enhancers	LPHN agonists: α-Latrotoxin Others: Atracotoxins (e.g., robustoxin, versutoxin) Crotoxin

See also: Receptor/signaling modulators • Muscarinic acetylcholine receptor modulators • Nicotinic acetylcholine receptor modulators

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