Ensaculin

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Ensaculin

Systematic (IUPAC) name
7-methoxy-6-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy]-3,4-dimethylchromen-2-one
Clinical data
Legal status	?
Pharmacokinetic data
Half-life	13.7 hours
Identifiers
CAS number	155773-59-4^Y
ATC code	None
PubChem	CID 208923
ChemSpider	181019^N
UNII	869PGR00AT^N
Chemical data
Formula	C₂₆H₃₂N₂O₅
Mol. mass	452.543
SMILES O=C/4Oc3cc(OC)c(OCCCN2CCN(c1ccccc1OC)CC2)cc3\C(=C\4C)C
InChI InChI=1S/C26H32N2O5/c1-18-19(2)26(29)33-23-17-24(31-4)25(16-20(18)23)32-15-7-10-27-11-13-28(14-12-27)21-8-5-6-9-22(21)30-3/h5-6,8-9,16-17H,7,10-15H2,1-4H3^N Key:FQELZLMTAPJJOL-UHFFFAOYSA-N^N
N (what is this?) (verify)

Ensaculin (KA-672) is a drug from the coumarin family, which has been researched as a potential treatment for dementia. It acts on a number of receptor systems, being both a weak NMDA antagonist and a 5HT_1A agonist.^[1]^[2] Animal studies have shown promising nootropic effects,^[3]^[4] although efficacy in humans has yet to be proven. It was well tolerated in human trials, with the main side effect being orthostatic hypotension (low blood pressure).^[5]

References

↑ Lishko, PV; Maximyuk, OP; Chatterjee, SS; Nöldner, M; Krishtal, OA (1998). "The putative cognitive enhancer KA-672.HCl is an uncompetitive voltage-dependent NMDA receptor antagonist". NeuroReport 9 (18): 4193–7. doi:10.1097/00001756-199812210-00035. PMID 9926872.
↑ Winter, JC; Helsley, SE; Rabin, RA (1998). "The discriminative stimulus effects of KA 672, a putative cognitive enhancer: evidence for a 5-HT1A component". Pharmacology, Biochemistry, and Behavior 60 (3): 703–7. doi:10.1016/S0091-3057(98)00043-4. PMID 9678654.
↑ Hoerr, R; Noeldner, M (2002). "Ensaculin (KA-672 HCl): a multitransmitter approach to dementia treatment". CNS Drug Reviews 8 (2): 143–58. PMID 12177685.
↑ Knauber, J; Müller, WE (2003). "Anseculin improves passive avoidance learning of aged mice". Pharmacological research : the official journal of the Italian Pharmacological Society 47 (3): 225–33. doi:10.1016/S1043-6618(02)00311-0. PMID 12591018.
↑ Sourgens, H; Hoerr, R; Biber, A; Steinbrede, H; Derendorf, H (1998). "KA 672-HCl, a neuronal activator against dementia: tolerability, safety, and preliminary pharmacokinetics after single and multiple oral doses in healthy male and female volunteers". Journal of clinical pharmacology 38 (4): 373–81. PMID 9590466.

v t e Piperazines

Simple piperazines (no additional rings)	1-Cyclohexylpiperazine Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES

Phenylpiperazines	Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin CSP-2503 Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Naphthylpiperazine Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635

Benzylpiperazines	2C-B-BZP Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Piberaline Piribedil Trimetazidine Vesnarinone

Diphenylalkylpiperazines (benzhydrylalkylpiperazines)	Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,783 GBR-12,935 GBR-13,069 GBR-13,098 GBR-13,119 Hydroxyzine Lidoflazine Manidipine Meclozine Oxatomide SNC-80 Vanoxerine

Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Prazitone Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone

Pyridinylpiperazines	Atevirdine Azaperone Mirtazapine Pyridinylpiperazine

Benzo(iso)thiazolyl piperazines	Lurasidone Perospirone Revospirone Tiospirone Ziprasidone

Tricyclics (piperazine attached via side chain)	Amoxapine Clopenthixol Clorotepine Clozapine Cyanothepin Doclothepin Docloxythepin Flupentixol Fluphenazine Isofloxythepin Loxapine Meperathiepin Metitepine Octomethothepin Olanzapine Opipramol Oxyclothepin Oxyprothepin Peradithiepin Perathiepin Perazine Perphenazine Pirenzepine Prochlorperazine Thiethylperazine Thiothixene Trifluoperazine Trifluthepin Zuclopenthixol

Others/Uncategorized	6-Nitroquipazine Azimilide Cinepazet Cyclohexylpiperazine Hexocyclium Indinavir JNJ-7777120 Lodenafil Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 Zipeprol

v t e Nootropics (N06B)

Acetylcholinesterases	Celastrus paniculatus Cymserine Donepezil Galantamine Huperzine A (Huperzia Serrata) Ladostigil Metrifonate Physostigmine Rivastigmine Tacrine

Adenosine antagonists	Caffeine

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

Ampakine-like	Sunifiram Unifiram

D₁ Agonists	6-Br-APB A-77636 Dihydrexidine Dinapsoline Doxanthrine SKF-81297

Eugeroics	Adrafinil Armodafinil JZ-IV-10 Fluorafinil Fluorenol Modafinil

GABA_A α₅ Inverse Agonists	α5IA L-655,708 PWZ-029 Ro4938581 Radequinil Suritozole TB-21007 Terbequinil ZK-93426

H₃ Antagonists	A-349,821 ABT-239 Ciproxifan Clobenpropit GSK-189,254 JNJ-5207852 Pitolisant

mACh Agonists	77-LH-28-1 ADX-47273 Alvameline Arecoline Cevimeline CI-1017 Milameline Sabcomeline Talsaclidine Tazomeline Xanomeline

nACh Agonists	AR-R17779 GTS-21 Cotinine Ispronicline Nicotine PHA-543,613 PNU-282,987 Pozanicline Rivanicline SIB-1553A SSR-180,711 TC-1827 TC-5619 WAY-317,538

NMDA agonists	GLYX-13

NMDA antagonists	Neramexane Sabeluzole Vinconate

Racetams	Aniracetam Brivaracetam Coluracetam Etiracetam Fasoracetam Levetiracetam Nebracetam Nefiracetam Noopept Oxiracetam Phenylpiracetam Piracetam Pramiracetam Rolziracetam Seletracetam

Neurogenics	NSI-189

Others	2CD-5EtO Alpha-GPC Acetylcarnitine Adafenoxate Amphetamine BAY 73-6691 Bifemelane Bilobalide (Ginkgo Biloba) C16 Carbenoxolone Cerlapirdine Centella asiatica Choline (Lecithin) Citicoline Cinnarizine Clitoria ternatea Cyprodenate Dimethylethanolamine Eleutherococcus senticosus Ergoloid Ensaculin Emoxypine Fipexide Guarana Idebenone Indeloxazine ISRIB Latrepirdine Leteprinim Linopirdine Stabilized R-(+)-lipoic acid (RLA) Meclofenoxate Methylene Blue Nicotinamide Nizofenone P7C3 Phosphatidylserine Pirisudanol PRL-8-53 PRX-03140 Pyritinol Razobazam Ro10-5824 RS-67,333 Rubidium S-17092 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Semax Shilajit Sulbutiamine Taltirelin Teniloxazine Tricyanoaminopropene Tyrosine Uncaria tomentosa Vincamine Vinpocetine Zacopride

Psychoanaleptics: Antidementia agents (N06D)

Anticholinesterases

Others

M: PSO/PSI

mepr

dsrd (o, p, m, p, a, d, s), sysi/epon, spvo

proc (eval/thrp), drug (N5A/5B/5C/6A/6B/6D)

Types of coumarins

Aglycones

O-Methylated	Fraxetin Herniarin (7-O-Methylumbelliferone) Osthol Scopoletin (6-Methoxyumbelliferone)

glycosides

Aesculin (Esculetin 6-O-glucoside)
Fraxin (Fraxetin glucoside)
Skimmin (Umbelliferone 7-O-glucoside)
Scopolin
Umbelliferone 7-apiosylglucoside

derivatives

Furanocoumarins

Aglycones

Angelicin
Marmesin
Psoralen
Vaginol
Xanthotoxol (8-Hydroxypsoralen)

O-Methylated	Bergapten (5-methoxypsoralen) Isopimpinellin (5,8-Dimethoxypsoralene) Methoxsalen (8-Methoxypsoralen) Trioxsalen (2,5,9-Trimethylpsoralen)

Furanocoumarin glycosides

Apterin (vaginol glucoside)

Meroterpene furanocoumarin ether

Oligomers

Dicoumarol

Synthetic

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