Ensaculin

Ensaculin
Clinical data

ATC code	none
Pharmacokinetic data
Biological half-life	13.7 hours
Identifiers
IUPAC name 7-methoxy-6-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy]-3,4-dimethylchromen-2-one
CAS Number	155773-59-4^Y
PubChem (CID)	208923
ChemSpider	181019^N
UNII	869PGR00AT^N
ChEMBL	CHEMBL1963107^N
Chemical and physical data
Formula	C₂₆H₃₂N₂O₅
Molar mass	452.543
3D model (Jmol)	Interactive image
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
^NY (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. doi:10.1111/j.1527-3458.2002.tb00220.x. 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. doi:10.1002/j.1552-4604.1998.tb04438.x. PMID 9590466.

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 Methoxypiperamide Piberaline Piribedil Sunifiram 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 Delavirdine 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 Cinepazic acid Cinepazide Cyclohexylpiperazine Hexocyclium Indinavir JNJ-7777120 Lodenafil Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 Zipeprol

Nootropics

Ampakines	CX-516 CX-546 CX-614 Farampator (CX-691) CX-717 IDRA-21 LY-404,187 LY-503,430 Nooglutyl Org 26576 PEPA S-18986

Cholinergics	mAChR agonists: 77-LH-28-1 ADX-47273 Alvameline Arecoline Cevimeline CI-1017 Milameline Sabcomeline Tazomeline Xanomeline nAChR agonists: AR-R17779 Bradanicline Cotinine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-282,987 Pozanicline Rivanicline SIB-1553A SSR-180,711 TC-1827 WAY-317,538 AChE inhibitors: Celastrus paniculatus Cymserine Donepezil Galantamine Huperzine A (Huperzia Serrata) Ladostigil Metrifonate Physostigmine Rivastigmine Tacrine Others: Alpha-GPC Choline Dimethylethanolamine Citicoline

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

Nutrients	Acetylcarnitine Choline Omega-3 fatty acids Magnesium threonate Phosphatidylserine Pyritinol Sulbutiamine Thiamine

Others	Aceglutamide Adafenoxate Bacopa monnieri BAY 73-6691 Bifemelane Bilobalide (Ginkgo biloba) C16 Carbenoxolone Centella asiatica Cinnarizine Ciproxifan Clitoria ternatea Cyprodenate Dihexa Edaravone Eleutherococcus senticosus Ergoloid Ensaculin Emoxypine Fipexide Ginseng Guarana Idebenone Indeloxazine ISRIB Leteprinim Linopirdine Meclofenoxate (centrophenoxine) Methylene blue Nizofenone Noopept NSI-189 P7C3 Pirisudanol Pitolisant PRL-8-53 Razobazam Rubidium S-17092 Semax Shilajit Suritozole Taltirelin Teniloxazine Tianeptine Tricyanoaminopropene Uncaria tomentosa Vincamine Vinpocetine

Psychoanaleptics: Antidementia agents (N06D)

AChE inhibitors	Donepezil Galantamine Huperzine A (Huperzia serrata) Rivastigmine Tacrine

Others	Bifemelane Ergoloid Meclofenoxate (centrophenoxine) Memantine Nicergoline

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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