PWZ-029

PWZ-029
Systematic (IUPAC) name

8-chloro-3-(methoxymethyl)-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one
Identifiers
PubChem	CID 9971547
ChEMBL	CHEMBL45346^N
Chemical data
Formula	C₁₄H₁₄ClN₃O₂
Molar mass	291.732 g/mol
SMILES ClC1=CC=C2C(C(N(CC3=C(COC)N=CN32)C)=O)=C1
^NY (what is this?) (verify)

PWZ-029 is a benzodiazepine derivative drug with nootropic effects developed by WiSys,^[1] It acts as a subtype-selective, mixed agonist-inverse agonist at the benzodiazepine binding site on the GABA_A receptor, acting as a partial inverse agonist at the α₅ subtype and a weak partial agonist at the α₃ subtype. This gives it a mixed pharmacological profile, producing at low doses memory-enhancing effects but with no convulsant or anxiogenic effects or muscle weakness, although at higher doses it produces some sedative effects.^[2]

References

↑ US Patent application US2006/258643 A1
↑ Savić MM, Clayton T, Furtmüller R, Gavrilović I, Samardzić J, Savić S, Huck S, Sieghart W, Cook JM. PWZ-029, a compound with moderate inverse agonist functional selectivity at GABA(A) receptors containing alpha5 subunits, improves passive, but not active, avoidance learning in rats. Brain Research. 2008 May 7;1208:150-9. doi:10.1016/j.brainres.2008.02.020 PMID 18394590

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 Talsaclidine 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 Phosphatidylserine Pyritinol Sulbutiamine Thiamine

Others	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 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

GABAergics

Receptor
(ligands)

GABA_A

Agonists	(+)-Catechin Bamaluzole Barbiturates (e.g., phenobarbital) BL-1020 DAVA Dihydromuscimol GABA Gabamide GABOB Gaboxadol (THIP) Homotaurine (tramiprosate, 3-APS) Ibotenic acid iso-THAZ iso-THIP Isoguvacine Isomuscimol Isonipecotic acid Kojic amine Lignans (e.g., honokiol) Monastrol Muscimol Neuroactive steroids (e.g., allopregnanolone) Org 20599 Phenibut Picamilon P4S Progabide Propofol Quisqualamine SL-75102 TACA TAMP Terpenoids (e.g., borneol) Thiomuscimol Tolgabide ZAPA

PAMs	(abridged; see here for a full list): α-EMTBL Alcohols (e.g., ethanol) Avermectins (e.g., ivermectin) Barbiturates (e.g., phenobarbital) Benzodiazepines (e.g., diazepam) Bromide compounds (e.g., potassium bromide) Carbamates (e.g., meprobamate) Carbamazepine Chloralose Chlormezanone Clomethiazole Dihydroergolines (e.g., ergoloid (dihydroergotoxine)) Etazepine Etifoxine Fenamates (e.g., mefenamic acid) Flavonoids (e.g., apigenin, hispidulin) Fluoxetine Flupirtine Imidazoles (e.g., etomidate) Kava constituents (e.g., kavain) Lanthanum Loreclezole Monastrol Neuroactive steroids (e.g., allopregnanolone, cholesterol) Niacin Nicotinamide (niacinamide) Nonbenzodiazepines (e.g., β-carbolines (e.g., abecarnil), cyclopyrrolones (e.g., zopiclone), imidazopyridines (e.g., zolpidem), pyrazolopyrimidines (e.g., zaleplon)) Norfluoxetine Petrichloral Phenols (e.g., propofol) Phenytoin Piperidinediones (e.g., glutethimide) Propanidid Pyrazolopyridines (e.g., etazolate) Quinazolinones (e.g., methaqualone) Retigabine (ezogabine) ROD-188 Skullcap constituents (e.g., baicalin) Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal)) Topiramate Valerian constituents (e.g., valerenic acid) Volatiles/gases (e.g., chloral hydrate, chloroform, diethyl ether, paraldehyde, sevoflurane)

Antagonists	Bicuculline Coriamyrtin Dihydrosecurinine Gabazine (SR-95531) Hydrastine Hyenachin (mellitoxin) PHP-501 Pitrazepin Securinine Sinomenine SR-42641 SR-95103 Thiocolchicoside Tutin

NAMs	1,3M1B 3M2B 17-Phenylandrostenol α5IA (LS-193,268) β-CCB β-CCE β-CCM β-CCP β-EMGBL Amiloride Anisatin β-Lactams (e.g., penicillins, cephalosporins, carbapenems) Basmisanil Bemegride Bilobalide CHEB Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin (+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142 (ZK-31906) Fiproles (e.g., fipronil) Flavonoids (e.g., amentoflavone, oroxylin A) Flumazenil Fluoroquinolones (e.g., ciprofloxacin) Flurothyl Furosemide Iomazenil (¹²³I) Isoallopregnanolone Isopregnanolone (sepranolone) L-655,708 Laudanosine Leptazol Lindane MaxiPost Morphine Morphine-3-glucuronide MRK-016 Naloxone Naltrexone Nicardipine Non-steroidal antiandrogens (e.g., apalutamide, bicalutamide, enzalutamide, flutamide, nilutamide) Oenanthotoxin Pentetrazol (metrazol) Phenylsilatrane Picrotoxin (i.e., picrotin and picrotoxinin) Pregnenolone sulfate Propybicyphat PWZ-029 Radequinil Ro 15-4513 Ro 19-4603 RO4882224 RO4938581 Sarmazenil SCS Suritozole TB-21007 TBOB TBPS TCS-1105 Terbequinil TETS Thujone U-93631 Zinc ZK-93426

GABA_A-ρ

Agonists	BL-1020 CACA CAMP Homohypotaurine GABA GABOB Ibotenic acid Isoguvacine Muscimol N⁴-Chloroacetylcytosine arabinoside Picamilon Progabide TACA TAMP Thiomuscimol Tolgabide

PAMs	Allopregnanolone Alphaxolone ATHDOC Lanthanides

Antagonists	(S)-2-MeGABA (S)-4-ACPBPA (S)-4-ACPCA 2-MeTACA 3-APMPA 4-ACPAM 4-GBA cis-3-ACPBPA CGP-36742 (SGS-742) DAVA Gabazine (SR-95531) Gaboxadol (THIP) I4AA Isonipecotic acid Loreclezole P4MPA P4S SKF-97541 SR-95318 SR-95813 TPMPA trans-3-ACPBPA ZAPA

NAMs	5α-Dihydroprogesterone Bilobalide Loreclezole Picrotoxin (picrotin, picrotoxinin) Pregnanolone ROD-188 THDOC Zinc

GABA_B

Agonists	1,4-Butanediol Aceburic acid Arbaclofen Arbaclofen placarbil Baclofen BL-1020 GABA Gabamide GABOB GBL GHB GHBAL GHV GVL Isovaline Lesogaberan Phenibut Picamilon Progabide Sodium oxybate SKF-97,541 SL 75102 Tolgabide

Antagonists	2-Hydroxysaclofen CGP-35348 CGP-46381 CGP-52432 CGP-54626 CGP-55845 CGP-64213 DAVA Homotaurine (tramiprosate, 3-APS) Phaclofen Saclofen SCH-50911 SKF-97541

NAMs	Compound 14

PAMs	ADX-71441 BHF-177 BHFF BSPP CGP-7930 CGP-13501 GS-39783 rac-BHFF

Transporter
(blockers)

GAT	4-Aminovaleric acid β-Alanine Arecaidine CI-966 DABA Deramciclane (EGIS-3886, EGYT-3886) EF-1502 Gabaculine Guvacine Ibotenic acid Muscimol Nipecotic acid NNC 05-2090 NO-711 Riluzole SKF-89976A SNAP-5114 TACA Tiagabine

VIAAT	β-Alanine Bafilomycin A1 Chicago sky blue 6B Evans blue GABA Glycine N-Butyric acid Nigericin Nipecotic acid Valinomycin Vigabatrin

Enzyme
(inhibitors)

GAD	3-Mercaptopropionic acid AAOA L-Allylglycine Semicarbazide

GABA-T	3-Hydrazinopropionic acid γ-Acetylenic-GABA AOAA EOS Gabaculine Isoniazid L-Cycloserine Phenelzine PEH Rosmarinic acid (lemon balm) Sodium valproate Valnoctamide Valproate pivoxil Valproate semisodium (divalproex sodium) Valproic acid Valpromide Vigabatrin

Others

Precursors	1,4-Butanediol GHB GHBAL Glutamate Glutamine

Analogues	Pregabalin 4-Methylpregabalin Atagabalin Gabapentin Gabapentin enacarbil Imagabalin Mirogabalin PD-200,347 PD-217,014 PD-299,685 Phenibut

Others	Vitamin B₆ GABA-T activators: 3-Methyl-GABA

See also: GHBergics • Glutamatergics • Glycinergics

Benzodiazepines

1,4-Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Bromazepam Camazepam Carburazepam Chlordiazepoxide Cinazepam Cinolazepam Clonazepam Clorazepate Cyprazepam Delorazepam Demoxepam Desmethylflunitrazepam Devazepide* Diazepam Diclazepam Doxefazepam Elfazepam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Flubromazepam Fletazepam Fludiazepam Flunitrazepam Flurazepam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Iclazepam Irazepine Kenazepine Ketazolam Lorazepam Lormetazepam Lufuradom* Meclonazepam Medazepam Menitrazepam Metaclazepam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nordazepam Nortetrazepam Oxazepam Phenazepam Pinazepam Pivoxazepam Prazepam Proflazepam Quazepam QH-II-66 Reclazepam RO4491533* Ro5-4864* Sulazepam Temazepam Tetrazepam Tifluadom* Tolufazepam Triflunordazepam Tuclazepam Uldazepam

1,5-Benzodiazepines	Arfendazam Clobazam CP-1414S Lofendazam Triflubazam

2,3-Benzodiazepines*	Girisopam GYKI-52466 GYKI-52895 Nerisopam Talampanel Tofisopam

Triazolobenzodiazepines	Adinazolam Alprazolam Clonazolam Estazolam Flubromazolam Nitrazolam Pyrazolam Triazolam

Imidazobenzodiazepines	Bretazenil Climazolam EVT-201 FG-8205 Flumazenil Imidazenil ¹²³I-Iomazenil L-655,708 Loprazolam Midazolam PWZ-029 Remimazolam Ro15-4513 Ro48-6791 Ro48-8684 Ro4938581 Sarmazenil SH-053-R-CH3-2′F

Oxazolobenzodiazepines	Cloxazolam Flutazolam Haloxazolam Mexazolam Oxazolam

Thienodiazepines	Bentazepam Clotiazepam

Thienotriazolodiazepines	Brotizolam Ciclotizolam Desmethyletizolam Etizolam Israpafant* JQ1*

Thienobenzodiazepines*	Olanzapine Telenzepine

Pyridodiazepines	Lopirazepam

Pyridotriazolodiazepines	Zapizolam

Pyrazolodiazepines	Razobazam* Ripazepam Zolazepam Zomebazam Zometapine*

Pyrrolodiazepines	Premazepam

Tetrahydroisoquinobenzodiazepines	Clazolam

Pyrrolobenzodiazepines*	Anthramycin

Benzodiazepine prodrugs	Avizafone Rilmazafone

* atypical activity profile (not GABA_A receptor ligands)

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