Sazetidine A

Sazetidine A
Identifiers
	IUPAC name 6-[5-[(2S)-2-Azetidinylmethoxy]-3-pyridinyl]-5-hexyn-1-ol;
CAS Number	820231-95-6
PubChem (CID)	11983356
ChemSpider	10155861
Chemical and physical data
Formula	C15H20N2O2
Molar mass	260.331
3D model (Jmol)	Interactive image
	SMILES OCCCCC#Cc1cc(cnc1)OCC2CCN2 ;
	InChI InChI=1S/C15H20N2O2/c18-8-4-2-1-3-5-13-9-15(11-16-10-13)19-12-14-6-7-17-14/h9-11,14,17-18H,1-2,4,6-8,12H2/t14-/m0/s1 ; Key:WONBUILDJNKYCB-AWEZNQCLSA-N ;
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Sazetidine A (AMOP-H-OH) is a drug which acts as a subtype selective partial agonist at α4β2 neural nicotinic acetylcholine receptors, acting as an agonist at (α4)2(β2)3 pentamers, but as an antagonist at (α4)3(β2)2 pentamers.^[1]^[2] It has potent analgesic effects in animal studies comparable to those of epibatidine, but with less toxicity,^[3] and also has antidepressant action.^[4]

References[edit]

^ Xiao Y; Fan H; Musachio JL; Wei ZL; Chellappan SK; Kozikowski AP; Kellar KJ (October 2006). "Sazetidine-A, a novel ligand that desensitizes alpha4beta2 nicotinic acetylcholine receptors without activating them". Molecular Pharmacology. 70 (4): 1454–60. doi:10.1124/mol.106.027318. PMID 16857741.
^ Zwart R; Carbone AL; Moroni M; Bermudez I; Mogg AJ; Folly EA; Broad LM; Williams AC; Zhang D; Ding C; Heinz BA; Sher E (June 2008). "Sazetidine-A is a potent and selective agonist at native and recombinant alpha 4 beta 2 nicotinic acetylcholine receptors". Molecular Pharmacology. 73 (6): 1838–43. doi:10.1124/mol.108.045104. PMID 18367540.
^ Cucchiaro G; Xiao Y; Gonzalez-Sulser A; Kellar KJ (September 2008). "Analgesic effects of Sazetidine-A, a new nicotinic cholinergic drug". Anesthesiology. 109 (3): 512–9. doi:10.1097/ALN.0b013e3181834490. PMID 18719450.
^ Kozikowski AP; Eaton JB; Bajjuri KM; Chellappan SK; Chen Y; Karadi S; He R; Caldarone B; Manzano M; Yuen PW; Lukas RJ (August 2009). "Chemistry and Pharmacology of Nicotinic Ligands Based on 6-5-(Azetidin-2-ylmethoxy) pyridin-3-ylhex-5-yn-1-ol (AMOP-H-OH) for Possible Use in Depression". Chemmedchem. 4 (8): 1279–91. doi:10.1002/cmdc.200900079. PMC 2955514. PMID 19569163.

[pmid16857741-1] Xiao Y; Fan H; Musachio JL; Wei ZL; Chellappan SK; Kozikowski AP; Kellar KJ (October 2006). "Sazetidine-A, a novel ligand that desensitizes alpha4beta2 nicotinic acetylcholine receptors without activating them". Molecular Pharmacology. 70 (4): 1454–60. doi:10.1124/mol.106.027318. PMID 16857741.

[pmid18367540-2] Zwart R; Carbone AL; Moroni M; Bermudez I; Mogg AJ; Folly EA; Broad LM; Williams AC; Zhang D; Ding C; Heinz BA; Sher E (June 2008). "Sazetidine-A is a potent and selective agonist at native and recombinant alpha 4 beta 2 nicotinic acetylcholine receptors". Molecular Pharmacology. 73 (6): 1838–43. doi:10.1124/mol.108.045104. PMID 18367540.

[pmid18719450-3] Cucchiaro G; Xiao Y; Gonzalez-Sulser A; Kellar KJ (September 2008). "Analgesic effects of Sazetidine-A, a new nicotinic cholinergic drug". Anesthesiology. 109 (3): 512–9. doi:10.1097/ALN.0b013e3181834490. PMID 18719450.

[pmid19569163-4] Kozikowski AP; Eaton JB; Bajjuri KM; Chellappan SK; Chen Y; Karadi S; He R; Caldarone B; Manzano M; Yuen PW; Lukas RJ (August 2009). "Chemistry and Pharmacology of Nicotinic Ligands Based on 6-5-(Azetidin-2-ylmethoxy) pyridin-3-ylhex-5-yn-1-ol (AMOP-H-OH) for Possible Use in Depression". Chemmedchem. 4 (8): 1279–91. doi:10.1002/cmdc.200900079. PMC 2955514. PMID 19569163.

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[2]

[3]

[4]

v t e Stimulants (category)

Adamantanes	Adaphenoxate Adapromine Amantadine Bromantane Chlodantane Gludantane Memantine Rimantadine

Adenosine antagonists	8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Paraxanthine SCH-58261 Theobromine Theophylline

Alkylamines	Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Levopropylhexedrine 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

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 JZ-IV-10 Modafinil

Oxazolines	4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone

Phenethylamines	1-(4-Methylphenyl)-2-aminobutane 1-Phenyl-2-(piperidin-1-yl)pentan-3-one 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fuoroamphetamine 2-Fuoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2-Phenyl-3-methylaminobutane 2,3-MDA 3-Fuoroamphetamine 3-Fluoroethamphetamine 3-Fluoromethcathinone 3-Methoxyamphetamine 3-Methylamphetamine 3,4-DMMC 4-BMC 4-CMC 4-Ethylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-Methylbuphedrone 4-Methylcathinone 4-MMA 4-Methylpentedrone 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amfepramone 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 Benzedrone Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Buphedrone Bupropion Butylone Camfetamine Cathine Cathinone Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethcathinone Ethylnorepinephrine Ethylone Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Feprosidnine Flephedrone Fludorex Formetorex Furfenorex Gepefrine Hexapradol Hexedrone HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine IMP Indanylamphetamine Iofetamine Isoetarine Isoethcathinone Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA MDBU MDEA MDMA MDMPEA MDOH MDPR MDPEA Mefenorex Mephedrone Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methcathinone Methedrone Methoxyphenamine Methylenedioxycathinone Methylone Mexedrone MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N-Benzyl-1-phenethylamine N-Ethylbuphedrone N-Ethylhexedrone N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine (drug) Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Pentedrone Pentylone Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Phthalimidopropiophenone Prenylamine Propylamphetamine Pseudoephedrine Ropinirole Salbutamol (Levosalbutamol) Sibutramine 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 MeOPP MBZP Vanoxerine

Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 1-(3,4-Dichlorophenyl)-1-(piperidin-2-yl)butane 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3-Chloromethylphenidate 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate Methylphenidate (Dexmethylphenidate) N-Methyl-3β-propyl-4β-(4-chlorophenyl)piperidine Nocaine Phacetoperane Pipradrol Propylphenidate SCH-5472

Pyrrolidines	2-Diphenylmethylpyrrolidine 5-DBFPV α-PPP α-PBP α-PHP 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	3-CPMT 3'-Chloro-3a-(diphenylmethoxy)tropane 4-fluorotropacocaine 4'-Fluorococaine AHN-1055 Altropane (IACFT) Brasofensine CFT (WIN 35,428) β-CIT (RTI-55) Cocaethylene Cocaine Dichloropane (RTI-111) Difluoropine FE-β-CPPIT FP-β-CPPIT Ioflupane (¹²³I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-105 RTI-112 RTI-113 RTI-117 RTI-120 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-154 RTI-171 RTI-177 RTI-183 RTI-193 RTI-194 RTI-199 RTI-202 RTI-204 RTI-229 RTI-241 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (β-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33 WF-60

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 2-Phenylcyclohexylamine 3,3-Diphenylcyclobutanamine Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Centanafadine Ciclazindol Clofenciclan Cropropamide Crotetamide D-161 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

v t e 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

Sazetidine A

References[edit]

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Identifiers

IUPAC name 6-[5-[(2S)-2-Azetidinylmethoxy]-3-pyridinyl]-5-hexyn-1-ol
CAS Number	820231-95-6^Y
PubChem (CID)	11983356
ChemSpider	10155861
Chemical and physical data
Formula	C₁₅H₂₀N₂O₂
Molar mass	260.331
3D model (Jmol)	Interactive image
SMILES OCCCCC#Cc1cc(cnc1)OCC2CCN2
InChI InChI=1S/C15H20N2O2/c18-8-4-2-1-3-5-13-9-15(11-16-10-13)19-12-14-6-7-17-14/h9-11,14,17-18H,1-2,4,6-8,12H2/t14-/m0/s1 Key:WONBUILDJNKYCB-AWEZNQCLSA-N
(verify)