Chemistry:A-366,833

A-366,833
Identifiers
	IUPAC name 5-[(1R,5S)-3,6-Diazabicyclo[3.2.0]hept-6-yl]pyridine-3-carbonitrile;
CAS Number	370882-41-0 ;
PubChem CID	9834234;
ChemSpider	8009955 ;
UNII	6XRK9HTJ6M;
ChEMBL	ChEMBL239931 ;
Chemical and physical data
Formula	C11H12N4
Molar mass	200.239 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	101.4–102.9 °C (214.5–217.2 °F)
	SMILES N#CC1=CN=CC(N2[C@]3([H])CNC[C@]3([H])C2)=C1;
	InChI InChI=1S/C11H12N4/c12-2-8-1-10(5-13-3-8)15-7-9-4-14-6-11(9)15/h1,3,5,9,11,14H,4,6-7H2/t9-,11-/m1/s1 ; Key:GPXAWLDGWSBLKM-MWLCHTKSSA-N ;
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Short description: Chemical compound

A-366,833 is a drug developed by Abbott, which acts as an agonist at neural nicotinic acetylcholine receptors selective for the α4β2 subtype, and has been researched for use as an analgesic, although it has not passed clinical trials.^[2] Its structure has a nicotinonitrile (3-cyanopyridine) core bound through C5 to the N6 of (1R,5S)-3,6-diazabicyclo[3.2.0]heptane.^[3]

References

↑ "Synthesis and structure-activity relationship studies of 3,6-diazabicyclo[3.2.0]heptanes as novel alpha4beta2 nicotinic acetylcholine receptor selective agonists". Journal of Medicinal Chemistry 50 (22): 5493–508. November 2007. doi:10.1021/jm070755h. PMID 17929796.
↑ "Central nicotinic receptors: structure, function, ligands, and therapeutic potential". ChemMedChem 2 (6): 746–67. June 2007. doi:10.1002/cmdc.200600207. PMID 17295372.
↑ "A-366833: a novel nicotinonitrile-substituted 3,6-diazabicyclo[3.2.0]-heptane alpha4beta2 nicotinic acetylcholine receptor selective agonist: Synthesis, analgesic efficacy and tolerability profile in animal models". Biochemical Pharmacology 74 (8): 1253–62. October 2007. doi:10.1016/j.bcp.2007.08.010. PMID 17854775.

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[1] "Synthesis and structure-activity relationship studies of 3,6-diazabicyclo[3.2.0]heptanes as novel alpha4beta2 nicotinic acetylcholine receptor selective agonists". Journal of Medicinal Chemistry 50 (22): 5493–508. November 2007. doi:10.1021/jm070755h. PMID 17929796.

[2] "Central nicotinic receptors: structure, function, ligands, and therapeutic potential". ChemMedChem 2 (6): 746–67. June 2007. doi:10.1002/cmdc.200600207. PMID 17295372.

[3] "A-366833: a novel nicotinonitrile-substituted 3,6-diazabicyclo[3.2.0]-heptane alpha4beta2 nicotinic acetylcholine receptor selective agonist: Synthesis, analgesic efficacy and tolerability profile in animal models". Biochemical Pharmacology 74 (8): 1253–62. October 2007. doi:10.1016/j.bcp.2007.08.010. PMID 17854775.

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[3]

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Alkylamines	Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Levopropylhexedrine Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane
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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
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Eugeroics	Adrafinil Armodafinil CRL-40,940 CRL-40,941 Fluorenol Modafinil
Oxazolines	4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines	1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fuoroamphetamine 2-Fuoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fuoroamphetamine 3-Fluoroethamphetamine 3-Fluoromethcathinone 3-Methoxyamphetamine 3-Methylamphetamine 3,4-DMMC 4-BMC 4-CMC 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-Methylbuphedrone 4-Methylcathinone 4-MEAP 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 Indanylamphetamine Iofetamine Isoetarine Isoethcathinone Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) 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-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 Solriamfetol 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 oMPP Vanoxerine
Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate JZ-IV-10 Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate SCH-5472
Pyrrolidines	2-Diphenylmethylpyrrolidine 5-DBFPV α-PPP α-PBP α-PHP α-PHPP 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
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ATC code: N06B

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Identifiers

IUPAC name 5-[(1R,5S)-3,6-Diazabicyclo[3.2.0]hept-6-yl]pyridine-3-carbonitrile
CAS Number	370882-41-0^Y
PubChem CID	9834234
ChemSpider	8009955^Y
UNII	6XRK9HTJ6M
ChEMBL	ChEMBL239931^Y
Chemical and physical data
Formula	C₁₁H₁₂N₄
Molar mass	200.239 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	101.4–102.9 °C (214.5–217.2 °F) ^[1]
SMILES N#CC1=CN=CC(N2[C@]3([H])CNC[C@]3([H])C2)=C1
InChI InChI=1S/C11H12N4/c12-2-8-1-10(5-13-3-8)15-7-9-4-14-6-11(9)15/h1,3,5,9,11,14H,4,6-7H2/t9-,11-/m1/s1^N Key:GPXAWLDGWSBLKM-MWLCHTKSSA-N^N
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