3-(p-Fluorobenzoyloxy)tropane

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3-(p-Fluorobenzoyloxy)tropane

Systematic (IUPAC) name
(1R,5S)-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-4-fluorobenzoate
Clinical data
Pregnancy cat.	?
Legal status	?
Routes	insufflated
Identifiers
CAS number	172883-97-5^Y
ATC code	?
PubChem	CID 5147770
ChemSpider	4321292^Y
Chemical data
Formula	C₁₅H₁₈F N O₂
Mol. mass	263.307
SMILES	eMolecules & PubChem
InChI InChI=1S/C15H18FNO2/c1-17-12-6-7-13(17)9-14(8-12)19-15(18)10-2-4-11(16)5-3-10/h2-5,12-14H,6-9H2,1H3^Y Key:YXDFSLSXLYAAPF-UHFFFAOYSA-N^Y
Y (what is this?) (verify)

3β-(p-Fluorobenzoyloxy)tropane, (8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 4-fluorobenzoic acid ester, 4-fluorotropacocaine, 3-pseudotropyl-4-fluorobenzoate, pFBT) is a tropane derivative drug which acts as a local anaesthetic, having around 30% the stimulant potency of cocaine but around the same potency as a local anaesthetic.^{[citation needed]} It has been investigated as a potential radiolabelled agent for studying receptor binding,^[1] but was not adopted for this application. The main application for fluorotropacocaine however has been as a designer drug analogue of cocaine, first detected by the EMCDDA in 2008,^[2]^[3] and subsequently sold as an ingredient of various "bath salt" powder products, usually mixed in combination with other stimulant drugs such as caffeine, dimethocaine, desoxypipradrol or substituted cathinone derivatives.^[4]^[5]

References

^ Ali M. Emran. New Trends in Radiopharmaceutical Synthesis, Quality Assurance, and Regulatory Control. Springer, 1991. p84. ISBN 0-306-44035-0
^ Wohlfarth, A.; Weinmann, W. (2010). "Bioanalysis of new designer drugs". Bioanalysis 2 (5): 965–979. doi:10.4155/bio.10.32. PMID 21083227. edit
^ Kavanagh P, Angelov D, O'Brien J, Fox J, O'Donnell C, Christie R, Power JD, McDermott SD. The syntheses and characterization 3β-(4-fluorobenzoyloxy)tropane (fluorotropacocaine) and its 3α isomer. Drug Testing and Analysis. 2011 Nov 18. DOI 10.1002/dta.362 PMID 22102564
^ An overview of new psychoactive substances and the outlets supplying them
^ Reitzel LA, Dalsgaard PW, Müller IB, Cornett C. Identification of ten new designer drugs by GC-MS, UPLC-QTOF-MS, and NMR as part of a police investigation of a Danish Internet company. Drug Testing and Analysis. 2011 Nov 18. doi: 10.1002/dta.358 PMID 22102551

v t e Stimulants (N06B)

Adamantanes	Adaphenoxate • Adapromine • Amantadine • Bromantane • Chlodantane • Gludantane • Memantine • Midantane

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

Alkylamines	Cyclopentamine • Cypenamine • Cyprodenate • Heptaminol • Isometheptene • Methylhexaneamine • Octodrine • Propylhexedrine • Tuaminoheptane

Arylcyclohexylamines	Benocyclidine • Dieticyclidine • Esketamine • Eticyclidine • Gacyclidine • Ketamine • Phencyclamine • Phencyclidine • Rolicyclidine • Tenocyclidine • Tiletamine

Benzazepines	6-Br-APB • SKF-77434 • SKF-81297 • SKF-82958

Cholinergics	A-84543 • A-366,833 • ABT-202 • ABT-418 • AR-R17779 • Altinicline • Anabasine • Arecoline • 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 • TC-5619 • Tebanicline • UB-165 • Varenicline • WAY-317,538

Convulsants	Anatoxin-a • Bicuculline • DMCM • Flurothyl • Gabazine • Pentetrazol • Picrotoxin • Strychnine • Thujone

Eugeroics	Adrafinil • Armodafinil • CRL-40941 • 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-Fluoroamphetamine • 2-Fluoromethamphetamine • 2-OH-PEA • 2-Phenyl-3-aminobutane • 2-Phenyl-3-methylaminobutane • 2,3-MDA • 3-Fluoroamphetamine • 3-Fluoroethamphetamine • 3-Fluoromethcathinone • 3-Methoxyamphetamine • 3-Methylamphetamine • 3,4-DMMC • 4-BMC • 4-Ethylamphetamine • 4-FA • 4-FMA • 4-MA • 4-MMA • 4-MTA • 6-FNE • Alfetamine • α-Ethylphenethylamine • Amfecloral • Amfepentorex • Amfepramone • Amidephrine • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Arbutamine • β-Methylphenethylamine • β-Phenylmethamphetamine • Benfluorex • Benzedrone • Benzphetamine • BDB (J) • BOH (Hydroxy-J) • BPAP • Buphedrone • Bupropion (Amfebutamone) • Butylone • Cathine • Cathinone • Chlorphentermine • Cinnamedrine • Clenbuterol • Clobenzorex • Cloforex • Clortermine • D-Deprenyl • Denopamine • Dimethoxyamphetamine • Dimethylamphetamine • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Dobutamine • DOPA (Dextrodopa, Levodopa) • Dopamine • Dopexamine • Droxidopa • EBDB (Ethyl-J) • Ephedrine • Epinephrine (Adrenaline) • Epinine (Deoxyepinephrine) • Etafedrine • Ethcathinone (Ethylpropion) • Ethylamphetamine (Etilamfetamine) • Ethylnorepinephrine (Butanefrine) • Ethylone • Etilefrine • Famprofazone • Fenbutrazate • Fencamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenmetramide • Fenproporex • Flephedrone • Fludorex • Furfenorex • Gepefrine • HMMA • Hordenine • Ibopamine • IMP • Indanylamphetamine • Isoetarine • Isoethcathinone • Isoprenaline (Isoproterenol) • L-Deprenyl (Selegiline) • Lefetamine • Lisdexamfetamine • Lophophine (Homomyristicylamine) • Manifaxine • MBDB (Methyl-J; "Eden") • MDA (Tenamfetamine) • MDBU • MDEA ("Eve") • MDMA ("Ecstasy", "Adam") • MDMPEA (Homarylamine) • MDOH • MDPR • MDPEA (Homopiperonylamine) • Mefenorex • Mephedrone • Mephentermine • Metanephrine • Metaraminol • Methamphetamine (Desoxyephedrine, Methedrine; Dextromethamphetamine, Levomethamphetamine) • Methoxamine • Methoxyphenamine • MMA • Methcathinone (Methylpropion) • Methedrone • Methoxyphenamine • Methylone • MMDA • MMDMA • MMMA • Morazone • N-Benzyl-1-phenethylamine • N,N-Dimethylphenethylamine • Naphthylamphetamine • Nisoxetine • Norepinephrine (Noradrenaline) • Norfenefrine • Norfenfluramine • Normetanephrine • Octopamine • Orciprenaline • Ortetamine • Oxilofrine • Paredrine (Norpholedrine, Oxamphetamine, Mycadrine) • PBA • PCA • PHA • Pargyline • Pentorex (Phenpentermine) • Pentylone • Phenatine • Phendimetrazine • Phenmetrazine • Phenpromethamine • Phentermine • Phenylalanine • Phenylephrine (Neosynephrine) • Phenylpropanolamine • Pholedrine • PIA • PMA • PMEA • PMMA • PPAP • Prenylamine • Propylamphetamine • Pseudoephedrine • Radafaxine • Ropinirole • Salbutamol (Albuterol; Levosalbutamol) • Sibutramine • Synephrine (Oxedrine) • Theodrenaline • Tiflorex (Flutiorex) • Tranylcypromine • Tyramine • Tyrosine • Xamoterol • Xylopropamine • Zylofuramine

Piperazines	2C-B-BZP • 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 • 3,4-Dichloromethylphenidate • 4-Benzylpiperidine • 4-Methylmethylphenidate • Desoxypipradrol • Difemetorex • Diphenylpyraline • Ethylphenidate • Methylnaphthidate • Methylphenidate (Dexmethylphenidate) • N-Methyl-3β-propyl-4β-(4-chlorophenyl)piperidine • Nocaine • Phacetoperane • Pipradrol • SCH-5472

Pyrrolidines	2-Diphenylmethylpyrrolidine • α-PPP • α-PBP • α-PVP • Diphenylprolinol • MDPPP • MDPBP • MDPV • MPBP • MPHP • MPPP • MOPPP • Naphyrone • PEP • Prolintane • Pyrovalerone

Tropanes	3-CPMT • 3'-Chloro-3α-(diphenylmethoxy)tropane • 3-Pseudotropyl-4-fluorobenzoate • 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

Others	1-(Thiophen-2-yl)-2-aminopropane • 2-Amino-1,2-dihydronaphthalene • 2-Aminoindane • 2-Aminotetralin • 2-MDP • 2-Phenylcyclohexylamine • 2-Phenyl-3,6-dimethylmorpholine • 3-Benzhydrylmorpholine • 3,3-Diphenylcyclobutanamine • 5-(2-Aminopropyl)indole • 5-Iodo-2-aminoindane • AL-1095 • Amfonelic acid • Amineptine • Amiphenazole • Atipamezole • Atomoxetine (Tomoxetine) • Bemegride • Benzydamine • BTQ • BTS 74,398 • Camfetamine • Carphedon • Ciclazindol • Cilobamine • Clofenciclan • Cropropamide • Crotetamide • Cypenamine • D-161 • Diclofensine • Dimethocaine • Efaroxan • Etamivan • EXP-561 • Fencamfamine • Fenpentadiol • Feprosidnine • G-130 • Gamfexine • Gilutensin • GSK1360707F • GYKI-52895 • Hexacyclonate • Idazoxan • Indanorex • Indatraline • JNJ-7925476 • JZ-IV-10 • Lazabemide • Leptacline • Levopropylhexedrine • Lomevactone • LR-5182 • Mazindol • Meclofenoxate • Medifoxamine • Mefexamide • Mesocarb • Methastyridone • Methiopropamine • N-Methyl-3-phenylnorbornan-2-amine • Nefopam • Nikethamide • Nomifensine • O-2172 • Oxaprotiline • Phthalimidopropiophenone • PNU-99,194 • Propylhexedrine • PRC200-SS • Rasagiline • Rauwolscine • Rubidium chloride • Setazindol • Tametraline • Tandamine • Trazium • UH-232 • Yohimbine

See also Sympathomimetic amines

Anesthetics: Local anesthetics - primarily sodium channel blockers (N01B)

Esters

Esters of aminobenzoic acid	Amylocaine Benzocaine Butacaine Butamben Chloroprocaine Dimethocaine Meprylcaine Metabutoxycaine Orthocaine Propoxycaine Procaine (Novocaine) Proxymetacaine Risocaine Tetracaine

Esters of benzoic acid	3-(p-Fluorobenzoyloxy)tropane Cocaine Cyclomethycaine Hexylcaine Piperocaine

Amides

Articaine
Bupivacaine # /Levobupivacaine/Ropivacaine
Carticaine
Cinchocaine
Etidocaine
Lidocaine #
Mepivacaine
Prilocaine
Trimecaine

Combinations

Anesthetic/anesthetic - Lidocaine/prilocaine

Anesthetic/vasoconstrictor - Iontocaine

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: PNS

anat(h/r/t/c/b/l/s/a)/phys(r)/devp/prot/nttr/nttm/ntrp

noco/auto/cong/tumr, sysi/epon, injr

proc, drug(N1B)

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