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Uses
CFT was first reported by Clarke and co-workers in 1973. This drug is known to function as a
“positive reinforcer” (although it is less likely to be self-administered by rhesus monkeys
than cocaine). Tritiated CFT is frequently used to map binding of novel ligands to the DAT,
although the drug also has some SERT affinity.
Radiolabelled forms of CFT have been used in humans and animals to map the distribution of
dopamine transporters in the brain. CFT was found to be particularly useful for this
application as a normal fluorine atom can be substituted with the radioactive isotope 18F
which is widely used in Positron emission tomography. Another radioisotope-substituted
analogue [11C]WIN-35,428 (where the carbon atom of either the N-methyl group, or the
methyl from the 2-carbomethoxy group of CFT, has been replaced with 11C) is now more
commonly used for this application, as it is quicker and easier in practice to make
radiolabelled CFT by methylating nor-CFT or 2-desmethyl-CFT than by reacting
methylecgonidine with parafluorophenylmagnesium bromide, and also avoids the
requirement for a licence to work with the restricted precursor ecgonine.
CFT is about as addictive as cocaine in animal studies, but is taken less often due to its longer
duration of action. Potentially this could make it a suitable drug to be used as a substitute for
cocaine, in a similar manner to how methadone is used as a substitute for opiates in treating
addiction.
Legal Status
CFT has no history of abuse in humans, but according to the chemical supplier Sigma-
Aldrich it is illegal in the USA (Schedule II) and Germany (Kontrollierte Droge) 1,
presumably due to its similar effects to cocaine; however CFT is not specifically listed as a
Schedule II drug on the DEA website 2 or on the German controlled drug schedule 3 and so it
is unclear on what basis Sigma-Aldrich has derived this legal information, although
provisions of the Federal Analog Act may be used by Sigma-Aldrich (and the DEA) to
presume its illegality. While CFT might well be considered a controlled substance analogue
in these countries there has never been any formal announcement by either the US or German
government of CFT being added to the controlled substances list.
CFT might possibly also be considered a controlled substance analogue of cocaine in Canada,
New Zealand and Australia, due to its related chemical structure to cocaine. According to
analog law one must consider structural similarity, and CFT might well not be considered
substantially similar to cocaine, having been derived by the removal of an ester linkage rather
than by simply substituting extra groups onto cocaine, although a para-fluoro group has also
been added to CFT. Also the intent of the user must be considered as well, so CFT would
probably not be considered illegal when it is being used solely for scientific research. The
relatively complex synthesis of CFT, as well as the fact that the main synthetic routes proceed
via the restricted intermediate compound ecgonine, make it fairly unlikely that CFT will
appear on the recreational market as a drug of abuse.
Toxicity
Sigma-Aldrich categorizes CFT as being a “very toxic” chemical and recommends the use of
gloves, goggles, protective apron and respirator while handling it, and states it must only be
used in a fume hood. However this description is not supported by the known toxicology of
CFT based on its widespread use in animals over a 30 year period and so this extreme caution
is difficult to reconcile with the chemical and pharmacological properties of the drug; this
may instead reflect concerns about its abuse potential rather than actual potential to cause
poisoning. The drug data sheet notes that serious side effects can occur following exposure to
CFT, including CNS stimulation, dilation of eye pupils, euphoria, breathing difficulties,
nervousness, restlessness, hypertension, fainting, paleness, arrhythmia, cardiac arrest,
convulsions, and death. Prolonged or repeated exposure to CFT may result in habituation or
addiction.
Administering 100mg/kg of CFT to rats only resulted in convulsions being reported, whereas
CIT had the ability to cause death at this dose.
See also
List of cocaine analogues
References
^ a b Wee S, Carroll FI, Woolverton WL. A Reduced Rate of In Vivo Dopamine Transporter
Binding is Associated with Lower Relative Reinforcing Efficacy of Stimulants.
Neuropsychopharmacology. 2006 Feb;31(2):351-62. PMID 15957006
^ Clarke RL, Daum SJ, Gambino AJ, Aceto MD, Pearl J, Levitt M, Cumiskey WR, Bogado
EF. Compounds affecting the central nervous system. 4. 3 Beta-phenyltropane-2-carboxylic
esters and analogs. Journal of Medicinal Chemistry. 1973 Nov;16(11):1260-7. PMID
4747968
^ Carroll FI, Runyon SP, Abraham P, Navarro H, Kuhar MJ, Pollard GT, Howard JL.
Monoamine transporter binding, locomotor activity, and drug discrimination properties of 3-
(4-substituted-phenyl)tropane-2-carboxylic acid methyl ester isomers. J Med Chem. 2004
Dec 2;47(25):6401-9. PMID 15566309
References
D’Mello GD, Goldberg DM, Goldberg SR, Stolerman IP. Conditioned taste aversion and
operant behaviour in rats: effects of cocaine and a cocaine analogue (WIN 35,428).
Neuropharmacology. 1979 Dec;18(12):1009-10.
Reith, MEA., Sershen H, Lajtha A. Saturable (3H)cocaine binding in central nervous system
of mouse. Life Sciences. 1980 Sep 22;27(12):1055-62.
Spealman RD, Bergman J, Madras BK. Self-administration of the high-affinity cocaine
analog 2 beta-carbomethoxy-3 beta-(4-fluorophenyl)tropane. Pharmacology Biochemistry
and Behaviour. 1991 Aug;39(4):1011-3.
Milius RA, Saha JK, Madras BK, Neumeyer JL. Synthesis and Receptor Binding of N-
Substituted Tropane Derivatives. High- Affinity Ligands for the Cocaine Receptor. Journal of
Medicinal Chemistry. 1991,34, 1728-1731
Cline EJ, Scheffel U, Boja JW, Carroll FI, Katz JL, Kuhar MJ. Behavioral effects of novel
cocaine analogs: a comparison with in vivo receptor binding potency. Journal of
Pharmacology and Experimental Therapeutics. 1992 Mar;260(3):1174-9.
Singh S. Chemistry, Design, and Structure-Activity Relationship of Cocaine Antagonists.
Chemistry Reviews, 2000. 100(3): 925-1024
Li SM, Campbell BL, Katz JL. Interactions of cocaine with dopamine uptake inhibitors or
dopamine releasers in rats discriminating cocaine. Journal of Pharmacology and
Experimental Therapeutics. 2006 Jun;317(3):1088-96.
Richard H. Kline, Jr., Jeremy Wright, Kristine M. Fox, and Mohyee E. Eldefrawi. Synthesis
of 3- Arylecgonine Analogues as Inhibitors of Cocaine Binding and Dopamine Uptake.
Journal of Medicinal Chemistry 1990, (33): 2024-2027.
Xu L, Trudell ML. Journal of Heterocyclic Chemistry. 1996; 33: 2037.
v  d  e
Phenyltropanes (classifications)
2-Carboxymethyl Esters
Troparil  WIN 35428  RTI-31  RTI-32  RTI-51  RTI-55
(3,4-Disubstituted Phenyl)-tropanes
Dichloropane  RTI-112  RTI-353
Arylcarboxy
RTI-113
Carboxyalkyl
RTI-121  RTI-150
Acyl
PTT/WF-11  WF-23  PIT/WF-21  WF-33
, Stereochemistry
RTI-352  RTI-274
, Stereochemistry
Brasofensine  Tesofensine  NS2359
Heterocycles: 3-Substituted-isoxazol-5-yl
RTI-177  RTI-336  RTI-371
Heterocycles: 3-Substituted-1,2,4-oxadiazole
RTI-126  RTI-371
N-alkyl
FP–CPPIT  FE–CPPIT  Altropane  Ioflupane (123I)
N-replaced (S,O,C)
Tropoxane
Irreversible
RTI-76
Nortropanes (N-demethylated)
NS2359 (GSK-372,475)
v  d  e
Stimulants
Adamantanes
Adaphenoxate Adapromine Amantadine Bromantane Chlodantane Gludantane Memantine
Midantane
Arylcyclohexylamines
Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine
Phencyclidine Rolicyclidine Tenocyclidine Tiletamine
Benzazepines
6-Br-APB 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
Convulsants
Anatoxin-a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine
Thujone
Eugeroics
Adrafinil Armodafinil Modafinil
Oxazolines
4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline
Thozalinone
Phenethylamines
2-Fluoroamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2-Phenyl-3-methylaminobutane
2,3-MDA 3-Fluoroamphetamine 3-Fluoromethcathinone 3-Methoxyamphetamine 3-
Methylamphetamine 4-BMC 4-Ethylamphetamine 4-FA 4-FMA 4-MA 4-MMA 4-MTA
Alfetamine -Ethylphenethylamine Amfecloral Amfepentorex Amfepramone Amidephrine
Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine
Atomoxetine (Tomoxetine) -Methylphenethylamine Benfluorex Benzphetamine BDB (J)
BOH (Hydroxy-J) BPAP Buphedrone Bupropion (Amfebutamone) Butylone Cathine
Cathinone Chlorphentermine Clenbuterol Clobenzorex 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) Ethylone
Etilefrine Fenbutrazate Fencamine Fencamfamine Fenethylline Fenfluramine
(Dexfenfluramine) Fenproporex Flephedrone Fludorex Furfenorex Gepefrine HMMA
Hordenine Ibopamine Indanorex IMP Indanylamphetamine Isoetarine 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 Naphthylamphetamine Nisoxetine Norepinephrine (Noradrenaline)
Norfenefrine Norfenfluramine Normetanephrine Octopamine Orciprenaline Ortetamine
Oxilofrine Paredrine (Norpholedrine, Oxamphetamine, Mycadrine) PBA PCA PHA
Pargyline Pentylone Phendimetrazine Phenmetrazine Phenpentermine 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 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119
MeOPP MBZP Vanoxerine
Piperidines
2-Benzylpiperidine 4-Benzylpiperidine Desoxypipradrol Diphemethoxidine Ethylphenidate
Methylnaphthidate Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol
SCH-5472
Pyrrolidines
-PPP -PBP -PVP MDPPP MDPBP MDPV MPBP MPHP MPPP MOPPP Naphyrone
Prolintane Pyrovalerone
Tropanes
3-Bis-(4-fluorophenyl)methoxytropane 3-CPMT 3-Pseudotropyl-4-fluorobenzoate Altropane
(IACFT) Brasofensine CFT (WIN 35,428) -CIT (RTI-55) Cocaethylene Cocaine
Dichloropane (RTI-111) Difluoropine FE–CPPIT FP–CPPIT Ioflupane (123I) Norcocaine
PIT PTT RTI-31 RTI-32 RTI-51 RTI-105 RTI-112 RTI-113 RTI-117 RTI-121 (IPCIT) RTI-
126 RTI-150 RTI-154 RTI-171 RTI-177 RTI-183 RTI-194 RTI-202 RTI-229 RTI-241 RTI-
336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (-CPT, WIN
35,065-2) Tropoxane WF-23 WF-33 WF-60
Xanthines
Aminophylline Caffeine Dimethazan Paraxanthine Theobromine Theophylline
Others
1-(Thiophen-2-yl)-2-aminopropane 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 2-
Aminotetralin 2-Diphenylmethylpyrrolidine 5-(2-Aminopropyl)indole AL-1095 Amfonelic
acid Amineptine Amiphenazole Atipamezole Bemegride Benzydamine BTQ BTS 74,398
Carphedon Ciclazindol Cilobamine Clofenciclan Cropropamide Crotetamide Diclofensine
Dimethocaine Diphenylprolinol Efaroxan Etamivan Feprosidnine Gamfexine Gilutensin
GYKI-52895 Hexacyclonate Idazoxan Indatraline JNJ-7925476 JZ-IV-10 Lazabemide
Leptacline LR-5182 Mazindol Meclofexonate Medifoxamine Mefexamide Mesocarb
Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline Phthalimidopropiophenone
Propylhexedrine PRC200-SS Rasagiline Rauwolscine Tametraline Tandamine U-23807A
UH-232 Yohimbine
See also Sympathomimetic amines
v  d  e
Dopaminergics
Receptor
Ligands
Agonists
Benzazepines: 6-Br-APB Fenoldopam SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958
SKF-83,959; Ergot-derivatives: Bromocriptine Cabergoline Dihydroergocryptine Lisuride
LSD Pergolide; Dihydrexidine-derivatives: 2-OH-NPA A-86,929 Dihydrexidine Dinapsoline
Dinoxyline Doxanthrine; Morphine-derivatives: Apomorphine Propylnorapomorphine;
Piperazines: ABT-724 Aripiprazole Piribedil WAY-100,635; Others: 7-OH-DPAT 8-OH-
PBZI A-68,930 A-77,636 A-412,997 ABT-670 Amantadine Aplindore CY-208,243
Etilevodopa Melevodopa Memantine PD-128,907 PF-219,061 Pramipexole Pukateine
Quinpirole RDS-127 Rimantadine Ropinirole Rotigotine SKF-89145 SKF-89626
Antagonists
Typical Antipsychotics: Acepromazine Azaperone Benperidol Bromperidol Clopenthixol
Chlorpromazine Chlorprothixene Droperidol Flupentixol Fluphenazine Fluspirilene
Haloperidol Loxapine Mesoridazine Methotrimeprazine Molindone Penfluridol Perazine
Periciazine Perphenazine Pimozide Prochlorperazine Promazine Sulforidazine Thioridazine
Thiothixene Trifluoperazine Triflupromazine Trifluperidol Zuclopenthixol; Atypical
Antipsychotics: Amisulpride Asenapine Clozapine Iloperidone Melperone Olanzapine
Paliperidone Perospirone Quetiapine Risperidone Sertindole Sulpiride Ziprasidone Zotepine;
Antiemetics: AS-8112 Alizapride Bromopride Clebopride Domperidone Metoclopramide
Thiethylperazine; Others: Amoxapine Blonanserin Buspirone Butaclamol N-Ethoxycarbonyl-
2-ethoxy-1,2-dihydroquinoline Ecopipam Eticlopride Fananserin Mosapramine Nafadotride
Nemonapride Nuciferine Raclopride Remoxipride SB-277,011-A SCH-23,390 SKF-83,566
SKF-83,959 Spiperone Spiroxatrine Stepholidine Tetrahydropalmatine Tiapride UH-232
Yohimbine
Reuptake
Inhibitors
Plasmalemmal
DAT Inhibitors
Piperazines: DBL-583 GBR-12,935 Nefazodone Vanoxerine; Piperidines: BTCP
Desoxypipradrol Dextromethylphenidate Ethylphenidate Methylnaphthidate Methylphenidate
Phencyclidine Pipradrol; Pyrrolidines: Diphenylprolinol Methylenedioxypyrovalerone
(MDPV) Naphyrone Prolintane Pyrovalerone; Tropanes: -CPPIT Altropane Brasofensine
CFT Cocaine Dichloropane Difluoropine FE–CPPIT FP–CPPIT Ioflupane (123I) Iometopane
RTI-112 RTI-113 RTI-121 RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 Tenocyclidine
Tesofensine Troparil Tropoxane WF-11 WF-23 WF-31 WF-33; Others: Amfonelic Acid
Amineptine Benzatropine (Benztropine) Bromantane BTQ BTS-74,398 Bupropion
(Amfebutamone) Ciclazindol Diclofensine Dimethocaine Dizocilpine DOV-102,677 DOV-
21,947 DOV-216,303 Etybenzatropine (Ethylbenztropine) Fencamine Fencamfamine GYKI-
52,895 Indatraline Ketamine Lefetamine LR-5182 Manifaxine Mazindol Medifoxamine
Mesocarb Nefopam Nomifensine NS-2359 O-2172 Propylamphetamine Radafaxine SEP-
225,289 SEP-227,162 Sibutramine Tametraline Tripelennamine
TRPC6 Activators
Adhyperforin Hyperforin
Vesicular
VMAT Inhibitors
Deserpidine Ibogaine Reserpine Tetrabenazine
Releasing
Agents
Morpholines: Phendimetrazine Phenmetrazine; Oxazolines: 4-Methylaminorex (4-MAR, 4-
MAX) Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone;
Phenethylamines (also Amphetamines, Cathinones, Phentermines, etc): 2-
Hydroxyphenethylamine (2-OH-PEA) 4-Methylamphetamine (4-MA) 4-
Methylmethamphetamine (4-MMA) Alfetamine Amfecloral Amfepentorex Amfepramone
Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil
-Methylphenethylamine (-Me-PEA) Benzodioxolylbutanamine (BDB)
Benzodioxolylhydroxybutanamine (BOH) Benzphetamine Buphedrone Butylone Cathine
Cathinone Clobenzorex Clortermine D-Deprenyl Dimethoxyamphetamine (DMA)
Dimethoxymethamphetamine (DMMA) Dimethylamphetamine Dimethylcathinone
(Dimethylpropion, Metamfepramone) Ethcathinone (Ethylpropion) Ethylamphetamine
Ethylbenzodioxolylbutanamine (EBDB) Ethylone Fenethylline Fenproporex Flephedrone
Fludorex Furfenorex Hordenine Indanorex Lophophine (Homomyristicylamine) Mefenorex
Mephedrone Methamphetamine (Desoxyephedrine, Methedrine; Dextromethamphetamine,
Levomethamphetamine) Methcathinone (Methylpropion) Methedrone
Methoxymethylenedioxyamphetamine (MMDA) Methoxymethylenedioxymethamphetamine
(MMDMA) Methylbenzodioxolylbutanamine (MBDB) Methylenedioxyamphetamine (MDA;
Tenamfetamine) Methylenedioxyethylamphetamine (MDEA)
Methylenedioxyhydroxyamphetamine (MDOH) Methylenedioxymethamphetamine (MDMA)
Methylenedioxymethylphenethylamine (MDMPEA; Homarylamine)
Methylenedioxyphenethylamine (MDPEA; Homopiperonylamine) Methylone Ortetamine
Parabromoamphetamine (PBA) Parachloroamphetamine (PCA) Parafluoroamphetamine
(PFA) Parafluoromethamphetamine (PFMA) Parahydroxyamphetamine (PHA)
Paraiodoamphetamine (PIA) Paramethoxyamphetamine (PMA)
Paramethoxyethylamphetamine (PMEA) Paramethoxymethamphetamine (PMMA) Paredrine
(Norpholedrine, Oxamphetamine) Phenethylamine (PEA) Pholedrine Phenpromethamine
Prenylamine Propylamphetamine Tiflorex (Flutiorex) Tyramine (TRA) Xylopropamine
Zylofuramine; Piperazines: 2,5-Dimethoxy-4-bromobenzylpiperazine (2C-B-BZP)
Benzylpiperazine (BZP) Methoxyphenylpiperazine (MeOPP; Paraperazine)
Methylbenzylpiperazine (MBZP) Methylenedioxybenzylpiperazine (MDBZP;
Piperonylpiperazine); Others: 2-Amino-1,2-dihydronaphthalene (2-ADN) 2-Aminoindane (2-
AI) 2-Aminotetralin (2-AT) 4-Benzylpiperidine (4-BP) Clofenciclan Cyclopentamine
Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate
Indanylaminopropane (IAP) Isometheptene Methylhexanamine Naphthylaminopropane
(NAP) Octodrine Phthalimidopropiophenone Propylhexedrine (PHX) Tuaminoheptane
(Tuamine)
Enzyme
Inhibitors
Anabolism
PAH Inhibitors
3,4-Dihydroxystyrene
TH Inhibitors
3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone
AAAD / DDC Inhibitors
Benserazide Carbidopa Methyldopa
Catabolism
MAO Inhibitors
Nonselective: Benmoxin Caroxazone Echinopsidine Furazolidone Hydralazine Iproclozide
Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide
Octamoxin Phenelzine Pheniprazine Phenoxypropazine Pivalylbenzhydrazine Procarbazine
Safrazine Tranylcypromine; MAO-A Selective: Amiflamine Bazinaprine Befloxatone Befol
Brofaromine Cimoxatone Clorgiline Esuprone Harmala alkaloids (Harmine, Harmaline,
Tetrahydroharmine, Harman, Norharman, etc) Methylene Blue Metralindole Minaprine
Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone Tyrima; MAO-B Selective: D-
Deprenyl L-Deprenyl (Selegiline) Ladostigil Lazabemide Milacemide Pargyline Rasagiline
COMT Inhibitors
Entacapone Tolcapone
DBH Inhibitors
Disulfiram Nepicastat Tropolone
Others
Precursors
L-Phenylalanine L-Tyrosine L-DOPA (Levodopa)
Cofactors
Ferrous Iron (Fe2+) Tetrahydrobiopterin Vitamin B3 (Niacin, Nicotinamide NADPH)
Vitamin B6 (Pyridoxine, Pyridoxamine, Pyridoxal Pyridoxal Phosphate) Vitamin B9 (Folic
Acid Tetrahydrofolic Acid) Vitamin C (Ascorbic Acid) Zinc (Zn2+)
Others
Activity Enhancers: Benzofuranylpropylaminopentane (BPAP) Phenylpropylaminopentane
(PPAP)
Categories: Cocaine | Dopamine reuptake inhibitors | Stimulants | Tropanes |
Sympathomimetic amines | Medical imaging | NeuroimagingHidden categories: Drugboxes
with an unspecified ATC code | Drug pages needing formula fontification

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