Bromantane: Wikis

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Bromantane
Systematic (IUPAC) name


N-(4-bromophenyl)adamantan-2-amine
Identifiers
CAS number	87913-26-6
ATC code	none
PubChem	4660557
Chemical data
Formula	C₁₆H₂₀Br N
Mol. mass	306.246 g/mol
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Legal
Routes	?

Bromantane is a stimulant drug developed in Russia during the late 1980s,^[1]^[2] which acts mainly by inhibiting the reuptake of both dopamine and serotonin in the brain,^[3]^[4]^[5]^[6] although it also has anticholinergic effects at very high doses.^[7]^[8] It was used as a doping agent to enhance athletic performance, and several athletes tested positive for the drug at the 1996 Atlanta Olympic Games,^[9] following which it was added to the banned list. Research on this class of drugs has been fairly extensive and a large family of derivatives are known, although bromantane remains the best studied,^[10] and human trials continue for applications such as increasing endurance under extreme conditions.^[11]

References

^ Krapivin SV, Sergeeva SA, Morozov IS. A quantitative pharmaco-electroencephalographic analysis of the action of bromantane. (Russian) Biulleten Eksperimental'noi Biologii i Meditsiny. 1993 Nov;116(11):515-8. PMID 8312546
^ I.S. Morozov, I.A. Ivanova and T.A. Lukicheva (2001). "Search for New Drugs: Actoprotector and Adaptogen properties of Adamantane Derivatives (A Review)". Pharma. Chem. J. 35: 235–238.
^ Grekhova TV, Gaĭnetdinov RR, Sotnikova TD, Krasnykh LM, Kudrin VS, Sergeeva SA, Morozov IS. The effect of bromantane, a new immunostimulant with psychostimulating action, on release and metabolism of dopamine in the dorsal striatum of freely moving rats: a microdialysis study. (Russian) Biulleten Eksperimental'noi Biologii i Meditsiny. 1995 Mar;119(3):302-4. PMID 7795203
^ Kudrin VS, Sergeeva SA, Krasnykh LM, Miroshnichenko II, Grekhova TV, Gaĭnetdinov RR. The effect of bromantane on the dopamin- and serotoninergic systems of the rat brain. (Russian) Eksperimental'naia i Klinicheskaia Farmakologiia. 1995 Jul-Aug;58(4):8-11. PMID 7580761
^ Morozov IS, Pukhova GS, Avdulov NA, Sergeeva SA, Spasov AA, Iezhitsa IN. The mechanisms of the neurotropic action of bromantan. (Russian) Eksperimental'naia i Klinicheskaia Farmakologiia. 1999 Jan-Feb;62(1):11-4. PMID 10198757
^ Seredenin SB, Miramedova AG. Analysis of pharmacological properties of bromantane. (Russian) Biulleten Eksperimental'noi Biologii i Meditsiny. 1999 Nov;128(11):529-31. PMID 10640239
^ Bugaeva LI, Verovskiĭ VE, Iezhitsa IN, Spasov AA. An acute toxicity study of bromantane. (Russian) Eksperimental'naia i Klinicheskaia Farmakologiia. 2000 Jan-Feb;63(1):57-61. PMID 10763112
^ Iezhitsa IN, Spasov AA, Bugaeva LI, Morozov IS. Toxic effect of single treatment with bromantane on neurological status of experimental animals. (Russian) Biulleten Eksperimental'noi Biologii i Meditsiny. 2002 Apr;133(4):380-3. PMID 12124651
^ Burnat P, Payen A, Le Brumant-Payen C, Hugon M, Ceppa F. Bromontan, a new doping agent. Lancet. 1997 Sep 27;350(9082):963-4. PMID 9314900
^ Morozov IS, Klimova NV, Sergeeva SA, Ivanova IA, Barchukov VG, Kovalev GI, Piatin BM, Avdiunina NI. Adamantane derivatives enhancing body's resistance to emergencies. (Russian) Vestnik Rossiiskoi Akademii Meditsinskikh Nauk. 1999;(3):28-32. PMID 10222828
^ Viatleva OA, Barchukov VG, Morozov IS, Salenko IuA, Zhirnov EN. The neuro- and psychophysiological effects of bromantane. (Russian) Voenno-Meditsinskii Zhurnal. 2000 Aug;321(8):61-5, 96. PMID 10998997

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-Methoxyamphetamine • 3-Methylamphetamine • 4-BMC • 4-Ethylamphetamine • 4-FA • 4-FMA • 4-MA • 4-MMA • 4-MTA • Alfetamine • α-Ethylphenethylamine • Amfecloral • Amfepentorex • Amidephrine • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Arbutamine • Atomoxetine (Tomoxetine) • β-Methylphenethylamine • Benfluorex • Benzphetamine • BDB (J) • BOH (Hydroxy-J) • BPAP • Buphedrone • Bupropion (Amfebutamone) • Butylone • Cathine • Cathinone • Chlorphentermine • Clenbuterol • Clobenzorex • Clortermine • D-Deprenyl • Denopamine • Diethylcathinone (Diethylpropion, Amfepramone) • 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) • Medifoxamine • 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 • 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	α-PPP • α-PBP • α-PVP • MDPPP • MDPBP • MDPV • MPBP • MPHP • MPPP • MOPPP • Naphyrone • Prolintane • Pyrovalerone

Tropanes	3α-Bis-(4-fluorophenyl)methoxytropane • 3-CPMT • 3-Pseudotropyl-4-fluorobenzoate • 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-112 • RTI-113 • RTI-121 (IPCIT) • RTI-126 • RTI-150 • RTI-171 • RTI-177 • RTI-336 • RTI-371 • RTI-386 • Tesofensine • Troparil (β-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 • 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 • 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

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 • 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: β-CPPIT • Altropane • Brasofensine • CFT • Cocaine • Dichloropane • Difluoropine • FE-β-CPPIT • FP-β-CPPIT • Ioflupane (¹²³I) • Iometopane • RTI-112 • RTI-113 • RTI-121 • RTI-126 • RTI-150 • RTI-177 • RTI-336 • Tenocyclidine • Tesofensine • Troparil • Tropoxane • WF-11 • WF-23 • WF-31 • WF-33; Others: Amfonelic Acid • Amineptine • Benzatropine • Bromantane • BTQ • BTS-74,398 • Bupropion (Amfebutamone) • Diclofensine • Dimethocaine • Dizocilpine • DOV-102,677 • DOV-21,947 • DOV-216,303 • Etybenzatropine • Fencamine • Fencamfamine • GYKI-52,895 • Indatraline • Ketamine • Lefetamine • LR-5182 • Manifaxine • 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 • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • β-Methylphenethylamine (β-Me-PEA) • Benzodioxolylbutanamine (BDB) • Benzodioxolylhydroxybutanamine (BOH) • Benzphetamine • Buphedrone • Butylone • Cathine • Cathinone • Clobenzorex • Clortermine • D-Deprenyl • Diethylcathinone (Diethylpropion, Amfepramone) • 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 • Furazolidone • Hydralazine • Iproclozide • Iproniazid • Isocarboxazid • Isoniazid • Linezolid • Mebanazine • Metfendrazine • Nialamide • Octamoxin • Phenelzine • Pheniprazine • Phenoxypropazine • Pivalylbenzhydrazine • Procarbazine • Safrazine • Tranylcypromine; MAO-A Selective: Befloxatone • Brofaromine • Cimoxatone • Clorgiline • Harmala alkaloids (Harmine, Harmaline, Tetrahydroharmine, Harman, Norharman, etc) • Metralindole • Minaprine • Moclobemide • Pirlindole • Toloxatone • Tyrima; MAO-B Selective: D-Deprenyl • L-Deprenyl (Selegiline) • Ladostigil • Lazabemide • 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)

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References