| Identification | Back Directory | [Name]
N-(2-ADAMANTYL)-N-(4-BROMOPHENYL)AMINE | [CAS]
87913-26-6 | [Synonyms]
bromantan
Boomantan
bromantane
AKOS BB-9852
2-(4-BROMOPHENYL)AMINOADAMANTANE
N-(4-bromophenyl)-2-adamantanamine
N-(2-ADAMANTYL)-N-(4-BROMOPHENYL)AMINE
N-(4-BroMophenyl)tricyclo[3.3.1.13,7]decan-2-aMine
Tricyclo[3.3.1.13,7]decan-2-aMine,N-(4-broMophenyl)-
n-(4-bromophenyl)-tricyclo(3.3.1.1(sup3.7))decan-2-amin | [EINECS(EC#)]
207-332-1 | [Molecular Formula]
C16H20BrN | [MDL Number]
MFCD02101627 | [MOL File]
87913-26-6.mol | [Molecular Weight]
306.24 |
| Chemical Properties | Back Directory | [Melting point ]
106-108°C | [Boiling point ]
404.8±28.0 °C(Predicted) | [density ]
1.388±0.06 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
Refrigerator | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly) | [form ]
Solid | [pka]
3.97±0.20(Predicted) | [color ]
White to Off-White | [InChI]
InChI=1S/C16H20BrN/c17-14-1-3-15(4-2-14)18-16-12-6-10-5-11(8-12)9-13(16)7-10/h1-4,10-13,16,18H,5-9H2 | [InChIKey]
LWJALJDRFBXHKX-UHFFFAOYSA-N | [SMILES]
C12CC3CC(CC(C3)C1NC1=CC=C(Br)C=C1)C2 |
| Hazard Information | Back Directory | [Description]
Bromantane(87913-26-6) is an adamantine derivate that has a bromaniline side chain. It has been used therapeutically in Russia as a psychostimulant and anxiolytic. It have serotonergic, dopaminergic and limited noradrenergic actions，similar tomesocarb. Bromantane was first detected in 1996(Ayotte and Goudreault 1999), but due to juridical problems nine doping cases at the Atlanta Olympic Games were classified without consequences for the athletes. It was included in the IOC list of prohibited substances in September 1996，shortly after the Olympic Games.
| [Uses]
N-(2-ADAMANTYL)-N-(4-BROMOPHENYL)AMINE is an adamantane derivative used as an anxiolytic agent.
| [Mechanism of action]
The mechanism of bromantane action is based on the facility to increase the activity of the lower centers of the central nervous system (the hypothalamus nuclei, the reticular nuclei of the operculum, the hippocampus). It does not exert any expressed action on noradrenergic mediators, but implements the activation properties through the dopaminergic system. Bromantane strengthens GABA-ergic mediation, reducing gene expression, supervising synthesis of GABA-transporters, and functioning as a return capture mediator. A potentiality for central serotonin holding effects is also assumed. | [Side effects]
Bromantane(87913-26-6) is said to have no addictive potential, and research done thus far shows that it doesn’t have serious side effects. Some users have reported having experienced brain fog, depression, and fatigue after the use of Bromantane. Nonetheless, there hasn't been sufficient research on Bromantane. Most of the trials have been conducted on rodents; therefore, its safety in humans is still uncertain.
| [Metabolism]
Bromantane, upon oral induction, is quickly but not fully absorbed from the gastrointestinal tract into the blood (bioavailability: 42%). It is quickly, and in large quantities, distributed over the tissues and organs, and is slowly eliminated from the body. Bromantane is highly lipophilic, is distributed into the lipids of brain and fat tissue and, finally, is deposited in adipose tissue. The speed of bromantane absorption from the gastrointestinal tract is much higher in women, so the half-life is respectively lower than in men. The time to achievement of the maximum concentration of blood bromantane is 2.75 hours in women, and 4.0 hours in men. The drug is metabolized in the liver, but its elimination occurs mostly through the adrenal gland. Bromantane metabolism is characterized mainly by hydroxylation in the 6th position of the adamantan cycle. All of the determined metabolites can be found in urine, even in two weeks after administration of bromantane (this last fact is important for doping control). |
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