Bromantane, ≥98%

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An atypical stimulant and anxiolytic with dopaminergic mechanisms. Immunomodulator. 

Chemical NameN-(4-Bromophenyl)adamantan-2-amine
SynonymsLadasten; Bromantan; 2-(4-Bromophenyl)aminoadamantane; 
CAS #87913-26-6
FormWhite powder
Molecular FormulaC16H20BrN
Molecular Weight306.247 g/mol
SolubilityEasily soluble in acetone, dioxane, diethyl ether, and choloform. Soluble in hexane. Slightly soluble in ethanol (produces toxic ethylbromides). Insoluble in water.

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Precaution and Disclaimer:

This Material is Sold For Research Use Only. Terms of Sale Apply. Not for Human Consumption, nor Medical, Veterinary, or Household Uses.

Chemical Information:

CAS Number:87913-26-6
Purity:≥98%
Molecular Weight:306.247 g/mol
Melting Point:105-107 °C
Molecular Formula:C16H20BrN
Synonyms: Ladasten; Bromantan; 2-(4-Bromophenyl)aminoadamantane ; N-(2-adamantyl)-N-(p-bromophenyl)-amine; N-(4-Bromophenyl)tricyclo[3.3.1.13,7]decan-2-amine
PubChem CID:4660557
SMILES:C1C2CC3CC1CC(C2)C3NC4=CC=C(C=C4)Br

 

Technical Information:

Application:Bromantane is an atypical stimulant and anxiolytic with dopaminergic and possible serotonergic effects that produces additional immunomodulation. 
Appearance:White powder
Physical State:Solid
Solubility:Easily soluble in acetone, dioxane, diethyl ether, and choloform. Soluble in hexane. Slightly soluble in ethanol (produces toxic ethylbromides). Insoluble in water
Storage:Store at room temperature or cooler, in a sealed airtight container, protected from heat, light and humidity.
Stability:Stable for at least two years when stored as above.

 

Background:

Bromantane (N-(4-Bromophenyl)adamantan-2-amine, Ladasten) is a stimulant and anxiolytic derivative of Adamantane, developed in Russia in the late 1980s. It is considered an atypical stimulant, and possesses both dopaminergic and possibly serotonergic effects. However, its exact mechanism of action has not yet been fully established.[1] Some resources refer to Bromantane as an actoprotective or adaptogen substance, with the ability to increase the release of dopamine in the dorsal stratium and to influence the immune system through modulation of T-cell production.[2]

Clinical studies show several pharmacological actions after administration in human subjects. These include increase resistance to overheating and decreased fatigue. As such, Bromantane is said to combine stimulant and anxiolytic effects. Further research has indicated that it accelerates physical restoration after exercise in normal conditions, as well as under hypoxic and hyperthermia stresses. Research has also indicated increased learning capacity and antagonism to sedative actions of tranquilizers, increased body temperature, improved movement coordination, and immunomodulation actions after administration in human and animal studies.[3]

Bromantane manufacture continued in Russia through the 1990s, with limited applications (mostly in sports medicine). It has been utilized in studies of patients with abnormal weakness/lack of energy (asthenic), and has been banned in sports by anti-doping authorities since 1997. [4]

 

Modes of action:

Although often referred to as a stimulant compound, Bromantane possesses distinct mechanisms of action when compared to ‘traditional’ psychostimulants (for example phenylethylamine derivatives). More precisely, it has been: 

shown to induce the genes whose products are involved in various signal pathways (APC, Rb, PKCIP, and PMCA), as well as the genes of cytoskeletal proteins (Tubα1 and actin), synaptic proteins (SynIA&IB and PLP), and enzymes (Gapdh and NSE).” (Vakhitova et al., 2004) [5]

While typical stimulants tend to either inhibit reuptake or induce the release of dopamine, it appears that Bromantane acts instead through genomic mechanisms, which produce rapid and long-lasting increases in the expression of tyrosine hydroxylase (TH) and aromatic L-amino acid decarboxylase (AAAD or DOPA decarboxylase), which are both key enzymes of the dopamine synthesis pathway.[6] These effects have been found to occur in a variety of regions of the brain, including the hypothalamus, striatum, ventral tegmental area, nucleus accumbens, and others.[7]

Research has indicated that amantadine and memantine (compounds of the same class as Bromantane) act as agonists on the σ receptor (K = 7.44 µM and 2.60 µM, respectively). The σ receptor is involved in the dopaminergic effects of memantine, and this mechanism of action may extend to similar compounds, possibly including Bromantane.[8]

Furthermore, animal studies have indicated that administration of Bromantane increases protein kinase C activity in the brain by up to twofold or more. The pharmacological effects of this compound appear to correspond to activation of cAMP-, Ca2+, and phospholipid-dependent protein kinases.[9]

 

Further Scientific research:

There is a fairly large amount of research available on free access journal websites like PubMed and PMC. The information below is intended to give a brief outline of a variety of studies, not a comprehensive account of the available research. 

 

Clinical Reviews:

There is room for further research into the mechanisms of action and pharmacology of this compound in human subjects. As yet, there are no publically accessible literature reviews or meta-analyses focussing on these parameters for this compound.

 

Human studies: 

In 2000, Russian researchers conducted a study on the EEG and psychophysiological effects of Bromantane in 10 healthy volunteers, against placebo. Results pointed to an increase in middle-frequency alpha-rhythm power with lowering of powers in delta- and beta1-bands (similar to many drugs with stimulant and antihypoxic properties. Effects seemed to increase the cognitive functional state and motor performance.[10]

In 1993, a Russian journal published results of a study looking into the effects of Bromantane on coping with and recovery from coacting high-temperature exposure (50 degrees C) and carbon dioxide exposure. Results showed an effective increase in stability of the human body against environmental stresses (adaptogenic effects).[11]

A recent study, published in 2015, examined the use of Ladasten (Bromantane) for weakness syndrome in incurable patients suffering from cancer. Results indicated that the combination of 100 mg Bronantane, 16 mg of ondansetron orally per day and 50 mg of agomelatine per night, appears to be more effective in therapy than standard drug regimes.[12]

In 2014, Russian researchers released results of a study looking into the effects of this compound as an actoprotector and antihypoxant, in terms of its use for short-term adaptation to changes in altitude (from 1670m to 3750m). Results indicated that a combination of metaprote and Bromantane (sold as Ladasten, and at a dosage of 100 – 125 mg) accelerated acclimatization to high altitude (established by red blood cell count and improved physical activity). Interestingly, adaptive changes in the energy supply system could be seen within the first day in the active group, while not being visible in the placebo group or hypoxen (0.5 mg) group until day 3.[13]

 

Toxicology Reviews:

In 2002, researchers looked into the potential for toxic effects of Bromantane administration, at a variety of dosages. As a dose of 30 – 300 mg/kg, the drug produced stimulatory effects, while larger dosages of 600 – 9,600 mg suppressed activity. At all studied doses, mydriasis (pupil dilation) was recorded. At large dosages, this compound caused increased respiration rate and depth, as well as vomiting, diarrhea, and polyuria in some animals.[14]

 

Animal studies:

A 2004 study added to the available research pertaining to the effects of this compound on sexual behaviour and pairing activity in mice. At a Bromantane dosage of 30 and 300 mg/kg (p.o.), sexual proceptivity was increased while chronic administration produced a dose-dependent increase in both proceptivity and receptivity. These effects were hypothesized to be related to dopaminergic interactions.[15]

 In 2011, researchers published their study looking into the effects of Ladasten on a variety of cytokines and behaviour in mice. Male mice were studied using a depression model (induced by a single i.p. injection of bacterial LPS. At doses of 30 – 50mg/kg, Bromantane produced significant decreases in the concentration of inflammatory markers TNF-α and IL-6 in blood plasma. As a reference, the compound was compared to imipramine and found to be more effective in immunomodulation. [16]

In 2007, a study was published looking into the effects of Bromantane and similar adamantine derivatives like memantine on dopaminergic neurotransmission. It was hypothesized that some behavioural effects are related to changes in catecholamine synthesis. Results showed that dosages of 50 mg/kg (p.o.) differentially regulates tyrosine hydroxylase mRNA and protein as well as dopamine and L-DOPA content in various areas of the brain. Furthermore, hippocampal synaptic plasticity was affected: short-term potentiation was transformed to longer-lasting forms of transmission. This suggests that ladasten (Bromantane) produces a reinforcement of short-term potentiation via protein synthesis and dopamine-dependent mechanisms.[17]

 

References:

 

  • [1]  Grekhova TV, Gainetdinov RR, Sotnikova TD, Krasnykh LM, Kudrin VS, Sergeeva SA, Morozov IS. (1995). Effect of bromantane, a new immunostimulating agent with psychostimulating activity, on the release and metabolism of dopamine in the striatum of freely moving rats. A microdialysis study. Bulletin of Experimental Biology and Medicine, 119(3):294–296.
  • [2] Spasov AA, Khamidova TV, Bugaeva LI et al. (2000). Adamantane derivatives: Pharmacological and toxicological properties (review). Pharm Chem J ,34:1.
  • [3] Morozov IS, Klimova NV, Sergeeva SA, Ivanova IA, Barchukov VG, Kovalev GI, Piatin BM, Avdiunina NI. (1999). [Adamantane derivatives enhancing body's resistance to emergencies]. (Article in Russian). Vestn Ross Akad Med Nauk, (3):28-32.
  • [4] Oliynyk S, Oh S. (2012). The Pharmacology of Actoprotectors: Practical Application for Improvement of Mental and Physical Performance. Biomolecules & Therapeutics, 20(5):446-456.
  • [5] Vakhitova YV, Yamidanov RS, Vakhitov VA, et al. (2005). cDNA macroarray analysis of gene expression changes in rat brain after a single administration of a 2-aminoadamantane derivatives. Mol Biol, 39: 244.
  • [6] Vakhitova IuV, Iamidanov RS, Seredinin SB. (2004). [Ladasten induces the expression of genes regulating dopamine biosynthesis in various structures of rat brain].” (Article in Russian). Eksp Klin Farmakol, 67(4):7-11.
  • [7] Vakhitova YV, Yamidanov RS, Vakhitov VA, Seredenin SB. (2005). The effect of ladasten on gene expression in the rat brain. Dokl Biochem Biophys, 401:150-3.
  • [8] Peeters M, Romieu P, Maurice T, Su TP, Maloteaux JM, Hermans E. (2004). Involvement of the sigma 1 receptor in the modulation of dopaminergic transmission by amantadine. Eur J Neurosci, 19(8):2212-20.
  • [9] Vakhitova IuV, Salimgareeva MKh, Seredenin SB. (2004). [Effect of ladasten on the proteinase C activity in the rat brain cells]. (Article in Russian). Eksp Klin Farmakol, 67(2):12-5.
  • [10] Viatleva OA, Barchukov VG, Morozov IS, Salenko IuA, Zhirnov EN. (2000). [The neuro- and psychophysiological effects of bromantane].” (Article in Russian). Voen Med Zh, 321(8):61-5, 96.
  • [11] Sedov AV, Lukicheva TA, Surovtsev NA, Akin'shin AV, Nazarov LIu, Miroshnik SV. (1993). [Experimental rationale for the use of drugs to increase the resistance of the human body to the combined action of carbon monoxide and hyperthermia]. (Article in Russian). Med Tr Prom Ekol, (9-10):10-1.
  • [12] Ryazankina AA, Rozengard SA, Glushchenko VA, Karitsky AP, Kvashnin AV. (2015). [Optimization of pharmacological therapy for weakness syndrome in incurable patients].” (Article in Russian). Vopr Onkol, 61(2):270-3.
  • [13] Kundashev UK, Zurdinov AZ, Barchukov VG. (2014). Possibilities of the pharmacological correction of adaptive reactions of human organism in short-term moving from middle to high altitude]. (Article in Russian). Eksp Klin Farmakol, 77(9):32-7.
  • [14] Kuzubova EA, Bugaeva LI, Spasov AA. (2004). [The effect of bromantan on the sexual behavior and conception in rats]. (Article in Russian). Eksp Klin Farmakol, 67(3):34-7.
  • [15] Tallerova AV, Kovalenko LP, Durnev AD, Seredenin SB. (2011). Effect of ladasten on the content of cytokine markers of inflammation and behavior of mice with experimental depression-like syndrome.” Bull Exp Biol Med, 152(1):58-60.
  • [16] Mikhaylova M, Vakhitova JV, Yamidanov RS, Salimgareeva MKh, Seredenin SB, Behnisch T. (2007). The effects of ladasten on dopaminergic neurotransmission and hippocampal synaptic plasticity in rats. Neuropharmacology, 53(5):601-8.
  • [17] Iezhitsa IN, Spasov AA, Bugaeva LI, Morozov IS. (2002). Toxic effect of single treatment with bromantane on neurological status of experimental animals. Bull Exp Biol Med, 133(4):380-3.

Precaution and Disclaimer:

This Material is Sold For Research Use Only. Terms of Sale Apply. Not for Human Consumption, nor Medical, Veterinary, or Household Uses.

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