Description
1-(2-adamantyl)azepane (systematic name per PubChem; older form: N-(2-adamantyl)hexamethyleneimine), crystalline powder, 1000 mg package. Material intended exclusively for laboratory and analytical in vitro research. Not for human or animal consumption, not a medicinal product, dietary supplement, food, or cosmetic.
Three different entities that must not be confused
For this molecule, separating the layers is especially important, because hemantane (himantane) was in Russia the subject not only of preclinical research but also of at least one published study involving patients. This does not, however, make it a medicinal product within the meaning of pharmaceutical law — the table below separates these layers explicitly:
| Entity | What it is | Status of hemantane |
|---|---|---|
| Chemical substance hemantane, CAS 299424-44-5 |
Chemical concept — a molecule of defined structure, registered in PubChem (CID 9838302) and in the MeSH thesaurus of the U.S. National Library of Medicine (C122112). | yes — this is the only entity this listing concerns |
| Clinically tested preparation himantane, formerly code A-7 |
Material administered to laboratory animals in preclinical studies and — in one published open-label study from 2008 — to patients with Parkinson’s disease, under clinical trial conditions. | this is not a registered medicinal product. In the databases searched (PubMed, PubChem) no evidence was found of registration under any trade name or of marketing authorization in any country — unlike, for example, bromantane, registered in Russia as Ladasten |
| Chemical reagent material offered here |
Material for laboratory and analytical work. Does not have, and cannot have, authorization for use in humans or animals — it has no pharmaceutical form or medicinal product documentation. | analytics, chemistry, reference standards |
The consequence is unambiguous. The study results cited further on this page come either from preclinical studies on laboratory animals, or from a single published clinical study in which patients were given an investigational preparation — not the analytical reagent sold on this page. None of these studies was conducted using the material offered in this shop, and the 2008 investigational preparation is not a commercially available medicine — it is a scientific publication describing a one-off clinical study, not a pharmaceutical offering. None of these results carries over to the offered reagent and none can be a basis for its use outside the laboratory.
Reagent identification card
| Systematic name (IUPAC, PubChem) | 1-(2-adamantyl)azepane |
|---|---|
| Older systematic name (MeSH) | N-(2-adamantyl)hexamethyleneimine |
| Common name | hemantan, hemantane, himantan / himantane, hymantane |
| Early laboratory code | A-7 |
| CAS Number | 299424-44-5 |
| Molecular formula | C16H27N |
| Molar mass | 233.39 g·mol−1 |
| Monoisotopic mass | 233.2143 Da |
| InChIKey | JAROVUWOMYMQCW-UHFFFAOYSA-N |
| SMILES | C1CCCN(CC1)C2C3CC4CC(C3)CC2C4 |
| PubChem CID | 9838302 |
| MeSH (Supplementary Concept) | C122112 |
| Form | white to off-white crystalline powder |
| Purity | ≥ 98% (HPLC) |
| Intended use | research reagent — not for human or animal consumption |
Note on the CAS number. Number 299424-44-5 comes from this product’s documentation. Neither PubChem (CID 9838302) nor the MeSH record (C122112, entry “N-(2-adamantyl)hexamethylenimine”) assigns this molecule a CAS number as a verified synonym in their own databases — both identify the compound by systematic name and structure, consistent with the data in the table above (C16H27N, approx. 233.4 g/mol). We state this directly rather than passing over it in silence: structural identity is independently confirmed in two NIH databases, whereas the CAS number itself could not be confirmed in those same sources.
The molecule’s lineage: the second branch of the Moscow 2-aminoadamantane program
Hemantane is not a random research molecule — it is the second, lesser-known branch of the same medicinal chemistry line from which bromantane, offered in our catalog, is derived. Both molecules share a common core: the 2-adamantyl substituent, i.e., an adamantane cage attached to the nitrogen atom at position 2, rather than at the bridgehead position 1 (as in amantadine or memantine). They differ in their substituents: bromantane carries a 4-bromophenyl ring, hemantane — a seven-membered azepane ring (older name: hexamethyleneimine).
Early work designated the molecule with the laboratory code A-7 — this is how it appears in publications from 2000–2001, including the classic electrophysiological paper by Sobolevsky and Yelshansky in The Journal of Physiology, describing the mechanism of NMDA channel block using the patch-clamp method. This is one of the few papers from that period to reach the international, English-language peer-reviewed literature rather than only Russian journals.
Later work was carried out at the V.V. Zakusov Institute of Pharmacology in Moscow — the same center bromantane comes from. Among the authors, the name Sergei Seredenin recurs; he led the team responsible for the first indexed bromantane paper from 1999, and for hemantane he appears as a co-author of a 2017 paper on the compound’s effect on ethanol consumption. This is no coincidence — both molecules originate from the same research program, despite different goals: bromantane was developed as an actoprotector, hemantane — as a potential anti-Parkinson’s agent acting via NMDA channel block.
Timeline
| 2000 | first indexed papers under the code A-7: a behavioral study with subchronic administration [1] and an independent electrophysiological paper in The Journal of Physiology, describing the mechanism of “trapping” NMDA channel block [2] |
|---|---|
| 2001 | evaluation of the effect on NMDA receptor ion channels by the patch-clamp method, IC50 in the low tens of µM [3]; first studies on immunotropic activity [4] and the effect on striatal monoamine levels by microdialysis [5] |
| 2003 | distribution of isotopically labeled ³H-himantane in brain and thymus structures [6]; evaluation of the effect on MAO activity [7]; study of the effect on rat embryo development [8] |
| 2004 | evaluation of neuroprotective action in an MPTP neurotoxicity model [9]; study of the effect on reproductive function and gonad morphology [10] |
| 2007 | mechanism of dopamine reuptake in rat striatum ex vivo [11] |
| 2008 | publication describing an open-label clinical study involving patients with Parkinson’s disease [12]; effect on the dopamine transporter DAT protein in striatum and cell culture [13] |
| 2010–2012 | evaluation of the effect on brain dopamine and serotonin receptors with subchronic administration [14]; pharmacokinetics in rats [15], absolute bioavailability in rabbits [16], and excretion in urine and feces [17] — a full pharmacokinetic profile in animal models |
| 2012–2019 | models of the early (premotor) stage of Parkinson’s disease [18], levodopa-induced dyskinesia [19] and hemiparkinsonian syndrome [20], cytoprotective action against the neurotoxin 6-hydroxydopamine [21], reduction of ethanol consumption [22], and alleviation of morphine withdrawal syndrome [23] |
| 2023–2024 | a topical anti-inflammatory formulation in an arthritis model [24], TRPV1-channel-dependent analgesic mechanisms [25], and EEG recording in a Parkinson’s disease model [26] |
Research centers
The literature on hemantane is, as with bromantane, almost exclusively Russian, with the exception of papers reaching international English-language journals (The Journal of Physiology, Bulletin of Experimental Biology and Medicine, Advanced Pharmaceutical Bulletin) — which matters when verifying source data.
- Institute of General Pathology and Pathophysiology (Moscow) — the center responsible for the early electrophysiological characterization of the NMDA channel using patch-clamp [2][3] and for the striatal monoamine microdialysis studies [5].
- V.V. Zakusov Institute of Pharmacology (Moscow) — the same center bromantane comes from. Most of the later work originates here: pharmacokinetics and bioavailability [15][16][17], Parkinson’s disease and neuroprotection models [9][18][19][20][21], addiction research [22][23], and the most recent papers from 2023–2024 [24][25][26].
Disclaimer for the entire section above and for the Timeline. This describes the history of scientific research from 2000–2024. Preclinical studies were conducted on laboratory animals, and the only study involving humans that was found [12] was an open-label clinical study using an investigational preparation, not a registered medicine. This is not a description of the properties of the offered material, does not constitute information on its use, and cannot be a basis for any use outside the laboratory. The offered reagent is not a medicinal product and must not be used in humans or animals.
Chemistry and what it means for the laboratory
The same core as bromantane, a different substituent
The similarity to bromantane does not end with the adamantane cage. Both molecules carry a substituent attached at position 2 of adamantane — rather than at the bridgehead position 1, as in amantadine or memantine — which has a direct structural consequence: substitution at position 2 does not generate a classical stereogenic center, owing to the local symmetry of the cage. As with bromantane, the material does not require enantiomer separation, which simplifies qualification as an analytical standard.
The difference lies in what is attached to the nitrogen. In bromantane it is an aromatic ring (4-bromophenyl); in hemantane — a saturated, seven-membered azepane ring. The nitrogen in this arrangement is tertiary: it carries no hydrogen atom, as can be seen in the computed descriptors below.
Physicochemical characteristics
| Parameter | Value | What it means |
|---|---|---|
| Partition coefficient (XLogP) | ≈ 3.9 | high lipophilicity — elutes late in reversed-phase chromatography |
| Topological polar surface area (TPSA) | 3.2 Å2 | extremely low — lower than in bromantane (12 Å2); typical of a tertiary hydrocarbon amine with no polar groups |
| Hydrogen bond donors | 0 | no N–H — tertiary nitrogen in the azepane ring |
| Hydrogen bond acceptors | 1 | only the lone electron pair on nitrogen |
| Rotatable bonds | 1 | rigid molecule — two rings connected by a single C–N bond |
| Heavy atoms | 17 | — |
Lipophilicity and solubility. The extremely low TPSA and absence of hydrogen bond donors mean that the free base of hemantane has minimal capacity to dissolve in water and dissolves well in organic solvents (DMSO, chloroform, ethanol). It is no coincidence that the MeSH thesaurus lists, alongside the molecule itself, a separate entry for its hydrochloride — the salt form in which the compound was administered to laboratory animals in the studies cited below, since it facilitates the preparation of aqueous solutions for injection. For analytical purposes (HPLC, LC-MS), stock solutions of the free base are prepared in an organic solvent.
No isotope signature. Unlike bromantane — where the bromine atom produces a characteristic pair of peaks in the mass spectrum — hemantane contains only carbon, hydrogen, and nitrogen, elements that are practically monoisotopic in the typical mass range. Identification by mass spectrometry therefore relies on exact molecular mass and retention time, not on an isotope pattern.
Mechanism described in the literature. Electrophysiologically, hemantane has been characterized as a non-competitive, “trapping” (trapping) NMDA channel blocker — using the patch-clamp method on rat hippocampal neurons, with an IC50 in the low tens of micromolar range [2][3]. This is the same general type of block described for amantadine and memantine, on a different structural core. Later work also linked hemantane’s action to the dopaminergic system (DAT transporter [11][13], dopamine receptors [14]) and to MAO-B activity [7].
Nomenclature and synonyms
- Hemantan / Hemantane — the most common form in the English-language literature after 2007;
- Himantan / Himantane and Hymantane — transliteration variants from Cyrillic, dominant in publications from 2000–2004; the same compound, not a different salt or analog;
- Gimantan — a name found in reagent suppliers’ commercial materials; not found in the PubMed or PubChem searches performed, so we treat it as an unconfirmed trade-name variant rather than a separately verified identifier;
- A-7 — the laboratory code from the first publications (2000–2001);
- N-(2-adamantyl)hexamethyleneimine — the older systematic name, used in the MeSH thesaurus; its hydrochloride is the salt form in which the compound was tested in animals;
- 1-(2-adamantyl)azepane — the current IUPAC systematic name per PubChem, the only one unambiguous regardless of bibliographic context.
The transliteration discrepancy has a bibliographic consequence: searching databases only under the term “hemantane” misses a significant part of the earlier literature, indexed under “himantane” or “hymantane”. When querying, it is worth combining all variants.
Laboratory use of the reagent
- reference material for confirming identity and purity by HPLC-UV;
- standard for LC-MS and GC-MS methods — chromatographic techniques coupled with mass spectrometry were used in the cited pharmacokinetic, bioavailability, and excretion studies [15][16][17];
- model compound in electrophysiology of NMDA receptor ion channels (patch-clamp technique), as an example of a “trapping”-type blocker [2][3];
- comparative material in the chemistry of adamantane derivatives — structural contrast with bromantane: the same 2-adamantyl substituent, a different amine fragment (azepane ring instead of 4-bromophenyl);
- standard for work with isotopically labeled compounds — ³H-himantane was used in the tissue distribution studies [6].
Storage, handling, and work safety
Store in the original, tightly closed packaging, in a dry and cool place, protected from light, separately from food and feed and out of the reach of children. Work only under laboratory conditions, using personal protective equipment: gloves, safety goggles, and laboratory clothing; weigh the powder under conditions that limit dust generation. Avoid inhaling dust and contact with skin and eyes. Handle waste in accordance with the regulations applicable to chemical waste at the site where the research is conducted.
Note on safety data. The literature contains preclinical studies of hemantane’s effect on embryonic development and gonad morphology in laboratory animals [8][10], which in itself signals a need for caution rather than removing it. This is not a complete toxicological profile — the data concerning the reagent in the form offered on this page are incomplete. The absence of documented hazard is not equivalent to the absence of hazard; the material should be handled with the caution appropriate for a substance with an unestablished human safety profile.
Regulatory status
In the databases searched (PubMed, PubChem) no evidence was found of hemantane’s registration as a medicinal product under any trade name, nor of marketing authorization in any country. One publication was found describing an open-label clinical study involving patients with Parkinson’s disease [12] — this is a record of a scientific study, not information on drug availability. The legal status of substances of this type can be subject to changes in national law — the buyer is responsible for verifying the legal status in the destination country before ordering. The offered material is a chemical reagent and has no authorization for any use in humans or animals.
Frequently Asked Questions
What is the difference between hemantane and bromantane?
Both have the same core — the 2-adamantyl substituent — and come from the same research center (V.V. Zakusov Institute of Pharmacology, Moscow). They differ in the amine fragment: bromantane carries a 4-bromophenyl ring, hemantane — a saturated azepane ring. The research programs under which they were developed also differ: bromantane as an actoprotector, hemantane as a potential anti-Parkinson’s agent.
Is hemantane (himantane) a registered medicine?
No evidence of this was found in the databases searched. One published open-label clinical study from 2008 was found, in which an investigational preparation was given to patients with Parkinson’s disease — this, however, is a scientific publication describing a study, not information about registration or market availability of a drug, and it is not what this page sells.
What is the chemical formula and molar mass of hemantane?
C16H27N; molar mass 233.39 g·mol−1 (PubChem), monoisotopic mass 233.2143 Da. InChIKey JAROVUWOMYMQCW-UHFFFAOYSA-N.
Is CAS number 299424-44-5 confirmed in scientific databases?
It comes from this product’s documentation. Neither PubChem nor MeSH assigns it to this molecule as a verified synonym — both databases confirm the compound’s identity through its systematic name and structure (consistent with the data in the identification card), not through this number. We state this directly so as not to imply a verification that could not be performed.
Are “Gimantan” and “hemantane” the same compound?
Probably yes — this is a name found in reagent suppliers’ commercial materials, pointing to the same molecule. However, it was not found in the PubMed or PubChem searches performed, so we treat it as an unconfirmed name variant rather than an independently verified identifier.
Is the reagent suitable for uses other than laboratory use?
No. The material is intended exclusively for laboratory and analytical research, not for human or animal consumption, is not a medicine, dietary supplement, food, or cosmetic, and cannot be used for medical, diagnostic, or consumption purposes.
How should hemantane be stored as a laboratory reagent?
In the original, tightly closed packaging, in a dry and cool place, protected from light, separately from food and feed and out of the reach of children.
What does hemantane dissolve in?
The free base dissolves well in organic solvents (DMSO, chloroform, ethanol), poorly in water — with XLogP ≈ 3.9 and an extremely low TPSA (3.2 Ų), stock solutions are prepared in an organic solvent. Animal studies used the hydrochloride form, which facilitates the preparation of aqueous solutions.
Does hemantane require enantiomer separation?
No. As with bromantane, substitution at position 2 of the adamantane cage does not generate a classical stereogenic center — the material does not require enantiomer separation.
What mechanism of action has been described for hemantane in preclinical studies?
Electrophysiologically, it has been characterized as a non-competitive, “trapping” NMDA channel blocker — the same general type of block described for amantadine and memantine. Later work also linked its action to the dopaminergic system and to monoamine oxidase type B activity. This description concerns only the history of scientific research, not the properties of the offered reagent.
Is a safety data sheet included with hemantane?
We provide the safety data sheet on request. Toxicological data for this molecule are incomplete — only selected preclinical studies are available (including the effect on embryonic development in animals); the material should be handled with the caution appropriate for a substance with an unestablished human safety profile.
How many scientific publications concern hemantane?
In the PubMed database under the terms hemantane/himantane/hymantane (as of September 2026), 38 records from 2000–2024 were found. In the Bibliography section below we cite 26 items covering the full thematic and chronological range of this set.
Bibliography
The items below come from the PubMed database (search under the terms hemantane / himantane / hymantane, 38 records in total, as of September 2026) and concern the history of research on the molecule. All items except [12] are preclinical studies in laboratory animals or in vitro studies. Item [12] is the only study involving humans that was found, conducted as an open-label clinical study using an investigational preparation — not using a chemical reagent. The whole list is cited as historical-scientific context and a bibliographic reference, not as information about the use of the offered material nor as an encouragement for any use.
- Val’dman EA (2000). Pharmacological activity of the new adamantane derivative — potential antiparkinson preparation during subchronic administration. Eksp Klin Farmakol. PMID 11109514.
- Sobolevsky AI, Yelshansky MV (2000). The trapping block of NMDA receptor channels in acutely isolated rat hippocampal neurones. J Physiol. PMID 10922002. doi:10.1111/j.1469-7793.2000.t01-2-00493.x.
- Elshanskaia MV, Sobolevskii AI, Val’dman EA et al. (2001). Effect of the potential antiparkinsonian agent adamantane derivative on ion channels of NMDA glutamate receptors. Eksp Klin Farmakol. PMID 11544796.
- Nezhinskaia GI, Val’dman EA, Nazarov PG (2001). Immunotropic activity of a potential antiparkinson agent himantane. Eksp Klin Farmakol. PMID 11548451.
- Andiarzhanova EA, Val’dman EA, Kudrin VS et al. (2001). Effect of the new potential anti-Parkinson agent, hymantane, on levels of monoamines and their metabolites in rat striatum (a microdialysis study). Eksp Klin Farmakol. PMID 11871228.
- Kovalev GI, Rodionov AP, Petrenko ES et al. (2003). Comparative study of the distribution of 3[H]-himantane in the brain structures and the thymus of rats. Eksp Klin Farmakol. PMID 12924235.
- Val’dman EA, Voronina TA, Aksenova LN et al. (2003). Effect of a new antiparkinsonian drug himantane on monoamine oxidase activity. Eksp Klin Farmakol. PMID 14650204.
- Durnev AD, Smol’nikova NM, Nemova EP et al. (2003). Effect of himantane on the rat embryo development. Eksp Klin Farmakol. PMID 14743708.
- Val’dman EA, Nerobkova LN, Voronina TA et al. (2004). Estimation of the protective effect of the novel potential antiparkinsonian agent himantane against MPTP neurotoxicity. Eksp Klin Farmakol. PMID 15079899.
- Smol’nikova NM, Nemova EP, Sorokina AV et al. (2004). The effect of hemantane on the generative function and gonad morphology in rats. Eksp Klin Farmakol. PMID 15707015.
- Abaimov DA, Kovalev GI (2007). The acute and subchronic effects of hemantane on [3H]-dopamine reuptake in rat striatal synaptosomes ex vivo. Eksp Klin Farmakol. PMID 18078034.
- Katunina EA, Petrukhova AV, Avakian GN et al. (2008). The possibilities of using himantane in the treatment of Parkinson’s disease. Zh Nevrol Psikhiatr Im S S Korsakova. PMID 18577930.
- Abaimov DA, Zenina-Antipova TA, Kovalev GI et al. (2008). Effect of antiparkinsonian drug himantane on the content of dopamine transporter DAT protein in rat striatum and cultured pheochromocytoma PC-12 cells. Bull Exp Biol Med. PMID 19039936. doi:10.1007/s10517-008-0083-9.
- Zimin IA, Kapitsa IG, Voronina TA et al. (2010). Effects of subchronic hemantane administration on dopamine and serotonin receptors in intact and MPP+-treated rat brain ex vivo. Eksp Klin Farmakol. PMID 21254589.
- Litvin EA, Bastrygin DV, Kolyvanov GB et al. (2011). Pharmacokinetics of hemantane in rats. Eksp Klin Farmakol. PMID 22288156.
- Litvin EA, Bastrygin DV, Kolyvanov GB et al. (2012). Absolute bioavailability of himantane in rabbits. Bull Exp Biol Med. PMID 22816084. doi:10.1007/s10517-012-1677-9.
- Litvin EA, Bastrygin DV, Kolyvanov GB et al. (2012). Excretion of himantane and its metabolites with the urine and feces in rats. Bull Exp Biol Med. PMID 22977850. doi:10.1007/s10517-012-1746-0.
- Nepoklonov AV, Kapitsa IG, Ivanova EA et al. (2012). Study of hemantane effects in rats on a model of early (premotor) stage of Parkinson’s disease. Eksp Klin Farmakol. PMID 23323324.
- Kapitsa IG, Ivanova EA, Kokshenev II et al. (2014). Influence of hemantane in injectable dosage form on levodopa-induced dyskinesia in rats with model parkinsonian syndrome. Eksp Klin Farmakol. PMID 25033563.
- Ivanova EA, Kapitsa IG, Val’dman EA et al. (2015). Anti-Parkinsonian Activity of Hemantane on a Model of Hemiparkinsonian Syndrome in Rats. Bull Exp Biol Med. PMID 26212814. doi:10.1007/s10517-015-2968-8.
- Logvinov IO, Antipova TA, Nepoklonov AV et al. (2016). Comparison of cytoprotective effects of hemantane and amantadine under conditions of 6-hydroxydopamine neurotoxin action on cultured human neuroblastoma cells. Eksp Klin Farmakol. PMID 27159951.
- Kolik LG, Nadorova AV, Seredenin SB (2017). Non-Competitive NMDA Receptor Antagonist Hemantane Reduces Ethanol Consumption in Long-Term Alcohol Experienced Rats. Bull Exp Biol Med. PMID 29177883. doi:10.1007/s10517-017-3946-0.
- Kolik LG, Konstantinopolsky MA (2019). Comparative Assessment of the Effectiveness of Noncompetitive NMDA Receptor Antagonists Amantadine and Hemantane in Morphine Withdrawal Syndrome Model. Bull Exp Biol Med. PMID 31020587. doi:10.1007/s10517-019-04430-2.
- Ivanova E, Matyushkin A, Sorokina A et al. (2024). Low-Affinity NMDA Receptor Antagonist Hemantane in a Topical Formulation Attenuates Arthritis Induced by Freund’s Complete Adjuvant in Rats. Adv Pharm Bull. PMID 38585463. doi:10.34172/apb.2024.002.
- Ivanova EA, Vasilchuk AG, Voronina TA (2024). Protein Kinase A Inhibitor Attenuates the Antinociceptive Effect of NMDA-Receptor Channel Antagonists in the Capsaicin Test in Mice. Bull Exp Biol Med. PMID 39093477. doi:10.1007/s10517-024-06162-4.
- Voronina NA, Kapitsa IG, Kucheryanu VG et al. (2024). Electric activity of the brain at early and late clinical stages of experimental modeling of Parkinson’s disease, an impact of hemantane. Zh Nevrol Psikhiatr Im S S Korsakova. PMID 39435789. doi:10.17116/jnevro2024124091129.
Identification data and computed descriptors from PubChem (CID 9838302) and the MeSH thesaurus (C122112).
Related reagents in our catalog
- Bromantane (CAS 87913-26-6) — the same 2-adamantyl core and the same research center (V.V. Zakusov Institute of Pharmacology); a different amine fragment and a different research program
- L-DOPA — in the cited literature, hemantane was studied in models of levodopa-induced dyskinesia in experimental parkinsonism; the connection is through a shared research model, not through structural similarity
Statement of product purpose
The offered material is a chemical reagent intended exclusively for research, analytical, and laboratory purposes. It is not intended for human or animal consumption. It is not a medicinal product, dietary supplement, food, medical device, or cosmetic. It must not be used for medical, diagnostic, therapeutic, prophylactic, or consumption purposes, administered to humans or animals, applied to the skin, or added to food, beverages, or feed. Sold exclusively to buyers engaged in research, scientific, or analytical activity, with laboratory facilities and the knowledge needed to safely handle chemical reagents. The buyer bears sole responsibility for the lawful and safe use of the reagent and for compliance with the regulations in force in the destination country.
