hemantane

{{Short description|Experimental antiparkinsonian agent and adamantane derivative}}

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| CAS_number = 299424-44-5

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| PubChem = 9838302

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| ChemSpiderID = 8014022

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| synonyms = Hymantane; Gimantan; N-Adamant-2-ylhexamethyleneimine; N-(2-Adamantyl)hexamethyleneimine

| IUPAC_name = 1-(2-adamantyl)azepane

| C=16 | H=27 | N=1

| SMILES = C1CCCN(CC1)C2C3CC4CC(C3)CC2C4

| StdInChI = 1S/C16H27N/c1-2-4-6-17(5-3-1)16-14-8-12-7-13(10-14)11-15(16)9-12/h12-16H,1-11H2

| StdInChIKey = JAROVUWOMYMQCW-UHFFFAOYSA-N

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Hemantane, or hymantane, also known as N-(2-adamantyl)hexamethyleneimine, is an experimental antiparkinsonian agent of the adamantane family that was never marketed.{{cite journal | vauthors = Abaimov DA, Kovalev GI | title=Sigma receptors as a pharmacological target for neuroprotectors. New horizons of pharmacotherapy of Parkinson disease | journal=Neurochemical Journal | volume=5 | issue=2 | date=2011 | issn=1819-7124 | doi=10.1134/S1819712411010028 | pages=83–91}} It was developed and studied in Russia.

It has been said to act as a low-affinity non-competitive NMDA receptor antagonist, as a selective MAO-B inhibitor, and as showing various other actions and effects such as modulation of the dopaminergic and serotonergic systems in the striatum.{{cite journal | vauthors = Fischler PV, Soyka M, Seifritz E, Mutschler J | title = Off-label and investigational drugs in the treatment of alcohol use disorder: A critical review | journal = Frontiers in Pharmacology | volume = 13 | issue = | pages = 927703 | date = 2022 | pmid = 36263121 | pmc = 9574013 | doi = 10.3389/fphar.2022.927703 | doi-access = free }} The drug has also been theorized to be a sigma receptor agonist, which is said to likely be involved in its dopaminergic effects. Analogues of hemantane, such as memantine and amantadine, share some of these actions, like NMDA receptor antagonism, sigma receptor agonism, and dopaminergic modulation.

The drug was first described by 2000.{{cite journal | vauthors = Val'dman EA | title = [Pharmacological activity of the new adamantane derivative--potential antiparkinson preparation during subchronic administration] | language = Russian | journal = Eksperimental'naia i Klinicheskaia Farmakologiia | volume = 63 | issue = 5 | pages = 3–6 | date = 2000 | pmid = 11109514 | doi = }}{{cite journal | vauthors = Andiarzhanova EA, Val'dman EA, Kudrin VS, Raevskiĭ KS, Voronina TA | title = [Effect of the new potential anti-Parkinson agent, hymantane, on levels of monoamines and their metabolites in rat striatum (a microdialysis study)] | language = Russian | journal = Eksperimental'naia i Klinicheskaia Farmakologiia | volume = 64 | issue = 6 | pages = 13–16 | date = 2001 | pmid = 11871228 | doi = }}

The dosage of gimantan is standardized to 50mg tablet strength.{{cite journal | vauthors = Tsvetkova EA, Volkova MY, Stepanenko OB, Kislyak NA, Shcherbakova OV, Avdyunina NI, Pyatin BM | title = Gimantan Tablets: Analysis and Standardization. | journal = Pharmaceutical Chemistry Journal | date = January 2002 | volume = 36 | issue = 1 | pages = 48-50 | doi = 10.1023/A:1015761110991 }}