Hemantane

Hemantane, or hymantane, also known as N-(2-adamantyl)hexamethyleneimine, is an experimental antiparkinsonian agent of the adamantane family that was never marketed.^[1] It was developed and studied in Russia.^[1]

Other namesHymantane; Gimantan; N-Adamant-2-ylhexamethyleneimine; N-(2-Adamantyl)hexamethyleneimine

CAS Number

299424-44-5

PubChem CID

9838302

ChemSpider

8014022

Quick facts Clinical data, Other names ...

Hemantane
Clinical data

Other names	Hymantane; Gimantan; N-Adamant-2-ylhexamethyleneimine; N-(2-Adamantyl)hexamethyleneimine
Identifiers
IUPAC name 1-(2-adamantyl)azepane
CAS Number	299424-44-5
PubChem CID	9838302
ChemSpider	8014022
Chemical and physical data
Formula	C₁₆H₂₇N
Molar mass	233.399 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1CCCN(CC1)C2C3CC4CC(C3)CC2C4
InChI InChI=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 Key:JAROVUWOMYMQCW-UHFFFAOYSA-N

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.^[1]^[2] The drug has also been theorized to be a sigma receptor agonist.^[1] Analogues of hemantane, such as memantine and amantadine, share some of these actions, like NMDA receptor antagonism, sigma receptor agonism, and dopaminergic modulation.^[1]

The drug was first described by 2000.^[3]^[4]

The dosage of gimantan is standardized to 50mg tablet strength.^[5]

Chemistry

Gimantan is synthesized via a modified Leuckart reaction, by heating adamantanone and azepane in the presence of formic acid.^[6]^[7]^[8]

References

[1]
Abaimov DA, Kovalev GI (2011). "Sigma receptors as a pharmacological target for neuroprotectors. New horizons of pharmacotherapy of Parkinson disease". Neurochemical Journal. 5 (2): 83–91. doi:10.1134/S1819712411010028. ISSN 1819-7124.
[2]
Fischler PV, Soyka M, Seifritz E, Mutschler J (2022). "Off-label and investigational drugs in the treatment of alcohol use disorder: A critical review". Frontiers in Pharmacology. 13 927703. doi:10.3389/fphar.2022.927703. PMC 9574013. PMID 36263121.
[3]
Val'dman EA (2000). "[Pharmacological activity of the new adamantane derivative--potential antiparkinson preparation during subchronic administration]". Eksperimental'naia i Klinicheskaia Farmakologiia (in Russian). 63 (5): 3–6. PMID 11109514.
[4]
Andiarzhanova EA, Val'dman EA, Kudrin VS, Raevskiĭ KS, Voronina TA (2001). "[Effect of the new potential anti-Parkinson agent, hymantane, on levels of monoamines and their metabolites in rat striatum (a microdialysis study)]". Eksperimental'naia i Klinicheskaia Farmakologiia (in Russian). 64 (6): 13–16. PMID 11871228.
[5]
Tsvetkova EA, Volkova MY, Stepanenko OB, Kislyak NA, Shcherbakova OV, Avdyunina NI, et al. (January 2002). "Gimantan Tablets: Analysis and Standardization". Pharmaceutical Chemistry Journal. 36 (1): 48–50. doi:10.1023/A:1015761110991.
[6]
Sergeeva MS, Grushevskaya LN, Pyatin BM, Avdyunina NI, Gaevaya LM, Klumova VS, et al. (November 2011). "Pharmaceutical analysis and standardization of gimantan parenteral dosage form". Pharmaceutical Chemistry Journal. 45 (8): 499–502. doi:10.1007/s11094-011-0664-1.
[7]
Seredenin SB, Voronina TA, Avdyunina NI, Pyatin BM, Morozov IS, Bykov NP, et al. (2010). "SU1825499 "N-(2-adamantyl)hexamethyleneimine hydrochloride with anticataleptic activity". Byull. Izobret. (in Russian). 4.
[8]
Tsvetkova EA, Volkova MY, Stepanenko OB, Avdyunina NI, Bol'shakova RF, Pyatin BM (November 2001). "Analysis and Standardization of the New Domestic Antiparkinsonian Drug Gimantan". Pharmaceutical Chemistry Journal. 35 (11): 635–638. doi:10.1023/A:1015158213734.

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Chemistry

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References

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