View source for Chemistry:Huprine X

{{Short description|Chemical compound}}
{{Drugbox
| IUPAC_name = (1S)-7-chloro-15-ethyl-10-azatetracyclo[11.3.1.0<sup>2,11</sup>.0<sup>4,9</sup>]heptadeca-2,4(9),5,7,10,14-hexaen-3-amine
| image = Huprine-X_structure.png
| width = 200px
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<!--Identifiers-->
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| PubChem = 3632
| ChemSpiderID = 3506
| ChEMBL = 143812
| DrugBank = DB04114
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| smiles = CCC1=CC2CC(C1)C3=C(C4=C(C=C(C=C4)Cl)N=C3C2)N

<!--Chemical data-->
| C=18 | H=19 | Cl=1 | N=2
| StdInChI = 1S/C18H19ClN2/c1-2-10-5-11-7-12(6-10)17-16(8-11)21-15-9-13(19)3-4-14(15)18(17)20/h3-5,9,11-12H,2,6-8H2,1H3,(H2,20,21)
| StdInChIKey = QTPHSDHUHXUYFE-UHFFFAOYSA-N
}}

'''Huprine X''' is a synthetic cholinergic compound developed as a hybrid between the natural product [[Chemistry:Huperzine A|Huperzine A]] and the synthetic drug [[Chemistry:Tacrine|tacrine]]. It is one of the most potent reversible inhibitors of [[Biology:Acetylcholinesterase|acetylcholinesterase]] known, with a binding affinity of 0.026nM,<ref>{{cite journal | vauthors = Camps P, Cusack B, Mallender WD, El Achab RE, Morral J, Muñoz-Torrero D, Rosenberry TL | title = Huprine X is a novel high-affinity inhibitor of acetylcholinesterase that is of interest for treatment of Alzheimer's disease | journal = Molecular Pharmacology | volume = 57 | issue = 2 | pages = 409–17 | date = February 2000 | pmid = 10648652 }}</ref> as well as showing direct agonist activity at both nicotinic and muscarinic [[Biology:Acetylcholine receptor|acetylcholine receptor]]s.<ref>{{cite journal | vauthors = Roman S, Vivas NM, Badia A, Clos MV | title = Interaction of a new potent anticholinesterasic compound (+/-)huprine X with muscarinic receptors in rat brain | journal = Neuroscience Letters | volume = 325 | issue = 2 | pages = 103–6 | date = June 2002 | pmid = 12044632 | doi = 10.1016/s0304-3940(02)00245-8 | s2cid = 30405842 }}</ref><ref>{{cite journal | vauthors = Roman S, Badia A, Camps P, Clos MV | title = Potentiation effects of (+/-)huprine X, a new acetylcholinesterase inhibitor, on nicotinic receptors in rat cortical synaptosomes | journal = Neuropharmacology | volume = 46 | issue = 1 | pages = 95–102 | date = January 2004 | pmid = 14654101 | doi = 10.1016/j.neuropharm.2003.08.005 | s2cid = 19189750 }}</ref> In animal studies it has [[Chemistry:Nootropic|nootropic]] and neuroprotective effects, and is used in research into [[Medicine:Alzheimer's disease|Alzheimer's disease]],<ref>{{cite journal | vauthors = Ratia M, Giménez-Llort L, Camps P, Muñoz-Torrero D, Clos MV, Badia A | title = Behavioural effects and regulation of PKCalpha and MAPK by huprine X in middle aged mice | journal = Pharmacology, Biochemistry, and Behavior | volume = 95 | issue = 4 | pages = 485–93 | date = June 2010 | pmid = 20363245 | doi = 10.1016/j.pbb.2010.03.013 | s2cid = 34525530 }}</ref><ref>{{cite journal | vauthors = Ratia M, Giménez-Llort L, Camps P, Muñoz-Torrero D, Pérez B, Clos MV, Badia A | title = Huprine X and huperzine A improve cognition and regulate some neurochemical processes related with Alzheimer's disease in triple transgenic mice (3xTg-AD) | journal = Neuro-Degenerative Diseases | year = 2013 | volume = 11 | issue = 3 | pages = 129–40 | pmid = 22626981 | doi = 10.1159/000336427 | s2cid = 46024586 }}</ref><ref>{{cite journal | vauthors = Giménez-Llort L, Ratia M, Pérez B, Camps P, Muñoz-Torrero D, Badia A, Clos MV | title = Behavioural effects of novel multitarget anticholinesterasic derivatives in Alzheimer's disease | journal = Behavioural Pharmacology | volume = 28 | issue = 2 and 3-Spec Issue | pages = 124–131 | date = April 2017 | pmid = 28125507 | doi = 10.1097/FBP.0000000000000292 }}</ref><ref>{{cite journal | vauthors = Relat J, Pérez B, Camps P, Muñoz-Torrero D, Badia A, Victòria Clos M | title = Huprine X Attenuates The Neurotoxicity Induced by Kainic Acid, Especially Brain Inflammation | journal = Basic & Clinical Pharmacology & Toxicology | volume = 122 | issue = 1 | pages = 94–103 | date = January 2018 | pmid = 28724203 | doi = 10.1111/bcpt.12852 | doi-access = free }}</ref> and although huprine X itself has not been researched for medical use in humans, a large family of related derivatives have been developed.<ref>{{cite journal | vauthors = Ronco C, Sorin G, Nachon F, Foucault R, Jean L, Romieu A, Renard PY | title = Synthesis and structure-activity relationship of Huprine derivatives as human acetylcholinesterase inhibitors | journal = Bioorganic & Medicinal Chemistry | volume = 17 | issue = 13 | pages = 4523–36 | date = July 2009 | pmid = 19473849 | doi = 10.1016/j.bmc.2009.05.005 }}</ref><ref>{{cite journal | vauthors = Ronco C, Foucault R, Gillon E, Bohn P, Nachon F, Jean L, Renard PY | title = New huprine derivatives functionalized at position 9 as highly potent acetylcholinesterase inhibitors | journal = ChemMedChem | volume = 6 | issue = 5 | pages = 876–88 | date = May 2011 | pmid = 21344648 | doi = 10.1002/cmdc.201000523 | s2cid = 10893910 }}</ref><ref>{{cite journal | vauthors = Galdeano C, Viayna E, Sola I, Formosa X, Camps P, Badia A, Clos MV, Relat J, Ratia M, Bartolini M, Mancini F, Andrisano V, Salmona M, Minguillón C, González-Muñoz GC, Rodríguez-Franco MI, Bidon-Chanal A, Luque FJ, Muñoz-Torrero D | display-authors = 6 | title = Huprine-tacrine heterodimers as anti-amyloidogenic compounds of potential interest against Alzheimer's and prion diseases | journal = Journal of Medicinal Chemistry | volume = 55 | issue = 2 | pages = 661–9 | date = January 2012 | pmid = 22185619 | doi = 10.1021/jm200840c }}</ref>


== References ==
{{Reflist}}

{{Acetylcholine metabolism and transport modulators}}

[[Category:Acetylcholinesterase inhibitors]]
[[Category:Heterocyclic compounds with 4 rings]]
[[Category:Chloroarenes]]
[[Category:Amines]]
[[Category:Nitrogen heterocycles]]


{{Sourceattribution|Huprine X}}