Huprine X

Huprine X
Identifiers
	IUPAC name (1S)-7-chloro-15-ethyl-10-azatetracyclo[11.3.1.02,11.04,9]heptadeca-2,4(9),5,7,10,14-hexaen-3-amine;
PubChem CID	3632;
DrugBank	DB04114;
ChemSpider	3506;
ChEMBL	ChEMBL143812;
Chemical and physical data
Formula	C18H19ClN2
Molar mass	298.81 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC1=CC2CC(C1)C3=C(C4=C(C=C(C=C4)Cl)N=C3C2)N;
	InChI InChI=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); Key:QTPHSDHUHXUYFE-UHFFFAOYSA-N;

Huprine X is a synthetic cholinergic compound developed as a hybrid between the natural product Huperzine A and the synthetic drug tacrine. It is one of the most potent reversible inhibitors of acetylcholinesterase known, with a binding affinity of 0.026nM,[1] as well as showing direct agonist activity at both nicotinic and muscarinic acetylcholine receptors.[2][3] In animal studies it has nootropic and neuroprotective effects, and is used in research into Alzheimer's disease,[4][5][6][7] and although huprine X itself has not been researched for medical use in humans, a large family of related derivatives have been developed.[8][9][10]

References

Camps P, Cusack B, Mallender WD, El Achab RE, Morral J, Muñoz-Torrero D, Rosenberry TL (February 2000). "Huprine X is a novel high-affinity inhibitor of acetylcholinesterase that is of interest for treatment of Alzheimer's disease". Molecular Pharmacology. 57 (2): 409–17. PMID 10648652.
Roman S, Vivas NM, Badia A, Clos MV (June 2002). "Interaction of a new potent anticholinesterasic compound (+/-)huprine X with muscarinic receptors in rat brain". Neuroscience Letters. 325 (2): 103–6. doi:10.1016/s0304-3940(02)00245-8. PMID 12044632. S2CID 30405842.
Roman S, Badia A, Camps P, Clos MV (January 2004). "Potentiation effects of (+/-)huprine X, a new acetylcholinesterase inhibitor, on nicotinic receptors in rat cortical synaptosomes". Neuropharmacology. 46 (1): 95–102. doi:10.1016/j.neuropharm.2003.08.005. PMID 14654101. S2CID 19189750.
Ratia M, Giménez-Llort L, Camps P, Muñoz-Torrero D, Clos MV, Badia A (June 2010). "Behavioural effects and regulation of PKCalpha and MAPK by huprine X in middle aged mice". Pharmacology, Biochemistry, and Behavior. 95 (4): 485–93. doi:10.1016/j.pbb.2010.03.013. PMID 20363245. S2CID 34525530.
Ratia M, Giménez-Llort L, Camps P, Muñoz-Torrero D, Pérez B, Clos MV, Badia A (2013). "Huprine X and huperzine A improve cognition and regulate some neurochemical processes related with Alzheimer's disease in triple transgenic mice (3xTg-AD)". Neuro-Degenerative Diseases. 11 (3): 129–40. doi:10.1159/000336427. PMID 22626981. S2CID 46024586.
Giménez-Llort L, Ratia M, Pérez B, Camps P, Muñoz-Torrero D, Badia A, Clos MV (April 2017). "Behavioural effects of novel multitarget anticholinesterasic derivatives in Alzheimer's disease". Behavioural Pharmacology. 28 (2 and 3-Spec Issue): 124–131. doi:10.1097/FBP.0000000000000292. PMID 28125507.
Relat J, Pérez B, Camps P, Muñoz-Torrero D, Badia A, Victòria Clos M (January 2018). "Huprine X Attenuates The Neurotoxicity Induced by Kainic Acid, Especially Brain Inflammation". Basic & Clinical Pharmacology & Toxicology. 122 (1): 94–103. doi:10.1111/bcpt.12852. PMID 28724203.
Ronco C, Sorin G, Nachon F, Foucault R, Jean L, Romieu A, Renard PY (July 2009). "Synthesis and structure-activity relationship of Huprine derivatives as human acetylcholinesterase inhibitors". Bioorganic & Medicinal Chemistry. 17 (13): 4523–36. doi:10.1016/j.bmc.2009.05.005. PMID 19473849.
Ronco C, Foucault R, Gillon E, Bohn P, Nachon F, Jean L, Renard PY (May 2011). "New huprine derivatives functionalized at position 9 as highly potent acetylcholinesterase inhibitors". ChemMedChem. 6 (5): 876–88. doi:10.1002/cmdc.201000523. PMID 21344648. S2CID 10893910.
Galdeano C, Viayna E, Sola I, Formosa X, Camps P, Badia A, et al. (January 2012). "Huprine-tacrine heterodimers as anti-amyloidogenic compounds of potential interest against Alzheimer's and prion diseases". Journal of Medicinal Chemistry. 55 (2): 661–9. doi:10.1021/jm200840c. PMID 22185619.

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[1] Camps P, Cusack B, Mallender WD, El Achab RE, Morral J, Muñoz-Torrero D, Rosenberry TL (February 2000). "Huprine X is a novel high-affinity inhibitor of acetylcholinesterase that is of interest for treatment of Alzheimer's disease". Molecular Pharmacology. 57 (2): 409–17. PMID 10648652.

[2] Roman S, Vivas NM, Badia A, Clos MV (June 2002). "Interaction of a new potent anticholinesterasic compound (+/-)huprine X with muscarinic receptors in rat brain". Neuroscience Letters. 325 (2): 103–6. doi:10.1016/s0304-3940(02)00245-8. PMID 12044632. S2CID 30405842.

[3] Roman S, Badia A, Camps P, Clos MV (January 2004). "Potentiation effects of (+/-)huprine X, a new acetylcholinesterase inhibitor, on nicotinic receptors in rat cortical synaptosomes". Neuropharmacology. 46 (1): 95–102. doi:10.1016/j.neuropharm.2003.08.005. PMID 14654101. S2CID 19189750.

[4] Ratia M, Giménez-Llort L, Camps P, Muñoz-Torrero D, Clos MV, Badia A (June 2010). "Behavioural effects and regulation of PKCalpha and MAPK by huprine X in middle aged mice". Pharmacology, Biochemistry, and Behavior. 95 (4): 485–93. doi:10.1016/j.pbb.2010.03.013. PMID 20363245. S2CID 34525530.

[5] Ratia M, Giménez-Llort L, Camps P, Muñoz-Torrero D, Pérez B, Clos MV, Badia A (2013). "Huprine X and huperzine A improve cognition and regulate some neurochemical processes related with Alzheimer's disease in triple transgenic mice (3xTg-AD)". Neuro-Degenerative Diseases. 11 (3): 129–40. doi:10.1159/000336427. PMID 22626981. S2CID 46024586.

[6] Giménez-Llort L, Ratia M, Pérez B, Camps P, Muñoz-Torrero D, Badia A, Clos MV (April 2017). "Behavioural effects of novel multitarget anticholinesterasic derivatives in Alzheimer's disease". Behavioural Pharmacology. 28 (2 and 3-Spec Issue): 124–131. doi:10.1097/FBP.0000000000000292. PMID 28125507.

[7] Relat J, Pérez B, Camps P, Muñoz-Torrero D, Badia A, Victòria Clos M (January 2018). "Huprine X Attenuates The Neurotoxicity Induced by Kainic Acid, Especially Brain Inflammation". Basic & Clinical Pharmacology & Toxicology. 122 (1): 94–103. doi:10.1111/bcpt.12852. PMID 28724203.

[8] Ronco C, Sorin G, Nachon F, Foucault R, Jean L, Romieu A, Renard PY (July 2009). "Synthesis and structure-activity relationship of Huprine derivatives as human acetylcholinesterase inhibitors". Bioorganic & Medicinal Chemistry. 17 (13): 4523–36. doi:10.1016/j.bmc.2009.05.005. PMID 19473849.

[9] Ronco C, Foucault R, Gillon E, Bohn P, Nachon F, Jean L, Renard PY (May 2011). "New huprine derivatives functionalized at position 9 as highly potent acetylcholinesterase inhibitors". ChemMedChem. 6 (5): 876–88. doi:10.1002/cmdc.201000523. PMID 21344648. S2CID 10893910.

[10] Galdeano C, Viayna E, Sola I, Formosa X, Camps P, Badia A, et al. (January 2012). "Huprine-tacrine heterodimers as anti-amyloidogenic compounds of potential interest against Alzheimer's and prion diseases". Journal of Medicinal Chemistry. 55 (2): 661–9. doi:10.1021/jm200840c. PMID 22185619.