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Revision as of 09:23, 21 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 461733743 of page Huperzine_A for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo').		Latest revision as of 00:31, 7 September 2024 edit HodgeBrad (talk | contribs)257 editsm Added a line and reference about it being used to help induce lucid dreaming.
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			{{Short description|Chemical compound}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
			{{cs1 config|name-list-style=vanc|display-authors=6}}
	{{chembox
			{{Drugbox
	| verifiedrevid = 451619690
			| Verifiedfields = changed
	| Name = Huperzine A
			| Watchedfields = changed
	| ImageFile = Huperzine A.png
			| verifiedrevid = 461740300
	| ImageSize = 200px
	| ImageName = Huperzine A		| image = Huperzine A.png
			| width = 200
	| ImageFile1 = HuperzineA3d.png
			| image2 = HuperzineA3d.png
	| ImageSize1 = 200px
			| width2 = 200
	| ImageName1 = Huperzine A 3d
	| IUPACName = (1''R'',9''S'',13''E'')- 1-Amino- 13-ethylidene- 11-methyl- 6-azatricyclo trideca- 2(7),3,10- trien- 5-one		| IUPAC_name = (1''R'',9''R'',13''E'')-1-Amino-13-ethylidene-11-methyl-6-azatricyclotrideca-2(7),3,10-trien-5-one
	| OtherNames = HupA		| synonyms = HupA
	| Section1 = {{Chembox Identifiers		<!--Identifiers-->
			| ATC_prefix = N06
			| ATC_suffix =
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}		| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank = DB01928		| DrugBank = DB01928
			| PubChem = 854026
	| SMILES = C\C2=C\\3CC=1NC(=O)\C=C/C=1(N)(C2)C/3=C\C
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEBI = 78330
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 395280		| ChEMBL = 395280
	| ChemSpiderID = 16736021		| ChemSpiderID = 16736021
			| UNII_Ref = {{fdacite|changed|FDA}}
	| InChI = 1/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3+/t10-,15+/m0/s1
			| UNII = 0111871I23
	| InChIKey = ZRJBHWIHUMBLCN-YQEJDHNABN
			| CAS_number_Ref = {{cascite|changed|??}}
			| CAS_number = 102518-79-6
			<!--Clinical data-->
			| tradename =
			| Drugs.com =
			| legal_AU =
			| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
			| legal_UK =
			| legal_US =
			| routes_of_administration = Oral
			<!--Pharmacokinetic data-->
			| bioavailability =
			| protein_bound =
			| metabolism =
			| elimination_half-life = 10-14h<ref>{{cite journal | vauthors = Li YX, Zhang RQ, Li CR, Jiang XH | title = Pharmacokinetics of huperzine A following oral administration to human volunteers | journal = European Journal of Drug Metabolism and Pharmacokinetics | volume = 32 | issue = 4 | pages = 183–187 | date = 2007 | pmid = 18348466 | doi = 10.1007/BF03191002 | s2cid = 2702029 }}</ref>
			| excretion =
			<!--Physical data-->
			| density =
			| melting_point = 217
			| melting_high = 219
			| melting_notes =
			| solubility =
			<!--Chemical data-->
			| C=15 | H=18 | N=2 | O=1
			| smiles = C/C=C/1\2CC3=C(1(CC(=C2)C)N)C=CC(=O)N3
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3+/t10-,15+/m0/s1		| StdInChI = 1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3+/t10-,15+/m0/s1
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = ZRJBHWIHUMBLCN-YQEJDHNASA-N		| StdInChIKey = ZRJBHWIHUMBLCN-YQEJDHNASA-N
	| CASNo_Ref = {{cascite|correct|??}}
	| CASNo = <!-- blanked - oldvalue: 102518-79-6 -->
	| RTECS =
	}}
	| Section2 = {{Chembox Properties
	| Formula = C<sub>15</sub>H<sub>18</sub>N<sub>2</sub>O
	| MolarMass = 242.32 g/mol
	| Appearance =
	| Density =
	| Solubility =
	| MeltingPt = 217–219 °C
	| BoilingPt =
	| pKb =
	}}
	<!--
	| </nowiki><sub>D</sub>]]
	| -147° (''c'' = 0.36, ])
	|-
	-->
	| Section7 = {{Chembox Hazards
	| ExternalMSDS =
	| MainHazards =
	| FlashPt =
	| RPhrases =
	| SPhrases =
	}}
	| Section8 = {{Chembox Related
	| OtherCpds =
	}}
	}}		}}
			'''Huperzine A''' is a naturally-occurring ] ] compound found in the ] '']''<ref name="Zangara2003"/> and in varying quantities in other food ''Huperzia'' species, including ''H. elmeri'', ''H. carinat'', and ''H. aqualupian''.<ref>{{cite journal | vauthors = Lim WH, Goodger JQ, Field AR, Holtum JA, Woodrow IE | title = Huperzine alkaloids from Australasian and southeast Asian Huperzia | journal = Pharmaceutical Biology | volume = 48 | issue = 9 | pages = 1073–1078 | date = September 2010 | pmid = 20731560 | doi = 10.3109/13880209.2010.485619 | doi-access = free }}</ref> Huperzine A has been investigated as a treatment for neurological conditions such as ], but a 2013 ] of those studies concluded that they were of poor methodological quality and the findings should be interpreted with caution.<ref name="meta2013">{{cite journal | vauthors = Yang G, Wang Y, Tian J, Liu JP | title = Huperzine A for Alzheimer's disease: a systematic review and meta-analysis of randomized clinical trials | journal = PLOS ONE | volume = 8 | issue = 9 | pages = e74916 | date = 2013 | pmid = 24086396 | pmc = 3781107 | doi = 10.1371/journal.pone.0074916 | doi-access = free | bibcode = 2013PLoSO...874916Y }}</ref><ref name=cochranemeta /> Huperzine A inhibits the breakdown of the ] ] (ACh) by the enzyme ]. It is also an antagonist of the NMDA-receptor. It is commonly available over the counter as a ] and marketed as a memory and concentration ].
			Huperzine A has also been noted to help induce ].<ref name="Ferris 2009">{{cite web|title=Lucid Dreaming: A Beginner's Guide|url=http://fourhourworkweek.com/2009/09/21/how-to-lucid-dream/|website=The Four Hour Work Week|accessdate=29 December 2016}}</ref>
			==Pharmacological effects==
			Huperzine A is extracted from '']''.<ref name="Zangara2003">{{cite journal | vauthors = Zangara A | title = The psychopharmacology of huperzine A: an alkaloid with cognitive enhancing and neuroprotective properties of interest in the treatment of Alzheimer's disease | journal = Pharmacology, Biochemistry, and Behavior | volume = 75 | issue = 3 | pages = 675–686 | date = June 2003 | pmid = 12895686 | doi = 10.1016/S0091-3057(03)00111-4 | s2cid = 36435892 }}</ref> It is a reversible ]<ref>{{cite journal | vauthors = Wang R, Yan H, Tang XC | title = Progress in studies of huperzine A, a natural cholinesterase inhibitor from Chinese herbal medicine | journal = Acta Pharmacologica Sinica | volume = 27 | issue = 1 | pages = 1–26 | date = January 2006 | pmid = 16364207 | doi = 10.1111/j.1745-7254.2006.00255.x | quote = Huperzine A (HupA), a novel alkaloid isolated from the Chinese herb Huperzia serrata, is a potent, highly specific and reversible inhibitor of acetylcholinesterase (AChE). | doi-access = free }}</ref><ref>{{cite book | url=https://books.google.com/books?id=a5AMBY9ekzcC&q=Huperzine&pg=PA191 | title=Herbs and Nutrients for the Mind: A Guide to Natural Brain Enhancers | publisher=Greenwood Publishing Group | vauthors = Meletis CD, Barke JE | date=2004 | pages=191 | isbn=978-0-275-98394-9}}</ref><ref name="Alzheimer 1996">{{cite journal | vauthors = Wang BS, Wang H, Wei ZH, Song YY, Zhang L, Chen HZ | title = Efficacy and safety of natural acetylcholinesterase inhibitor huperzine A in the treatment of Alzheimer's disease: an updated meta-analysis | journal = Journal of Neural Transmission | volume = 116 | issue = 4 | pages = 457–465 | date = April 2009 | pmid = 19221692 | doi = 10.1007/s00702-009-0189-x | s2cid = 8655284 }}</ref><ref>{{cite journal | vauthors = Tang XC, He XC, Bai DL | title=Huperzine A: A novel acetylcholinesterase inhibitor | journal=Drugs of the Future | date=1999 | volume=24 | issue=6 | pages=647 | doi=10.1358/dof.1999.024.06.545143 }}</ref> and ] antagonist<ref>{{cite journal | vauthors = Coleman BR, Ratcliffe RH, Oguntayo SA, Shi X, Doctor BP, Gordon RK, Nambiar MP | title = -Huperzine A treatment protects against N-methyl-D-aspartate-induced seizure/status epilepticus in rats | journal = Chemico-Biological Interactions | volume = 175 | issue = 1–3 | pages = 387–395 | date = September 2008 | pmid = 18588864 | doi = 10.1016/j.cbi.2008.05.023 }}</ref> that crosses the ].<ref>{{cite journal | vauthors = Patocka J | title = Huperzine A--an interesting anticholinesterase compound from the Chinese herbal medicine | journal = Acta Medica | volume = 41 | issue = 4 | pages = 155–157 | date = 1998 | pmid = 9951045 | doi = 10.14712/18059694.2019.181 | doi-access = free }}</ref> ] is an enzyme that catalyzes the breakdown of the neurotransmitter ACh and other choline esters that function as neurotransmitters. The structure of the complex of huperzine A with acetylcholinesterase has been determined by ] (PDB code: ; ).<ref>{{cite journal | vauthors = Raves ML, Harel M, Pang YP, Silman I, Kozikowski AP, Sussman JL | title = Structure of acetylcholinesterase complexed with the nootropic alkaloid, (-)-huperzine A | journal = Nature Structural Biology | volume = 4 | issue = 1 | pages = 57–63 | date = January 1997 | pmid = 8989325 | doi = 10.1038/nsb0197-57 | s2cid = 236518 }}</ref>
			Huperzine A has been investigated as a possible treatment for diseases characterized by ] such as ],<ref name="Zangara2003" /><ref name="r1">{{cite journal | vauthors = Bai DL, Tang XC, He XC | title = Huperzine A, a potential therapeutic agent for treatment of Alzheimer's disease | journal = Current Medicinal Chemistry | volume = 7 | issue = 3 | pages = 355–374 | date = March 2000 | pmid = 10637369 | doi = 10.2174/0929867003375281 }}</ref> and there is some evidence from small-scale studies that it can benefit cognitive functioning, global clinical status, and ability to engage in ] (ADLs) among individuals with the disease. In a 2016 ],<ref>{{cite journal | vauthors = Laver K, Dyer S, Whitehead C, Clemson L, Crotty M | title = Interventions to delay functional decline in people with dementia: a systematic review of systematic reviews | journal = BMJ Open | volume = 6 | issue = 4 | pages = e010767 | date = April 2016 | pmid = 27121704 | pmc = 4854009 | doi = 10.1136/bmjopen-2015-010767 }}</ref> huperzine A was associated with a ] of 1.48 (], 0.95-2.02) compared to placebo on measures of ADL among people with dementia, but the evidence was very low-quality and uncertain. In a 2022 umbrella review,<ref>{{cite journal | vauthors = Fan F, Liu H, Shi X, Ai Y, Liu Q, Cheng Y | title = The Efficacy and Safety of Alzheimer's Disease Therapies: An Updated Umbrella Review | journal = Journal of Alzheimer's Disease | volume = 85 | issue = 3 | pages = 1195–1204 | date = 2022-02-01 | pmid = 34924395 | doi = 10.3233/JAD-215423 | s2cid = 245311001 }}</ref> huperzine A was associated with broad benefits to dementia patients' cognitive functioning, but the degree of ] in measurements and outcomes of the reviewed studies indicated ] toward huperzine A benefit.
			==Adverse effects==
			Huperzine A may present with mild ] side effects such as nausea, vomiting, and diarrhea.<ref name="cochranemeta">{{cite journal | vauthors = Li J, Wu HM, Zhou RL, Liu GJ, Dong BR | veditors = Wu HM | title = Huperzine A for Alzheimer's disease | journal = The Cochrane Database of Systematic Reviews | volume = CD005592 | issue = 2 | pages = CD005592 | date = April 2008 | pmid = 18425924 | doi = 10.1002/14651858.CD005592.pub2 }}</ref> Slight muscle twitching and slurred speech might also occur, as well as ] and sweating. The use of huperzine A during pregnancy and lactation is not recommended due to the lack of sufficient safety data.<ref name="Natural Standard">{{cite web|title=Huperzine A|url=https://naturalmedicines.therapeuticresearch.com/databases/food,-herbs-supplements/professional.aspx?productid=764#safety|website=Natural Standard: The Authority on Integrative Medicine |publisher=Natural Standard|access-date=29 October 2014}}</ref>
			==Drug interactions==
			Huperzine A may have ] if taken with drugs causing ], such as ]s,<ref name="pepping">{{cite journal | vauthors = Pepping J | title = Huperzine A | journal = American Journal of Health-System Pharmacy | volume = 57 | issue = 6 | pages = 530, 533-530, 534 | date = March 2000 | pmid = 10754762 | doi = 10.1093/ajhp/57.6.530 | doi-access = free }}</ref> which may decrease heart rate. Theoretically, there may be possible additive cholinergic effects if huperzine A is taken with other ]s or ] agents.<ref>{{cite journal | vauthors = Skolnick AA | title = Old Chinese herbal medicine used for fever yields possible new Alzheimer disease therapy | journal = JAMA | volume = 277 | issue = 10 | pages = 776 | date = March 1997 | pmid = 9052690 | doi = 10.1001/jama.1997.03540340010004 }}</ref>
			==Safety==
			Huperzine A, in spite of the possible cholinergic side effects, seems to have a wide margin of safety. ] studies show huperzine A to be non-toxic even when administered at 50-100 times the human therapeutic dose. The extract is active for 6 hours at a dose of 2 μg/kg with no remarkable side effects.<ref name="Safety">{{cite journal | vauthors = Lallement G, Baille V, Baubichon D, Carpentier P, Collombet JM, Filliat P, Foquin A, Four E, Masqueliez C, Testylier G, Tonduli L, Dorandeu F | title = Review of the value of huperzine as pretreatment of organophosphate poisoning | journal = Neurotoxicology | volume = 23 | issue = 1 | pages = 1–5 | date = May 2002 | pmid = 12164543 | doi = 10.1016/S0161-813X(02)00015-3 }}</ref>
			==Other possible uses==
			Huperzine A might be useful in the treatment of ] by preventing damage to the ] caused by such agents.
			<ref name="Poisoning">{{cite web|title=Review of the Value of Huperzine as Pretreatment of Organophosphate Poisoning|url=https://nutritionreview.org/2013/04/huperzinea/|website=Nutrition Review|date=22 April 2013}}</ref>
			<ref name="Poisoning2">{{cite journal | vauthors = Liu L, Sun JX | title = | journal = Wei Sheng Yan Jiu = Journal of Hygiene Research | volume = 34 | issue = 2 | pages = 224–226 | date = March 2005 | pmid = 15952670 | url = https://europepmc.org/article/med/15952670 }}</ref>
			==Synthesis==
			Two scalable and efficient ] of huperzine A have been reported.<ref>{{cite journal | vauthors = un MK, Wüstmann DJ, Herzon SB | title=A robust and scalable synthesis of the potent neuroprotective agent (−)-huperzine A | journal=Chemical Science | date=2011 | volume=2 | issue=11 | pages=2251–2253 | doi=10.1039/C1SC00455G | s2cid=98224866 }}</ref><ref>{{cite journal | vauthors = Tudhope SR, Bellamy JA, Ball A, Rajasekar D, Azadi-Ardakani M, Meera HS, Gnanadeepam JM, Saiganesh R, Gibson F, He L, Behrens CH | title=Development of a Large-Scale Synthetic Route to Manufacture (−)-Huperzine A | journal=Organic Process Research & Development | date=2012 | volume=16 | issue=4 | pages=635–642 | doi=10.1021/op200360b }}</ref>
			== References ==
			{{Reflist|2}}
			== External links ==
			* in ]
			{{Antidementia}}
			{{Acetylcholine metabolism and transport modulators}}
			{{Ionotropic glutamate receptor modulators}}
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