Peganum harmala: Difference between revisions

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{{BotanyBox/Peganum harmala}}
{{BotanyBox/Peganum harmala}}
'''''Peganum harmala''''', commonly called '''Syrian rue''', '''harmel''', '''espand''', '''esfand''', '''wild rue''', '''African rue''', or '''aspand''', is a plant native to the eastern Iranian region west to India. It has also spread invasively throughout Arizona, California, Montana, Nevada, Oregon, Texas and Washington.<ref>https://plants.usda.gov/core/profile?symbol=PEHA</ref> The plant itself produces seeds which contain harmala alkaloids and is easily accessible and legal to purchase online.
'''''Peganum harmala''''', commonly called '''Syrian rue''', '''harmel''', '''espand''', '''esfand''', '''wild rue''', '''African rue''', or '''aspand''', is a plant native to the eastern Iranian region west to India. It has also spread invasively throughout Arizona, California, Montana, Nevada, Oregon, Texas and Washington.<ref>{{Citation | title=USDA Plants Database | url=https://plants.usda.gov/home/plantProfile?symbol=PEHA}}</ref> The plant itself produces seeds which contain harmala alkaloids and is easily accessible and legal to purchase online.


==Chemistry==
==Chemistry==
[[File:Syrianrueseeds.jpg|150px|thumbnail|left|Syrian rue seeds]]
[[File:Syrianrueseeds.jpg|150px|thumbnail|left|Syrian rue seeds]]


Powdered syrian rue seeds act as a MAOI at doses of 2-5g.
Powdered syrian rue seeds act as a RIMA at doses of 2-5g.
Syrian rue seeds contain several different harmala alkaloids at slightly varying percentages. Only some are monoamine oxidase A inhibitors. In one study, total harmala alkaloids were at least 5.9% of dried weight.<ref>http://www.phcogrev.com/article.asp?issn=0973-7847;year=2013;volume=7;issue=14;spage=199;epage=212;aulast=Moloudizargari</ref><ref>http://www.tandfonline.com/doi/abs/10.1080/15563650701323205</ref><ref name=partial/> Seed extracts were potent reversible and competitive inhibitors of MAO-A but poor inhibitors of MAO-B.<ref name="new1" />
Syrian rue seeds contain several different harmala alkaloids at slightly varying percentages. Only some are monoamine oxidase A inhibitors. In one study, total harmala alkaloids were at least 5.9% of dried weight.<ref>{{cite journal | vauthors=((Moloudizargari, M.)), ((Mikaili, P.)), ((Aghajanshakeri, S.)), ((Asghari, M.)), ((Shayegh, J.)) | journal=Pharmacognosy Reviews | title=Pharmacological and therapeutic effects of Peganum harmala and its main alkaloids | volume=7 | issue=14 | pages=199 | date= 2013 | url=http://www.phcogrev.com/article/2013/7/14/1041030973-7847120524 | issn=0973-7847 | doi=10.4103/0973-7847.120524}}</ref><ref>{{cite journal | vauthors=((Yuruktumen, A.)), ((Karaduman, S.)), ((Bengi, F.)), ((Fowler, J.)) | journal=Clinical Toxicology | title=Syrian rue tea: A recipe for disaster | volume=46 | issue=8 | pages=749–752 | date=1 January 2008 | url=https://doi.org/10.1080/15563650701323205 | issn=1556-3650 | doi=10.1080/15563650701323205}}</ref><ref name="partial" /> Seed extracts were potent reversible and competitive inhibitors of MAO-A but poor inhibitors of MAO-B.<ref name="new1" />


Total harmala alkaloids were at least 5.9% of dried weight, in one study.<ref name=partial/>
Total harmala alkaloids were at least 5.9% of dried weight, in one study.<ref name="partial" />


{| class="wikitable sortable" style="text-align: center"
{{Peganum harmala alkaloids}}
|-
! Alkaloid
! Content
! Type
|-
! [[Desoxypeganine]]<ref>https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3841998/</ref>
|
| MAO-A<ref>{{cite journal |last1=Algorta |first1=J |last2=Pena |first2=MA |last3=Maraschiello |first3=C |last4=Alvarez-González |first4=A |last5=Maruhn |first5=D |last6=Windisch |first6=M |last7=Mucke |first7=HA |title=Phase I clinical trial with desoxypeganine, a new cholinesterase and selective MAO-A inhibitor: tolerance and pharmacokinetics study of escalating single oral doses. |journal=Methods and findings in experimental and clinical pharmacology |date=March 2008 |volume=30 |issue=2 |pages=141-7 |doi=10.1358/mf.2008.30.2.1159649 |pmid=18560630}}</ref>
|-
! [[Harmalicidine]]<ref>{{cite journal |last1=Lamchouri |first1=F |last2=Zemzami |first2=M |last3=Jossang |first3=A |last4=Abdellatif |first4=A |last5=Israili |first5=ZH |last6=Lyoussi |first6=B |title=Cytotoxicity of alkaloids isolated from Peganum harmala seeds. |journal=Pakistan journal of pharmaceutical sciences |date=July 2013 |volume=26 |issue=4 |pages=699-706 |pmid=23811445}}</ref>
|
|
|-
! [[Harmaline]] (harmidine)
| 0.25%<ref name=partial/>–0.79%<ref name=chroma/>–5.6%<ref name=new1/>
| [[Reversible inhibitor of monoamine oxidase A]] (RIMA)
|-
! [[Harmalol]]
| 0.6%<ref name=new1/>–3.90%<ref name=partial/>
|
|-
! [[Harmane]] (harman)
| 0.16%<ref name=partial>{{cite journal |vauthors=Hemmateenejad B, Abbaspour A, Maghami H, Miri R, Panjehshahin MR |title=Partial least squares-based multivariate spectral calibration method for simultaneous determination of beta-carboline derivatives in Peganum harmala seed extracts |journal=Anal. Chim. Acta |volume=575 |issue=2 |pages=290–9 |date=August 2006 |pmid=17723604 |doi=10.1016/j.aca.2006.05.093}}</ref>
| MAO-A and MAO B<ref>{{cite journal |last1=Herraiz |first1=T |last2=Chaparro |first2=C |title=Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee. |journal=Life sciences |date=18 January 2006 |volume=78 |issue=8 |pages=795-802 |doi=10.1016/j.lfs.2005.05.074 |pmid=16139309}}</ref>
|-
! [[Harmine]] (banisterine, telepathine)
| 0.44%<ref name=chroma>{{cite journal |vauthors=Pulpati H, Biradar YS, Rajani M |title=High-performance thin-layer chromatography densitometric method for the quantification of harmine, harmaline, vasicine, and vasicinone in Peganum harmala |journal=J AOAC Int |volume=91 |issue=5 |pages=1179–85 |year=2008 |doi=10.1093/jaoac/91.5.1179 |pmid=18980138|doi-access=free }}</ref>–1.84%<ref name=partial/>–4.3%<ref name=new1>{{cite journal |vauthors=Herraiz T, González D, Ancín-Azpilicueta C, Arán VJ, Guillén H |title=beta-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO) |journal=Food Chem. Toxicol. |volume=48 |issue=3 |pages=839–45 |date=March 2010 |pmid=20036304 |doi=10.1016/j.fct.2009.12.019}}</ref> – The coatings of the seeds are said to contain large amounts of harmine.<ref name=cdfa/>
| [[Reversible inhibitor of monoamine oxidase A]] (RIMA)
|-
! [[Tetrahydroharmine]] (THH)
| 0.1%<ref name=new1/>
| [[Serotonine reuptake inhibitor]]<ref name="pmid10404423">{{cite journal |last=Callaway |first=James C. |last2=McKenna |first2=Dennis |author-link2=Dennis McKenna |last3=Grob |first3=Charles S. |title=Pharmacokinetics of hoasca alkaloids in healthy humans |journal=[[Journal of Ethnopharmacology]] |volume=65 |issue=3 |pages=243–56 |date=June 1999 |pmid=10404423 |issn=0279-1072 |doi=10.1016/S0378-8741(98)00168-8|display-authors=etal}}</ref>
|-
! [[Vasicine]] (peganine)<ref name=nook/>
| 0.25%<ref name=chroma/>
|
|-
! [[Vasicinone]]<ref name=nook/>
| 0.0007%<ref name=chroma/>
|
|}


==Toxicity and harm potential==
==Toxicity and harm potential==
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====Cholinergics====
====Cholinergics====
[[Cholinergic]] substances combined with ''Peganum harmala'' can cause a [https://en.wikipedia.org/wiki/Cholinergic_crisis cholinergic crisis] because the plant contains several acetylcholinesterase inhibitors (AChEIs):
[[Cholinergic]] substances combined with ''Peganum harmala'' can cause a [https://en.wikipedia.org/wiki/Cholinergic_crisis cholinergic crisis] because the plant contains several acetylcholinesterase inhibitors (AChEIs):
* Desoxypeganine<ref>Studies in Natural Products Chemistry, Volume 43, page 43</ref>
 
* Harmaline<ref name="Pubmed-19784581">https://www.ncbi.nlm.nih.gov/pubmed/19784581</ref>
*Desoxypeganine<ref>{{cite book | vauthors=((Kubo, M.)), ((Esumi, T.)), ((Imagawa, H.)), ((Fukuyama, Y.)) | date= 2014 | chapter=Studies in Natural Products Chemistry | title=Chemical Diversity of Vibsane-Type Diterpenoids and Neurotrophic Activity and Synthesis of Neovibsanin | publisher=Elsevier | volume=43 | pages=41–78 | url=https://linkinghub.elsevier.com/retrieve/pii/B9780444634306000023 | doi=10.1016/B978-0-444-63430-6.00002-3 | isbn=9780444634306}}</ref>
* Harmine<ref name="Pubmed-19784581" />
*Harmaline<ref name="Pubmed-19784581">{{cite journal | vauthors=((Zheng, X.)), ((Zhang, Z.)), ((Chou, G.)), ((Wu, T.)), ((Cheng, X.)), ((Wang, C.)), ((Wang, Z.)) | journal=Archives of Pharmacal Research | title=Acetylcholinesterase inhibitive activity-guided isolation of two new alkaloids from seeds of Peganum nigellastrum Bunge by an in vitro TLC- bioautographic assay | volume=32 | issue=9 | pages=1245–1251 | date= September 2009 | issn=0253-6269 | doi=10.1007/s12272-009-1910-x}}</ref>
* Harmol<ref name="Pubmed-19784581" />
*Harmine<ref name="Pubmed-19784581" />
* Vasicine (possible)<ref>https://journals.plos.org/plosone/article?id=10.1371/journal.pone.0122366</ref>
*Harmol<ref name="Pubmed-19784581" />
*Vasicine (possible)<ref>{{cite journal | vauthors=((Liu, W.)), ((Shi, X.)), ((Yang, Y.)), ((Cheng, X.)), ((Liu, Q.)), ((Han, H.)), ((Yang, B.)), ((He, C.)), ((Wang, Y.)), ((Jiang, B.)), ((Wang, Z.)), ((Wang, C.)) | journal=PLOS ONE | title=In Vitro and In Vivo Metabolism and Inhibitory Activities of Vasicine, a Potent Acetylcholinesterase and Butyrylcholinesterase Inhibitor | volume=10 | issue=4 | pages=e0122366 | date=7 April 2015 | url=https://journals.plos.org/plosone/article?id=10.1371/journal.pone.0122366 | issn=1932-6203 | doi=10.1371/journal.pone.0122366}}</ref>


====Drug use in pregnancy====
====Drug use in pregnancy====
''Peganum harmala'' can induce miscarriage. It has traditionally been used as an abortifacient agent in Morocco, North Africa, and the Middle East.<ref>https://www.hindawi.com/journals/criem/2014/783236/</ref> It is believed that quinazoline alkaloids such as vasicine and vasicinone are responsible for the abortifacient activity of the plant.<ref>https://www.sciencedirect.com/topics/agricultural-and-biological-sciences/zygophyllaceae</ref>
''Peganum harmala'' can induce miscarriage. It has traditionally been used as an abortifacient agent in Morocco, North Africa, and the Middle East.<ref>{{cite journal | vauthors=((Berdai, M. A.)), ((Labib, S.)), ((Harandou, M.)) | journal=Case Reports in Emergency Medicine | title=Peganum harmala L. Intoxication in a Pregnant Woman | volume=2014 | pages=e783236 | date=14 May 2014 | url=https://www.hindawi.com/journals/criem/2014/783236/ | issn=2090-648X | doi=10.1155/2014/783236}}</ref> It is believed that quinazoline alkaloids such as vasicine and vasicinone are responsible for the abortifacient activity of the plant.<ref>{{Citation | title=Zygophyllaceae - an overview, ScienceDirect Topics | url=https://www.sciencedirect.com/topics/agricultural-and-biological-sciences/zygophyllaceae}}</ref>
 
==Legal issues==
In the United States, it is considered an invasive, noxious weed in the following states: Arizona (prohibited noxious weed), California (A listed noxious weed), Colorado (A listed noxious weed), Nevada (noxious weed), New Mexico (class B noxious weed), and Oregon (A designated weed, under quarantine). This may require land owners to exterminate infestations on their land or be fined, and allows access to government grants to buy herbicides to do so. It is illegal to sell plants of this species in the states listed above.<ref name=PLANTS/><ref name=Oregon1>{{cite news |last=Alexanian |first=Kev |date=2007–2014 |title=AFRICAN RUE, Now That's What I Call A Weed! |url=https://co.crook.or.us/Portals/0/WeedsWarriorsGuidetoCrookCounty.pdf |work=Central Oregonian |pages=11–12 |location=Crook County, Oregon |access-date=4 March 2019 |archive-date=30 September 2015 |archive-url=https://web.archive.org/web/20150930133937/http://co.crook.or.us/Portals/0/WeedsWarriorsGuideToCrookCounty.pdf |url-status=dead }}</ref><ref>{{cite news |last=Alexanian |first=Kev |date=2007–2014 |title=CROOK COUNTY'S NOXIOUS WEED LIST, How We Got This Way |url=https://co.crook.or.us/Portals/0/WeedsWarriorsGuidetoCrookCounty.pdf |work=Central Oregonian |pages=113–114 |location=Crook County, Oregon |access-date=4 March 2019 |archive-date=30 September 2015 |archive-url=https://web.archive.org/web/20150930133937/http://co.crook.or.us/Portals/0/WeedsWarriorsGuideToCrookCounty.pdf |url-status=dead }}</ref><ref>{{cite news |last=Alexanian |first=Kev |date=2007–2014 |title=GRANTS A GO-GO, Got Weeds? There May Be Financial Help on the Horizon |url=https://co.crook.or.us/Portals/0/WeedsWarriorsGuidetoCrookCounty.pdf |work=Central Oregonian |pages=117–118 |location=Crook County, Oregon |access-date=4 March 2019 |archive-date=30 September 2015 |archive-url=https://web.archive.org/web/20150930133937/http://co.crook.or.us/Portals/0/WeedsWarriorsGuideToCrookCounty.pdf |url-status=dead }}</ref> Since 2005, with caveats, the cultivation, possession or sale of this species is also illegal in Louisiana.{{citation needed|date=December 2022}}
 
Since 2005, the possession of the seeds, the plant itself, and the alkaloids [[harmine]] and [[harmaline]], which it contains, is illegal in France.<ref>{{cite book |last=Bruneton |first=J. |date=2009 |title=Pharmacognosie, Phytochimie, Plantes médicinales |language=fr |edition=4 |location=Paris |publisher=Lavoisier}}</ref> In Finland the plant is officially listed as a medicinal plant, which means one would require a doctors prescription to acquire it. In Canada, harmaline is illegal.<ref>{{cite web |url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/page-2.html|title=Controlled Drugs and Substances Act (S.C 1996, c.19)|website=Justice Laws Website|date=19 September 2019|access-date=25 September 2019}}</ref> In Australia, harmala alkaloids are illegal.{{citation needed|date=December 2022}}


==See also==
==See also==
*[[Harmala alkaloids]]
*[[Harmala alkaloids]]
*[[Soma (Haoma)]]
*[[Soma (Haoma)]]
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==External links==
==External links==
*[[wikipedia:Peganum harmala|''Peganum harmala'' (Wikipedia)]]
*[[wikipedia:Peganum harmala|''Peganum harmala'' (Wikipedia)]]
*[https://erowid.org/plants/syrian_rue/syrian_rue.shtml Syrian rue (Erowid)]
*[https://erowid.org/plants/syrian_rue/syrian_rue.shtml Syrian rue (Erowid)]
*[https://www.drugs.com/npp/syrian-rue.html Syrian rue (Drugs.com)]
*[https://drugs-forum.com/wiki/Syrian_Rue Syrian rue (Drugs-Forum)]
*[https://drugs-forum.com/wiki/Syrian_Rue Syrian rue (Drugs-Forum)]


==References==
==References==
<references/>
<references />


[[Category:Plant]]
[[Category:Plant]]
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[[Category:Acetylcholinesterase inhibitor]]
[[Category:Acetylcholinesterase inhibitor]]
[[Category:Cytochrome P450 inhibitor]]
[[Category:Cytochrome P450 inhibitor]]
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