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Peganum harmala

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Peganum harmala
P. harmala in the nature.
Taxonomical nomenclature
Kingdom Plantae
Unranked Angiosperms
Unranked Eudicots
Unranked Rosids
Order Sapindales
Family Nitrariaceae
Genus Peganum
Species P. harmala
Common nomenclature
Common names Espand, Esfand, Syrian rue
Constituents
Active constituents Harmala alkaloid

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.[1] The plant itself produces seeds which contain harmala alkaloids and is easily accessible and legal to purchase online.

Chemistry

Syrian rue seeds

Powdered syrian rue seeds act as a MAOI 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.[2][3][4] Seed extracts were potent reversible and competitive inhibitors of MAO-A but poor inhibitors of MAO-B.[5]

Total harmala alkaloids were at least 5.9% of dried weight, in one study.[4]

Alkaloid Content Type
Desoxypeganine[6] MAO-A[7]
Harmalicidine[8]
Harmaline (harmidine) 0.25%[4]–0.79%[9]–5.6%[5] Reversible inhibitor of monoamine oxidase A (RIMA)
Harmalol 0.6%[5]–3.90%[4]
Harmane (harman) 0.16%[4] MAO-A and MAO B[10]
Harmine (banisterine, telepathine) 0.44%[9]–1.84%[4]–4.3%[5] – The coatings of the seeds are said to contain large amounts of harmine.[11] Reversible inhibitor of monoamine oxidase A (RIMA)
Tetrahydroharmine (THH) 0.1%[5] Serotonine reuptake inhibitor[12]
Vasicine (peganine)[13] 0.25%[9]
Vasicinone[13] 0.0007%[9]

Toxicity and harm potential

Dangerous interactions

See the MAOI page for substances that may cause dangerous interaction.


Cholinergics

Cholinergic substances combined with Peganum harmala can cause a cholinergic crisis because the plant contains several acetylcholinesterase inhibitors (AChEIs):

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.[17] It is believed that quinazoline alkaloids such as vasicine and vasicinone are responsible for the abortifacient activity of the plant.[18]

See also

References

  1. ↑ https://plants.usda.gov/core/profile?symbol=PEHA
  2. ↑ http://www.phcogrev.com/article.asp?issn=0973-7847;year=2013;volume=7;issue=14;spage=199;epage=212;aulast=Moloudizargari
  3. ↑ http://www.tandfonline.com/doi/abs/10.1080/15563650701323205
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 Hemmateenejad B, Abbaspour A, Maghami H, Miri R, Panjehshahin MR (August 2006). "Partial least squares-based multivariate spectral calibration method for simultaneous determination of beta-carboline derivatives in Peganum harmala seed extracts". Anal. Chim. Acta. 575 (2): 290–9. doi:10.1016/j.aca.2006.05.093. PMID 17723604. 
  5. ↑ 5.0 5.1 5.2 5.3 5.4 Herraiz T, González D, Ancín-Azpilicueta C, Arán VJ, Guillén H (March 2010). "beta-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO)". Food Chem. Toxicol. 48 (3): 839–45. doi:10.1016/j.fct.2009.12.019. PMID 20036304. 
  6. ↑ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3841998/
  7. ↑ Algorta, J; Pena, MA; Maraschiello, C; Alvarez-González, A; Maruhn, D; Windisch, M; Mucke, HA (March 2008). "Phase I clinical trial with desoxypeganine, a new cholinesterase and selective MAO-A inhibitor: tolerance and pharmacokinetics study of escalating single oral doses". Methods and findings in experimental and clinical pharmacology. 30 (2): 141–7. doi:10.1358/mf.2008.30.2.1159649. PMID 18560630. 
  8. ↑ Lamchouri, F; Zemzami, M; Jossang, A; Abdellatif, A; Israili, ZH; Lyoussi, B (July 2013). "Cytotoxicity of alkaloids isolated from Peganum harmala seeds". Pakistan journal of pharmaceutical sciences. 26 (4): 699–706. PMID 23811445. 
  9. ↑ 9.0 9.1 9.2 9.3 Pulpati H, Biradar YS, Rajani M (2008). "High-performance thin-layer chromatography densitometric method for the quantification of harmine, harmaline, vasicine, and vasicinone in Peganum harmala". J AOAC Int. 91 (5): 1179–85. doi:10.1093/jaoac/91.5.1179 Freely accessible. PMID 18980138. 
  10. ↑ Herraiz, T; Chaparro, C (18 January 2006). "Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee". Life sciences. 78 (8): 795–802. doi:10.1016/j.lfs.2005.05.074. PMID 16139309. 
  11. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named cdfa
  12. ↑ Callaway, James C.; McKenna, Dennis; Grob, Charles S.; et al. (June 1999). "Pharmacokinetics of hoasca alkaloids in healthy humans". Journal of Ethnopharmacology. 65 (3): 243–56. doi:10.1016/S0378-8741(98)00168-8. ISSN 0279-1072. PMID 10404423. 
  13. ↑ 13.0 13.1 Cite error: Invalid <ref> tag; no text was provided for refs named nook
  14. ↑ Studies in Natural Products Chemistry, Volume 43, page 43
  15. ↑ 15.0 15.1 15.2 https://www.ncbi.nlm.nih.gov/pubmed/19784581
  16. ↑ https://journals.plos.org/plosone/article?id=10.1371/journal.pone.0122366
  17. ↑ https://www.hindawi.com/journals/criem/2014/783236/
  18. ↑ https://www.sciencedirect.com/topics/agricultural-and-biological-sciences/zygophyllaceae
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