Peganum harmala

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Peganum harmala
Peganum harmala.jpg
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 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.[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]

Beta-carboline[6] Content
1-hydroxy-7-methoxy-β-carboline
2-aldehyde-tetrahydroharmine
3-hydroxylated harmine
6-methoxytetrahydro-1-norharmanone
8-hydroxy-harmine
Acetylnorharmine
Desoxypeganine[7]
Dihydroruine
Dipegene
Harmalacidine (HMC)
Harmalacinine
Harmalanine
Harmalicine
Harmalidine
Harmaline (dihydroharmine, DHH, harmidine) 0.25%[4]–0.79%[8]–5.6%[5]
Harmalol 0.6%[5]–3.90%[4]
Harmane (harman) 0.16%[4]
Harmic acid
Harmic acid methyl ester
Harmine (banisterine, telepathinec, yageine) 0.44%[8]–1.84%[4]–4.3%[5] – The coatings of the seeds are said to contain large amounts of harmine.[9]
Harmine N-oxide
Harmol
Isoharmine
Isopeganine
Norharman
Norharmine (tetrahydro-beta-carboline)
Pegaharmine A
Pegaharmine B
Pegaharmine C
Pegaharmine D
Pegaharmine E
Pegaharmine F
Pegaharmine G
Pegaharmine H
Pegaharmine I
Pegaharmine J
Pegaharmine K
Peganine A
Peganine B
Peganumal A
Peganumal B
Peganumine A
Peganumine B
Ruine
Tetrahydroharman
Tetrahydroharmine (THH, leptaflorine) 0.1%[5]
Tetrahydroharmol
Tetrahydronorharman

Toxicity and harm potential

Dangerous interactions

Skull and crossbones darktextred2.png

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.[13] It is believed that quinazoline alkaloids such as vasicine and vasicinone are responsible for the abortifacient activity of the plant.[14]

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.[15][16][17][18] Since 2005, with caveats, the cultivation, possession or sale of this species is also illegal in Louisiana.[citation needed]

Since 2005, the possession of the seeds, the plant itself, and the alkaloids harmine and harmaline, which it contains, is illegal in France.[19] 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.[20] In Australia, harmala alkaloids are illegal.[citation needed]

See also

External links

References

  1. ↑ USDA Plants Database 
  2. ↑ Moloudizargari, M., Mikaili, P., Aghajanshakeri, S., Asghari, M., Shayegh, J. (2013). "Pharmacological and therapeutic effects of Peganum harmala and its main alkaloids". Pharmacognosy Reviews. 7 (14): 199. doi:10.4103/0973-7847.120524. ISSN 0973-7847. 
  3. ↑ Yuruktumen, A., Karaduman, S., Bengi, F., Fowler, J. (1 January 2008). "Syrian rue tea: A recipe for disaster". Clinical Toxicology. 46 (8): 749–752. doi:10.1080/15563650701323205. ISSN 1556-3650. 
  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. ↑ "Table 4 | Peganum spp.: A Comprehensive Review on Bioactivities and Health-Enhancing Effects and Their Potential for the Formulation of Functional Foods and Pharmaceutical Drugs". www.hindawi.com. 
  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. ↑ 8.0 8.1 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. 
  9. ↑ "African rue or Harmel". cdfa.ca.gov. Archived from the original on 22 October 2015. Retrieved 17 February 2021. 
  10. ↑ Kubo, M., Esumi, T., Imagawa, H., Fukuyama, Y. (2014). "Studies in Natural Products Chemistry". Chemical Diversity of Vibsane-Type Diterpenoids and Neurotrophic Activity and Synthesis of Neovibsanin. 43. Elsevier. pp. 41–78. doi:10.1016/B978-0-444-63430-6.00002-3. ISBN 9780444634306. 
  11. ↑ 11.0 11.1 11.2 Zheng, X., Zhang, Z., Chou, G., Wu, T., Cheng, X., Wang, C., Wang, Z. (September 2009). "Acetylcholinesterase inhibitive activity-guided isolation of two new alkaloids from seeds of Peganum nigellastrum Bunge by an in vitro TLC- bioautographic assay". Archives of Pharmacal Research. 32 (9): 1245–1251. doi:10.1007/s12272-009-1910-x. ISSN 0253-6269. 
  12. ↑ Liu, W., Shi, X., Yang, Y., Cheng, X., Liu, Q., Han, H., Yang, B., He, C., Wang, Y., Jiang, B., Wang, Z., Wang, C. (7 April 2015). "In Vitro and In Vivo Metabolism and Inhibitory Activities of Vasicine, a Potent Acetylcholinesterase and Butyrylcholinesterase Inhibitor". PLOS ONE. 10 (4): e0122366. doi:10.1371/journal.pone.0122366. ISSN 1932-6203. 
  13. ↑ Berdai, M. A., Labib, S., Harandou, M. (14 May 2014). "Peganum harmala L. Intoxication in a Pregnant Woman". Case Reports in Emergency Medicine. 2014: e783236. doi:10.1155/2014/783236. ISSN 2090-648X. 
  14. ↑ Zygophyllaceae - an overview, ScienceDirect Topics 
  15. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named PLANTS
  16. ↑ Alexanian, Kev (2007–2014). "AFRICAN RUE, Now That's What I Call A Weed!" (PDF). Central Oregonian. Crook County, Oregon. pp. 11–12. Archived from the original (PDF) on 30 September 2015. Retrieved 4 March 2019.  Unknown parameter |url-status= ignored (help)
  17. ↑ Alexanian, Kev (2007–2014). "CROOK COUNTY'S NOXIOUS WEED LIST, How We Got This Way" (PDF). Central Oregonian. Crook County, Oregon. pp. 113–114. Archived from the original (PDF) on 30 September 2015. Retrieved 4 March 2019.  Unknown parameter |url-status= ignored (help)
  18. ↑ Alexanian, Kev (2007–2014). "GRANTS A GO-GO, Got Weeds? There May Be Financial Help on the Horizon" (PDF). Central Oregonian. Crook County, Oregon. pp. 117–118. Archived from the original (PDF) on 30 September 2015. Retrieved 4 March 2019.  Unknown parameter |url-status= ignored (help)
  19. ↑ Bruneton, J. (2009). Pharmacognosie, Phytochimie, Plantes médicinales (in French) (4 ed.). Paris: Lavoisier. 
  20. ↑ "Controlled Drugs and Substances Act (S.C 1996, c.19)". Justice Laws Website. 19 September 2019. Retrieved 25 September 2019. 


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