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 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]

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 A
Peganumal B
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]

See also

External links

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. "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/91.5.1179Freely accessible. PMID 18980138. 
  9. "African rue or Harmel". cdfa.ca.gov. Archived from the original on 22 October 2015. Retrieved 17 February 2021. 
  10. Studies in Natural Products Chemistry, Volume 43, page 43
  11. 11.0 11.1 11.2 https://www.ncbi.nlm.nih.gov/pubmed/19784581
  12. https://journals.plos.org/plosone/article?id=10.1371/journal.pone.0122366
  13. https://www.hindawi.com/journals/criem/2014/783236/
  14. https://www.sciencedirect.com/topics/agricultural-and-biological-sciences/zygophyllaceae