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== Occurrence in nature ==
== Occurrence in nature ==
Various plants contain harmaline including ''[[Peganum harmala]]'' (Syrian Rue) as well as the hallucinogenic drink [[ayahuasca]], which is traditionally brewed using ''[[Banisteriopsis caapi]]''.
Various plants contain harmaline including ''[[Peganum harmala]]'' (Syrian Rue) as well as the hallucinogenic beverage [[ayahuasca]], which is traditionally brewed using ''[[Banisteriopsis caapi]]''.
Present at 3% by dry weight, the harmala alkaloids may be extracted from the
Present at 3% by dry weight, the harmala alkaloids may be extracted from the
Syrian Rue seeds.<ref name=erowid>{{ cite web | url = http://www.erowid.org/plants/syrian_rue/syrian_rue_info9.shtml | title = Syrian Rue | publisher = Erowid }}</ref>
Syrian Rue seeds.<ref name=erowid>{{ cite web | url = http://www.erowid.org/plants/syrian_rue/syrian_rue_info9.shtml | title = Syrian Rue | publisher = Erowid }}</ref>
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The harmala alkaloids are psychoactive in humans.<ref name = erowid/>
The harmala alkaloids are psychoactive in humans.<ref name = erowid/>
Harmaline is shown to act as an [[acetylcholinesterase inhibitor]].<ref>{{ cite journal | author = Zheng, X. Y.; Zhang, Z. J.; Chou, G. X.; Wu, T.; Cheng, X. M.; Wang, C. H.; Wang, Z. T. | title = Acetylcholinesterase inhibitive activity-guided isolation of two new alkaloids from seeds of ''Peganum nigellastrum'' Bunge by an ''in vitro'' TLC-bioautographic assay | journal = Archives of Pharmacological Research | year = 2009 | volume = 32 | issue = 9 | pages = 1245–1251 | pmid = 19784581 | doi = 10.1007/s12272-009-1910-x | url = http://www.springerlink.com/content/2561160164458518/ }}</ref> Harmaline also stimulates [[striatum|striatal]] dopamine release in rats at very high dose levels.<ref>{{ cite journal | author = Schwarz, M. J.; Houghton, P. J.; Rose, S.; Jenner, P.; Lees, A. D. | title = Activities of Extract and Constituents of ''Banisteriopsis caapi'' Relevant to Parkinsonism | journal = Pharmacology Biochemistry and Behavior | year = 2003 | volume = 75 | issue = 3 | pages = 627–633 | doi = 10.1016/S0091-3057(03)00129-1 }}</ref> Since harmaline is a [[reversible inhibitor of monoamine oxidase A]], it could, in theory, induce both [[serotonin syndrome]] and [[hypertensive crises]] in combination with serotonergic and catecholaminergic drugs respectively. Harmaline containing plant and tryptamine containing plants are used in ayahausca brews. The inhibitory effects on monoamine oxidase allows [[Dimethyltryptamine|dimethyltryptamine (DMT)]], the psychologically prominent chemical in the mixture, to bypass the extensive first-pass metabolism it undergoes upon ingestion; allowing a psychologically active quantity of the chemical to exist in the brain for a perceivable period of time.<ref name=Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions.>{{ cite web | url = http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3028383/ | title = Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions. | publisher = NCBI }}</ref>
Harmaline is shown to act as an [[acetylcholinesterase inhibitor]].<ref>{{ cite journal | author = Zheng, X. Y.; Zhang, Z. J.; Chou, G. X.; Wu, T.; Cheng, X. M.; Wang, C. H.; Wang, Z. T. | title = Acetylcholinesterase inhibitive activity-guided isolation of two new alkaloids from seeds of ''Peganum nigellastrum'' Bunge by an ''in vitro'' TLC-bioautographic assay | journal = Archives of Pharmacological Research | year = 2009 | volume = 32 | issue = 9 | pages = 1245–1251 | pmid = 19784581 | doi = 10.1007/s12272-009-1910-x | url = http://www.springerlink.com/content/2561160164458518/ }}</ref> Harmaline also stimulates [[striatum|striatal]] dopamine release in rats at very high dose levels.<ref>{{ cite journal | author = Schwarz, M. J.; Houghton, P. J.; Rose, S.; Jenner, P.; Lees, A. D. | title = Activities of Extract and Constituents of ''Banisteriopsis caapi'' Relevant to Parkinsonism | journal = Pharmacology Biochemistry and Behavior | year = 2003 | volume = 75 | issue = 3 | pages = 627–633 | doi = 10.1016/S0091-3057(03)00129-1 }}</ref> Since harmaline is a [[reversible inhibitor of monoamine oxidase A]], it could, in theory, induce both [[serotonin syndrome]] and [[hypertensive crises]] in combination with tyramine, serotonergics, catecholaminergics drugs or prodrugs. Harmaline containing plant and tryptamine containing plants are used in ayahausca brews. The inhibitory effects on monoamine oxidase allows [[Dimethyltryptamine|dimethyltryptamine (DMT)]], the psychologically prominent chemical in the mixture, to bypass the extensive first-pass metabolism it undergoes upon ingestion; allowing a psychologically active quantity of the chemical to exist in the brain for a perceivable period of time.<ref name=Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions.>{{ cite web | url = http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3028383/ | title = Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions. | publisher = NCBI }}</ref> Harmaline forces the anabolic metabolism of serotonin into [[normelatonin]] or [[n-acetylserotonin]], and then to melatonin, the body's principle sleep-regulating hormone and a powerful antioxidant.


United States [[Patent]] Number 5591738 describes a method for treating various chemical dependencies via the administration of harmaline and or other beta-carbolines.<ref name=fpo>{{ cite patent | country = US | number = 5591738 | status = patent | inventor = Howard Lotsof | title = Method of Treating Chemical Dependency Using β-Carboline Alkaloids, Derivatives and Salts thereof | gdate = 1997-01-07 }}</ref>
United States [[Patent]] Number 5591738 describes a method for treating various chemical dependencies via the administration of harmaline and or other beta-carbolines.<ref name=fpo>{{ cite patent | country = US | number = 5591738 | status = patent | inventor = Howard Lotsof | title = Method of Treating Chemical Dependency Using β-Carboline Alkaloids, Derivatives and Salts thereof | gdate = 1997-01-07 }}</ref>
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A study found that a single injection of 40&nbsp;mg/kg in rats or 3 x 25&nbsp;mg/kg spread over 3 days had visible neurotoxic effects.<ref>{{ cite journal | author = O'Hearn, E.; Molliver, M. E. | title = Degeneration of Purkinje Cells in Parasagittal Zones of the Cerebellar Vermis after Treatment with Ibogaine or Harmaline | journal = Neuroscience | year = 1993 | volume = 55 | issue = 2 | pages = 303–310 | pmid = 8377927 | doi = 10.1016/0306-4522(93)90500-F }}</ref>
A study found that a single injection of 40&nbsp;mg/kg in rats or 3 x 25&nbsp;mg/kg spread over 3 days had visible neurotoxic effects.<ref>{{ cite journal | author = O'Hearn, E.; Molliver, M. E. | title = Degeneration of Purkinje Cells in Parasagittal Zones of the Cerebellar Vermis after Treatment with Ibogaine or Harmaline | journal = Neuroscience | year = 1993 | volume = 55 | issue = 2 | pages = 303–310 | pmid = 8377927 | doi = 10.1016/0306-4522(93)90500-F }}</ref>


Harmaline is known to act as a [[histamine N-methyltransferase]] inhibitor,<ref>{{cite journal|last=Cumming|first=P|author2=Vincent SR|title=Inhibition of histamine-N-methyltransferase (HNMT) by fragments of 9-amino-1,2,3,4-tetrahydroacridine (tacrine) and by beta-carbolines|journal=Biochemical Pharmacology|date=September 1992|year=1992|volume=44|issue=5|pages=989–992|doi=10.1016/0006-2952(92)90133-4|pmid=1530666}}</ref> this explains how harmaline elicits its [[Wakefulness-promoting agent|wakefulness-promoting effects]].
Harmaline is known to act as a [[histamine N-methyltransferase]] inhibitor.<ref>{{cite journal|last=Cumming|first=P|author2=Vincent SR|title=Inhibition of histamine-N-methyltransferase (HNMT) by fragments of 9-amino-1,2,3,4-tetrahydroacridine (tacrine) and by beta-carbolines|journal=Biochemical Pharmacology|date=September 1992|year=1992|volume=44|issue=5|pages=989–992|doi=10.1016/0006-2952(92)90133-4|pmid=1530666}}</ref> this explains how harmaline elicits its [[Wakefulness-promoting agent|wakefulness-promoting effects]].


==See also==
==See also==

Revision as of 20:40, 5 August 2014

Harmaline
Clinical data
Dependence
liability		Negligible/Non-existent
Routes of
administration		Ingestion
Legal status
Legal status
  • AU: S9 (Prohibited substance)
Identifiers
  • 7-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.594 Edit this at Wikidata
Chemical and physical data
FormulaC13H14N2O
Molar mass214.263 g/mol g·mol−1
3D model (JSmol)
Melting point232–234 °C (450–453 °F)
  • C\C2=N\CCc1c3ccc(OC)cc3nc12
  • InChI=1S/C13H14N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7,15H,5-6H2,1-2H3 checkY
  • Key:RERZNCLIYCABFS-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Harmaline is a fluorescent psychoactive indole alkaloid from the group of harmala alkaloids and beta-carbolines. It is the reduced hydrogenated form of harmine.

Occurrence in nature

Various plants contain harmaline including Peganum harmala (Syrian Rue) as well as the hallucinogenic beverage ayahuasca, which is traditionally brewed using Banisteriopsis caapi. Present at 3% by dry weight, the harmala alkaloids may be extracted from the Syrian Rue seeds.[1]

Effects

Harmaline and harmine fluoresce under ultraviolet light. These three extractions indicate that the middle one has a higher concentration of the two compounds.

Harmaline is a central nervous system stimulant and a "reversible inhibitor of MAO-A (RIMA)".[2] This means that the risk of a hypertensive crisis, a dangerous high blood pressure crisis from eating tyramine-rich foods such as cheese, is likely lower with harmaline than with irreversible MAOIs such as phenelzine.

The harmala alkaloids are psychoactive in humans.[1] Harmaline is shown to act as an acetylcholinesterase inhibitor.[3] Harmaline also stimulates striatal dopamine release in rats at very high dose levels.[4] Since harmaline is a reversible inhibitor of monoamine oxidase A, it could, in theory, induce both serotonin syndrome and hypertensive crises in combination with tyramine, serotonergics, catecholaminergics drugs or prodrugs. Harmaline containing plant and tryptamine containing plants are used in ayahausca brews. The inhibitory effects on monoamine oxidase allows dimethyltryptamine (DMT), the psychologically prominent chemical in the mixture, to bypass the extensive first-pass metabolism it undergoes upon ingestion; allowing a psychologically active quantity of the chemical to exist in the brain for a perceivable period of time.Cite error: The <ref> tag has too many names (see the help page). Harmaline forces the anabolic metabolism of serotonin into normelatonin or n-acetylserotonin, and then to melatonin, the body's principle sleep-regulating hormone and a powerful antioxidant.

United States Patent Number 5591738 describes a method for treating various chemical dependencies via the administration of harmaline and or other beta-carbolines.[5]

In a study Harmaline has also been found to induce "vasorelaxant effects" in "isolated rat aorta."[6]

A study found that a single injection of 40 mg/kg in rats or 3 x 25 mg/kg spread over 3 days had visible neurotoxic effects.[7]

Harmaline is known to act as a histamine N-methyltransferase inhibitor.[8] this explains how harmaline elicits its wakefulness-promoting effects.

See also

References

  1. ^ a b "Syrian Rue". Erowid.
  2. ^ Massaro, E. J. (2002). Handbook of Neurotoxicology. Totowa, NJ: Humana Press. p. 237. ISBN 0-89603-796-7.
  3. ^ Zheng, X. Y.; Zhang, Z. J.; Chou, G. X.; Wu, T.; Cheng, X. M.; Wang, C. H.; Wang, Z. T. (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 Pharmacological Research. 32 (9): 1245–1251. doi:10.1007/s12272-009-1910-x. PMID 19784581.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ Schwarz, M. J.; Houghton, P. J.; Rose, S.; Jenner, P.; Lees, A. D. (2003). "Activities of Extract and Constituents of Banisteriopsis caapi Relevant to Parkinsonism". Pharmacology Biochemistry and Behavior. 75 (3): 627–633. doi:10.1016/S0091-3057(03)00129-1.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ^ US patent 5591738, Howard Lotsof, "Method of Treating Chemical Dependency Using β-Carboline Alkaloids, Derivatives and Salts thereof", issued 1997-01-07 
  6. ^ Berrougui, H.; Martin-Cordero, C.; Khalil, A.; Hmamouchi, M.; Ettaib, A.; Marhuenda, E.; Herrera, M. D. (2006). "Vasorelaxant Effects of Harmine and Harmaline Extracted from Peganum harmala L. Seeds in Isolated Rat Aorta". Pharmacological Research. 54 (2): 150–157. doi:10.1016/j.phrs.2006.04.001. PMID 16750635.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ^ O'Hearn, E.; Molliver, M. E. (1993). "Degeneration of Purkinje Cells in Parasagittal Zones of the Cerebellar Vermis after Treatment with Ibogaine or Harmaline". Neuroscience. 55 (2): 303–310. doi:10.1016/0306-4522(93)90500-F. PMID 8377927.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  8. ^ Cumming, P; Vincent SR (September 1992). "Inhibition of histamine-N-methyltransferase (HNMT) by fragments of 9-amino-1,2,3,4-tetrahydroacridine (tacrine) and by beta-carbolines". Biochemical Pharmacology. 44 (5): 989–992. doi:10.1016/0006-2952(92)90133-4. PMID 1530666.{{cite journal}}: CS1 maint: date and year (link)

External links

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