Chemistry:Harmaline

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Short description: Chemical compound
Harmaline
Harmalin.svg
Harmaline-from-xtal-Mercury-3D-bs.png
Clinical data
Dependence
liability		N/A
Routes of
administration		Ingestion
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC13H14N2O
Molar mass214.268 g·mol−1
3D model (JSmol)
Melting point232–234 °C (450–453 °F)
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Harmaline is a fluorescent indole alkaloid from the group of harmala alkaloids and beta-carbolines. It is the partly 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 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.

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

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 plants and tryptamine-containing plants are used in ayahuasca brews. The inhibitory effects on monoamine oxidase allows dimethyltryptamine (DMT), the psychoactively 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.[5] Harmaline forces the anabolic metabolism of serotonin into N-acetylserotonin (normelatonin), and then to melatonin, the body's principal 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.[6]

A study has reported the antiviral activity of Harmaline against Herpes Simplex Virus 1 and 2 (HSV-1 and HSV-2) by inhibiting immediate early transcription of the virus at noncytotoxic concentration.[7]

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

Legal status

Australia

Harmala alkaloids are considered Schedule 9 prohibited substances under the Poisons Standard (October 2015).[9] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[9]

Canada

Harmaline and Harmalol are considered Schedule III controlled substances by the Controlled Drugs and Substances Act. Every person found to be in possession of a Schedule III drug is guilty of an indictable offence and liable to imprisonment for a term not exceeding three years; or for a first offence, guilty on summary conviction, to a fine not exceeding one thousand dollars or to imprisonment for a term not exceeding six months, or to both. Every person found to be trafficking a Schedule III drug is guilty of an indictable offence and liable to imprisonment for a term not exceeding ten years, or is guilty on summary conviction (first-time offenders) and liable to imprisonment for a term not exceeding eighteen months.[10]

See also

References

  1. ↑ 1.0 1.1 "Peganum Harmala pamphlet: Syrian Rue". Erowid. http://www.erowid.org/plants/syrian_rue/syrian_rue_info9.shtml. 
  2. ↑ Handbook of Neurotoxicology. Totowa, NJ: Humana Press. 2002. p. 237. ISBN 978-0-89603-796-0. https://books.google.com/books?id=2c2K-epbCDQC&q=harmaline+antidepressant&pg=PA237. 
  3. ↑ "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): 1245–51. September 2009. doi:10.1007/s12272-009-1910-x. PMID 19784581. https://repositorio.unal.edu.co/handle/unal/80277. 
  4. ↑ "Activities of extract and constituents of Banisteriopsis caapi relevant to parkinsonism". Pharmacology, Biochemistry, and Behavior 75 (3): 627–33. June 2003. doi:10.1016/S0091-3057(03)00129-1. PMID 12895680. 
  5. ↑ "Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions". Current Drug Metabolism 11 (8): 659–66. October 2010. doi:10.2174/138920010794233495. PMID 20942780. 
  6. ↑ Lotsof H, "Method of Treating Chemical Dependency Using β-Carboline Alkaloids, Derivatives and Salts thereof", US patent 5591738, issued 1997-01-07
  7. ↑ "A dihydro-pyrido-indole potently inhibits HSV-1 infection by interfering the viral immediate early transcriptional events". Antiviral Research 105: 126–134. May 2014. doi:10.1016/j.antiviral.2014.02.007. PMID 24576908. 
  8. ↑ "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): 989–92. September 1992. doi:10.1016/0006-2952(92)90133-4. PMID 1530666. 
  9. ↑ 9.0 9.1 "Poisons Standard October 2015". Australian Government. 30 September 2015. https://www.comlaw.gov.au/Details/F2015L01534. 
  10. ↑ "Controlled Drugs and Substances Act (S.C 1996, c.19)". 19 September 2019. https://laws-lois.justice.gc.ca/eng/acts/c-38.8/page-2.html. 

Further reading



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