Harmaline

Harmaline
IUPAC name

7-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole
Identifiers
CAS number 304-21-2 Y
PubChem 5280951
ChemSpider 10211258 Y
UNII CN58I4TOET Y
KEGG C06536 Y
ChEBI CHEBI:28172 Y
ChEMBL CHEMBL340807 Y
Jmol-3D images Image 1
Properties
Molecular formula C13H14N2O
Molar mass 214.263 g/mol
Melting point

232–234 °C[1]
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

Contents

Occurrence in nature

Various plants contain harmaline including Banisteriopsis caapi (a jungle vine) and Peganum harmala (Syrian Rue) as well as the hallucinogenic drink ayahuasca, which is traditionally brewed using Banisteriopsis caapi. Also passionflower (Passiflora incarnata) and tobacco.[2]

Present at 3% by dry weight, the harmala alkaloids may be extracted from the Syrian Rue seeds.[3]

Effects

Harmaline is a central nervous system stimulant and a "reversible inhibitor of MAO-A (RIMA)."[4] It being a reversible MAO-A inhibitor means that it competes with tyramine for binding to MAO-A, so foods containing some tyramine can be safely consumed (wine and aged cheese should probably be avoided for 12 hours prior to consuming harmaline containing plants). The reversibility means that, instead of binding permanently to MAO-A for weeks until the body replaces the MAO-A enzyme molecules, harmaline binds only transiently, so tyramine can be metabolized as well by competing with harmaline for the binding site on the enzyme.[5] This means that the risk of a hypertensive crisis, a dangerous high blood pressure crisis from eating tyramine-rich foods such as cheese, is potentially lower with harmaline than with non-reversible MAOIs such as phenelzine, especially after 24 hours following ingestion. Do not mix MAO inhibitors (i.e. the harmala alkaloids) with any of the following: cheese, especially aged cheese, beer, mine, pickled herrings, snails, chicken livers, yeast products, figs, raisans, pickles, sauerkraut, coffee, chocolate soy sauce, cream or yogurt. [6]

The harmala alkaloids are psychoactive in man at oral doses of 25 to 750 milligrams. A small dose (25.50 milligrams) is a CNS stimulant. it increases mental activity and produces a pleasant dreamy state for several hours. The larger doses-- 200 milligrams up to 750 milligrams-- yield the hallucinogenic effects. The experience usually begins within one hour and often lasts six hours or more.[7]

Harmaline is shown to act as an acetylcholinesterase inhibitor.[8] Harmaline also stimulates striatal dopamine release in rat at very high dose levels.[9] Depending upon the dosage, harmaline induces temporary oneirophrenia and ataxia. Harmaline, on the higher end of its safe dosage range, has hallucinogenic properties, but it differentiates itself significantly from the "classical" hallucinogens in its pharmacology. Since harmaline is a reversible monoamine oxidase inhibitor, it could increase the effect of some drugs problematically. Harmaline causes no known physical or psychological dependence.

United States Patent Number 5591738 describes a method for treating various chemical dependencies via the administration of harmaline and or other beta-carbolines.[10]

Claudio Naranjo has studied potential applications of harmal alkaloids in psychotherapy.

Harmaline has also been shown to induce "vasorelaxant effects" in "isolated rat aorta."[11]

Harmaline has both protective and toxic effects on neurons.[10] For the harmaline experiments a single injection of 40mg/kg in rats or 3 x 25mg/kg spread over 3 days had very visible neurotoxic effects. [12]

Approximately 1.5 mg harmala alkaloids per kilogram body mass is all that is needed to activate oral DMT. [13]

Harmaline is known to act as a histamine N-methyltransferase inhibitor.

History

In the year 1841 harmaline was isolated from Peganum harmala by Goegel.[10] It was first synthesized in 1930 by Hasenfratz.[10]

References

  1. ^ Data from the Sigma Aldrich Catalog (German)
  2. ^ http://www.answers.com/topic/passionflower
  3. ^ http://www.erowid.org/plants/syrian_rue/syrian_rue_info9.shtml
  4. ^ Massaro, Edward J. (2002). Handbook of neurotoxicology. Totowa, NJ: Humana Press. p. 237. ISBN 0-89603-796-7. http://books.google.com/?id=2c2K-epbCDQC&pg=PA237&lpg=PA237&dq=harmaline+antidepressant. 
  5. ^ Youdim MB, Weinstock M (Jan 2004). "Therapeutic applications of selective and non-selective inhibitors of monoamine oxidase A and B that do not cause significant tyramine potentiation". Neurotoxicology 25 (1–2): 243–50. doi:10.1016/S0161-813X(03)00103-7. PMID 14697899. 
  6. ^ http://www.erowid.org/plants/syrian_rue/syrian_rue_info9.shtml
  7. ^ http://www.erowid.org/plants/syrian_rue/syrian_rue_info9.shtml
  8. ^ Zheng XY, Zhang ZJ, Chou GX, Wu T, Cheng XM, Wang CH, Wang ZT. (Sep 2009). "Acetylcholinesterase inhibitive activity-guided isolation of two new alkaloids from seeds of Peganum nigellastrum Bunge by an in vitro TLC- bioautographic assay". Arch Pharm Res. 32 (9): 1245–51. doi:10.1007/s12272-009-1910-x. PMID 19784581. http://www.springerlink.com/content/2561160164458518/. 
  9. ^ M. J. Schwarza, P. J. Houghtona, S. Roseb, P. Jennerb and A. D. Leesc (June 2003). "Activities of extract and constituents of Banisteriopsis caapi relevant to parkinsonism". Pharmacology Biochemistry and Behavior 75 (3): 627–33. doi:10.1016/S0091-3057(03)00129-1. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6T0N-48V972J-3&_user=10&_coverDate=06%2F30%2F2003&_rdoc=1&_fmt=high&_orig=search&_sort=d&_docanchor=&view=c&_searchStrId=1428794180&_rerunOrigin=google&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=c86ea82a1fedc0f2bc6e029e5f7bb880. 
  10. ^ a b c d Method of treating chemical dependency using .beta.-carboline alkaloids, derivatives and salts thereof
  11. ^ Berrougui H, Martin-Cordero C, Khalil A, Hmamouchi M, Ettaib A, Marhuenda E, Herrera MD (Aug 2006). "Vasorelaxant effects of harmine and harmaline extracted from Peganum harmala L. seeds in isolated rat aorta". Pharmacol Res. 54 (2): 150–7. doi:10.1016/j.phrs.2006.04.001. PMID 16750635. 
  12. ^ http://www.ncbi.nlm.nih.gov/pubmed/8377927
  13. ^ http://www.erowid.org/plants/syrian_rue/syrian_rue_dose.shtml

External links