Chembox new
Name = Harmaline
ImageFile = Harmaline.png ImageName = Harmaline
IUPACName = 7-methoxy-1-methyl
[3,4-b] indole [http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5280951 PubChem] ]
Section1 = Chembox Identifiers
CASNo = 304-21-2


Section2 = Chembox Properties
Formula = C13H14N2O.]
MolarMass = 214.263 g/mol.]
MeltingPt = 232–234 °C [http://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/51330 Data from the Sigma Aldrich Catalog (German)] ]

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

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.


Harmaline is a central nervous system stimulant and a "reversible inhibitor of MAO-A (RIMA)." [ [http://books.google.com/books?id=2c2K-epbCDQC&pg=PA237&lpg=PA237&dq=harmaline+antidepressant&source=web&ots=IrcpVr4R_H&sig=5FvlysKKEN7Hb4_YjfgoZM8rsTg Edward J. Massaro, Handbook of Neurotoxicology] ] 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. [ [http://www.ncbi.nlm.nih.gov/pubmed/14697899?ordinalpos=21&itool=EntrezSystem2.PEntrez.Pubmed.Pubmed_ResultsPanel.Pubmed_RVDocSum Therapeutic applications of selective and non-sele... [Neurotoxicology. 2004 - PubMed Result ] ] 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 MAOI's, especially after 24 hours following ingestion.

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. [http://www.freepatentsonline.com/5591738.html Method of treating chemical dependency using .beta.-carboline alkaloids, derivatives and salts thereof] ]

Harmaline has also been shown to induce "vasorelaxant effects" in "isolated rat aorta." [ [http://grande.nal.usda.gov/ibids/index.php?mode2=detail&origin=ibids_references&therow=800566 Berrougui,-H; Martin-Cordero,-C; Khalil,-A; Hmamouchi,-M; Ettaib,-A; Marhuenda,-E; Herrera,-M-D. Vasorelaxant effects of harmine and harmaline extracted from Peganum harmala L. seeds in isolated rat aorta. Pharmacol-Res. 2006 Aug; 54(2): 150-7] ]

Harmaline has both protective and toxic effects on neurons..]


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

External links

* [http://www.erowid.org/library/books_online/tihkal/tihkal13.shtml TIHKAL, #13]

* [http://www3.interscience.wiley.com/cgi-bin/abstract/112228825/ABSTRACT?CRETRY=1&SRETRY=0 Antileishmanial activity of harmaline and other tryptamine derivatives] A. Tudor Evans, Simon L. Croft, Department of Medical Protozoology, London School of Hygiene and Tropical Medicine, Keppel Street, London WCIE 7HT, UK

* [http://www.aapspharmaceutica.com/search/view.asp?ID=78110 Study Indicating that Harmaline is a Free Radical Scavenger]


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Look at other dictionaries:

  • Harmaline — Structure du harmaline Général Nom IUPAC 7 méthoxy 1 méthyl 4,9 dihydro 3H β carboline …   Wikipédia en Français

  • Harmaline — Har ma*line (h[aum]r m[.a]*l[i^]n or l[=e]n), n. [Cf. F. harmaline See {Harmel}.] (Chem.) An alkaloid found in the plant Peganum harmala. It forms bitter, yellow salts. [1913 Webster] …   The Collaborative International Dictionary of English

  • harmaline — [ aʀmalin] n. f. ÉTYM. XXe; de harmale, et ine. ❖ ♦ Chim., pharm. Alcaloïde extrait des graines et de la racine de harmale (Peganum harmala), employé comme vermifuge …   Encyclopédie Universelle

  • harmaline — noun The reduced hydrated form of harmine …   Wiktionary

  • harmaline — An amine oxidase inhibitor and a central nervous system stimulant; obtained from the seeds of Peganum harmala (family Zygophyllaceae) and from Banisteria caapi (family Malpighiaceae); has been used in parkinsonism. SYN: harmidine. * * *… …   Medical dictionary

  • harmaline — (har ma li n ) s. f. Terme de chimie. Substance qu on trouve dans les graines de peganum harmala, L …   Dictionnaire de la Langue Française d'Émile Littré

  • harmaline — har·ma·line …   English syllables

  • harmaline — ˈhärməˌlēn, lə̇n noun ( s) Etymology: International Scientific Vocabulary harmal + ine : a crystalline alkaloid C13H14N2O found in harmal seeds; dihydro harmine * * * harˈmalin, harˈmaline, harˈmin or harˈmine noun …   Useful english dictionary

  • 304-21-2 — Harmaline Harmaline Structure du harmaline Général Nom IUPAC 7 méthoxy 1 méthyl 4,9 dihydro 3H β carboline …   Wikipédia en Français

  • C13H14N2O — Harmaline Harmaline Structure du harmaline Général Nom IUPAC 7 méthoxy 1 méthyl 4,9 dihydro 3H β carboline …   Wikipédia en Français

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