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It occurs in a number of different plants, most notably the [[Syrian rue]] and ''[[Banisteriopsis caapi]]''.<ref name=":3">{{Cite journal|display-authors=etal|vauthors=Djamshidian A|date=2015|title=Banisteriopsis caapi, a Forgotten Potential Therapy for Parkinson's Disease?|journal=Movement Disorders Clinical Practice|volume=3|issue=1|pages=19–26|doi=10.1002/mdc3.12242|pmc=6353393|pmid=30713897}}</ref> Harmine [[Enzyme inhibitor#Reversible inhibitors|reversibly inhibits]] [[monoamine oxidase A]] (MAO-A), an [[enzyme]] which breaks down [[monoamine]]s, making it a [[Reversible inhibitor of monoamine oxidase A]] (RIMA). Harmine does not inhibit [[MAO-B]].<ref name=":4">{{Cite journal|vauthors=Frecska E, Bokor P, Winkelman M|date=2016|title=The Therapeutic Potentials of Ayahuasca: Possible Effects against Various Diseases of Civilization|journal=Frontiers in Pharmacology|volume=7|page=35|doi=10.3389/fphar.2016.00035|pmc=4773875|pmid=26973523|doi-access=free}}</ref> Harmine is also known as '''banisterin''', '''banisterine''', '''telopathin''', '''telepathine''', '''leucoharmine'''<ref>{{Cite journal|vauthors=Allen JR, Holmstedt BR|date=1980|title=The simple β-carboline alkaloids|url=http://www.sciencedirect.com/science/article/pii/S0031942200837735|journal=Phytochemistry|volume=19|issue=8|pages=1573–1582|doi=10.1016/S0031-9422(00)83773-5|bibcode=1980PChem..19.1573A }}</ref> and '''yagin''', '''yageine'''.<ref name=":3" /><ref>{{Cite web|title=SciFinderⁿ Login|url=https://sso.cas.org/as/authorization.oauth2?response_type=code&client_id=scifinder-n&redirect_uri=https%3A%2F%2Fscifinder-n.cas.org%2Fpa%2Foidc%2Fcb&state=eyJ6aXAiOiJERUYiLCJhbGciOiJkaXIiLCJlbmMiOiJBMTI4Q0JDLUhTMjU2Iiwia2lkIjoiOW0iLCJzdWZmaXgiOiJPYUUxeEsuMTYzNjk1NzY3NSJ9..5wCwUVpvCohoxPuelNXYXA.FNzx1epEQU7XKLOIfKZw9sFA-B1xNTEJgrzQ3t6LTSZGpsIoqRWrKcfqzIvqUOHUkXhmsiLU0o-ToIDwBwtkRgCXCFGmriUzgjRjfYFFj_bV6D9Ecb8-EqZHjZ4UgJIq50LntW-yXQfE73B0Zup-Xg.hnJD-6Ednl699nsrpZYPiw&nonce=h0ZRbLU6gzzg6-oVhiSyO9fWRRA-jI4HtH1MHoWUARg&scope=openid%20address%20email%20phone%20profile&vnd_pi_requested_resource=https%3A%2F%2Fscifinder-n.cas.org%2FsearchDetail%2Fsubstance%2F618e06e87bbc3e6eeb0be381%2FsubstanceDetails&vnd_pi_application_name=SciFinder-nIDF|access-date=2021-11-12|website=sso.cas.org}}</ref> == Biosynthesis == The coincident occurrence of [[β-carboline]] alkaloids and [[serotonin]] in ''[[Peganum harmala]]'' indicates the presence of two very similar, interrelated biosynthetic pathways, which makes it difficult to definitively identify whether free [[tryptamine]] or L-[[tryptophan]] is the precursor in the biosynthesis of harmine.<ref name=":0">{{cite journal |author1=Berlin Jochen |author2=Rugenhagen Christiane |author3=Greidziak Norbert |author4=Kuzovkina Inna |author5=Witte Ludger |author6=Wray Victor | year = 1993 | title = Biosynthesis of Serotonin and Beta-carboline Alkaloids in Hairy Root Cultures of Peganum Harmala|journal = Phytochemistry | volume = 33 | issue = 3| pages = 593–97 | doi=10.1016/0031-9422(93)85453-x|bibcode=1993PChem..33..593B }}</ref> However, it is postulated that L-tryptophan is the most likely precursor, with tryptamine existing as an intermediate in the pathway. The following figure shows the proposed biosynthetic scheme for harmine.<ref name=":1">{{cite journal |author1=Nettleship Lesley |author2=Slaytor Michael | year = 1974 | title = Limitations of Feeding Experiments in Studying Alkaloid Biosynthesis in Peganum Harmala Callus Cultures|journal = Phytochemistry | volume = 13 | issue = 4| pages = 735–42 | doi=10.1016/s0031-9422(00)91406-7|bibcode=1974PChem..13..735N }}</ref> The [[Shikimate pathway|Shikimate acid pathway]] yields the aromatic amino acid, L-tryptophan. Decarboxylation of L-tryptophan by [[aromatic L-amino acid decarboxylase]] (AADC) produces tryptamine ('''I'''), which contains a [[nucleophilic]] center at the C-2 carbon of the [[indole]] ring due to the adjacent nitrogen atom that enables the participation in a [[Mannich reaction|Mannich-type reaction]]. Rearrangements enable the formation of a [[Schiff base]] from tryptamine, which then reacts with pyruvate in '''II''' to form a β-carboline [[carboxylic acid]]. The β-carboline carboxylic acid subsequently undergoes [[decarboxylation]] to produce 1-methyl β-carboline '''III'''. [[Hydroxylation]] followed by [[methylation]] in '''IV''' yields [[harmaline]]. The order of O-methylation and hydroxylation have been shown to be inconsequential to the formation of the harmaline intermediate.<ref name=":0" /> In the last step '''V''', the oxidation of harmaline is accompanied by the loss of water and effectively generates harmine. [[File:Harmine Biosynthesis.png|left|Proposed biosynthesis of harmine from L-tryptophan|border|frameless|500px]] The difficulty distinguishing between L-tryptophan and free tryptamine as the precursor of harmine biosynthesis originates from the presence of the serotonin biosynthetic pathway, which closely resembles that of harmine, yet necessitates the availability of free tryptamine as its precursor.<ref name=":0" /> As such, it is unclear if the decarboxylation of L-tryptophan, or the incorporation of pyruvate into the basic tryptamine structure is the first step of harmine biosynthesis. However, feeding experiments involving the feeding of one of tryptamine to hairy root cultures of ''P. harmala'' showed that the feeding of tryptamine yielded a great increase in serotonin levels with little to no effect on β-carboline levels, confirming that tryptamine is the precursor for serotonin, and indicating that it is likely only an intermediate in the biosynthesis of harmine; otherwise, comparable increases in harmine levels would have been observed.<ref name=":1" /> == Uses == ===Monoamine oxidase inhibitor=== Harmine is a [[Reversible inhibitor of monoamine oxidase A|RIMA]], as it [[Reversible inhibitor|reversibly inhibits]] monoamine oxidase A ([[MAO-A]]), but not [[MAO-B]].<ref name=":4" /> Oral or intravenous harmine doses ranging from 30 to 300&nbsp;mg may cause agitation, [[bradycardia]] or [[tachycardia]], blurred vision, [[hypotension]], [[paresthesias]]. Serum or plasma harmine concentrations may be measured as a confirmation of diagnosis. The plasma elimination [[half-life]] of harmine is on the order of 1–3 hours.<ref>R. Baselt, ''Disposition of Toxic Drugs and Chemicals in Man'', 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 727-728.</ref> Medically significant amounts of harmine occur in the plants [[Syrian rue]] and ''[[Banisteriopsis caapi]]''. These plants also contain notable amounts of [[harmaline]],<ref name=":3" /> which is also a RIMA.<ref name=":4" /> The psychoactive [[ayahuasca]] brew is made from ''B. caapi'' stem bark usually in combination with [[dimethyltryptamine]] (DMT) containing ''[[Psychotria viridis]]'' leaves. DMT is a [[psychedelic drug]], but it is not orally active unless it is ingested with MAOIs. This makes harmine a vital component of the ayahuasca brew with regard to its ability to induce a [[psychedelic experience]].<ref>{{Cite journal|display-authors=etal|vauthors=Jonathan H|date=2019|title=Ayahuasca: Psychological and Physiologic Effects, Pharmacology and Potential Uses in Addiction and Mental Illness|journal=Current Neuropharmacology|volume=17|issue=2|pages=108–128|doi=10.2174/1570159X16666180125095902|pmc=6343205|pmid=29366418}}</ref> Syrian rue or synthetic harmine is sometimes used to substitute ''B. caapi'' in the oral use of DMT.<ref>{{Cite journal|display-authors=etal|vauthors=Simão AY|date=2019|title=Toxicological Aspects and Determination of the Main Components of Ayahuasca: A Critical Review|journal=Medicines|volume=6|issue=4|pages=106|doi=10.3390/medicines6040106|pmid=31635364|pmc=6963515|doi-access=free}}</ref> === Other === [[File:Harmaline Harmine.jpg|thumb|right|175px|[[Harmaline]] and harmine [[fluoresce]] under [[ultraviolet light]]. These three extractions indicate that the middle one has a higher concentration of the two compounds.]] Harmine is a useful fluorescent pH indicator. As the pH of its local environment increases, the fluorescence emission of harmine decreases. Due to its MAO-A specific binding, [[carbon-11]] [[Radioactive tracer|labeled]] harmine can be used in [[positron emission tomography]] to study MAO-A dysregulation in several psychiatric and neurologic illnesses.<ref>{{Cite journal|author1 = Nathalie Ginovart|author2 = Jeffrey H. Meyer |author-link2 = Jeffrey H. Meyer|author3 = Anahita Boovariwala|author4 = Doug Hussey|author5 = Eugenii A. Rabiner|author6 = Sylvain Houle|author-link6 = Sylvain Houle|author7 = Alan A. Wilson|title = Positron emission tomography quantification of &#91;<sup>11</sup>C&#93;-harmine binding to monoamine oxidase-A in the human brain|journal = [[Journal of Cerebral Blood Flow & Metabolism]]|year = 2006|volume = 26|pages = 330–344|doi = 10.1038/sj.jcbfm.9600197|pmid = 16079787|issue = 3|doi-access = free}}</ref> Harmine was used as an [[antiparkinsonian]] medication since the late 1920s until the early 1950s. It was replaced by other medications.<ref name=":2" /> == Research == === Pancreatic islet cell proliferation === Harmine is currently the only known [[drug]] that induces proliferation (rapid [[mitosis]] and subsequent mass growth) of pancreatic [[Alpha cell|alpha]] (α) and [[Beta cell|beta]] (β) cells in adult humans.<ref>{{cite journal |last1=Wang |first1=P. |title=Induction of human pancreatic beta cell replication by inhibitors of dual specificity tyrosine regulated kinase |journal=Nature Medicine |date=2015 |volume=21 |issue=4 |pages=383–388 |doi=10.1038/nm.3820 |pmid=25751815 |pmc=4690535 }}</ref> These [[Pancreatic islets|islet]] sub-cells are normally resistant to growth stimulation in the [[adult]] stage of a human's life, as the cell mass plateaus at around age 10 and remains virtually unchanged. == Adverse effects == {{More citations needed section|date=November 2024}} A 2024 Phase 1 clinical trial investigating pharmaceutical-grade harmine hydrochloride in healthy adults found that the maximum tolerated dose (MTD) is approximately 2.7 mg/kg body weight.<ref>{{cite journal |last1=Ables |first1=Jessica L |last2=Israel |first2=Leah |year=2024 |title=A Phase 1 single ascending dose study of pure oral harmine in healthy volunteers |journal=Journal of Psychopharmacology |doi=10.1177/02698811241273772|pmc=11549898 }}</ref> Below this threshold, harmine is generally well-tolerated with minimal adverse effects. Above 2.7 mg/kg, common adverse effects include nausea and vomiting, which typically occur 60-90 minutes after ingestion. Other reported effects include drowsiness, dizziness, and impaired concentration. These effects are generally mild to moderate in severity and resolve within several hours. No serious adverse cardiovascular effects were observed at any dose tested (up to 500 mg), though rare instances of transient hypotension occurred during episodes of vomiting. Unlike some traditional preparations containing harmine (such as Ayahuasca), pure harmine did not cause diarrhea in study participants. The study found that adverse effects were more common in participants with lower body weight when given fixed doses, leading the researchers to conclude that 2.7 mg/kg represents a more useful threshold than fixed dosing. == Natural sources == Harmine is found in a wide variety of different organisms, most of which are plants. [[Alexander Shulgin]] lists about thirty different species known to contain harmine, including seven species of [[butterfly]] in the family [[Nymphalidae]].<ref>{{Cite book | author = Shulgin, Alexander |author-link = Alexander Shulgin |author2 = Shulgin, Ann |author-link2 = Ann Shulgin | year = 1997 | title = TiHKAL: The Continuation | publisher = [[Transform Press]] | isbn = 0-9630096-9-9 |title-link = TiHKAL |pages =713–714}}</ref> The harmine-containing plants include [[tobacco]], ''[[Peganum harmala]]'', two species of [[passiflora]], and numerous others. [[Lemon balm]] (''Melissa officinalis'') contains harmine.<ref>{{cite journal | title = Harmala Alkaloids as Bee Signaling Chemicals | author = Natalie Harrington | volume = 1 | issue = 1 | year = 2012 | journal = Journal of Student Research |url=http://www.jofsr.com/index.php/path/article/view/30 | pages = 23–32| doi = 10.47611/jsr.v1i1.30 | doi-access = free }}</ref> In addition to ''[[Banisteriopsis caapi|B. caapi]]'', at least three members of the [[Malpighiaceae]] contain harmine, including two more ''Banisteriopsis'' species and the plant ''[[Callaeum antifebrile]]''. Callaway, Brito and Neves (2005) found harmine levels of 0.31–8.43% in ''B. caapi'' samples.<ref>{{Cite journal |author1=Callaway J. C. |author2=Brito G. S. |author3=Neves E. S. | year = 2005 | title = Phytochemical analyses of Banisteriopsis caapi and Psychotria viridis | journal = [[Journal of Psychoactive Drugs]] | volume = 37 | issue = 2 | pages = 145–150 | pmid = 16149327 | doi = 10.1080/02791072.2005.10399795 |s2cid=30736017 }}</ref> The family [[Zygophyllaceae]], which ''P. harmala'' belongs to, contains at least two other harmine-bearing plants: ''[[Peganum nigellastrum]]'' and ''[[Zygophyllum fabago]]''. == History == J. Fritzsche was the first to isolate and name harmine. He isolated it from the husks of ''[[Peganum harmala]]'' seeds in 1848. The related [[harmaline]] was already isolated and named by Fr. Göbel in 1837 from the same plant.<ref>{{Cite journal|date=1848|title=Bestandtheile der Samen von Peganum Harmala|url=https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/jlac.18480640353|journal=Justus Liebigs Annalen der Chemie|language=en|volume=64|issue=3|pages=360–369|doi=10.1002/jlac.18480640353}}</ref><ref name=":2" /> The pharmacology of harmine was not studied in detail until 1895.<ref name=":2" /> The structures of harmine and harmaline were determined in 1927 by Richard Helmuth Fredrick Manske and colleagues.<ref>{{Cite journal|vauthors=Manske RH, Perkin, WH, Robinson R|date=1927|title=Harmine and harmaline. Part IX. A synthesis of harmaline|url=https://pubs.rsc.org/en/content/articlelanding/1927/jr/jr9270000001|journal=Journal of the Chemical Society|pages=1–14|doi=10.1039/JR9270000001}}</ref><ref>{{Cite patent|number=5591738|title=Method of treating chemical dependency using β-carboline alkaloids, derivatives and salts thereof|pubdate=1997-01-07|invent1=Lotsof|inventor1-first=Howard S.|assign=NDA International Inc.|country=US}}</ref> In 1905, the Colombian naturalist and chemist, Rafael Zerda-Bayón suggested the name telepathine to the then unknown [[hallucinogenic]] ingredient in [[ayahuasca]] brew.<ref name=":3" /><ref name=":2" /> "Telepathine" comes from "[[telepathy]]", as Zerda-Bayón believed that ayahuasca induced telepathic visions.<ref name=":3" /><ref>{{Cite journal|last=Baldo|first=Benjamin|date=1920|title=Telepathy and Telepathine|url=https://www.samorini.it/doc1/alt_aut/ad/baldo-telepathy-and-telepathin.pdf|url-status=live|journal=American Druggist|volume=68|issue=4|pages=15|archive-url=https://web.archive.org/web/20201023045312/https://www.samorini.it/doc1/alt_aut/ad/baldo-telepathy-and-telepathin.pdf|archive-date=2020-10-23}}</ref> In 1923, the Colombian chemist, Guillermo Fischer-Cárdenas was the first to isolate harmine from ''[[Banisteriopsis caapi]]'', which is an important herbal component of ayahuasca brew. He called the isolated harmine "telepathine".<ref name=":3" /> This was solely to honor Zerda-Bayón, as Fischer-Cárdenas found that telepathine had only mild non-hallucinogenic effects in humans.<ref>{{cite thesis|last=Fischer-Cárdenas|first=Guillermo|date=1923|title=Estudio sobre el principio activo del Yagé|type=PhD|chapter=V. Encephalitis lethargica: New strategies in the therapy of parkinsonism|publisher=Universidad Nacional|chapter-url=https://www.samorini.it/doc1/alt_aut/ad/cardenas.pdf|access-date=2020-11-22}}</ref> In 1925, Barriga Villalba, professor of chemistry at the University of Bogotá, isolated harmine from ''B. caapi'', but named it "yajéine",<ref name=":2">{{cite thesis|last=Foley|first=Paul Bernard|date=2001|title=Beans, roots and leaves: a brief history of the pharmacological therapy of parkinsonism|degree=PhD|chapter=V. Encephalitis lethargica: New strategies in the therapy of parkinsonism|publisher=Bavarian Julius Maximilian University|url=https://nbn-resolving.org/urn:nbn:de:bvb:20-1181975|chapter-url=https://d-nb.info/96446392X/34|access-date=2020-11-22|pages=166–180}}</ref> which in some texts is written as "yageine".<ref name=":3" /> In 1927, F. Elger, who was a chemist working at [[Hoffmann-La Roche]], isolated harmine from ''B. caapi''. With the assistance of Professor [[Robert Robinson (chemist)|Robert Robinson]] in Manchester, Elger showed that harmine (which was already isolated in 1848) was identical with telepathine and yajéine.<ref>{{Cite journal|last=Elger|first=F.|date=1928|title=Über das Vorkommen von Harmin in einer südamerikanischen Liane (Yagé)|url=https://onlinelibrary.wiley.com/doi/abs/10.1002/hlca.19280110113|journal=Helvetica Chimica Acta|language=en|volume=11|issue=1|pages=162–166|doi=10.1002/hlca.19280110113}}</ref><ref name=":2" /> In 1928, [[Louis Lewin]] isolated harmine from ''B. caapi'', and named it "banisterine",<ref>{{Cite journal|last=Schultes|first=RE|date=1982|title=The beta-carboline Hallucinogens of South America|url=http://www.tandfonline.com/doi/abs/10.1080/02791072.1982.10471930|journal=Journal of Psychoactive Drugs|volume=14|issue=3|pages=205–220|doi=10.1080/02791072.1982.10471930|pmid=6754896}}</ref> but this supposedly novel compound was soon also shown to be harmine.<ref name=":2" /> Harmine was first patented by Jialin Wu and others who invented ways to produce new harmine derivatives with enhanced antitumor activity and lower toxicity to human nervous cells.<ref>{{cite patent|country=EP|number=1634881|title=Harmine derivatives, intermediates used in their preparations, preparation processes and use thereof|pubdate=2006-03-15|inventor1-last=Wu|inventor1-first=Jialin |inventor2-last=Chen|inventor2-first= Qi |inventor3-last=Cao|inventor3-first= Rihui |inventor4-last= YU F HUASHIDAN ; WANG ZIHOU ; PENG WENLIE |assign=Xinjiang Huashidan Pharmaceutical Research Co. }}</ref> == Legal status == ===Australia=== Harmala alkaloids are considered Schedule 9 prohibited substances under the [[Standard for the Uniform Scheduling of Medicines and Poisons|Poisons Standard]] (October 2015).<ref name="Poisons Standard">Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534</ref> 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.<ref name="Poisons Standard" /> Exceptions are made when in herbs, or preparations, for therapeutic use such as: (a) containing 0.1 per cent or less of harmala alkaloids; or (b) in divided preparations containing 2&nbsp;mg or less of harmala alkaloids per recommended daily dose.<ref name="Poisons Standard" /> == References == {{Reflist}} == External links == *[http://tihkal.info/read.php?domain=tk&id=14 Harmine entry in TiHKAL • info] {{Hallucinogens}} {{Monoamine metabolism modulators}} {{Tryptamines}} [[Category:Indole alkaloids]] [[Category:Alkaloids found in Nicotiana]] [[Category:Beta-Carbolines]] [[Category:Monoamine oxidase inhibitors]] [[Category:Phenol ethers]] </textarea><div class="templatesUsed"><div 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