# Harmane > Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Harmane > Markdown URL: https://mediated.wiki/source/Harmane.md > Source: https://en.wikipedia.org/wiki/Harmane > Source revision: 1355563515 > License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/) {{short description|Chemical compound}} {{Chembox | ImageFile = Harmane.svg | ImageClass = skin-invert-image | ImageSize = 220px | ImageFile2 = Harmane 3D BS.png | ImageClass2 = bg-transparent | ImageSize2 = 220px | PIN = 1-Methyl-9''H''-pyrido[3,4-''b'']indole | OtherNames = Harman, 1-Methyl-β-carboline, Aribine, Aribin, Locuturine, Locuturin, Loturine, Passiflorin, 1-Methylnorharman, NSC 54439 |Section1={{Chembox Identifiers | CASNo = 486-84-0 | CASNo_Ref = {{cascite|correct|CAS}} | UNII = 82D6J0535P | UNII_Ref = {{fdacite|correct|FDA}} | PubChem = 5281404 | EINECS = 207-642-2 | ChemSpiderID = 4444755 | SMILES = CC1=NC=CC2=C1NC3=CC=CC=C23 | InChI = 1/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H3 | InChIKey = PSFDQSOCUJVVGF-UHFFFAOYAA | StdInChI = 1S/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H3 | StdInChIKey = PSFDQSOCUJVVGF-UHFFFAOYSA-N | RTECS = | MeSHName = | ChEBI = 5623 | KEGG = C09209}} |Section2={{Chembox Properties | C=12 | H=10 | N=2 | Appearance = | Density = | MeltingPtC = 235-238 | BoilingPt = | Solubility = Soluble to 10 mM in 1 eq. HCl methanol: soluble 50 mg/ml}} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} '''Harmane''', or '''harman''', also known as '''1-methyl-β-carboline''', is a [heterocyclic amine](/source/heterocyclic_amine) and [β-carboline](/source/substituted_%CE%B2-carboline) found in a variety of foods including [coffee](/source/coffee),{{cite journal | pmid = 16139309 | year = 2006 | last1 = Herraiz | first1 = T | title = Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee | journal = Life Sciences | volume = 78 | issue = 8 | pages = 795–802 | last2 = Chaparro | first2 = C | doi = 10.1016/j.lfs.2005.05.074 }} sauces,{{Cite journal | doi = 10.1080/02652030400019844| pmid = 15764332| title = Relative exposure toβ-carbolines norharman and harman from foods and tobacco smoke| journal = Food Additives and Contaminants| volume = 21| issue = 11| pages = 1041–50| year = 2004| last1 = Herraiz | first1 = T.| bibcode = 2004FACon..21.1041H| s2cid = 216644379}} and cooked meat.{{cite journal | pmid = 17497412 | pmc = 4993204 | year = 2007 | last1 = Louis | first1 = E. D. | title = Quantification of the neurotoxic beta-carboline harmane in barbecued/grilled meat samples and correlation with level of doneness | journal = Journal of Toxicology and Environmental Health, Part A | volume = 70 | issue = 12 | pages = 1014–9 | last2 = Zheng | first2 = W | last3 = Jiang | first3 = W | last4 = Bogen | first4 = K. T. | last5 = Keating | first5 = G. A. | doi = 10.1080/15287390601172015 | bibcode = 2007JTEHA..70.1014L }} It is also present in [tobacco smoke](/source/Tobacco_smoking).{{cite journal | doi = 10.1016/j.bbrc.2004.11.033| pmid = 15582589| title = Human monoamine oxidase is inhibited by tobacco smoke: β-carboline alkaloids act as potent and reversible inhibitors| journal = Biochemical and Biophysical Research Communications| volume = 326| issue = 2| pages = 378–86| year = 2005| last1 = Herraiz| first1 = Tomas| last2 = Chaparro| first2 = Carolina| bibcode = 2005BBRC..326..378H}} Harmane is related to other alkaloids, [harmine](/source/harmine) and [harmaline](/source/harmaline), found in 1837 in the plant ''[Peganum harmala](/source/Peganum_harmala)''.{{cite web |last1=Claude Lotfi |title=Contribution à l'étude du Peganum harmala (L.) (Hermel) |url=http://chimie.these.free.fr/CHIMTHE%20056.htm |date=1967}} The name derives from the Arabic word for the plant, {{Lang|ar|حَرْمَل|rtl=yes}} ({{Lang|ar-latn|ḥarmal}}). In humans, harmane is a potent tremor-producing neurotoxin.{{Cite journal|last1=Louis|first1=Elan D|last2=Jiang|first2=Wendy|last3=Pellegrino |first3=Kathryn M|last4=Rios|first4=Eileen|last5=Factor-Litvak|first5=Pam|last6=Henchcliffe |first6=Claire|last7=Zheng|first7=Wei|date=2008|title=Elevated blood harmane (1-methyl-9H-pyrido[3,4-b]indole) concentrations in essential tremor|journal=Neurotoxicology|volume=29|issue=2|pages=294–300|doi=10.1016/j.neuro.2007.12.001|pmid=18242711|pmc=2291546 |bibcode=2008NeuTx..29..294L }} Harmane has been found to inhibit the early stages of the growth of the [malaria](/source/malaria) parasite in the gut of [mosquito](/source/mosquito)es infected by the bacterium ''[Delftia tsuruhatensis](/source/Delftia_tsuruhatensis)'', and can be absorbed by the mosquitoes upon contact.{{Cite journal |last1=Huang |first1=Wei |last2=Rodrigues |first2=Janneth |last3=Bilgo |first3=Etienne |last4=Tormo |first4=José R. |last5=Challenger |first5=Joseph D. |last6=De Cozar-Gallardo |first6=Cristina |last7=Pérez-Victoria |first7=Ignacio |last8=Reyes |first8=Fernando |last9=Castañeda-Casado |first9=Pablo |last10=Gnambani |first10=Edounou Jacques |last11=Hien |first11=Domonbabele François de Sales |last12=Konkobo |first12=Maurice |last13=Urones |first13=Beatriz |last14=Coppens |first14=Isabelle |last15=Mendoza-Losana |first15=Alfonso |date=2023-08-04 |title=Delftia tsuruhatensis TC1 symbiont suppresses malaria transmission by anopheline mosquitoes |url=https://www.science.org/doi/10.1126/science.adf8141 |journal=Science |language=en |volume=381 |issue=6657 |pages=533–540 |doi=10.1126/science.adf8141 |pmid=37535741 |bibcode=2023Sci...381..533H |issn=0036-8075|hdl=10044/1/105278 |s2cid=260440907 |hdl-access=free }}{{Cite news |last=Offord |first=Catherine |date=3 August 2023 |title=Microbe stops mosquitoes from harboring malaria parasite |work=[Science](/source/Science_(journal)) |url=https://www.science.org/content/article/microbe-stops-mosquitoes-harboring-malaria-parasite}}{{cite web |last1=Naomi Grimley |title=Chance discovery helps fight against malaria |url=https://www.bbc.com/news/health-66394117 |publisher=BBC |date=Aug 4, 2023}} ==Pharmacology== ===Pharmacodynamics=== Harmane is a [potent](/source/potency_(pharmacology)) [reversible inhibitor of monoamine oxidase A](/source/reversible_inhibitor_of_monoamine_oxidase_A) (RIMA), with an {{Abbrlink|IC50|half-maximal inhibitory concentration}} of 60{{nbsp}}nM.{{cite journal | vauthors = Saro G, Johne S, Latino DA, Moine F, van der Toorn M, Mathis C, Veljkovic E | title = Monoamine Oxidase Inhibitors Present in Tobacco Modulate Dopamine Balance Via the Dopamine Transporter | journal = ACS Chem Neurosci | volume = 16 | issue = 6 | pages = 1117–1131 | date = March 2025 | pmid = 40033845 | pmc = 11926787 | doi = 10.1021/acschemneuro.4c00789 | url = }} It is also a weak [dopamine reuptake inhibitor](/source/dopamine_reuptake_inhibitor) (DRI), with an {{Abbr|IC50|half-maximal inhibitory concentration}} of 1,490{{nbsp}}nM at the [dopamine transporter](/source/dopamine_transporter) (DAT). Harmane shows weak [affinity](/source/affinity_(pharmacology)) for the serotonin [5-HT2B](/source/5-HT2B_receptor) and [5-HT2C receptor](/source/5-HT2C_receptor)s (Ki = 267{{nbsp}}nM and 1,135{{nbsp}}nM, respectively), but not for the serotonin [5-HT2A receptor](/source/5-HT2A_receptor) (Ki = >10,000{{nbsp}}nM).{{cite journal | last1=Foley | first1=Caroline A. | last2=Al-Issa | first2=Yazan A. | last3=Hiller | first3=Kathryn P. | last4=Mulcahy | first4=Seann P. | title=Synthesis and Structure–Activity Relationships of 1-Aryl-β-carbolines as Affinity Probes for the 5-Hydroxytryptamine Receptor | journal=ACS Omega | volume=4 | issue=6 | date=30 June 2019 | issn=2470-1343 | doi=10.1021/acsomega.9b01111 | pages=9807–9812 | doi-access=free }} It has been found to be inactive as an [agonist](/source/agonist) of the serotonin 5-HT2A receptor.{{cite journal | vauthors = Rabin RA, Regina M, Doat M, Winter JC | title = 5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens | journal = Pharmacol Biochem Behav | volume = 72 | issue = 1–2 | pages = 29–37 | date = May 2002 | pmid = 11900766 | doi = 10.1016/s0091-3057(01)00720-1 | url = }} Harmane fails to substitute for the [psychedelic drug](/source/psychedelic_drug) [DOM](/source/DOM_(drug)) in rodent [drug discrimination](/source/drug_discrimination) tests.{{cite journal | vauthors = Glennon RA, Young R, Jacyno JM, Slusher M, Rosecrans JA | title = DOM-stimulus generalization to LSD and other hallucinogenic indolealkylamines | journal = Eur J Pharmacol | volume = 86 | issue = 3–4 | pages = 453–459 | date = January 1983 | pmid = 6572591 | doi = 10.1016/0014-2999(83)90196-6 | url = }} This is similar to the case of [harmine](/source/harmine) but is in contrast to [harmaline](/source/harmaline) and [6-methoxyharmalan](/source/6-methoxyharmalan). ==Chemistry== Harmane is a [methyl](/source/methyl)ated [derivative](/source/derivative_(chemistry)) of [β-carboline](/source/substituted_%CE%B2-carboline) with the molecular formula C12H10N2. ==Natural occurrence== {| class="wikitable sortable" |+ Plant sources |- ! Family !! Plant |- | Rubiaceae || ''[Coffea arabica](/source/Coffea_arabica)'' |- | Solanaceae || ''[Nicotiana tabacum](/source/Nicotiana_tabacum)''{{cite journal | last1=Poindexter | first1=E.H. | last2=Carpenter | first2=R.D. | title=The isolation of harmane and norharmane from tobacco and cigarette smoke | journal=Phytochemistry | volume=1 | issue=3 | year=1962 | issn=0031-9422 | doi=10.1016/s0031-9422(00)82825-3 | pages=215–221| bibcode=1962PChem...1..215P }} |- | Theaceae || ''[Camellia sinensis](/source/Camellia_sinensis)''{{Cite journal|last1=Jiao|first1=Ye|last2=Yan|first2=Yan|last3=He|first3=Zhiyong|last4=Gao|first4=Daming|last5=Qin|first5=Fang|last6=Lu|first6=Mei|last7=Xie|first7=Mingyong|last8=Chen|first8=Jie|last9=Zeng|first9=Maomao|date=2018-06-20|title=Inhibitory effects of catechins on β-carbolines in tea leaves and chemical model systems|journal=Food & Function|volume=9|issue=6|pages=3126–3133|doi=10.1039/c7fo02053h|issn=2042-650X|pmid=29789822}} |} In 1962, Poindexter ''et al.'' found that there was very little harmane in tobacco, but a significant amount in tobacco smoke. They showed that it is produced from [tryptophan](/source/tryptophan) by the heat of burning the tobacco. ==Society and culture== ===Legal status=== ====Canada==== Harmane is not a [controlled substance](/source/controlled_substance) in [Canada](/source/Canada) as of 2025.{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=19 January 2026}} == See also == * [Substituted β-carboline](/source/Substituted_%CE%B2-carboline) * [Harmine](/source/Harmine) == References == {{Reflist}} ==External links== * [https://isomerdesign.com/pihkal/explore/5402 Harman - Isomer Design] {{Monoamine metabolism modulators}} {{Monoamine reuptake inhibitors}} {{Tryptamines}} Category:Beta-Carbolines Category:Dopamine reuptake inhibitors Category:Malaria Category:Monoamine oxidase inhibitors --- Adapted from the Wikipedia article [Harmane](https://en.wikipedia.org/wiki/Harmane) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Harmane?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.