Harmane

{{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-9H-pyrido[3,4-b]indole

| OtherNames = Harman, 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 (harman) is a heterocyclic amine found in a variety of foods including 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.| 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.{{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}}

Harmane is related to other alkaloids, harmine and harmaline, found in 1837 in the plant 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 }} Harmane has been found to inhibit the early stages of the growth of the malaria parasite in the gut of mosquitoes infected by the bacterium 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 |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}}