harmaline

Summary

Summary: A beta-carboline alkaloid isolated from seeds of PEGANUM.

Top Publications

  1. Miwa H, Kubo T, Suzuki A, Kihira T, Kondo T. A species-specific difference in the effects of harmaline on the rodent olivocerebellar system. Brain Res. 2006;1068:94-101 pubmed
    The rodent model of harmaline-induced tremor has been widely used for experimental analysis of tremor. Activation of the olivocerebellar system plays a key role in tremor-generating mechanisms...
  2. Jimenez J, Riverón Negrete L, Abdullaev F, Espinosa Aguirre J, Rodriguez Arnaiz R. Cytotoxicity of the beta-carboline alkaloids harmine and harmaline in human cell assays in vitro. Exp Toxicol Pathol. 2008;60:381-9 pubmed publisher
    ..the toxicities of one full aromatic beta-carboline alkaloid (harmine) and one dihydro-beta-carboline alkaloid (harmaline) were evaluated by means of two in vitro human cell assays: the cytochalasin-B blocked micronucleus (CBMN) assay ..
  3. Martin F, Thu Le A, Handforth A. Harmaline-induced tremor as a potential preclinical screening method for essential tremor medications. Mov Disord. 2005;20:298-305 pubmed
    ..Although harmaline tremor is a well known animal model of ET, it has not found utility as a preclinical drug screen and has not ..
  4. Martin F, Handforth A. Carbenoxolone and mefloquine suppress tremor in the harmaline mouse model of essential tremor. Mov Disord. 2006;21:1641-9 pubmed
    ..whether the gap junction blockers heptanol, octanol, carbenoxolone, and mefloquine suppress tremor in the mouse harmaline model, and performed an open-treatment clinical study of mefloquine for essential tremor...
  5. Miwa H. Rodent models of tremor. Cerebellum. 2007;6:66-72 pubmed
    This review focuses on rodent models of tremor, particularly those induced by pharmacological agents. Harmaline is one of the most frequently used tremor-generating drugs and harmaline-induced tremor is regarded as a model of essential ..
  6. Paterson N, Malekiani S, Foreman M, Olivier B, Hanania T. Pharmacological characterization of harmaline-induced tremor activity in mice. Eur J Pharmacol. 2009;616:73-80 pubmed publisher
    b>Harmaline-induced tremor in rodents is a model of essential tremor. We utilized a novel assay to quantify tremor activity in mice and found that tremor activity was dependent on harmaline dose...
  7. Rizwan ul Haq M, Gong L, Hu M, Luo J. Apolipophorin III and transmission electron microscopy as toxicity indicators for harmaline and tea saponin in Spodoptera exigua (Noctuidae: Lepidoptera). Chemosphere. 2011;85:995-1001 pubmed publisher
    ..III, traditionally known for lipid transport in insects is fairly established as toxicity indicator against harmaline and tea saponin during this study...
  8. Splettstoesser F, Bonnet U, Wiemann M, Bingmann D, Büsselberg D. Modulation of voltage-gated channel currents by harmaline and harmane. Br J Pharmacol. 2005;144:52-8 pubmed
    ..The aim of this study was to investigate the effects of harmaline and harmane on voltage-activated calcium- (I(Ca(V))), sodium- (I(Na(V))) and potassium (I(K(V)))-channel ..
  9. Nakagawa Y, Suzuki T, Ishii H, Ogata A, Nakae D. Mitochondrial dysfunction and biotransformation of ?-carboline alkaloids, harmine and harmaline, on isolated rat hepatocytes. Chem Biol Interact. 2010;188:393-403 pubmed publisher
    The cytotoxic effects and biotransformation of harmine and harmaline, which are known ?-carboline alkaloids and potent hallucinogens, were studied in freshly isolated rat hepatocytes...

More Information

Publications62

  1. Beitz A, Saxon D. Harmaline-induced climbing fiber activation causes amino acid and peptide release in the rodent cerebellar cortex and a unique temporal pattern of Fos expression in the olivo-cerebellar pathway. J Neurocytol. 2004;33:49-74 pubmed
    ..In the present study, climbing fibers were activated with harmaline and rats or mice were implanted with a microdialysis probe or a microperfusion probe, respectively, to measure ..
  2. Wang X, Geng Y, Wang D, Shi X, Liu J. Separation and purification of harmine and harmaline from Peganum harmala using pH-zone-refining counter-current chromatography. J Sep Sci. 2008;31:3543-7 pubmed publisher
    ..From 1.2 g of the crude extract, 554 mg harmine and 325 mg harmaline were obtained each with a purity of over 96% as determined by HPLC...
  3. Ledoux M, Lorden J. Abnormal spontaneous and harmaline-stimulated Purkinje cell activity in the awake genetically dystonic rat. Exp Brain Res. 2002;145:457-67 pubmed
    ..In this study, both spontaneous and harmaline-stimulated single-unit Purkinje cell recordings were obtained from awake normal and dystonic rats...
  4. Zappala A, Parenti R, La Delia F, Cicirata V, Cicirata F. Expression of connexin57 in mouse development and in harmaline-tremor model. Neuroscience. 2010;171:1-11 pubmed publisher
    ..hypothesis was tested by searching for the expression of the Cx57 transcripts in the mouse cerebellum of the harmaline-tremor model...
  5. Arshaduddin M, Kadasah S, Al Deeb S, Al Moutaery K, Tariq M. Exacerbation of harmaline-induced tremor by imipramine. Pharmacol Biochem Behav. 2005;81:9-14 pubmed
    ..In the present investigation attempt was made to study the effect of imipramine on harmaline-induced tremor in rats. Male Sprague Dawley rats weighing 115+/-2.5 g were given harmaline (10 mg/kg, i.p...
  6. Berrougui H, Martín Cordero C, Khalil A, Hmamouchi M, Ettaib A, Marhuenda E, et al. Vasorelaxant effects of harmine and harmaline extracted from Peganum harmala L. seeds in isolated rat aorta. Pharmacol Res. 2006;54:150-7 pubmed
    The present work describes the mechanisms involved in the vasorelaxant effect of harmine and harmaline. These alkaloids induce in a dose-dependent manner the relaxation in the aorta precontracted with noradrenaline or KCl...
  7. Mehta H, Saravanan K, Mohanakumar K. Serotonin synthesis inhibition in olivo-cerebellar system attenuates harmaline-induced tremor in Swiss albino mice. Behav Brain Res. 2003;145:31-6 pubmed
    ..depletor, on the neurochemical processes that occur synchronously in olivary nucleus (ON) and cerebellum during harmaline-induced tremor in mice...
  8. Kartal M, Altun M, Kurucu S. HPLC method for the analysis of harmol, harmalol, harmine and harmaline in the seeds of Peganum harmala L. J Pharm Biomed Anal. 2003;31:263-9 pubmed
    A simple and sensitive method for separation and determination of harmol, harmalol, harmine and harmaline has been developed and validated...
  9. Wang G, Fowler S. Concurrent quantification of tremor and depression of locomotor activity induced in rats by harmaline and physostigmine. Psychopharmacology (Berl). 2001;158:273-80 pubmed
    Both harmaline and physostigmine are known to produce whole-body tremors in rodents, yet there is little quantitative information on the differential frequency characteristics of these tremors or on other possible motor effects of these ..
  10. Welsh J. Systemic harmaline blocks associative and motor learning by the actions of the inferior olive. Eur J Neurosci. 1998;10:3307-20 pubmed
    ..conditioning involving tongue protrusion were developed using the rat to test whether: (a) the indole alkaloid harmaline blocks associative learning via actions within the inferior olive, and (b) the inferior olive is required for ..
  11. El Gendy M, Soshilov A, Denison M, El Kadi A. Harmaline and harmalol inhibit the carcinogen-activating enzyme CYP1A1 via transcriptional and posttranslational mechanisms. Food Chem Toxicol. 2012;50:353-62 pubmed publisher
    Dioxins are known to cause several human cancers through activation of the aryl hydrocarbon receptor (AhR). Harmaline and harmalol are dihydro-?-carboline compounds present in several medicinal plants such as Peganum harmala...
  12. Kolasiewicz W, Kuter K, Nowak P, Pastuszka A, Ossowska K. Lesion of the cerebellar noradrenergic innervation enhances the harmaline-induced tremor in rats. Cerebellum. 2011;10:267-80 pubmed publisher
    ..synchronous activation of the glutamatergic olivo-cerebellar pathway has been suggested to be crucial for the harmaline-induced tremor...
  13. Park S, Kim Y, Kim Y, Park G, Lee S. Beta-carboline alkaloids harmaline and harmalol induce melanogenesis through p38 mitogen-activated protein kinase in B16F10 mouse melanoma cells. BMB Rep. 2010;43:824-9 pubmed publisher
    ..carboline alkaloids including harmaline and harmalol are widely distributed in the environment including several plant families and alcoholic beverages...
  14. Milner T, Cadoret G, Lessard L, Smith A. EMG analysis of harmaline-induced tremor in normal and three strains of mutant mice with Purkinje cell degeneration and the role of the inferior olive. J Neurophysiol. 1995;73:2568-77 pubmed
    1. The effects of intraperitoneal injections of 10 mg/kg harmaline were tested in normal mice and three strains of cerebellar mutant mice with Purkinje cell degeneration...
  15. Du W, Aloyo V, Harvey J. Harmaline competitively inhibits [3H]MK-801 binding to the NMDA receptor in rabbit brain. Brain Res. 1997;770:26-9 pubmed
    b>Harmaline, a beta-carboline derivative, is known to produce tremor through a direct activation of cells in the inferior olive. However, the receptor(s) through which harmaline acts remains unknown...
  16. Lee C, Han E, Jang Y, Han J, Ha H, Kim D. Protective effect of harmalol and harmaline on MPTP neurotoxicity in the mouse and dopamine-induced damage of brain mitochondria and PC12 cells. J Neurochem. 2000;75:521-31 pubmed
    The present study elucidated the protective effect of beta-carbolines (harmaline, harmalol, and harmine) on oxidative neuronal damage...
  17. Kim D, Jang Y, Han E, Lee C. Protective effect of harmaline and harmalol against dopamine- and 6-hydroxydopamine-induced oxidative damage of brain mitochondria and synaptosomes, and viability loss of PC12 cells. Eur J Neurosci. 2001;13:1861-72 pubmed
    The present study elucidated the protective effect of beta-carbolines (harmaline, harmalol and harmine) against oxidative damage of brain mitochondria, synaptosomes and PC12 cells induced by either dopamine or 6-hydroxydopamine...
  18. Yu A, Idle J, Krausz K, Küpfer A, Gonzalez F. Contribution of individual cytochrome P450 isozymes to the O-demethylation of the psychotropic beta-carboline alkaloids harmaline and harmine. J Pharmacol Exp Ther. 2003;305:315-22 pubmed
    ..Cytochromes P450 1A1 (18.5), 1A2 (20), and 2D6 (100) catalyzed the O-demethylation of harmaline, and CYP1A1 (98...
  19. Di Giorgio C, Delmas F, Ollivier E, Elias R, Balansard G, Timon David P. In vitro activity of the beta-carboline alkaloids harmane, harmine, and harmaline toward parasites of the species Leishmania infantum. Exp Parasitol. 2004;106:67-74 pubmed
    Harmane, harmine, and harmaline were investigated for their in vitro antileishmanial activity toward parasites of the species Leishmania infantum...
  20. Kolasiewicz W, Kuter K, Wardas J, Ossowska K. Role of the metabotropic glutamate receptor subtype 1 in the harmaline-induced tremor in rats. J Neural Transm (Vienna). 2009;116:1059-63 pubmed publisher
    ..32 mg/kg sc strongly enhances tremor of forelimbs, head and trunk, hypolocomotion, and ataxia induced by harmaline (7.5 mg/kg ip) in rats. JNJ 16259685 inhibited locomotor and exploratory activity per se...
  21. Arshaduddin M, Al Kadasah S, Biary N, Al Deeb S, Al Moutaery K, Tariq M. Citalopram, a selective serotonin reuptake inhibitor augments harmaline-induced tremor in rats. Behav Brain Res. 2004;153:15-20 pubmed
    ..The present study was undertaken to investigate the effect of chronic citalopram treatment on harmaline-induced tremors in rats...
  22. Zaker F, Oody A, Arjmand A. A study on the antitumoral and differentiation effects of peganum harmala derivatives in combination with ATRA on leukaemic cells. Arch Pharm Res. 2007;30:844-9 pubmed
    ..The present study was an evaluation of proliferation, cytotoxicity and differentiation of harmine and harmaline on HL60 cells, alone or in combination with ATRA and G-CSF...
  23. Saify Z, Farhad J, Mushtaq N, Noor F, Akhtar S, Arif M, et al. Antibacterial activity of 1-methyl-7-methoxy-beta-carboline and its phenacyl and coumarine analogues. Pak J Pharm Sci. 2005;18:39-41 pubmed
    Antibacterial activity of 1-methyl-7-methoxy-beta-carboline (harmaline) and its phenacyl and coumarine analogues 1-(3-nitro-phenyl)-(2-(7-methoxy-1-methyl-1,3,4,9-tetrahydro-beta-carbolin-2-yl)-ethanone (II), 1-(3,4-dihydroxy-phenyl)-2-(..
  24. Shahinas D, Macmullin G, Benedict C, Crandall I, Pillai D. Harmine is a potent antimalarial targeting Hsp90 and synergizes with chloroquine and artemisinin. Antimicrob Agents Chemother. 2012;56:4207-13 pubmed publisher
    ..These findings have implications for the development of novel therapeutic combinations that are synergistic with existing antimalarials. ..
  25. Frecska E. Ayahuasca versus violence--a case report. Neuropsychopharmacol Hung. 2008;10:103-6 pubmed
  26. Shen H, Jiang X, Winter J, Yu A. Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions. Curr Drug Metab. 2010;11:659-66 pubmed
    ..5-MeO-DMT is often used with MAO-A inhibitors such as harmaline. Concurrent use of harmaline reduces 5-MeO-DMT deamination metabolism and leads to a prolonged and increased ..
  27. Moura D, Rorig C, Vieira D, Henriques J, Roesler R, Saffi J, et al. Effects of beta-carboline alkaloids on the object recognition task in mice. Life Sci. 2006;79:2099-104 pubmed
    ..b>Harmaline, a dihydro beta-carboline and inverse agonist of the MK-801 binding site on the N-methyl-d-aspartate (NMDA) ..
  28. Lee S, Boron W, Parker M. Substrate specificity of the electrogenic sodium/bicarbonate cotransporter NBCe1-A (SLC4A4, variant A) from humans and rabbits. Am J Physiol Renal Physiol. 2013;304:F883-99 pubmed publisher
    ..in human, rabbit, and rat renal preparations is substantially influenced by lithium, sulfite, oxalate, and harmaline. These data were taken as evidence for the presence of distinct Na(+) and CO(3)(2-) binding sites in NBCe1-A, ..
  29. Riba J, McIlhenny E, Valle M, Bouso J, Barker S. Metabolism and disposition of N,N-dimethyltryptamine and harmala alkaloids after oral administration of ayahuasca. Drug Test Anal. 2012;4:610-6 pubmed publisher
    ..plant tea obtained from Banisteriopsis caapi, which contains ?-carboline alkaloids, chiefly harmine, harmaline and tetrahydroharmine...
  30. Wang Y, Samoylenko V, Tekwani B, Khan I, Miller L, Chaurasiya N, et al. Composition, standardization and chemical profiling of Banisteriopsis caapi, a plant for the treatment of neurodegenerative disorders relevant to Parkinson's disease. J Ethnopharmacol. 2010;128:662-71 pubmed publisher
    ..The usefulness of Banisteriopsis caapi has been established for alleviating symptoms of neurological disorders including Parkinson's disease...
  31. Monsef H, Ghobadi A, Iranshahi M, Abdollahi M. Antinociceptive effects of Peganum harmala L. alkaloid extract on mouse formalin test. J Pharm Pharm Sci. 2004;7:65-9 pubmed
    ..To evaluate the effect of Peganum harmala (Syrian rue) a wild-growing flowering plant belonging to the family Zygophylaceae and found abundantly in Iran on formalin-induced pain response in mice...
  32. Louis E. Re-thinking the biology of essential tremor: from models to morphology. Parkinsonism Relat Disord. 2014;20 Suppl 1:S88-93 pubmed publisher
    ..This shift in paradigm opens the door for research that aims to identify the primary set of molecular triggers and the cascade of molecular/cellular events that accompany this disease. ..
  33. Gołembiowska K, Berghauzen Maciejewska K, Gorska A, Kaminska K, Ossowska K. A partial lesion of the substantia nigra pars compacta and retrorubral field decreases the harmaline-induced glutamate release in the rat cerebellum. Brain Res. 2013;1537:303-11 pubmed publisher
    ..SNC) and retrorubral field (RRF) on the glutamatergic transmission in the cerebellum and tremor induced by harmaline in rats...
  34. Zhao T, Zheng S, Zhang B, Li Y, Bligh S, Wang C, et al. Metabolic pathways of the psychotropic-carboline alkaloids, harmaline and harmine, by liquid chromatography/mass spectrometry and NMR spectroscopy. Food Chem. 2012;134:1096-105 pubmed publisher
    The ?-carboline alkaloids, harmaline and harmine, are present in hallucinogenic plants Ayahuasca and Peganum harmala, and in a variety of foods...
  35. Petzel D. Na(+)/H(+) exchange in mosquito Malpighian tubules. Am J Physiol Regul Integr Comp Physiol. 2000;279:R1996-2003 pubmed
    ..7 +/- 0.6 and -0.3 +/- 0.3 x 10(-3) pH/s, respectively. These results indicate that mosquito Malpighian tubules possess a Na(+)/H(+) exchanger...
  36. Storch A, Hwang Y, Gearhart D, Beach J, Neafsey E, Collins M, et al. Dopamine transporter-mediated cytotoxicity of beta-carbolinium derivatives related to Parkinson's disease: relationship to transporter-dependent uptake. J Neurochem. 2004;89:685-94 pubmed
    ..Our data suggest that DAT-mediated cellular uptake of 2[N]-methylated betaCs represents a potential mechanism for selective toxicity towards dopaminergic neurons and may be relevant for the pathogenesis of Parkinson's disease...
  37. Milasin J, Buffo A, Carulli D, Andjus P, Strata P. MAPK activation in cerebellar basket cell terminals after harmaline treatment. Ann N Y Acad Sci. 2005;1048:411-7 pubmed
    ..In the present study we used Western blotting and immunohistochemistry to examine the effects of harmaline administration on the phosphorylation state of three MAPKs: the extracellular signal-regulated kinase (ERK1/2), ..
  38. Jiang X, Shen H, Mager D, Yu A. Pharmacokinetic interactions between monoamine oxidase A inhibitor harmaline and 5-methoxy-N,N-dimethyltryptamine, and the impact of CYP2D6 status. Drug Metab Dispos. 2013;41:975-86 pubmed publisher
    ..Our recent study has demonstrated that coadministration of monoamine oxidase A (MAO-A) inhibitor harmaline (5 mg/kg) increases systemic exposure to 5-MeO-DMT (2 mg/kg) and active metabolite bufotenine...
  39. Zayed R, Wink M. Beta-carboline and quinoline alkaloids in root cultures and intact plants of Peganum harmala. Z Naturforsch C. 2005;60:451-8 pubmed
    ..beta-Carboline alkaloids, such as harmine, harmaline dominate in normal and root cultures transformed by Agrobacterium rhizogenes, as well as in roots and fruits of ..
  40. Helsley S, Rabin R, Winter J. The effects of beta-carbolines in rats trained with ibogaine as a discriminative stimulus. Eur J Pharmacol. 1998;345:139-43 pubmed
    ..In a previous report from our laboratory harmaline completely substituted for ibogaine (83.5%)...
  41. Vidová M, Bobalova J, Smigán P. Harmaline-resistant mutant of Methanothermobacter thermautotrophicus with a lesion in Na(+)/H(+) antiport. Gen Physiol Biophys. 2011;30 Spec No:S54-60 pubmed publisher
    A spontaneous mutant of Methanothermobacter thermautotrophicus resistant to the Na(+)/H(+) antiporter inhibitor harmaline was isolated...
  42. Petroselli G, Erra Balsells R, Gara P, Bilmes G. Photoacoustic and luminescence characterization of nitrogen heterocyclic aromatic UV-MALDI matrices in solution. Photochem Photobiol Sci. 2012;11:1062-8 pubmed publisher
    ..3AQ), 2-(2-aminoethylamino)-5-nitropyridine (AAN) and 3,4-dihydro-7-methoxy-1-methyl-9H-pyrido[3,4-b] indole (harmaline, HLA) in acetonitrile solutions is described...
  43. Arshad N, Zitterl Eglseer K, Hasnain S, Hess M. Effect of Peganum harmala or its beta-carboline alkaloids on certain antibiotic resistant strains of bacteria and protozoa from poultry. Phytother Res. 2008;22:1533-8 pubmed publisher
    ..b>Harmaline was found to be in the highest concentration followed by harmine and harmalol, whereas harmane could not be ..
  44. Hilber P, Chapillon P. Effects of harmaline on anxiety-related behavior in mice. Physiol Behav. 2005;86:164-7 pubmed
    b>Harmaline (HA) is a beta-carboline commonly known to provoke motor alterations through activation of cells in the inferior olive...
  45. Movafeghi A, Abedini M, Fathiazad F, Aliasgharpour M, Omidi Y. Floral nectar composition of Peganum harmala L. Nat Prod Res. 2009;23:301-8 pubmed publisher
    ..These findings may confer a better understanding upon outcrossing processes and favour the plant-pollinator relationships...
  46. Callaway J. Fast and slow metabolizers of Hoasca. J Psychoactive Drugs. 2005;37:157-61 pubmed
    ..This age-old method compensates for metabolic variations between individuals and variations in both the alkaloid profile and strength of the hoasca...
  47. Frostholm A, Evans J, Cummings S, Rotter A. Harmaline-induced changes in gamma aminobutyric acid(A) receptor subunit mRNA expression in murine olivocerebellar nuclei. Brain Res Mol Brain Res. 2000;85:200-8 pubmed
    ..The tremorgen, harmaline, causes a bursting pattern of activity in inferior olivary neurons, the effects of which are transmitted ..
  48. Dahhaoui M, Stelz T, Caston J. Effects of lesion of the inferior olivary complex by 3-acetylpyridine on learning and memory in the rat. J Comp Physiol A. 1992;171:657-64 pubmed
    ..The effects of the inferior olivary complex lesion are obviously different according to the task to be learnt, suggesting that these two tasks do not require the integrity of the same nervous structures. ..
  49. Gerardy J, Dresse A. Comparative effects of dehydropirlindole and other compounds on rat brain monoamine oxidase type A. Prog Neuropsychopharmacol Biol Psychiatry. 2002;26:75-9 pubmed
    ..The aim of this work is to compare the inhibitory potency of DHP with three reference compounds: harmaline, befloxatone and clorgyline; the two former are reversible inhibitors and the later is an irreversible inhibitor ..
  50. Halberstadt A, Buell M, Masten V, Risbrough V, Geyer M. Modification of the effects of 5-methoxy-N,N-dimethyltryptamine on exploratory behavior in rats by monoamine oxidase inhibitors. Psychopharmacology (Berl). 2008;201:55-66 pubmed publisher
    ..a combination of psychoactive plants that contribute the active components N,N-dimethyltryptamine (DMT) and 5-methoxy-DMT (5-MeO-DMT), as well as the monoamine oxidase (MAO) inhibitors (MAOIs) harmine and harmaline for oral activity.
  51. Tariq M, Arshaduddin M, Biary N, Al Moutaery K, Al Deeb S. 2-deoxy-D-glucose attenuates harmaline induced tremors in rats. Brain Res. 2002;945:212-8 pubmed
    ..investigation attempt was made to study the effect of 2-deoxyglucose (2DG) a glycolytic pathway inhibitor on harmaline induced tremor in rats. Wistar rats of either sex weighing 100+/-3 g were given harmaline (10 mg/kg, i.p...
  52. Fowler S, Zarcone T, Vorontsova E, Chen R. Motor and associative deficits in D2 dopamine receptor knockout mice. Int J Dev Neurosci. 2002;20:309-21 pubmed
    ..operant response performance, lick dynamics (force, rhythm), grip strength, and tremor in response to harmaline challenge...
  53. Zhan X, Graf W. Harmaline attenuates voltage--sensitive Ca(2+) currents in neurons of the inferior olive. J Pharm Pharm Sci. 2012;15:657-68 pubmed
    b>Harmaline is one member of a class of tremorgenic harmala alkaloids that have been implicated in neuroprotective effects and neurodegenerative disorders...