Developments in harmine pharmacology - Implications for ayahuasca use and drug-dependence treatment

Progress in Neuro-Psychopharmacology and Biological Psychiatry

Volumn 39, Issue 2, 2012, Pages 263-272

  Brierley, Daniel I ^a   Davidson, Colin ^a  

^a ST GEORGE'S UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

5 HT2; Ayahuasca; Dopamine transporter; DYRK1A; Harmine; Imidazoline

Indexed keywords

AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AYAHUASCA; BANISTERIOPSIS CAAPI EXTRACT; CLORGYLINE; DOPAMINE; DOPAMINE TRANSPORTER; DUAL SPECIFICITY TYROSINE PHOSPHORYLATION REGULATED KINASE 1A; EPIGALLOCATECHIN GALLATE; HARMINE; IMIDAZOLINE I2 RECEPTOR; MIRTAZAPINE; MOCLOBEMIDE; MODAFINIL; MONOAMINE OXIDASE INHIBITOR; N,N DIMETHYLTRYPTAMINE; OLANZAPINE; PARGYLINE; PLACEBO; PLANT EXTRACT; PROTEIN TYROSINE KINASE; PSYCHEDELIC AGENT; RISPERIDONE; SELEGILINE; SEROTONIN; SEROTONIN 2A RECEPTOR; UNCLASSIFIED DRUG;

ALCOHOL ABUSE; ALCOHOLISM; BANISTERIOPSIS; BANISTERIOPSIS CAAPI; CLINICAL TRIAL (TOPIC); COCAINE DEPENDENCE; DEPRESSION; DOSE RESPONSE; DRUG BLOOD LEVEL; DRUG DEPENDENCE; DRUG MECHANISM; DRUG MEGADOSE; DRUG METABOLISM; ENZYME INHIBITION; HUMAN; LOW DRUG DOSE; MEMBRANE TRANSPORT; NEUROTRANSMISSION; NONHUMAN; PARKINSON DISEASE; PHASE 3 CLINICAL TRIAL (TOPIC); REVIEW; SINGLE DRUG DOSE; TOXICITY TESTING; WITHDRAWAL SYNDROME;

ALCOHOLISM; ANIMALS; BANISTERIOPSIS; COCAINE-RELATED DISORDERS; HARMINE; HUMANS; MONOAMINE OXIDASE INHIBITORS; N,N-DIMETHYLTRYPTAMINE; RECURRENCE;

EID: 84866986674     PISSN: 02785846     EISSN: 18784216     Source Type: Journal    
DOI: 10.1016/j.pnpbp.2012.06.001     Document Type: Review

References (163)

1. Adayev T., Wegiel J., Hwang Y.W. Harmine is an ATP-competitive inhibitor for dual-specificity tyrosine phosphorylation-regulated kinase 1A (Dyrk1A). Arch Biochem Biophys 2010, 507(2):212-218.
2. Afshar M., Knapp C.M., Sarid-Segal O., Devine E., Colaneri L.S., Tozier L., et al. The efficacy of mirtazapine in the treatment of cocaine dependence with comorbid depression. Am J Drug Alcohol Abuse 2012, 38(2):181-186.
3. Amato L., Minozzi S., Pani P.P., Davoli M. Antipsychotic medications for cocaine dependence. Cochrane Database Syst Rev 2007, 3(3):CD006306.
4. Anderson N.J., Seif I., Nutt D.J., Hudson A.L., Robinson E.S. Autoradiographical distribution of imidazoline binding sites in monoamine oxidase A deficient mice. J Neurochem 2006, 96(6):1551-1559.
5. Aricioglu-Kartal F., Kayir H., Tayfun Uzbay I. Effects of harman and harmine on naloxone-precipitated withdrawal syndrome in morphine-dependent rats. Life Sci 2003, 73(18):2363-2371.
6. Bain J., Plater L., Elliott M., Shpiro N., Hastie C.J., McLauchlan H., et al. The selectivity of protein kinase inhibitors: a further update. Biochem J 2007, 408(3):297-315.
7. Barbosa P.C., Cazorla I.M., Giglio J.S., Strassman R. A six-month prospective evaluation of personality traits. Psychiatric symptoms and quality of life in ayahuasca-naive subjects. J Psychoactive Drugs 2009, 41(3):205-212.
8. Becker W., Sippl W. Activation, regulation, and inhibition of DYRK1A. FEBS J 2011, 278(2):246-256.
9. Berry M.D., Juorio A.V., Paterson I.A. The functional role of monoamine oxidases A and B in the mammalian central nervous system. Prog Neurobiol 1994, 42(3):375-391.
10. Bour S., Iglesias-Osma M.C., Marti L., Duro P., Garcia-Barrado M.J., Pastor M.F., et al. The imidazoline I2-site ligands BU 224 and 2-BFI inhibit MAO-A and MAO-B activities, hydrogen peroxide production, and lipolysis in rodent and human adipocytes. Eur J Pharmacol 2006, 552(1-3):20-30.
11. Brierley D., Davidson C. Effect of harmine on electrically evoked dopamine efflux in the rat nucleus accumbens core and shell brain slice. Proceedings of the British Pharmacological Society 2011, [at http://www.pa2online.org/abstracts/Vol9Issue3abst002P.pdf].
12. Bubar M.J., Cunningham K.A. Prospects for serotonin 5-HT2R pharmacotherapy in psychostimulant abuse. Prog Brain Res 2008, 172:319-346.
13. Bullis R.K. The "vine of the soul" vs. the controlled substances act: implications of the hoasca case. J Psychoactive Drugs 2008, 40(2):193-199.
14. Bunzow J.R., Sonders M.S., Arttamangkul S., Harrison L.M., Zhang G., Quigley D.I., et al. Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor. Mol Pharmacol 2001, 60(6):1181-1188.
15. Cakic V., Potkonyak J., Marshall A. Dimethyltryptamine (DMT): subjective effects and patterns of use among Australian recreational users. Drug Alcohol Depend 2010, 111(1-2):30-37.
16. Callaway J.C. Fast and slow metabolizers of hoasca. J Psychoactive Drugs 2005, 37(2):157-161.
17. Callaway J.C., Grob C.S. Ayahuasca preparations and serotonin reuptake inhibitors: a potential combination for severe adverse interactions. J Psychoactive Drugs 1998, 30(4):367-369.
18. Callaway J.C., McKenna D.J., Grob C.S., Brito G.S., Raymon L.P., Poland R.E., et al. Pharmacokinetics of hoasca alkaloids in healthy humans. J Ethnopharmacol 1999, 65(3):243-256.
19. Callaway J.C., Grob C.S., McKenna D.J., Nichols D.E., Shulgin A., Tupper K.W. A demand for clarity regarding a case report on the ingestion of 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) in an ayahuasca preparation. J Anal Toxicol 2006, 30(6):406-407. [author reply 407].
20. Carlezon W.A., Thomas M.J. Biological substrates of reward and aversion: a nucleus accumbens activity hypothesis. Neuropharmacology 2009, 56(Suppl. 1):122-132.
21. Chen-Hwang M.C., Chen H.R., Elzinga M., Hwang Y.W. Dynamin is a minibrain kinase/dual specificity Yak1-related kinase 1A substrate. J Biol Chem 2002, 277(20):17597-17604.
22. Conner S.D., Schmid S.L. Regulated portals of entry into the cell. Nature 2003, 422(6927):37-44.
23. Cunningham K.A., Bubar M.J., Anastasio N.C. The serotonin 5-ht2c receptor in medial prefrontal cortex exerts rheostatic control over the motivational salience of cocaine-associated cues: new observations from preclinical animal research. Neuropsychopharmacology 2010, 35(12):2319-2321.
24. Cunningham K.A., Fox R.G., Anastasio N.C., Bubar M.J., Stutz S.J., Moeller F.G., et al. Selective serotonin 5-HT(2C) receptor activation suppresses the reinforcing efficacy of cocaine and sucrose but differentially affects the incentive-salience value of cocaine- vs. sucrose-associated cues. Neuropharmacology 2011, 61(3):513-523.
25. Cuny G.D., Ulyanova N.P., Patnaik D., Liu J.F., Lin X., Auerbach K., et al. Structure-activity relationship study of beta-carboline derivatives as haspin kinase inhibitors. Bioorg Med Chem Lett 2012, 22(5):2015-2019.
26. Dackis C.A., Kampman K.M., Lynch K.G., Pettinati H.M., O'Brien C.P. A double-blind, placebo-controlled trial of modafinil for cocaine dependence. Neuropsychopharmacology 2005, 30(1):205-211.
27. Dackis CA, Kampman KM, Lynch KG, Plebani JG, Pettinati HM, Sparkman T, et al. A double-blind, placebo-controlled trial of modafinil for cocaine dependence. J Subst Abuse Treat in press. http://dx.doi.org/10.1016/j.jsat.2011.12.014.
28. Davidson C., Lazarus C., Xiong X., Lee T.H., Ellinwood E.H. 5-HT2 receptor antagonists given in the acute withdrawal from daily cocaine injections can reverse established sensitization. Eur J Pharmacol 2002, 453(2-3):255-263.
29. De La Garza R., Newton T.F., Kalechstein A.D. Risperidone diminishes cocaine-induced craving. Psychopharmacology (Berl) 2005, 178(2-3):347-350.
30. Desmarais J.E., Looper K.J. Interactions between tamoxifen and antidepressants via cytochrome P450 2D6. J Clin Psychiatry 2009, 70(12):1688-1697.
31. Doering-Silveira E., Grob C.S., de Rios M.D., Lopez E., Alonso L.K., Tacla C., et al. Report on psychoactive drug use among adolescents using ayahuasca within a religious Context. J Psychoactive Drugs 2005, 37(2):141-144.
32. Drucker G., Raikoff K., Neafsey E.J., Collins M.A. Dopamine uptake inhibitory capacities of beta-carboline and 3,4-dihydro-beta-carboline analogs of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) oxidation products. Brain Res 1990, 509(1):125-133.
33. Eglen R.M., Hudson A.L., Kendall D.A., Nutt D.J., Morgan N.G., Wilson V.G., et al. 'Seeing through a glass darkly': casting light on imidazoline 'I' sites. Trends Pharmacol Sci 1998, 19(9):381-390.
34. Elkashef A., Fudala P.J., Gorgon L., Li S.H., Kahn R., Chiang N., et al. Double-blind, placebo-controlled trial of selegiline transdermal system (STS) for the treatment of cocaine dependence. Drug Alcohol Depend 2006, 85(3):191-197.
35. Fabregas J.M., Gonzalez D., Fondevila S., Cutchet M., Fernandez X., Barbosa P.C., et al. Assessment of addiction severity among ritual users of ayahuasca. Drug Alcohol Depend 2010, 111(3):257-261.
36. Farah A. Atypicality of atypical antipsychotics. Prim. Care Companion J Clin Psychiatry 2005, 7(6):268-274.
37. Farzin D., Mansouri N. Antidepressant-like effect of harmane and other beta-carbolines in the mouse forced swim test. Eur Neuropsychopharmacol 2006, 16(5):324-328.
38. Farzin D., Haghparast A., Motaman S., Baryar F., Mansouri N. Effects of harmane and other beta-carbolines on apomorphine-induced licking behavior in rat. Pharmacol Biochem Behav 2011, 98(2):215-219.
39. Filip M., Bubar M.J., Cunningham K.A. Contribution of serotonin (5-HT) 5-HT2 receptor subtypes to the discriminative stimulus effects of cocaine in rats. Psychopharmacology (Berl) 2006, 183(4):482-489.
40. Fletcher P.J., Rizos Z., Noble K., Higgins G.A. Impulsive action induced by amphetamine, cocaine and MK801 is reduced by 5-HT(2C) receptor stimulation and 5-HT(2A) receptor blockade. Neuropharmacology 2011, 61(3):468-477.
41. Fontanilla D., Johannessen M., Hajipour A.R., Cozzi N.V., Jackson M.B., Ruoho A.E. The hallucinogen N,N-dimethyltryptamine (DMT) is an endogenous sigma-1 receptor regulator. Science 2009, 323(5916):934-937.
42. Fortunato J.J., Reus G.Z., Kirsch T.R., Stringari R.B., Stertz L., Kapczinski F., et al. Acute harmine administration induces antidepressive-like effects and increases BDNF levels in the rat hippocampus. Prog Neuropsychopharmacol Biol Psychiatry 2009, 33(8):1425-1430.
43. Fortunato J.J., Reus G.Z., Kirsch T.R., Stringari R.B., Fries G.R., Kapczinski F., et al. Chronic administration of harmine elicits antidepressant-like effects and increases BDNF levels in rat hippocampus. J Neural Transm 2010, 117(10):1131-1137.
44. Fortunato J.J., Reus G.Z., Kirsch T.R., Stringari R.B., Fries G.R., Kapczinski F., et al. Effects of beta-carboline harmine on behavioral and physiological parameters observed in the chronic mild stress model: further evidence of antidepressant properties. Brain Res Bull 2010, 81(4-5):491-496.
45. Freedland C.S., Mansbach R.S. Behavioral profile of constituents in ayahuasca, an Amazonian psychoactive plant mixture. Drug Alcohol Depend 1999, 54(3):183-194.
46. Frison G., Favretto D., Zancanaro F., Fazzin G., Ferrara S.D. A case of beta-carboline alkaloid intoxication following ingestion of Peganum harmala seed extract. Forensic Sci Int 2008, 179(2-3):e37-e43.
47. Frost D., Meechoovet B., Wang T., Gately S., Giorgetti M., Shcherbakova I., et al. Beta-carboline compounds, including harmine, inhibit DYRK1A and tau phosphorylation at multiple Alzheimer's disease-related sites. PLoS One 2011, 6(5):e19264.
48. Gable R.S. Risk assessment of ritual use of oral dimethyltryptamine (DMT) and harmala alkaloids. Addiction 2007, 102(1):24-34.
49. Garrett M.C., Soares-da-Silva P. Role of type A and B monoamine oxidase on the formation of 3,4-dihydroxyphenylacetic acid (DOPAC) in tissues from the brain of the rat. Neuropharmacology 1990, 29(10):875-879.
50. Gaujac A., Aquino A., Navickiene S., de Andrade J.B. Determination of N,N-dimethyltryptamine in Mimosa tenuiflora inner barks by matrix solid-phase dispersion procedure and GC-MS. J Chromatogr B Analyt Technol Biomed Life Sci 2012, 881-882:107-110.
51. Gerlach M., Youdim M.B., Riederer P. Pharmacology of selegiline. Neurology 1996, 47(6 Suppl 3):S137-S145.
52. Glennon R.A., Dukat M., Grella B., Hong S., Costantino L., Teitler M., et al. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend 2000, 60(2):121-132.
53. Gockler N., Jofre G., Papadopoulos C., Soppa U., Tejedor F.J., Becker W. Harmine specifically inhibits protein kinase DYRK1A and interferes with neurite formation. FEBS J 2009, 276(21):6324-6337.
54. Grabowski J., Rhoades H., Stotts A., Cowan K., Kopecky C., Dougherty A., et al. Agonist-like or antagonist-like treatment for cocaine dependence with methadone for heroin dependence: two double-blind randomized clinical trials. Neuropsychopharmacology 2004, 29(5):969-981.
55. Grella B., Dukat M., Young R., Teitler M., Herrick-Davis K., Gauthier C.B., et al. Investigation of hallucinogenic and related β-carbolines. Drug Alcohol Depend 1998, 50(2):99-107.
56. Grella B., Teitler M., Smith C., Herrick-Davis K., Glennon R.A. Binding of beta-carbolines at 5-HT(2) serotonin receptors. Bioorg Med Chem Lett 2003, 13(24):4421-4425.
57. Grob C.S., McKenna D.J., Callaway J.C., Brito G.S., Neves E.S., Oberlaender G., et al. Human psychopharmacology of hoasca, a plant hallucinogen used in ritual context in Brazil. J Nerv Ment Dis 1996, 184(2):86-94.
58. Gulley J.M., Zahniser N.R. Rapid regulation of dopamine transporter function by substrates. Blockers and presynaptic receptor ligands. Eur J Pharmacol 2003, 479(1-3):139-152.
59. Halpern J.H. Hallucinogens: an update. Curr Psychiatry Rep 2003, 5(5):347-354.
60. Halpern J.H., Pope H.G. Hallucinogens on the internet: a vast new source of underground drug information. Am J Psychiatry 2001, 158(3):481-483.
61. Halpern J.H., Sewell R.A. Hallucinogenic botanicals of America: a growing need for focused drug education and research. Life Sci 2005, 78(5):519-526.
62. Halpern J.H., Sherwood A.R., Passie T., Blackwell K.C., Ruttenber A.J. Evidence of health and safety in American members of a religion who use a hallucinogenic sacrament. Med Sci Monit 2008, 14(8):SR15-SR22.
63. Hamsa T., Kuttan G. Studies on anti-metastatic and anti-invasive effects of harmine using highly metastatic murine B16F-10 melanoma cells. J Environ Pathol Toxicol Oncol 2011, 30(2):123-137.
64. Hill S.L., Thomas S.H. Clinical toxicology of newer recreational drugs. Clin Toxicol (Phila) 2011, 49(8):705-719.
65. Ho M.C., Cherng C.G., Tsai Y.P., Chiang C.Y., Chuang J.Y., Kao S.F., et al. Chronic treatment with monoamine oxidase-b inhibitors decreases cocaine reward in mice. Psychopharmacology (Berl) 2009, 205(1):141-149.
66. Holmstedt B.R., Lindgren J.E. Chemical constituents and pharmacology of South American snuffs. Ethnopharmacologic search for psychoactive drugs 1967, 339. US Public Health Service Publication, Washington, DC, USA. 1st ed. D.H. Efron, B.R. Holmstedt, N.S. Kline (Eds.).
67. Holt A. Imidazoline binding sites on receptors and enzymes: emerging targets for novel antidepressant drugs?. J Psychiatry Neurosci 2003, 28(6):409-414.
68. Holt A., Berry M.D., Boulton A.A. On the binding of monoamine oxidase inhibitors to some sites distinct from the MAO active site, and effects thereby elicited. Neurotoxicology 2004, 25(1-2):251-266.
69. Husbands S.M., Glennon R.A., Gorgerat S., Gough R., Tyacke R., Crosby J., et al. Beta-carboline binding to imidazoline receptors. Drug Alcohol Depend 2001, 64(2):203-208.
70. Iurlo M., Leone G., Schilstrom B., Linner L., Nomikos G., Hertel P., et al. Effects of harmine on dopamine output and metabolism in rat striatum: role of monoamine oxidase-A inhibition. Psychopharmacology (Berl) 2001, 159(1):98-104.
71. Kampman K.M., Pettinati H., Lynch K.G., Sparkman T., O'Brien C.P. A pilot trial of olanzapine for the treatment of cocaine dependence. Drug Alcohol Depend 2003, 70(3):265-273.
72. Kim H., Sablin S.O., Ramsay R.R. Inhibition of monoamine oxidase A by beta-carboline derivatives. Arch Biochem Biophys 1997, 337(1):137-142.
73. Kim D.H., Jang Y.Y., Han E.S., Lee C.S. 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(10):1861-1872.
74. Kim Y., Park J., Song W.J., Chang S. Overexpression of Dyrk1A causes the defects in synaptic vesicle endocytosis. Neurosignals 2010, 18(3):164-172.
75. Kimura A., Tyacke R.J., Minchin M.C., Nutt D.J., Hudson A.L. Identification of an I(2) binding protein from rabbit brain. Ann N Y Acad Sci 2003, 1009:364-366.
76. Knoll J. (-)Deprenyl (selegiline): past, present and future. Neurobiology (Bp) 2000, 8(2):179-199.
77. Knowles I.D., Ramage A.G. Evidence for a role for central 5-HT2B as well as 5-HT2A receptors in cardiovascular regulation in anaesthetized rats. Br J Pharmacol 1999, 128(3):530-542.
78. Labate B.C., Feeney K. Ayahuasca and the process of regulation in brazil and internationally: implications and challenges. Int J Drug Policy 2012, 23(2):154-161.
79. Lewis A., Miller J.H., Lea R.A. Monoamine oxidase and tobacco dependence. Neurotoxicology 2007, 28(1):182-195.
80. Li R., Peng N., Li X.P., Le W.D. (-)-Epigallocatechin gallate regulates dopamine transporter internalization via protein kinase C-dependent pathway. Brain Res 2006, 1097(1):85-89.
81. Li Y., Sattler R., Yang E.J., Nunes A., Ayukawa Y., Akhtar S., et al. Harmine, a natural beta-carboline alkaloid, upregulates astroglial glutamate transporter expression. Neuropharmacology 2011, 60(7-8):1168-1175.
82. Lopez-Munoz F., Alamo C. Monoaminergic neurotransmission: the history of the discovery of antidepressants from 1950s until today. Curr Pharm Des 2009, 15(14):1563-1586.
83. Louis E.D., Zheng W., Applegate L., Shi L., Factor-Litvak P. Blood harmane concentrations and dietary protein consumption in essential tremor. Neurology 2005, 65(3):391-396.
84. Ma Y., Wink M. The beta-carboline alkaloid harmine inhibits BCRP and can reverse resistance to the anticancer drugs mitoxantrone and camptothecin in breast cancer cells. Phytother Res 2010, 24(1):146-149.
85. Mabit M. Takiwasi: ayahuasca and shamanism in addiction therapy. MAPS Bull 1996, 6(3):32-34.
86. Mabit J. Using indigenous medicinal knowledge to treat drug addiction. MAPS Bull 2002, 12(2):25-32.
87. Manyam B.V., Sanchez-Ramos J.R. Traditional and complementary therapies in Parkinson's disease. Adv Neurol 1999, 80:565-574.
88. Martinez de Lagran M., Bortolozzi A., Millan O., Gispert J.D., Gonzalez J.R., Arbones M.L., et al. Dopaminergic deficiency in mice with reduced levels of the dual-specificity tyrosine-phosphorylated and regulated kinase 1A, Dyrk1A(+/-). Genes Brain Behav 2007, 6(6):569-578.
89. Mazur-Kolecka B., Golabek A., Kida E., Rabe A., Hwang Y.W., Adayev T., et al. Effect of Dyrk1a activity inhibition on development of neuronal progenitors isolated from Ts65Dn mice. J Neurosci Res 2012, 90(5):999-1010.
90. McBride M.C. Bufotenine: toward an understanding of possible psychoactive mechanisms. J Psychoactive Drugs 2000, 32(3):321-331.
91. McIlhenny E.H., Riba J., Barbanoj M.J., Strassman R., Barker S.A. Methodology for determining major constituents of ayahuasca and their metabolites in blood. Biomed Chromatogr 2012, 26(3):301-313.
92. McKenna D.J. Clinical investigations of the therapeutic potential of ayahuasca: rationale and regulatory challenges. Pharmacol Ther 2004, 102(2):111-129.
93. McKenna D.J., Towers G.H., Abbott F. Monoamine oxidase inhibitors in South American hallucinogenic plants: tryptamine and beta-carboline constituents of ayahuasca. J Ethnopharmacol 1984, 10(2):195-223.
94. Measham F., Moore K., Newcombe R., Smith Z. Tweaking, bombing, dabbing and stockpiling: the emergence of mephedrone and the perversity of prohibition. Drugs Alcohol Today 2010, 10(1; 10):14-21.
95. Mendelson S.D., Gorzalka B.B. Harmine reverses the inhibition of lordosis by the 5-HT2 antagonists pirenperone and ketanserin in the female rat. Pharmacol Biochem Behav 1986, 25(1):111-115.
96. Meneguz A., Betto P., Ricciarello G. Different effects of harmine on plasma concentrations of l-DOPA and on cerebral dopamine metabolism in rabbits and rats. Pharmacology 1994, 48(6):360-366.
97. Metzner R. Hallucinogenic drugs and plants in psychotherapy and shamanism. J Psychoactive Drugs 1998, 30(4):333-341.
98. Miralles A., Esteban S., Sastre-Coll A., Moranta D., Asensio V.J., Garcia-Sevilla J.A. High-affinity binding of beta-carbolines to imidazoline I2B receptors and MAO-A in rat tissues: norharman blocks the effect of morphine withdrawal on DOPA/noradrenaline synthesis in the brain. Eur J Pharmacol 2005, 518(2-3):234-242.
99. Moura D.J., Rorig C., Vieira D.L., Henriques J.A., Roesler R., Saffi J., et al. Effects of beta-carboline alkaloids on the object recognition task in mice. Life Sci 2006, 79(22):2099-2104.
100. Murakami N., Bolton D., Hwang Y.W. Dyrk1A binds to multiple endocytic proteins required for formation of clathrin-coated vesicles. Biochemistry 2009, 48(39):9297-9305.
101. Musgrave I.F., Badoer E. Harmane produces hypotension following microinjection into the RVLM: possible role of I(1)-imidazoline receptors. Br J Pharmacol 2000, 129(6):1057-1059.
102. Neafsey E.J., Albores R., Gearhart D., Kindel G., Raikoff K., Tamayo F., et al. Methyl-beta-carbolinium analogs of MPP+ cause nigrostriatal toxicity after substantia nigra injections in rats. Brain Res 1995, 675(1-2):279-288.
103. Newton T.F., De La Garza R., Fong T., Chiang N., Holmes T.H., Bloch D.A., et al. A comprehensive assessment of the safety of intravenous methamphetamine administration during treatment with selegiline. Pharmacol Biochem Behav 2005, 82(4):704-711.
104. Ogawa Y., Nonaka Y., Goto T., Ohnishi E., Hiramatsu T., Kii I., et al. Development of a novel selective inhibitor of the down syndrome-related kinase Dyrk1A. Nat Commun 2010, 1(7):1-9.
105. Ott J. Ayahuasca analogues Pangean Entheogens 1994, Natural Products Company, Kennewick, WA, USA. 1st ed.
106. Ott J. Pharmahuasca: human pharmacology of oral DMT plus harmine. J Psychoactive Drugs 1999, 31(2):171-177.
107. Ott J. Pharmanopo-psychonautics: human intranasal, sublingual, intrarectal, pulmonary and oral pharmacology of bufotenine. J Psychoactive Drugs 2001, 33(3):273-281.
108. Paterson L.M., Tyacke R.J., Robinson E.S., Nutt D.J., Hudson A.L. In vitro and in vivo effect of BU99006 (5-isothiocyanato-2-benzofuranyl-2-imidazoline) on I2 binding in relation to MAO: evidence for two distinct I2 binding sites. Neuropharmacology 2007, 52(2):395-404.
109. Pepper J.P., Baumann M.H., Ayestas M., Rothman R.B. Inhibition of MAO-A fails to alter cocaine-induced increases in extracellular dopamine and norepinephrine in rat nucleus accumbens. Brain Res Mol Brain Res 2001, 87(2):184-189.
110. Peraile I., Torres E., Mayado A., Izco M., Lopez-Jimenez A., Lopez-Moreno J.A., et al. Dopamine transporter down-regulation following repeated cocaine: implications for 3,4-methylenedioxymethamphetamine-induced acute effects and long-term neurotoxicity in mice. Br J Pharmacol 2010, 159(1):201-211.
111. Pimpinella G., Palmery M. Interaction of beta-carbolines with central dopaminergic transmission in mice: structure-activity relationships. Neurosci Lett 1995, 189(2):121-124.
112. Pockros L.A., Pentkowski N.S., Swinford S.E., Neisewander J.L. Blockade of 5-HT2A receptors in the medial prefrontal cortex attenuates reinstatement of cue-elicited cocaine-seeking behavior in rats. Psychopharmacology (Berl) 2011, 213(2-3):307-320.
113. Raddatz R., Parini A., Lanier S.M. Imidazoline/guanidinium binding domains on monoamine oxidases, relationship to subtypes of imidazoline-binding proteins and tissue-specific interaction of imidazoline ligands with monoamine oxidase b. J Biol Chem 1995, 270(46):27961-27968.
114. Reid M.S., Casadonte P., Baker S., Sanfilipo M., Braunstein D., Hitzemann R., et al. A placebo-controlled screening trial of olanzapine, valproate, and coenzyme Q10/l-carnitine for the treatment of cocaine dependence. Addiction 2005, 100(Suppl. 1):43-57.
115. Reniers J., Robert S., Frederick R., Masereel B., Vincent S., Wouters J. Synthesis and evaluation of beta-carboline derivatives as potential monoamine oxidase inhibitors. Bioorg Med Chem 2011, 19(1):134-144.
116. Reus G.Z., Stringari R.B., de Souza B., Petronilho F., Dal-Pizzol F., Hallak J.E., et al. Harmine and imipramine promote antioxidant activities in prefrontal cortex and hippocampus. Oxid Med Cell Longev 2010, 3(5):325-331.
117. Riba J., Rodriguez-Fornells A., Urbano G., Morte A., Antonijoan R., Montero M., et al. Subjective effects and tolerability of the South American psychoactive beverage ayahuasca in healthy volunteers. Psychopharmacology (Berl) 2001, 154(1):85-95.
118. Riba J., Valle M., Urbano G., Yritia M., Morte A., Barbanoj M.J. Human pharmacology of ayahuasca: subjective and cardiovascular effects, monoamine metabolite excretion, and pharmacokinetics. J Pharmacol Exp Ther 2003, 306(1):73-83.
119. Riba J., McIlhenny E.H., Valle M., Bouso J.C., Barker S.A. Metabolism and Disposition of N, N-Dimethyltryptamine and Harmala Alkaloids After Oral Administration of Ayahuasca. Drug Test. Anal 2012, 4(7-8):610-616.
120. Robinson E.S., Anderson N.J., Crosby J., Nutt D.J., Hudson A.L. Endogenous beta-carbolines as clonidine-displacing substances. Ann N Y Acad Sci 2003, 1009:157-166.
121. Rodd R. Reassessing the cultural and psychopharmacological significance of Banisteriopsis caapi: preparation, classification and use among the Piaroa of Southern Venezuela. J Psychoactive Drugs 2008, 40(3):301-307.
122. Rollema H., Wilson G.G., Lee T.C., Folgering J.H., Flik G. Effect of co-administration of varenicline and antidepressants on extracellular monoamine concentrations in rat prefrontal cortex. Neurochem Int 2011, 58(1):78-84.
123. Runyon S.P., Carroll F.I. Dopamine transporter ligands: recent developments and therapeutic potential. Curr Top Med Chem 2006, 6(17):1825-1843.
124. Saavedra J.M., Axelrod J. Psychotomimetic N-methylated tryptamines: formation in brain in vivo and in vitro. Science 1972, 175(4028):1365-1366.
125. Samoylenko V., Rahman M.M., Tekwani B.L., Tripathi L.M., Wang Y.H., Khan S.I., et al. Banisteriopsis caapi, a unique combination of MAO inhibitory and antioxidative constituents for the activities relevant to neurodegenerative disorders and parkinson's disease. J Ethnopharmacol 2010, 127(2):357-367.
126. Sanchez-Blazquez P., Boronat M.A., Olmos G., Garcia-Sevilla J.A., Garzon J. Activation of I(2)-imidazoline receptors enhances supraspinal morphine analgesia in mice: a model to detect agonist and antagonist activities at these receptors. Br J Pharmacol 2000, 130(1):146-152.
127. Satomura K., Takase B., Hamabe A., Ashida K., Hosaka H., Ohsuzu F., et al. Sarpogrelate, a specific 5HT2-receptor antagonist, improves the coronary microcirculation in coronary artery disease. Clin Cardiol 2002, 25(1):28-32.
128. Saura Marti J., Kettler R., Da Prada M., Richards J.G. Molecular neuroanatomy of MAO-A and MAO-B. J Neural Transm Suppl 1990, 32:49-53.
129. Scheidweiler K.B., Spargo E.A., Kelly T.L., Cone E.J., Barnes A.J., Huestis M.A. Pharmacokinetics of cocaine and metabolites in human oral fluid and correlation with plasma concentrations after controlled administration. Ther Drug Monit 2010, 32(5):628-637.
130. Schifano F., Deluca P., Baldacchino A., Peltoniemi T., Scherbaum N., Torrens M., et al. Drugs on the web; the Psychonaut 2002 EU project. Prog Neuropsychopharmacol Biol Psychiatry 2006, 30(4):640-646.
131. Schmid J.T., Jungaberle H., Verres R. Subjective theories about (self-)treatment with ayahuasca. AOC 2010, 21(2):188-204.
132. Schmidt M.M., Sharma A., Schifano F., Feinmann C. "Legal highs" on the net-evaluation of UK-based websites, products and product information. Forensic Sci Int 2011, 206(1-3):92-97.
133. Schmitt K.C., Reith M.E. Regulation of the dopamine transporter: aspects relevant to psychostimulant drugs of abuse. Ann N Y Acad Sci 2010, 1187:316-340.
134. Schwarz M.J., Houghton P.J., Rose S., Jenner P., Lees A.D. Activities of extract and constituents of Banisteriopsis caapi relevant to parkinsonism. Pharmacol Biochem Behav 2003, 75(3):627-633.
135. Seifert A., Allan L.A., Clarke P.R. DYRK1A phosphorylates caspase 9 at an inhibitory site and is potently inhibited in human cells by harmine. FEBS J 2008, 275(24):6268-6280.
136. Shen H.W., Jiang X.L., Winter J.C., Yu A.M. Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions. Curr Drug Metab 2010, 11(8):659-666.
137. Shi C.C., Chen S.Y., Wang G.J., Liao J.F., Chen C.F. Vasorelaxant effect of harman. Eur J Pharmacol 2000, 390(3):319-325.
138. Shulgin A., Shulgin A. Tihkal: the continuation 1997, Transform Press, US. D. Joy (Ed.).
139. Sitz J.H., Baumgartel K., Hammerle B., Papadopoulos C., Hekerman P., Tejedor F.J., et al. The Down syndrome candidate dual-specificity tyrosine phosphorylation-regulated kinase 1A phosphorylates the neurodegeneration-related septin 4. Neuroscience 2008, 157(3):596-605.
140. Sklerov J., Levine B., Moore K.A., King T., Fowler D. A fatal intoxication following the ingestion of 5-methoxy-N,N-DImethyltryptamine in an ayahuasca preparation. J Anal Toxicol 2005, 29(8):838-841.
141. Smelson D.A., Williams J., Ziedonis D., Sussner B.D., Losonczy M.F., Engelhart C., et al. A double-blind placebo-controlled pilot study of risperidone for decreasing cue-elicited craving in recently withdrawn cocaine dependent patients. J Subst Abuse Treat 2004, 27(1):45-49.
142. Smelson D.A., Ziedonis D., Williams J., Losonczy M.F., Williams J., Steinberg M.L., et al. The efficacy of olanzapine for decreasing cue-elicited craving in individuals with schizophrenia and cocaine dependence: a preliminary report. J Clin Psychopharmacol 2006, 26(1):9-12.
143. Sorkina T., Hoover B.R., Zahniser N.R., Sorkin A. Constitutive and protein kinase C-induced internalization of the dopamine transporter is mediated by a clathrin-dependent mechanism. Traffic 2005, 6(2):157-170.
144. Stahl S.M., Felker A. Monoamine oxidase inhibitors: a modern guide to an unrequited class of antidepressants. CNS Spectr 2008, 13(10):855-870.
145. Stolc S. Indole derivatives as neuroprotectants. Life Sci 1999, 65(18-19):1943-1950.
146. Storch A., Hwang Y.I., Gearhart D.A., Beach J.W., Neafsey E.J., Collins M.A., et al. Dopamine transporter-mediated cytotoxicity of beta-carbolinium derivatives related to Parkinson's disease: relationship to transporter-dependent uptake. J Neurochem 2004, 89(3):685-694.
147. Strassman R.J., Qualls C.R. Dose-response study of N,N-dimethyltryptamine in humans. I. Neuroendocrine, autonomic, and cardiovascular effects. Arch Gen Psychiatry 1994, 51(2):85-97.
148. Su T.P., Hayashi T., Vaupel D.B. When the endogenous hallucinogenic trace amine N,N-dimethyltryptamine meets the sigma-1 receptor. Sci Signal 2009, 2(61):pe12.
149. Szara I., Sai-Halasz A., Boszormenyi Z. Dimethyltryptamine as a new psychotic agent. Acta Physiol Hung 1957, 11:78-79. (Suppl.).
150. Topping D. Ayahuasca and cancer: one man's experience. MAPS Bull 1998, 8(3):22-26.
151. Tupper K.W. The globalization of ayahuasca: harm reduction or benefit maximization?. Int J Drug Policy 2008, 19(4):297-303.
152. Vandenbrink B.M., Foti R.S., Rock D.A., Wienkers L.C., Wahlstrom J.L. Prediction of CYP2D6 drug interactions from in vitro data: evidence for substrate-dependent inhibition. Drug Metab Dispos 2012, 40(1):47-53.
153. Venton B.J., Seipel A.T., Phillips P.E., Wetsel W.C., Gitler D., Greengard P., et al. Cocaine increases dopamine release by mobilization of a synapsin-dependent reserve pool. J Neurosci 2006, 26(12):3206-3209.
154. Villegier A.S., Salomon L., Granon S., Changeux J.P., Belluzzi J.D., Leslie F.M., et al. Monoamine oxidase inhibitors allow locomotor and rewarding responses to nicotine. Neuropsychopharmacology 2006, 31(8):1704-1713.
155. Volkow N.D., Wang G.J., Fischman M.W., Foltin R.W., Fowler J.S., Abumrad N.N., et al. Relationship between subjective effects of cocaine and dopamine transporter occupancy. Nature 1997, 386:827-830.
156. Wang Y.H., Samoylenko V., Tekwani B.L., Khan I.A., Miller L.S., Chaurasiya N.D., 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(3):662-671.
157. Wegiel J., Kuchna I., Nowicki K., Frackowiak J., Dowjat K., Silverman W.P., et al. Cell type- and brain structure-specific patterns of distribution of minibrain kinase in human brain. Brain Res 2004, 1010(1-2):69-80.
158. Weinreb O., Amit T., Bar-Am O., Youdim M.B. Rasagiline: a novel anti-Parkinsonian monoamine oxidase-B inhibitor with neuroprotective activity. Prog Neurobiol 2010, 92(3):330-344.
159. Yu A.M., Idle J.R., Krausz K.W., Kupfer A., Gonzalez F.J. 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(1):315-322.
160. Zahniser N.R., Sorkin A. Rapid regulation of the dopamine transporter: role in stimulant addiction?. Neuropharmacology 2004, 47(Suppl. 1):80-91.
161. Zayara A.E., McIver G., Valdivia P.N., Lominac K.D., McCreary A.C., Szumlinski K.K. Blockade of nucleus accumbens 5-HT2A and 5-HT2C receptors prevents the expression of cocaine-induced behavioral and neurochemical sensitization in rats. Psychopharmacology (Berl) 2011, 213(2-3):321-335.
162. Zhao T., He Y.Q., Wang J., Ding K.M., Wang C.H., Wang Z.T. Inhibition of human cytochrome P450 enzymes 3A4 and 2D6 by beta-carboline alkaloids, harmine derivatives. Phytother Res 2011, 25(11):1671-1677.
163. Zhou S.F. Polymorphism of human cytochrome P450 2D6 and its clinical significance: part I. Clin Pharmacokinet 2009, 48(11):689-723.