Bufotenine: Toward an Understanding of Possible Psychoactive Mechanisms

REFERENCES

• Aghajanian , G. K. and Hailgler , H. J. 1975 . Hallucinogenic indoleamines: Preferential action upon presynaptic serotonin receptors . Psychopharmacology Communication , I ( 6 ) : 619 – 29 .
   Google Scholar
• Almaula , N. , Ebersole , B. J. , Ballesteros , J. A. , Weinstein , H. and Sealfon , S. C. 1996a . Contribution of a helix 5 locus to selectivity of hallucinogenic and non hallucinogenic ligands for the human 5-hydroxytryptamine2A and 5-hydroxytryptamine2C receptors: Direct and indirect effects of ligand affinity mediated by the same locus . Molecular Pharmacology , 50 : 34 – 42 .
   PubMed Web of Science ®Google Scholar
• Almaula , N. , Ebersole , B. J. , Zhang , D. , Weinstein , H. and Sealfon , S. C. 1996b . Mapping the binding site pocket of the serotonin 5-hydroxytryptamine2A receptor . Journal of Biological Chemistry , 271 ( 25 ) : 14672 – 75 .
   PubMed Web of Science ®Google Scholar
• Barfknecht , C. F. and Nichols , D. E. 1975 . Correlation of psychomimetic activity of phenethylamines and amphetamines with l-octanol-water partition coefficients . Journal of Medicinal Chemistry , 18 ( 2 ) : 208 – 10 .
   PubMed Web of Science ®Google Scholar
• Berger , G. , Maziere , M. , Marazano , C. and Comar , D. 1978 . Carbon II labeling of the psychoactive drug O-methyl-bufotenine and its distribution in the animal organism . European Journal of Nuclear Medicine , 3 ( 2 ) : 101 – 04 .
   PubMedGoogle Scholar
• Borne , R. F. 1994 . “ Serotonin: The neurotransmitter for the '90s. ” . In Drug Topics 108 October 10
   Google Scholar
• Burris , K. D. , Breeding , M. and Sanders-Bush , E. 1991 . (+)Lysergic acid diethylamide, but not its non hallucinogenic congeners, is a potent serotonin 5HT1C receptor agonist . Journal of Pharmacology and Experimental Therapeutics , 258 ( 3 ) : 891 – 96 .
   PubMed Web of Science ®Google Scholar
• Chen , K. K. and Kovarikova , A. 1967 . Pharmacology and toxicology of toad venom . Journal of Pharmaceutical Science , 56 : 1535 – 41 .
   PubMed Web of Science ®Google Scholar
• Chilton , W. S. , Bigwood , J. and Jensen , R. E. 1979 . Psilocin, bufotenine, and serotonin: Historical and biosynthetic observations . Journal of Psychedelic Drugs , 11 ( 1–2 ) : 61 – 9 .
   PubMed Web of Science ®Google Scholar
• Choudhary , M. S. , Craigo , S. and Roth , B. L. 1993 . A single point mutation (Phe340 => Leu340) of a conserved phenylalanine abolishes 4- [125I]Iodo-(2,5-dimethoxy)phenylisopropylamine and [3H]ketanserin binding to 5-hydroxytryptamine2 receptors . Molecular Pharmacology , 43 : 755 – 61 .
   PubMed Web of Science ®Google Scholar
• Choudhary , M. S. , Sachs , N. , Uluer , A. , Glennon , R. A. , Westkaemper , R. B. and Roth , B. L. 1995 . Differential ergoline and ergopeptine binding to 5-hydroxytryptamine2A receptors: Ergolines require an aromatic residue at position 340 for high affinity binding . Molecular Pharmacology , 47 : 450 – 57 .
   PubMed Web of Science ®Google Scholar
• Coe , M. and Deihl , R. 1980 . In the Land of the Olmec. Austin, Texas : University of Texas Press. .
   Google Scholar
• Cornfield , L. J. and Nelson , D. 1991 . “ Biochemistry of 5-hydroxytryptamine receptor subtypes: coupling to second messenger systems. ” . In Serotonin Receptor Subtypes: Basic and Clinical Aspects. Edited by: Peroutka , S. J. New York : Wiley-Liss. .
   Google Scholar
• Daly , J. W. , Myers , C. W. and Whittaker , N. 1987 . Further classification of skin alkaloids from neotropical poison frogs (Dedrobatidae), with a general survey of toxic/noxious csubstances in the amphibia . Toxicon , 24 ( 10 ) : 1023 – 95 .
   Web of Science ®Google Scholar
• Davis , W. 1985 . The Serpent and the Rainbow. New York : Simon & Schuster. .
   Google Scholar
• Davis , W. and Weil , A. T. 1992 . Identity of a New World psychoactive toad . Ancient Mesoamerica , 3 ( 1 ) : 51 – 9 .
   Google Scholar
• de Smet , P. A.G.M. 1985 . Ritual Enemas and Snuffs in the Americas. Amsterdam : Centre for Latin American Research and Documentation. .
   Google Scholar
• Donnelly , D. , Findlay , J. B.C. and Blundell , T. L. 1994 . The evolution and structure of aminergic G protein-coupled receptors . Receptor Channels , 2 : 61 – 78 .
   PubMedGoogle Scholar
• Fabing , H. D. and Hawkins , J. R. 1956 . Intravenous bufotenine injection in the human being . Science , 123 : 886 – 87 .
   PubMed Web of Science ®Google Scholar
• Fiorella , D. , Rabin , R. A. and Winter , J. C. 1995a . The role of the 5-HT2A and 5-HT2C receptors in the stimulus effect of hallucinogenic drugs I: Antagonist correlation analysis . Psychopharmacology , 121 : 347 – 56 .
   PubMed Web of Science ®Google Scholar
• Fiorella , D. , Rabin , R. A. and Winter , J. C. 1995b . The role of the 5-HT2A and 5-HT2C receptors in the stimulus effect of hallucinogenic drugs II: Reassessment of LSD false positives . Psychopharmacology , 121 : 357 – 63 .
   PubMed Web of Science ®Google Scholar
• Fiorella , D. , Rabin , R. A. and Winter , J. C. 1995c . The role of the 5-HT2A and 5-HT2C receptors in the stimulus effect of hallucinogenic drugs III: The mechanistic basis for super sensitivity to the LSD stimulus following serotonin depletion . Psychopharmacology , 121 : 364 – 72 .
   PubMed Web of Science ®Google Scholar
• Fuller , R. W. , Snoddy , H. D. and Perry , K. W. 1995 . Tissue distribution. metabolism and effects of bufotenine administered to rats . Neuropharmacology , 34 ( 7 ) : 799 – 804 .
   PubMed Web of Science ®Google Scholar
• Furst , P. , ed. 1972, 1990 . The Flesh of the Gods: The Ritual Use of Hallucinogens. Prospect Heights, Illinois : Waveland Press. .
   Google Scholar
• Furst , P. 1981 . “ Jaguar baby or toad mother: A new look at an old problem in Olmec iconography. ” . In The Olmec and Their Neighbors, Essays in Memory of Matthew W. Stirling. Edited by: Benson , E. P. Washington, D.C. : Dumbarton Oaks Research Library and Collections. .
   Google Scholar
• Gennaro , A. R. , ed. 1990 . Remington's Pharmaceutical Sciences. , 18th Ed. Easton, Pennsylvania : Mack Publishing Co. .
   Google Scholar
• Geyer , M. A. , Warbritton , J. D. , Menkes , D. M. , Zook , J. A. and Mandel , A. J. 1975 . Opposite effects of intraventricular serotonin and bufotenin on rat startle responses . Pharmacology, Biochemistry and Behavior , 3 ( 4 ) : 687 – 91 .
   PubMed Web of Science ®Google Scholar
• Glennon , R. A. 1994 . “ Classical hallucinogens: An introductory overview. ” . In Hallucinogens: An Update Edited by: Lin , G. C. and Glennon , R. A. Washington, DC : U.S. Department of Health and Human Services. . NIDA Research Monograph 146
   Google Scholar
• Glennon , R. A. and Dukat , M. 1995 . “ Serotonin receptor subtypes. ” . In Psychopharmacology: The Fourth Generation of Progress. Edited by: Bloom , F. E. and Kupfer , D. J. New York : Raven Press. .
   Google Scholar
• Glennon , R. A. , Westkaemper , R. B. and Bartyzel , P. 1991 . “ Medicinal chemistry of serotonergic agents. ” . In Serotonin Receptor Subtypes: Basic and Clinical Aspects. Edited by: Peroutka , S. J. New York : Wiley-Liss. .
   Google Scholar
• Glennon , R. A. , Dukat , M. , El-Bermawy , M. , Law , H. , De Los Angeles , J. , Teitler , M. , King , A. and Herrick-Davis , K. 1994 . Influence of amine substitutes on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines . Journal of Medicinal Chemistry , 37 ( 13 ) : 1929 – 35 .
   PubMed Web of Science ®Google Scholar
• Glennon , R. A. , Gessner , P. K. , Godse , D. D. and Kline , B. 1979 . Bufotenine esters . Journal of Medicinal Chemistry , 22 ( 11 ) : 1414 – 16 .
   PubMed Web of Science ®Google Scholar
• Guyton , A. C. 1991 . Textbook of Medical Physiology. Philadelphia : W.B. Saunders Company. .
   Google Scholar
• Hardebo , J. E. and Ownman , C. 1980 . Barrier mechanisms for neurotransmitter monoamines and the precursors at the blood-brain interface . Annals of Neurology , 8 ( 1 ) : 1 – 31 .
   PubMed Web of Science ®Google Scholar
• Hardman , J. G. and Limbird , L. E. , eds. 1996 . Goodman and Gillman's The Pharmacological Basis of Therapeutics, , 9th Ed. New York : McGraw-Hill. .
   Google Scholar
• Hitt , M. and Ettinger , D. D. 1986 . Toad toxicity . New England Journal of Medicine , 314 : 1517
   PubMed Web of Science ®Google Scholar
• Huang , K. N. and Julius , D. 1991 . “ Molecular characterization of three serotonin receptor subtypes. ” . In Serotonin Receptor Subtypes: Basic and Clinical Aspects. Edited by: Peroutka , S. J. New York : Wiley-Liss. .
   Google Scholar
• Hungen , K. V. , Roberts , S. and Hill , D. F. 1975 . Interactions between lysergic acid diethylamide and dopamine-sensitive adenyl cyclase systems in rat brain . Brain Research , 94 ( 1 ) : 57 – 66 .
   PubMed Web of Science ®Google Scholar
• Jacob , P. and Shulgin , A. T. 1994 . “ Structure-activity relationships of the classical hallucinogens and their analogs. ” . In Hallucinogens: An Update. Edited by: Lin , G. C. and Glennon , R. A. Washington, D.C : U.S. Department of Health ad Human Services. . NIDA Research Monograph 146
   Google Scholar
• Johansson , B. B. 1989 . “ Hypertension and the blood-brain barrier. ” . In Implications of the Blood-Brain Barrier and Its Manipulation. Edited by: Neuwelt , E. A. Volume 2 , New York : Plenum Medical Book Company. .
   Google Scholar
• Johansson , B. B. and Martinsson , L. 1980 . The blood-brain barrier in adrenaline-induced hypertension. Circadian variations and modification by beta-adrenoreceptor antagonists . Acta Neurologica Scandinavica , 62 ( 2 ) : 96 – 102 .
   PubMed Web of Science ®Google Scholar
• Johansson , B. B. and Martinsson , L. 1979 . Blood-brain barrier to albumin in awake rats in acute hypertension induced by adrenaline, noradrenaline or angiotensin . Acta Neurologica Scandinavica , 60 ( 4 ) : 193 – 97 .
   PubMed Web of Science ®Google Scholar
• Johnson , M. P. , Loncharich , R. J. , Baez , M. and Nelson , D. L. 1993 . Species variations in transmembrane region V of the 5-hydroxytryptamine type 2A receptor alter the structure-activity relationship of certain ergo lines and tryptamines . Molecular Pharmacology , 45 : 277 – 86 .
   Web of Science ®Google Scholar
• Kantor , R. E. , Dudlettes , S. D. and Shulgin , A. T. 1980 . 5-methoxy-alpha-methyl-tryptamine, a hallucinogenic homolog of serotonin . Biological Psychiatry , 15 ( 2 ) : 349 – 52 .
   PubMed Web of Science ®Google Scholar
• Kennedy , A. B. 1982 . Ecce Bufo: The toad in nature and in Olmec iconography . Current Anthropology , 23 ( 3 ) : 273 – 90 .
   Web of Science ®Google Scholar
• Kristiansen , K. and Dahl , S. G. 1996 . Molecular modeling of serotonin, ketanserin, ritanserin and their 5-HT2C receptor interactions . European Journal of Pharmacology , 306 : 195 – 210 .
   PubMed Web of Science ®Google Scholar
• Lyttle , T. , Goldstein , D. and Gartz , J. 1996 . Bufo toads and bufotenine: Fact and fiction surrounding an alleged psychedelic . Journal of Psychoactive Drugs , 28 ( 3 ) : 267 – 90 .
   PubMed Web of Science ®Google Scholar
• Marek , G. J. and Aghajanian , G. K. 1996 . LSD and the phenethylamine hallucinogen DOI are potent agonists at the 5-HT2A receptors on inter neurons in rat piriform cortex . Journal of Pharmacology and Experimental Therapeutics , 278 ( 3 ) : 1373 – 82 .
   PubMed Web of Science ®Google Scholar
• Marieb , E. N. 1992 . Human Anatomy and Physiology, , 2nd Ed. Redwood City, California : Benjamin/Cummings Publishing Company. .
   Google Scholar
• McClue , S. J. , Brazell , C. and Stahl , S. M. 1989 . Hallucinogenic drugs are partial agonists of the human platelet shape change response: A physiological model of the 5-HT2 receptor . Biological Psychiatry , 26 ( 3 ) : 297 – 302 .
   PubMed Web of Science ®Google Scholar
• McKenna , D. J. and Towers , G. H.N. 1984 . Biochemistry and pharmacology of tryptamines and beta-carbolines, a minireview . Journal of Psychoactive Drugs , 16 : 347 – 58 .
   PubMed Web of Science ®Google Scholar
• McLeod , W. R. and Sitaram , B. R. 1985 . Bufotenine reconsidered . Acta Psychiatrica Scandinavica , 72 : 447 – 50 .
   PubMed Web of Science ®Google Scholar
• Migliaccio , G. P. , Shieh , T-L. N. , Byrn , S. R. , Hathaway , B. A. and Nichols , D. E. 1981 . Comparison of solution conformational preferences for the hallucinogens bufotenine and psilocin using 360-MHz proton NMR spectroscopy . Journal of Medicinal Chemistry , 24 ( 2 ) : 206 – 09 .
   PubMed Web of Science ®Google Scholar
• Newton , R. A. , Phipps , S. L. , Flanigan , N. R. , Newberry , N. R. , Carey , J. E. , Kumar , C. , McDonald , B. , Chen , C. and Elliott , J. M. 1996 . Characterisation of human 5-hydroxytryptamine2A and 5-hydroxytryptamine2C receptors expressed in the human neuroblastoma cell line SH-SYSY: Comparative stimulation by hallucinogenic drugs . Journal of Neurochemistry , 67 ( 6 ) : 2521 – 31 .
   PubMed Web of Science ®Google Scholar
• Peroutka , S. J. 1991 . “ The molecular pharmacology of 5-hydroxytryptamine receptor subtypes. ” . In Serotonin Receptor Subtypes: Basic and Clinical Aspects. Edited by: Peroutka , S. J. New York : Wiley-Liss. .
   Google Scholar
• Peroutka , S. J. 1985 . Selective labeling of 5-HTIA and 5-HTIB binding sites in bovine brain . Brain Research , 344 ( 1 ) : 167 – 71 .
   PubMed Web of Science ®Google Scholar
• Pfaff , R. C. , Huang , X. , Marona-Lewicka , D. , Oberlander , R. and Nichols , D. 1994 . “ Lysergamides revisited. ” . In Hallucinogens: An Update. Edited by: Lin , G. C. and Glennon , R. A. Washington, D.C. : U.S. Department of Health and Human Services. . NIDA Research Monograph 146
   Google Scholar
• Reilly , F. K. III . 1989 . The shaman in transformation pose: A study of the theme of rulership in Olmec art . Record of the Art Museum, Princeton University , 48 ( 2 ) : 4 – 21 .
   Google Scholar
• Roth , B. L. , Chaudhary , M. S. , Kahn , N. and Uluer , A. Z. 1997a . High-affinity agonist binding is not sufficient for agonist efficacy at 5-hydroxytryptamine2A receptors: Evidence in favor of a modified ternary complex model . Journal of Pharmacology and Experimental Therapeutics , 280 ( 2 ) : 576 – 83 .
   PubMed Web of Science ®Google Scholar
• Roth , B. L. , Shoham , M. , Choudhary , M. S. and Kahn , N. 1997b . Identification of conserved aromatic residues essential for agonist binding and second messenger production at 5-HT2A receptors . Molecular Pharmacology , 52 ( 2 ) : 259 – 66 .
   PubMed Web of Science ®Google Scholar
• Sanders-Bush , E. 1994 . “ Neurochemical evidence that hallucinogenic drugs are 5-HTIC receptor agonists: What next?. ” . In Hallucinogens: An Update. Edited by: Lin , G. C. and Glennon , R. A. Washington, D.C. : U.S. Department of Health and Human Services. . NIDA Research Monograph 146
   Google Scholar
• Sanders-Bush , E. and Canton , H. 1995 . “ Serotonin receptors: Signal transduction pathways. ” . In Psychopharmacology: The Fourth Generation of Progress. Edited by: Broom , F. E. and Kupfer , D. New York : Raven Press. .
   Google Scholar
• Sanders-Bush , E. , Oates , J. A. and Bush , M. T. 1976 . Metabolism of bufotenine-21–14 C in human volunteers . Life Sciences , 19 ( 9 ) : 1407 – 12 .
   PubMed Web of Science ®Google Scholar
• Schultes , R. E. 1990 . “ [1972]. An overview of hallucinogens in the western hemisphere. ” . In Flesh of the Gods, The Ritual Use of Hallucinogens. Edited by: Furst , P. Prospect Heights, Illinois : Waveland Press. .
   Google Scholar
• Shih , J. C. , Chen , K. and Gallaher , T. K. 1995 . “ Molecular biology of serotonin receptors: A basis for understanding and addressing brain function. ” . In Psychopharmacology: The Fourth Generation of Progress. Edited by: Broom , F. E. and Kupfer , D. New York : Raven Press. .
   Google Scholar
• Shih , J. C. , Chen , K. and Gallaher , T. K. 1994 . “ Structure and function of serotonin 5-HT2 receptors. ” . In Hallucinogens: An Update. Edited by: Lin , G. C. and Glennon , R. A. Washington, D.C. : U.S. Department of Health and Human Services. . NIDA Research Monograph 146
   Google Scholar
• Sokrab , T-E. O. , Johansson , B. B. , Tengvar , C. , Kalimo , H. and Olsson , Y. 1988 . Adrenaline-induced hypertension: morphological consequences of the blood-brain barrier disturbance . Acta Neurologica Scandinavica , 77 ( 5 ) : 387 – 96 .
   PubMed Web of Science ®Google Scholar
• Takahashi , T. , Takahashi , Z. , Ido , T. , Yanai , K. , Iwata , R. , Lshiwata , K. and Nozoe , S. 1985 . 11C-labeling of indolealkylamine alkaloids and the comparative study of their tissue distributions . International Journal of Applied Radiation and Isotopes , 36 ( 1 ) : 965 – 69 .
   PubMedGoogle Scholar
• Trumpp-Kallmeyer , S. , Hoflack , J. , Bruinvels , A. and Hiber , M. F. 1992 . Modeling of G-protein-coupling receptors: Application to dopamine, adrenaline, serotonin, acetylcholine, and mammalian opsin receptors . Journal of Medicinal Chemistry , 35 : 3448 – 62 .
   PubMed Web of Science ®Google Scholar
• Vogel , W. H. and Evans , B. D. 1977 . Structure-activity-relationships of certain hallucinogenic substances based on brain levels . Life Sciences , 20 ( 10 ) : 1629 – 36 .
   PubMed Web of Science ®Google Scholar
• Wang , C-D. , Gallaher , T. K. and Shih , J. C. 1993 . Site-directed mutagenesis of the serotonin 5-hydroxytryptamine2 receptor: Identification of amino acids necessary for ligand binding and receptor activation . Molecular Pharmacology , 43 : 931 – 40 .
   PubMed Web of Science ®Google Scholar
• Wasson , R. G. 1990 . “ [1972]. The divine mushroom of immortality. ” . In Flesh of the Gods, The Ritual Use of Hallucinogens Edited by: Furst , P. Prospect Heights, Illinois : Waveland Press, Inc. .
   Google Scholar
• Wasson , R. G. 1980 . The Wondrous Mushroom: Mycolatry in Mesoamerica. New York : McGraw-Hill. .
   Google Scholar
• Weinstein , H. , Zhang , D. and Ballesteros , J. A. 1994 . “ Hallucinogens acting at 5-HT receptors: Towards a mechanistic understanding at atomic resolution. ” . In Hallucinogens: An Update. Edited by: Lin , G. C. and Glennon , R. A. Washington, D.C. : U.S. Department of Health and Human Services. . NIDA Research Monograph 146
   Google Scholar
• Westkaemper , R. B. and Glennon , R. A. 1994 . “ Molecular modeling of the interaction of LSD and other hallucinogens with 5-HT2 receptors. ” . In Hallucinogens: An Update. Edited by: Lin , G. C. and Glennon , R. A. Washington, D.C : U.S Department of Health and Human Services. . NIDA Research Monograph 146
   Google Scholar
• Zunkeler , B. , Carson , R. E. , Olson , J. , Blasberg , R. G. , De Vroom , H. , Lutz , R. J. , Saris , S. C. , Wright , D. C. , Kammerer , W. , Patronas , N. J. , Dedrick , R. L. , Herscovitch , P. and Oldfield , E. H. 1996 . Quantification and pharmacokinetics of blood-brain barrier disruption in humans . Journal of Neurosurgery , 85 ( 6 ) : 1056 – 65 .
   PubMed Web of Science ®Google Scholar