bufotenin

Summary

Summary: A hallucinogenic serotonin analog found in frog or toad skins, mushrooms, higher plants, and mammals, especially in the brains, plasma, and urine of schizophrenics. Bufotenin has been used as a tool in CNS studies and misused as a psychedelic.

Top Publications

  1. Almaula N, Ebersole B, Zhang D, Weinstein H, Sealfon S. Mapping the binding site pocket of the serotonin 5-Hydroxytryptamine2A receptor. Ser3.36(159) provides a second interaction site for the protonated amine of serotonin but not of lysergic acid diethylamide or bufotenin. J Biol Chem. 1996;271:14672-5 pubmed
    ..This interaction serves to orient the ligands in the binding pocket and may influence the degree of receptor activation. ..
  2. Halberstadt A, Nichols D, Geyer M. Behavioral effects of ?,?,?,?-tetradeutero-5-MeO-DMT in rats: comparison with 5-MeO-DMT administered in combination with a monoamine oxidase inhibitor. Psychopharmacology (Berl). 2012;221:709-18 pubmed publisher
    ..These results demonstrate that deuterated tryptamines may be useful in behavioral and pharmacological studies to mimic the effects of tryptamine/MAOI combinations. ..
  3. Moretti C, Gaillard Y, Grenand P, Bevalot F, Prevosto J. Identification of 5-hydroxy-tryptamine (bufotenine) in takini (Brosimumacutifolium Huber subsp. acutifolium C.C. Berg, Moraceae), a shamanic potion used in the Guiana Plateau. J Ethnopharmacol. 2006;106:198-202 pubmed
    ..acutifolium C.C. Berg that is found in the same area of the eastern Guianas. ..
  4. Roth B, Shoham M, Choudhary M, Khan N. Identification of conserved aromatic residues essential for agonist binding and second messenger production at 5-hydroxytryptamine2A receptors. Mol Pharmacol. 1997;52:259-66 pubmed
    ..These results demonstrate that highly conserved aromatic residues residing in neighboring helices provide the optimum environment for both agonist binding and activation of 5-HT2A receptors. ..
  5. Brubacher J, Lachmanen D, Ravikumar P, Hoffman R. Efficacy of digoxin specific Fab fragments (Digibind) in the treatment of toad venom poisoning. Toxicon. 1999;37:931-42 pubmed
    ..00003 for mortality and p = 0.009 for seizures). Digoxin specific Fab fragments are effective in the treatment of Chan Su poisoning in mice and may be effective for poisoning by other cardioactive steroids of the bufadienolide class. ..
  6. Lyttle T, Goldstein D, Gartz J. Bufo toads and bufotenine: fact and fiction surrounding an alleged psychedelic. J Psychoactive Drugs. 1996;28:267-90 pubmed
    ..Finally, to promote further investigation, a comprehensive bibliography is provided that charts the history of the Bufo toad and bufotenine. ..
  7. Berg K, Cropper J, Niswender C, Sanders Bush E, Emeson R, Clarke W. RNA-editing of the 5-HT(2C) receptor alters agonist-receptor-effector coupling specificity. Br J Pharmacol. 2001;134:386-92 pubmed
    ..3. Consistent with our previous report, the efficacy order of two 5-HT receptor agonists (TFMPP and bufotenin) was reversed for AA release and IP accumulation at the non-edited receptor thus demonstrating agonist ..
  8. Takeda N. Serotonin-degradative pathways in the toad (Bufo bufo japonicus) brain: clues to the pharmacological analysis of human psychiatric disorders. Comp Biochem Physiol Pharmacol Toxicol Endocrinol. 1994;107:275-81 pubmed
  9. Grover L, Farley J, Auerbach S. Serotonin involvement during in vitro conditioning of Hermissenda. Brain Res Bull. 1989;22:363-72 pubmed
    ..Yohimbine, an alpha 2-receptor antagonist, was without effect. These results, and those in the accompanying papers, suggest that serotonin modulates Type B photoreceptor excitability during associative conditioning. ..

More Information

Publications39

  1. Yanase E, Ohno M, Harakawa H, Nakatsuka S. Isolation of N,N-dimethyl and N-methylserotonin 5-O-?-glucosides from immature Zanthoxylum piperitum seeds. Biosci Biotechnol Biochem. 2010;74:1951-2 pubmed
    ..Their structures were determined by multi-step conversion reactions and spectroscopic analyses. Immature seeds of Z. piperitum contained extremely high levels of compounds 1a and 1b of approximately 0.29% and 0.15% (w/w), respectively. ..
  2. Siegel D, McDaniel S. The frog prince: tale and toxicology. Am J Orthopsychiatry. 1991;61:558-62 pubmed
    b>Bufotenin is a substance present in the skin of some common species of frogs, and its ingestion (such as would occur in licking or kissing a frog) can result in vivid hallucinations...
  3. Barker S, McIlhenny E, Strassman R. A critical review of reports of endogenous psychedelic N, N-dimethyltryptamines in humans: 1955-2010. Drug Test Anal. 2012;4:617-35 pubmed publisher
    ..The review also discusses the shortcomings of the existing data in light of more recent findings and how these may be overcome. Suggestions for the future directions of endogenous psychedelics research are offered. ..
  4. Kärkkäinen J, Räisänen M. Nialamide, an MAO inhibitor, increases urinary excretion of endogenously produced bufotenin in man. Biol Psychiatry. 1992;32:1042-8 pubmed
    ..to a normal man who volunteered in two separate trials (total intake 300 mg and 1000 mg, respectively), and his bufotenin excretion was followed by consecutive urine samples...
  5. Williams G, Smith D, Smith D. 5-HT3 receptors are not involved in the modulation of the K(+)-evoked release of [3H]5-HT from spinal cord synaptosomes of rat. Neuropharmacology. 1992;31:725-33 pubmed
    ..These results support the idea that 5-HT3 receptors do not act as nerve terminal autoreceptors in the spinal cord of the rat. ..
  6. Balzer I, Hardeland R. Effects of indoleamines and short photoperiods on the encystment of Gonyaulax polyedra. Chronobiol Int. 1992;9:260-5 pubmed
    ..and N,N-dimethyl-5-methoxytryptamine, and, at high concentrations, their respective precursors, serotonin and bufotenin, are capable of inducing cyst formation at 20 degrees C and in LD 12:12, whereas N-acetyl-serotonin does not ..
  7. Shen H, Wu C, Jiang X, Yu A. Effects of monoamine oxidase inhibitor and cytochrome P450 2D6 status on 5-methoxy-N,N-dimethyltryptamine metabolism and pharmacokinetics. Biochem Pharmacol. 2010;80:122-8 pubmed publisher
    ..These findings indicate that MAOI largely affects 5-MeO-DMT metabolism and pharmacokinetics, as well as bufotenine formation that is mediated by CYP2D6. ..
  8. Ott J. Pharmañopo-psychonautics: human intranasal, sublingual, intrarectal, pulmonary and oral pharmacology of bufotenine. J Psychoactive Drugs. 2001;33:273-81 pubmed
    ..Salient phytochemical and psychonautic literature is reviewed, and isolation of bufotenine from Anadenanthera seeds detailed (with one table and eight references). ..
  9. Vishwanathan K, Bartlett M, Stewart J. Determination of antimigraine compounds rizatriptan, zolmitriptan, naratriptan and sumatriptan in human serum by liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2000;14:168-72 pubmed
    ..3% and accuracy (%error) was less than 9.8% for all components. The limits of detection (LOD) for the method were 250 pg/mL for sumatriptan and 100 pg/mL for the remaining analytes based on a signal-to-noise ratio of 3. ..
  10. Berg K, Maayani S, Goldfarb J, Scaramellini C, Leff P, Clarke W. Effector pathway-dependent relative efficacy at serotonin type 2A and 2C receptors: evidence for agonist-directed trafficking of receptor stimulus. Mol Pharmacol. 1998;54:94-104 pubmed
    ..Rational drug design that optimizes preferential effector activity within a group of receptor-selective drugs holds the promise of increased selectivity in clinically useful agents. ..
  11. McPherson D, Blankenship J. Neuronal modulation of foot and body-wall contractions in Aplysia californica. J Neurophysiol. 1992;67:23-8 pubmed
    ..5-HT immunoreactivity is present in axons associated with foot and body-wall muscle. 5. Bath-applied 5-HT causes rhythmic bursting in the modulatory neurons. It appears likely that they are homologous to the POP cells of A. brasiliana. ..
  12. Takeda N, Ikeda R, Ohba K, Kondo M. Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. Neuroreport. 1995;6:2378-80 pubmed
    ..Only two of 200 urine specimens from healthy controls were positive for bufotenine. Thus, the presence and levels of bufotenine might be useful and important markers of some psychiatric disorders...
  13. Boulenguez P, Chauveau J, Segu L, Morel A, Lanoir J, Delaage M. A new 5-hydroxy-indole derivative with preferential affinity for 5-HT1B binding sites. Eur J Pharmacol. 1991;194:91-8 pubmed
    ..These derivatives could be of great interest for ultrastructural and behavioral studies relevant to 5-HT1B sites. ..
  14. Di Renzo G, Marino A. [Serotonin receptor subtypes. Considerations on their physiological role and therapeutic prospects]. Clin Ter. 1990;133:3-7 pubmed
    ..The development of specific agonists and antagonists to these different types of receptors suggests the possibility of a selective use of these drugs in the treatment of various disorders. ..
  15. Sitaram B, McLeod W. Observations on the metabolism of the psychotomimetic indolealkylamines: implications for future clinical studies. Biol Psychiatry. 1990;28:841-8 pubmed
    ..The implications of our observation for the interpretation of past clinical studies and the design of future ones is discussed. ..
  16. Roth B, Choudhary M, Khan N, Uluer A. High-affinity agonist binding is not sufficient for agonist efficacy at 5-hydroxytryptamine2A receptors: evidence in favor of a modified ternary complex model. J Pharmacol Exp Ther. 1997;280:576-83 pubmed
    ..These results are consistent with recent models of G protein-receptor functioning (e.g., modified ternary complex model) that predict that additional transition states of the receptor-ligand complex are essential for agonist efficacy...
  17. Sitaram B, Lockett L, McLeish M, Hayasaka Y, Blackman G, McLeod W. Gas chromatographic-mass spectroscopic characterisation of the psychotomimetic indolealkylamines and their in vivo metabolites. J Chromatogr. 1987;422:13-23 pubmed
    ..We now describe the combination of liquid chromatography with gas chromatography-mass spectrometry for the unequivocal verification of a number of structurally characteristic metabolites of the psychotomimetic indolealkylamines...
  18. Kärkkäinen J, Forsstrom T, Tornaeus J, Wahala K, Kiuru P, Honkanen A, et al. Potentially hallucinogenic 5-hydroxytryptamine receptor ligands bufotenine and dimethyltryptamine in blood and tissues. Scand J Clin Lab Invest. 2005;65:189-99 pubmed
  19. Martin R, Schürenkamp J, Gasse A, Pfeiffer H, Kohler H. Determination of psilocin, bufotenine, LSD and its metabolites in serum, plasma and urine by SPE-LC-MS/MS. Int J Legal Med. 2013;127:593-601 pubmed publisher
    ..3 %. Processed samples were stable in the autosampler for at least 2 days. Furthermore, freeze/thaw and long-term stability were investigated. The method was successfully applied to authentic serum and urine samples. ..
  20. 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
    ..In addition, the pharmacokinetic and pharmacodynamic drug-drug interactions between harmaline and 5-MeO-DMT, potential involvement of CYP2D6 pharmacogenetics, and risks of 5-MeO-DMT intoxication are discussed. ..
  21. Emanuele E, Colombo R, Martinelli V, Brondino N, Marini M, Boso M, et al. Elevated urine levels of bufotenine in patients with autistic spectrum disorders and schizophrenia. Neuro Endocrinol Lett. 2010;31:117-21 pubmed
    ..Our results indicate that elevated urine levels of the endogeneous psychotomimetic molecule bufotenine may play a role in ASD and schizophrenia, and can be correlated with hyperactivity scores in autism. ..
  22. Kostakis C, Byard R. Sudden death associated with intravenous injection of toad extract. Forensic Sci Int. 2009;188:e1-5 pubmed publisher
    ..It also shows the difficulties that may be associated with attempting to identify low levels of organic toxins in postmortem specimens necessitating a targeted screening approach guided by information obtained at the death scene...
  23. Costa T, Morales R, Brito J, Gordo M, Pinto A, Bloch C. Occurrence of bufotenin in the Osteocephalus genus (Anura: Hylidae). Toxicon. 2005;46:371-5 pubmed
    b>Bufotenin (5-hydroxy-N,N-dimetyltryptamine) is a tryptamine alkaloid widely spread among anuran families as a component of their chemical defense system, acting as a potent hallucinogenic factor, showing similar activity to LSD upon ..
  24. Ebersole B, Visiers I, Weinstein H, Sealfon S. Molecular basis of partial agonism: orientation of indoleamine ligands in the binding pocket of the human serotonin 5-HT2A receptor determines relative efficacy. Mol Pharmacol. 2003;63:36-43 pubmed
  25. Revial G, Jabin I, Lim S, Pfau M. Aromatization of 1,6,7,7a-tetrahydro-2H-indol-2-ones by a novel process. Preparation of key-intermediate methyl 1-benzyl-5-methoxy-1H-indole-3-acetate and the syntheses of serotonin, melatonin, and bufotenin. J Org Chem. 2002;67:2252-6 pubmed
    ..Aromatization of 10 was then accomplished with POCl(3), leading directly to the key-intermediate title compound 11 in 74% yield from ketone 6. Serotonin, melatonin, and bufotenin were then obtained by standard reactions.
  26. Fuller R, Snoddy H, Perry K. Tissue distribution, metabolism and effects of bufotenine administered to rats. Neuropharmacology. 1995;34:799-804 pubmed
    ..These experiments indicate that bufotenine is rapidly eliminated, in part by type A monoamine oxidase, after its injection into rats and that bufotenine penetrates the blood-brain barrier poorly. ..
  27. Kärkkäinen J, Räisänen M, Huttunen M, Kallio E, Naukkarinen H, Virkkunen M. Urinary excretion of bufotenin (N,N-dimethyl-5-hydroxytryptamine) is increased in suspicious violent offenders: a confirmatory study. Psychiatry Res. 1995;58:145-52 pubmed
    ..paranoid symptoms or whose violent actions had been directed against family members had higher urinary levels of bufotenin than other violent offenders...
  28. Barry T, Petzinger G, Zito S. GC/MS comparison of the West Indian aphrodisiac "Love Stone" to the Chinese medication "chan su": bufotenine and related bufadienolides. J Forensic Sci. 1996;41:1068-73 pubmed
    ..quot; The data demonstrate that the aphrodisiac was also derived from toads. ..
  29. Brubacher J, Ravikumar P, Bania T, Heller M, Hoffman R. Treatment of toad venom poisoning with digoxin-specific Fab fragments. Chest. 1996;110:1282-8 pubmed
    ..To our knowledge, this is the first reported use of digoxin Fab fragments to treat toad venom poisoning. ..
  30. Forsstrom T, Tuominen J, Kärkkäinen J. Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS. Scand J Clin Lab Invest. 2001;61:547-56 pubmed
    ..Method, procedure, considerations, statistical evaluations and urine sample spectra are presented...