Erratum to: Correlating the metabolic stability of psychedelic 5-HT 2A agonists with anecdotal reports of human oral bioavailability (Neurochemical Research DOI: 10.1007/s11064-014-1253-y);Correlating the Metabolic Stability of Psychedelic 5-HT 2A Agonists with Anecdotal Reports of Human Oral Bioavailability

Neurochemical Research

Volumn 39, Issue 10, 2014, Pages 2018-2023

  Leth Petersen, Sebastian ^a   Bundgaard, Christoffer ^b   Hansen, Martin ^a   Carnerup, Martin A ^b   Kehler, Jan ^b   Kristensen, Jesper Langgaard ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b H LUNDBECK A S   (Denmark)

Author keywords

5 HT 2A agonists; Microsomal stability; N benzylphenethylamines; Phenethylamines; Psychedelics

Indexed keywords

MESCALINE; PHENETHYLAMINE DERIVATIVE; PSYCHEDELIC AGENT; SEROTONIN 2A AGONIST; SEROTONIN 2A RECEPTOR; SEROTONIN 2C RECEPTOR; SEROTONIN AGONIST;

ARTICLE; DRUG BIOAVAILABILITY; DRUG STABILITY; FIRST PASS EFFECT; HUMAN; HUMAN CELL; HYDROXYLATION; INTRINSIC CLEARANCE; LIVER MICROSOME; BIOAVAILABILITY; DRUG EFFECTS; ORAL DRUG ADMINISTRATION;

ADMINISTRATION, ORAL; BIOLOGICAL AVAILABILITY; HUMANS; RECEPTOR, SEROTONIN, 5-HT2A; SEROTONIN RECEPTOR AGONISTS;

EID: 84918767399     PISSN: 03643190     EISSN: 15736903     Source Type: Journal    
DOI: 10.1007/s11064-014-1280-8     Document Type: Erratum

References (37)

1. Schultes RE, Hofmann A (1979) Plants of the gods: origins of hallucinogenic use. Alfred van der Marck Editions, New York
2. Harman WW, McKim RH, Mogar RE, Fadiman J, Stolaroff MJ (1966) Psychedelic agents in creative problem solving: a pilot study. Psychol Rep 19:211–227
3. UNODC, World Drug Report (2013) United Nations publication, Sales no. E.13.XI.6
4. Vollenweider FX, Vollenweider-Scherpenhuyzen MF, Bäbler A, Vogel H, Hell D (1998) Psilocybin induces schizophrenia-like psychosis in humans via a serotonin-2 agonist action. Neuroreport 9(17):3897–3902
5. Griffiths RR, Richards WA, McCann U, Jesse R (2006) Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual significance. Psychopharmacology 187(3):268–283
6. Griffiths R, Richards W, Johnson M, McCann U, Jesse R (2008) Mystical-type experiences occasioned by psilocybin mediate the attribution of personal meaning and spiritual significance 14 months later. J Psychopharmacol 22(6):621–632
7. Griffiths RR, Johnson MW, Richards WA, Richards BD, McCann U, Jesse R (2011) Psilocybin occasioned mystical-type experiences: immediate and persisting dose-related effects. Psychopharmacology 218:649–665
8. Grob CS, Danforth AL, Chopra GS, Hagerty M, McKay CR, Halberstadt AL, Greer GR (2011) Pilot study of psilocybin treatment for anxiety in patients with advanced-stage cancer. Arch Gen Psychiatry 68(1):71–78
9. Krebs TS, Johansen PØ (2012) Lysergic acid diethylamide (LSD) for alcoholism: meta-analysis of randomized controlled trials. J Psychopharmacol 26(7):994–1002
10. Moreno FA, Wiegand CB, Taitano EK, Delgado PL (2006) Safety, tolerability, and efficacy of psilocybin in 9 patients with obsessive-compulsive disorder. J Clin Psychiatry 67(11):1735–1740
11. Coyle JR, Presti DE, Baggott MJ (2012) Quantitative analysis of narrative reports of psychedelic drugs. arXiv:1206.0312v1
12. Nichols DE (2012) Structure–activity relationships of serotonin 5-HT2A agonists. WIREs Membr Transp Signal 1:559–579
13. Holmstedt B, Liljestrand G (1963) (eds) Readings in pharmacology. Macmillan, New York
14. Blaazer AR, Smid P, Kruse CG (2008) Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT(2A) receptors. ChemMedChem 9:1299–1309
15. Juncosa JI Jr, Hansen M, Bonner LA, Cueva JP, Maglathlin R, McCorvy JD, Marona-Lewicka D, Lill MA, Nichols DE (2013) Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands. ACS Chem Neurosci 4(1):96–109
16. Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL (2014) ACS Chem Neurosci. doi:10.1021/cn400216u
17. Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, Lehel S, Herth MM, Madsen J, Kristensen J, Begtrup M, Knudsen GM (2011) Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers. Eur J Nucl Med Mol Imaging 38(4):681–693
18. Ettrup A, Holm S, Hansen M, Wasim M, Santini MA, Palner M, Madsen J, Svarer C, Kristensen JL, Knudsen GM (2013) Preclinical safety assessment of the 5-HT2A receptor agonist PET radioligand [11C] Cimbi-36. Mol Imaging Biol 15(4):376–383
19. Gibbons S (2012) ‘Legal highs’-novel and emerging psychoactive drugs: a chemical overview for the toxicologist. Clin Toxicol (Phila) 50(1):15–24
20. Hill SL, Doris T, Gurung S, Katebe S, Lomas A, Dunn M, Blain P, Thomas SH (2013) Severe clinical toxicity associated with analytically confirmed recreational use of 25I-NBOMe: case series. Clin Toxicol (Phila) 51(6):487–492
21. http://www.erowid.org/chemicals/nbome/nbome_effects.shtml
22. http://www.erowid.org/chemicals/2cc_nbome/2cc_nbome_dose.shtml
23. Shulgin A, Shulgin A (1991) PIHKAL: a chemical love story. Transform Press, Berkeley
24. Carmo H, Hengstler JG, de Boer D, Ringel M, Remião F, Carvalho F, Fernandes E, dos Reys LA, Oesch F, de Bastos LM (2005) Metabolic pathways of 4-bromo-2,5-dimethoxyphenethylamine (2C-B): analysis of phase I metabolism with hepatocytes of six species including human. Toxicology 206(1):75–89
25. Kanamori T, Tsujikawa K, Ohmae Y, Iwata YT, Inoue H, Kishi T, Nakahama T, Inouye Y (2005) A study of the metabolism of methamphetamine and 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in isolated rat hepatocytes. Forensic Sci Int 148(2–3):131–137
26. Carmo H, de Boer D, Remião F, Carvalho F, dos Reys LA, de Bastos LM (2004) Metabolism of the designer drug 4-bromo-2,5 dimethoxyphenethylamine (2C-B) in mice, after acute administration. J Chromatogr B Anal Technol Biomed Life Sci 811(2):143–152
27. Theobald DS, Maurer HH (2006) Studies on the metabolism and toxicological detection of the designer drug 2,5-dimethoxy-4-methyl-beta-phenethylamine (2C-D) in rat urine using gas chromatographic/mass spectrometric techniques. J Mass Spectrom 41(11):1509–1519
28. Theobald DS, Maurer HH (2006) Studies on the metabolism and toxicological detection of the designer drug 4-ethyl-2,5-dimethoxy-beta-phenethylamine (2C-E) in rat urine using gas chromatographic-mass spectrometric techniques. J Chromatogr B Anal Technol Biomed Life Sci 842(2):76–90
29. Kanamori T, Kuwayama K, Tsujikawa K, Miyaguchi H, Iwata YT, Inoue H (2011) Synthesis and identification of urinary metabolites of 4-iodo-2,5-dimethoxyphenethylamine. J Forensic Sci 56(5):1319–1323
30. Theobald DS, Staack RF, Puetz M, Maurer HH (2005) New designer drug 2,5-dimethoxy-4-ethylthio-beta-phenethylamine (2C-T-2): studies on its metabolism and toxicological detection in rat urine using gas chromatography/mass spectrometry. J Mass Spectrom 40(9):1157–1172
31. Theobald DS, Fehn S, Maurer HH (2005) New designer drug, 2,5-dimethoxy-4-propylthio-beta-phenethylamine (2C-T-7): studies on its metabolism and toxicological detection in rat urine using gas chromatography/mass spectrometry. J Mass Spectrom 40(1):105–116
32. Obach RS (2001) The prediction of human clearance from hepatic microsomal metabolism data. Curr Opin Drug Discov Devel 4(1):36–44
33. Chao P, Uss AS, Cheng KC (2010) Use of intrinsic clearance for prediction of human hepatic clearance. Expert Opin Drug Metab Toxicol 6(2):189–198
34. Rowland M, Tozer TN (1995) Clinical pharmacokinetics: concepts and applications, 3rd edn. Lippincott Williams & Wilkins, Media
35. Ma Q, Lu AY (2008) The challenges of dealing with promiscuous drug-metabolizing enzymes, receptors and transporters. Curr Drug Metab 9(5):374–383
36. Charalampous KD, Walker KE, Kinross-Wright J (1966) Metabolic fate of mescaline in man. Psychopharmacologia 9(1):48–63
37. Wager TT, Hou X, Verhoest PR, Villalobos A (2010) Moving beyond rules: the development of a central nervous system multiparameter optimization (CNS MPO) approach to enable alignment of drug-like properties. ACS Chem Neurosci 1(6):435–449