1. bookVolume 69 (2019): Edizione 4 (December 2019)
Dettagli della rivista
Prima pubblicazione
28 Feb 2007
Frequenza di pubblicazione
4 volte all'anno
Accesso libero

Evaluation of phenylethylamine type entactogens and their metabolites relevant to ecotoxicology – a QSAR study

Pubblicato online: 21 Oct 2019
Volume & Edizione: Volume 69 (2019) - Edizione 4 (December 2019)
Pagine: 563 - 584
Accettato: 24 Jul 2019
Dettagli della rivista
Prima pubblicazione
28 Feb 2007
Frequenza di pubblicazione
4 volte all'anno

1. H. Jungaberle, S. Thal, A. Zeuch, A. Rougemont-Bücking, M. von Heyden, H. Aicher and M. Scheidegger, Positive psychology in the investigation of psychedelics and entactogens: a critical review, Neuropharmacology142 (2018) 179–199; https://doi.org/10.1016/j.neuropharm.2018.06.03410.1016/j.neuropharm.2018.06.03429964094Search in Google Scholar

2. D. E. Nichols, Differences between the mechanism of action of MDMA, MBDB, and the classic hallucinogens. Identification of a new therapeutic class: entactogens, J. Psychoactive Drugs18 (1986) 305–313; https://doi.org/10.1080/02791072.1986.1047236210.1080/02791072.1986.104723622880944Search in Google Scholar

3. L. Iversen, M. White and R. Treble, Designer psychostimulants: pharmacology and differences, Neuropharmacology87 (2014) 59–65; https://doi.org/10.1016/j.neuropharm.2014.01.01510.1016/j.neuropharm.2014.01.01524456744Search in Google Scholar

4. R. W. Freudenmann, F. Öxler and S. Bernschneider-Reif, The origin of MDMA (ecstasy) revisited: The true story reconstructed from the original documents, Addiction10 (2006) 1241–1245; https://doi.org//10.1111/j.1360-0443.2006.01511.xSearch in Google Scholar

5. K. S. Leung and L. B. Cottler, Ecstasy and other club drugs: a review of recent epidemiologic studies, Curr. Opin. Psychiatry. 21 (2008) 234–241; https://doi.org/10.1097/YCO.0b013e3282f9b1f110.1097/YCO.0b013e3282f9b1f118382220Search in Google Scholar

6. E. Gouzoulis-Mayfrank, Differential actions of an entactogen compared to a stimulant and a hallucinogen in healthy humans, Heffter Rev. Psychodelic Res. 2 (2001) 64–72.Search in Google Scholar

7. A. Aouidate, A. Ghaleb, M. Ghamali, S. Chtita, M. Choukrad, A. Sbai, M. Bouachrine and T. Lakhlifi, Combining DFT and QSAR studies for predicting psychotomimetic activity of substituted phenethylamines using statistical methods, J. Taibah. Univ. Sci.10 (2016) 787–796; https://doi.org/10.1016/j.jtusci.2016.07.00110.1016/j.jtusci.2016.07.001Search in Google Scholar

8. M. E. Liechti, Novel psychoactive substances (designer drugs): overview and pharmacology of modulators of monoamine signaling, Swiss. Med. Wkly.145 (2015) w14043; https://doi.org/10.4414/smw.2015.1404310.4414/smw.2015.1404325588018Search in Google Scholar

9. D. M. McDowell and H. D. Kleber, MDMA: its history and pharmacology, Psychiatr. Ann.24 (1994) 127–130.10.3928/0048-5713-19940301-06Search in Google Scholar

10. A. C. Parrott, Chronic tolerance to recreational MDMA (3,4-methylenedioxymethamphetamine) or Ecstasy, J. Psychopharmacol.19 (2005) 71–83; https://doi.org/10.1177/026988110504890010.1177/026988110504890015671132Search in Google Scholar

11. A. C. Parrott, Human psychobiology of MDMA or ‘Ecstasy’: an overview of 25 years of empirical research, Hum. Psychopharmacol.28 (2013) 289–307; https://doi.org/10.1002/hup.231810.1002/hup.231823881877Search in Google Scholar

12. T. S. Ray, Constructing the ecstasy of MDMA from its component mental organs: Proposing the primer/probe method, Med. Hypothesis87 (2016) 48–60; https://doi.org/10.1016/j.mehy.2015.12.01810.1016/j.mehy.2015.12.01826826641Search in Google Scholar

13. D. E. Nichols, Psychedelics, Pharmacol. Rev. 68 (2016) 264–355; https://doi.org/10.1124/pr.115.01147810.1124/pr.115.011478481342526841800Search in Google Scholar

14. F. X. Vollenweider, Brain mechanisms of hallucinogens and entactogens, Dialogues Clin Neurosci.3 (2001) 265–279.10.31887/DCNS.2001.3.4/fxvollenweiderSearch in Google Scholar

15. D. Quinteros-Muñoz, P. Sáez-Briones, G. Díaz-Véliz, S. Mora-Gutiérrez, M. Rebolledo-Fuentes, and B. K. Cassels, Behavioral profiles in rats distinguish among “ecstasy”, methamphetamine and 2,5-dimethoxy-4-iodoamphetamine: Mixed effects for “ecstasy” analogues, Behav. Neurosci.124 (2010) 662–676, https://doi.org/10.1037/a002082710.1037/a002082720939666Search in Google Scholar

16. A. Garcia-Romeu, B. Kersgaard and P. H. Addy, Clinical applications of hallucinogens: A Review, Exp. Clin. Psychphamacol. 24 (2016) 229–268; https://doi.org/10.1037/pha000008410.1037/pha0000084500168627454674Search in Google Scholar

17. M. C. Mithoefer, M. T. Wagner, A. T. Mithoefer, L. Jerome and R. Doblin, The safety and efficacy of ±3,4-methylenedioxymethamphetamine-assisted psychotherapy in subjects with chronic, treatment resistant posttraumatic stress disorder: the first randomized controlled pilot study, J. Psychopharmacol.25 (2010) 439–452; http://dx.doi.org/10.1177/026988111037837110.1177/0269881110378371312237920643699Search in Google Scholar

18. A. C. Wagner, M. C. Mithoefer, A. T. Mithoefer and C. M. Monson, Combining cognitive-behavioral conjoint therapy for PTSD with 3,4-methylenedioxymethamphetamine (MDMA): A case example, J. Psychoactive Drugs51 (2019) 166–173; https://doi.org/10.1080/02791072.2019.158902810.1080/02791072.2019.158902830890035Search in Google Scholar

19. W. Barone, J. Beck, M. Mitsunaga-Whitten and P. Perl, Perceived benefits of MDMA-assisted psychotherapy beyond symptom reduction: qualitative follow-up study of a clinical trial for individuals with treatment-resistant PTSD, J. Psychoactive Drugs51 (2019) 199–208; https://doi.org/10.1080/02791072.2019.158080510.1080/02791072.2019.158080530849288Search in Google Scholar

20. A. L. Danforth, Embracing neurodiversity in psychedelic science: A mixed-methods inquiry into the MDMA experiences of autistic adults, J. Psychoactive Drugs51 (2019) 146–154; https://doi.org/10.1080/02791072.2019.158711610.1080/02791072.2019.158711630909821Search in Google Scholar

21. E. Dyck, Psychedelics and dying care: A historical look at the relationship between psychedelics and palliative care, J. Psychoactive Drugs51 (2019) 102–107; https://doi.org/10.1080/02791072.2019.158130810.1080/02791072.2019.158130830821651Search in Google Scholar

22. MDMA Investigator’s Brochure U.S. 10th Edition: 10 July 2018, https://s3-us-west-1.amazonaws.com/mapscontent/research-archive/mdma/MAPS_2018_MDMA_Investigators_Brochure_Edition10_10JUL2018.pdf.Search in Google Scholar

23. A. P. Hall and J. A. Henry, Acute toxic effects of ‘Ecstasy’ (MDMA) and related compounds: overview of pathophysiology and clinical management, Br. J. Anaesth.96 (2006) 678–685; https://doi.org/10.1093/bja/ael07810.1093/bja/ael07816595612Search in Google Scholar

24. M. Ferigolo, A. G. da S. Machado, N. B. Oliveira and H. M. T. Barros, Ecstasy intoxication: the toxicological basis for treatment, Rev. Hosp. Clín. Fac. Med. S. Paulo58 (2003) 332–341.Search in Google Scholar

25. M. J. Baggott, K. J. Garrison, J. R. Coyle, G. P. Galloway, A. J. Barnes, M. A. Huestis and J. E. Mendelson, Effects of the psychedelic amphetamine MDA (3,4-methylenedioxyamphetamine) in healthy volunteers, J. Psychoactive Drugs51 (2019) 108–117; https://doi.org/10.1080/02791072.2019.159356010.1080/02791072.2019.1593560Search in Google Scholar

26. M. Edland-Gryt, S. Sandberg and W. Pedersen, From ecstasy to MDMA: Recreational drug use, symbolic boundaries, and drug trends, Int. J. Drug Policy5 (2017) 1–8; https://doi.org/10.1016/j.drug-po.2017.07.030Search in Google Scholar

27. A. C. Parrott, L. A. Downey, C. A. Roberts, C. Montgomery, R. Bruno and H. C. Fox, Recreational 3,4-methylenedioxymethamphetamine or ‘ecstasy’: current perspective and future research prospects, J. Psychopharmacol.31 (2017) 959–966; https://doi.org/10.1177/026988111771192210.1177/0269881117711922Search in Google Scholar

28. R. Bruno, A. J. Matthews, M. Dunn, R. Alati, F. McIlwraith, S. Hickey, L. Burns and N. Sindicich, Emerging psychoactive substance use among regular ecstasy users in Australia, Drug Alcohol Depend.124 (2012) 19–25; https://doi.org/10.1016/j.drugalcdep.2011.11.02010.1016/j.drugalcdep.2011.11.020Search in Google Scholar

29. M. D. Krasowski, Drug-assisted Sexual Assaults: Toxicology, Fatality, and Analytical Challenge, in Critical Issues in Alcohol and Drugs of Abuse Testing (Ed. A. Dasgupta), 2nd ed., Academic Press, Elsevier Inc., London 2019, p.p. 225–236.10.1016/B978-0-12-815607-0.00018-6Search in Google Scholar

30. H. Kalant, The pharmacology and toxicology of “ecstasy” (MDMA) and related drugs, CMAJ165 (2001) 917–928.Search in Google Scholar

31. R. de la Torre, M. Farré, P. N. Roset, C. H. Lopez, M. Mas, J. Ortuño, E. Menoyo, N. Pizarro, J. Segura and J. Cami, Pharmacology of MDMA in humans, Ann. N. Y. Acad Sci.914 (2000) 225–937; https://doi.org/10.1111/j.1749-6632.2000.tb05199.x10.1111/j.1749-6632.2000.tb05199.xSearch in Google Scholar

32. S. B. Holmes, A. K. Banerjee and W. D. Alexander, Hyponatraemia and seizures after ecstasy use, Postgrad. Med. J. 75 (1999) 32–33; https://doi.org/10.1136/pgmj.75.879.3210.1136/pgmj.75.879.32Search in Google Scholar

33. K. A. Graeme, New drugs of abuse, Emerg. Med. Clin. North. Am. 18 (2000) 625–636; https://doi.org/10.1016/S0733-8627(05)70150-410.1016/S0733-8627(05)70150-4Search in Google Scholar

34. C. Eiden, P. Cathala, N. Fabresse, Y. Galea, J. C. Mathieu-Daude, E. Baccino and E. H. Peyrière, A case of drug-facilitated sexual assault involving 3,4-methylenedioxy-methylamphetamine, J. Psychoactive Drugs45 (2013) 94–97; https://doi.org/10.1080/02791072.2013.76357310.1080/02791072.2013.76357323662335Search in Google Scholar

35. A. L. van Nuijs, S. Castiglioni, I. Tarcomnicu, C. Postigo, M. Lopez de Alda, H. Neels, E. Zuccato, D. Barcelo and A. Covaci, Illicit drug consumption estimations derived from wastewater analysis: a critical review, Sci. Total. Environ.409 (2011) 3564–3577; https://doi.org/10.1016/j.scitotenv.2010.05.03010.1016/j.scitotenv.2010.05.03020598736Search in Google Scholar

36. E. Zuccato and S. Castiglioni, Illicit drugs in the environment, Philos. Trans. A Math. Phys. Eng. Sci.367 (2009) 3965–3978; https://doi.org/10.1098/rsta.2009.010710.1098/rsta.2009.010719736230Search in Google Scholar

37. S. Karolack, T. Nefau, E. Bailly, A. Solgadi and Y. Levi, Estimation of illicit drugs consumption by wastewater analysis in Paris area (France), Forensic Sci. Int.200 (2010) 153–160; https://doi.org/1016/j.forsciint.2010.04.00710.1016/j.forsciint.2010.04.007Search in Google Scholar

38. M. Huerta-Fontela, M. T. Galceran, J. Martin-Alonso and F. Ventura, Occurrence of psychoactive stimulatory drugs in wastewaters in north-eastern Spain, Sci. Total. Environ.397 (2008) 31–40; https://doi.org/10.1016/j.scitotenv.2008.02.05710.1016/j.scitotenv.2008.02.057Search in Google Scholar

39. M. S. Lowless, M. Waldman, R. Franczkiewicz and R. D. Clark, Using Chemoinformatics in Drug Discovery, in New Approaches to Drug Discovery, Handbook of Experimental Pharmacology (Eds. U. Nielsch, U. Fuhrmann, S. Jaroch), Springer, Berlin 2015, pp. 232, 139–170.Search in Google Scholar

40. C. L. Russom, S. P. Bradbury, S. J. Broderius, D. E. Hammermeister and R. A. Drummond, Predicting modes of toxic action from chemical structure: Acute toxicity in the fathead minnow (Pimephales promelas), Environ. Toxicol.16 (1997) 948–967; https://doi.org/10.1002/etc.562016051410.1002/etc.5620160514Search in Google Scholar

41. H. Zhu, A. Tropsha, D. Fourches, A. Varnek, E. Papa, P. Gramatica, T. Oberg, P. Dao, A. Cherkasov and I. V. Tetko, Combinatorial QSAR modeling of chemical toxicants tested against Tetrahymena pyriformis, J. Chem. Inf. Model.48 (2008) 766–784; https://doi.org/10.1021/ci700443v10.1021/ci700443vSearch in Google Scholar

42. A. Golbamaki, A. Cassano, A. Lombardo, Y. Moggio, M. Colafranceschi and E. Benfenati, Comparison of in silico models for prediction of Daphnia magna acute toxicity, SAR QSAR Environ. Res.25 (2014) 673–694; https://doi.org/10.1080/1062936X.2014.92304110.1080/1062936X.2014.923041Search in Google Scholar

43. J. L. Hamelink and A. Spacie, Fish and chemicals: The process of accumulation, Annu. Rev. Pharmacol. Toxicol.17 (1977) 167–177; https://doi.org/10.1146/annurev.pa.17.040177.00112310.1146/annurev.pa.17.040177.001123Search in Google Scholar

44. Z. Zhan, L. Li, S. Tian, X. Zhen and Y. Li, Prediction of chemical biodegradability using computational methods, Mol. Simulat.43 (2017) 1277–1290; https://doi.org/10.1080/08927022.2017.132855610.1080/08927022.2017.1328556Search in Google Scholar

45. J. Kirchmair, M. J. Williamson, J. D. Tyzack, L. Tan, P. J. Bond, A. Bender and Robert C. Glen, Computational prediction of metabolism: sites, products, SAR, P450. Enzyme dynamics, and mechanisms, J. Chem. Inf. Model. 52 (2012) 617–648; dx.doi.org/10.1021/ci200542mSearch in Google Scholar

46. T. T. Abraham, A. J. Barnes, R. H. Lowe, E. A. Kolbrich Spargo, G. Milman, S. O. Pirnay, D. A. Gorelick, R. S. Goodwin and M. A. Huestis, Urinary MDMA, MDA, HMMA, and HMA excretion following controlled MDMA administration to humans, J. Anal. Toxicol.33 (2009) 439–446; https://doi.org/10.1093/jat/33.8.43910.1093/jat/33.8.439Search in Google Scholar

47. C. Burgess, A. Donohoe and M. Gill, Agony and ecstasy: a review of MDMA effects and toxicity, Eur. Psychiatry15 (2000) 287–294; https://doi.org/10.1016/S0924-9338(00)00396-510.1016/S0924-9338(00)00396-5Search in Google Scholar

48. R. L. Hartman, N. A. Desrosiers, A. J. Barnes, K. Yun, K. B. Scheidweiler, E. A. Kolbrich-Spargo, D. A. Gorelick, R. S. Goodwin and M. A. Huestis, 3,4-Methylenedioxymethamphetamine (MDMA) and metabolites disposition in blood and plasma following controlled oral administration, Anal. Bioanal. Chem. 406 (2014) 587–599; https://doi.org/10.1007/s00216-013-7468-y10.1007/s00216-013-7468-y449291624232751Search in Google Scholar

49. F. Schifano, A bitter pill. Overview of ecstasy (MDMA, MDA) related fatalities, Psychopharmacology173 (2004) 242–248; https://doi.org/10.1007/s00213-003-1730-510.1007/s00213-003-1730-5Search in Google Scholar

50. D. Trachsel, M. Hadorn and F. Baumberger, Synthesis of fluoro analogues of 3,4-(methylenedioxy) amphetamine (MDA) and its derivatives, Chem. Biodivers.3 (2006) 326–336; https://doi.org/10.1002/cbdv.20069003510.1002/cbdv.200690035Search in Google Scholar

51. R. G. Pearce, R. W. Setzer, J. L. Davis and J. F. Wambaugh, Evaluation and calibration of high-throughput predictions of chemical distribution to tissues, J. Pharmacokinet. Pharmacodyn.44 (2017) 549–565; https://doi.org/10.1007/s10928-017-9548-710.1007/s10928-017-9548-7Search in Google Scholar

52. F. Cheng, Y. Ikenaga, Y. Zhou, Y. Yu, W. Li, J. Shen, Z. Du, L. Chen, C. Xu, G. Liu, P. W. Lee, Y. Tang, In silico assessment of chemical biodegradability, J. Chem. Inf. Model. 52 (2012) 655–669; https://doi.org/10.1021/ci200622d10.1021/ci200622dSearch in Google Scholar

53. L. Moriguchi, S. Hirono, Q. Liu, I. Nakagome and Y. Matsushita, Simple method of calculating octanol/water partition coefficient, Chem. Pharm. Bull.40 (1992) 127–130.10.1248/cpb.40.127Search in Google Scholar

54. T. I. Oprea, J. Gottfries, V. Sherbukhin, P. Svensson and T. C. Kuhler, Chemical information management in drug discovery: optimizing the computational and combinatorial chemistry interfaces, J. Mol. Graph. Model.18 (2000) 512–524; https://doi.org/10.1016/S1093-3263(00)00066-810.1016/S1093-3263(00)00066-8Search in Google Scholar

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