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Part of the book series: Topics in the Neurosciences ((TNSC,volume 9))

Abstract

There can never be a complete history of any intensely controversial topic whose proponents and skeptics state their beliefs with equal confidence. Some historical facts will rest uncontested. Many facts will be clothed in opinions that will color the way the facts are to be interpreted. Other facts will never be publicly known, for reasons of legality or privacy. And some facts may simply be irretrievably lost.

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References

  1. Verfahren zur Darstellung von Alkyloxyaryl-. Dialkyloxyaryl- und Alkylenedioxyaryl- aminopropanen bzw. deren am Stickstoff monoalkylierten Derivaten, 1914. German Patent #274,350 filed December 24. 1912. issued May 16. 1914. and assigned to E. Merck in Darmstadt

    Google Scholar 

  2. Formyl derivatives of secondary bases. 1920. German patent #334,555, assigned to E. Merck Chetn. Absr 17: 1804a.

    Google Scholar 

  3. Care must be taken with the term pipcronylacetone. This term has been used commercially in reference to two distinct chemical individuals, vis.. 1-(3,4-methylenedioxyphenyl)-2- propanone: and l-(3.4-methylenedioxyphenyl)-3-butanone. Only the former compound, also known unambiguously as either 3,4-methylenedioxyphenylacetone or 3,4-methylene- dioxybenzyl methyl ketone, gives rise ultimately to MDMA. For chemical and pharmacological details, see: Shulgin. A T. and Jacob III. P. 1982. Potential misrepresentation of 3,4-methlenedioxyphenyl-amphetamine (MDA). A toxicological warning. J. Anal. Toxicol 6:71 –75 For a toxicologkal study of the products following the use of the latter (wrong) ketone, see reference 9.

    Google Scholar 

  4. Elks, J. and Hey, DH.. 1943. ß-3.4-methylenedioxyphenylisopropylamine J. Chem Soc. pp 15–16

    Google Scholar 

  5. Ichiro. H.. 1952. a-Methyl-3.4-methylenedioxyphenethylamine, Japanese patent 1770 (’52). Chem. Abst. 48: 2097b.

    Google Scholar 

  6. Biniecki, S.. Muszynski. E.. Jagiellowicz. H.. and Chojnacka. Z. 1962. Preparation of l.N- dimethylveratrylethylamine and I.N-dimethylpiperonylethylamine. Acta Polon. Pharm. 1931–35, and Chem. Abst. 58: 3334f.

    Google Scholar 

  7. Braun. U. Shulgin, AT., and Braun. G.. 1980. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J Pharm Sci 69:192–195

    Article  PubMed  CAS  Google Scholar 

  8. Anderson III. G M.. Braun. G., Braun. U.. Nichols. D.E.. and Shulgin. A.T.. 1978. Absolute configuration and psychotomimetic activity. NIDA Research Monograph #22. pp. 8–15.

    Google Scholar 

  9. Davis, WM. and Borne, RF., 1984. Pharmacological investigation of compounds related to 3.4-methylenedioxyamphetamine. Subst. Alcohol Action/Misuse 5:105–110.

    CAS  Google Scholar 

  10. O’Brien. BA., Bonicamp, JM.. and Jones. DW., 1982. Differentiation of amphetamine and its major hallucinogenic derivatives using thin layer chromatography. J. Anal. Toxicol 6:143–147.

    PubMed  Google Scholar 

  11. Fujisawa. T. and Deguchi, Y., 1954. Utilization of safrole as medical raw material. VI. New synthesis of 3,4-methylenedsoxybenzyl methyl ketone. I.J. Pharm. Soc. Jpn. 74:975–977. and Chem. Abst. 44: 10958i.

    Google Scholar 

  12. Hansson, R.C., 1987. Clandestine laboratories production of MDMA 3.4-methylenedioxymethamphetamine. Analog 9 (3): 1–10.

    Google Scholar 

  13. Binicrki. S. and Krajewtki. E.. 1960. Preparation of dl-l-(3.4-methylenedioxyphenyl)-2- (methylamino)propane. Acta Polon. Pharm. 17: 421–425.

    Google Scholar 

  14. Frith, C.H., 1986. Report: 28-day oral toxicity of methylenedioxymethamphetamine hydrochloride (MDMA) in rats Protocol No. F.MD-SC-002. Toxicology Pathology Associates, Little Rock. AR.

    Google Scholar 

  15. Gehlert. D.R. Schmidt. C.J.. Wu. L., and Lovenberg, W., 1985 Evidence for specific methyknedioxymethamphetamine(Ecstasy) binding sites in the rat brain. Eur. J. Pharmacol. 119: 135–136.

    Google Scholar 

  16. Bailey. K.. By. AW.. Legault. D.. and Verner. D.. 1975. Identificatsonolthe N-methylated analogs of the hallucinogenic amphetamines and some isomers. J. Assoc. Off. Anal. Chem 58:62–69.

    PubMed  CAS  Google Scholar 

  17. Sreenivasan, V.R., 1972 Problems in identification of methylenedioxy and methoxy amphetamines. J. Crim. Law 63: 304–312.

    Google Scholar 

  18. Gaston. T.R. and Rasmusseti. G.T., 1972. Identification of 3,4-methylenedioxymethamphetamine. Microgram 5: 60–63.

    Google Scholar 

  19. Eichrncier. L S. and Caplis. M E. 1975 The forensic chemist; an analytical detective. Anal. Chem. 47:841 A–844A.

    Google Scholar 

  20. Ruybal, R 1986 Microcrystallinc test for MDMA Microgram 19: 79–80.

    Google Scholar 

  21. Renfroe. C.L.. 1986 MDMA on the street: Analysis anonymous. J. Psychoactive Drugs 18: 363–369.

    Google Scholar 

  22. Sedgwick. B.. Lo. P.. and Yoe. M,, 1986. Screening and confirmation of 3,4- methylenedioxymethamphetamine (MDMA) in urine Evaluation of 1000 specimens Abstracts of the CAT/SOFT Meetings. Oct 29–Nov, 1. 1986. Reno/Lake Tahoc, NV.

    Google Scholar 

  23. Shaw. MA. and Peel. HW. 1975. Thin-layer chromatography of 3.4-methylenedioxy- amphetaimne and other phenethylamine derivatives. J. Chromatog. 104:201–204.

    Article  CAS  Google Scholar 

  24. Hearn. W.L., Hime. G. and Andollo, W. 1986. Recognizing Ecstasy: Adam and Eve. the MDA derivatives — analytical profiles. Abstracts of the CAT/SOFT Meetings. Oct. 29–Nov. 1. 1986. Reno/Lake Tahoe, NV.

    Google Scholar 

  25. Ruangyuttikarn. W and Moody. D.E., 1988. Comparison of three commercial amphetamine immunoassays for detection of methamphetamine, methylenedioxyamphetamine. methylenedioxymethamphetamine. and methylenedioxyethvlamphetamine J. Anal. Toxicol. 12: 229–233.

    Google Scholar 

  26. Nogglcjr. F,T., DeRuiter, J., and Long, M.J., 1986. Spectrophotometry and liquid chromatographic identification of 3.4-methylenedioxyphenylisopropylamine and its N-methyl and N-ethyl homologs J Assoc. Off. Anal. Chem. 69: 681–686.

    Google Scholar 

  27. Noggle Jr, FT., DeRuiter. J.. McMillan. CL.. and Clark, CR.. 1987. Liquid chromatographic analysis of some N-alkyl-3.4- methylenedioxyamphetamines J. Liq. Chromatog 10:2497–2504

    Article  CAS  Google Scholar 

  28. Hardman. H.F.. Haavik, C.O.. and Seevers. M.H.. 1973. Relationship of the structure of mescaline and seven analogs to toxicity and behavior in five species of laboratory animals. Tox. Appl. Pharmacol. 25: 299–309

    Google Scholar 

  29. Davis. W.M.. Hatoum. H.T., and Wate«. I.W.. 1987 Toxicity of MIM (3.4- methylenedioxyamphetamine) considered for relevance to hazards of MDMA (Ecstasy) abuse. Alcohol Drug Res. 7: 123–134.

    Google Scholar 

  30. George, D.J. and Wolf. H.H.. 1966. Dose-lethality curves for d-amphetamine in isolated and aggregated mice. Life Sci. 5: 1583–1590.

    Article  PubMed  CAS  Google Scholar 

  31. Harris. L.S., 1985. Preliminary report on the dependence liability and abuse potential of methylenedioxymethamphetamine (MDMA). Document entered into evidence Re: MDMA Scheduling Docket No. 84–48. U.S. Department of Justice. Drug Enforcement Administration. October 16. 1985.

    Google Scholar 

  32. Frith, CH.. Chang. LW.. Lattin. DL.. Walls. RC.. Hamm. J., and Doblin. R. 1987, Toxicity of meth vlenedioxy methainpheuminc (MDMA) in the dog and the rat. Fund Appl. Toxicol. 9: 110–119.

    Article  CAS  Google Scholar 

  33. Slikker Jr. W.. Ali. S.F., Scallet. A.C.. and Frith. C.H.. 1986. Mcthylcncdioxmethamphe- taminc (MDMA) produces long lasting alterations m the serotoninergic system of rat brain. Soc. Neurosci. Abst. 12: 363.

    Google Scholar 

  34. O’Hearn, E.. Battaglia. G.. DeSouza. E.B.. Kubar. M.J.. and MolKvir. M.E.. 1986. Systemic MDA and MDMA, psychotropic substituted amphetamines, produce serotonin neurotoxicity. Soc. Neurosci. Abst. 12: 1233.

    Google Scholar 

  35. Goad. P.T., 1985. Acute and subacute toxicity study of methylenedioxymethamphetamine in rats. Project Report. Intox Laboratories. Redfield, AR

    Google Scholar 

  36. Dowling. G.P.. McDonough III. E.T.. and Bost. R.O., 1987. “Eve” and “Ecstasy”: A report of five deaths associated with the use of MDEA and MDMA JAMA 257: 1615–1617.

    Google Scholar 

  37. Hayner. G.N. and McKinney, IL, 1986 The darkside of Ecstasy. J. Psychoactive Drugs 18341–347.

    Google Scholar 

  38. Brown, C. and Osterloh. J., 1987. Multiple severe complications from recreaooiul ingestion of MDMA (Ecstasy). JAMA 258: 780–781.

    Article  PubMed  CAS  Google Scholar 

  39. Smilkstein, M.J., Smolinski. S.C.. and Rumack. B.H., 1987. A case of MAO inhibitor/ MDMA interaction: Agony after Ecstasy. Clin. Toxicol. 25: 149–159.

    Article  CAS  Google Scholar 

  40. Verebey. K.. Alrazi, J. and Jaffe, J.H.. 1988. The complications of “Ecstasy” ( MDMA ). JAMA 259: 1649–1650.

    Google Scholar 

  41. Reynolds, P.C., 1986 Personal communication.

    Google Scholar 

  42. Buchanan. J .. 1985. Ecstasy in the emergency department. Clin. Toxicol. Update 7:1–4.

    Google Scholar 

  43. Peroutka, S.J., Pascoe, N., and Faull, K.F., 1987. Monoamine metabolites in the cerebrospinal fluid of recreational users of 3.4- methylenedioxymethamphetamine (MDMA; “Ecstasy”). Res Commun. Subst. Abuse 8: 125–138.

    Google Scholar 

  44. Shulgin, A.T. and Nichols, D.E., 1978. Characterization of three new psychotomimetics. In The Psychopharmacology of Hallucinogens ( Stillman and Willette, eds). New York: Pergamon Press, pp. 74–83.

    Google Scholar 

  45. Greer, G., 1983. MDMA: A new psychotropic compound and its effects in humans. Privately published 333 Rosario Hill, Sante Fe. NM 87501. Copyright 1983.

    Google Scholar 

  46. Greer, G. and Tolbert. R., 1986. Subjective reports of the effects of MDMA in a clinical setting. J. Psychoactive Drugs 18: 319–327

    PubMed  CAS  Google Scholar 

  47. Greer, G, 1985. Recommended protocol for MDMA sessions. Pnvately Published 333 Rosario Hill. Sante Fe. NM 87501. Copyright 1985.

    Google Scholar 

  48. Greer, G. 1985. Using MDMA in psychotherapy. Advances 2: 57–59.

    Google Scholar 

  49. Tatar. A. and Naranjo, C., 1985. MDMA in der Grappenpsychotherapie. Symposium: “Uber den derjenigen Stand der Forschung auf dem tiebiet der psychoaktiven Substanzen,” Nov. 29–Dec. 12, 1985, in Hirschhorn/Neckar. Germany.

    Google Scholar 

  50. Wolfson, P.E., 1986. Meetings at the edge with Adam: A man for all seasons. J. Psychoactive Drugs 18: 329–333.

    PubMed  CAS  Google Scholar 

  51. Siegel, R K, 1986. MDMA, nonmedical use and intoxication. J. Psychoactive Drugs 18: 349–354.

    PubMed  CAS  Google Scholar 

  52. Buffum. J. and Moser. C.. 1986 MDMA and human sexual function. J Psychoactive Drugs 18: 355–359.

    Google Scholar 

  53. Adamson. S.. 1985 Through the gateway of the heart: Accounts of experiences with MDMA and other empathogenic substances. San Francisco. CA: Four Trees Publication.

    Google Scholar 

  54. Downing. J .. 1986 The psychological and physiological effects of MDMA on normal volunteers. J. Psychoactive Drugs 18:335–340.

    PubMed  CAS  Google Scholar 

  55. Peroutka. S.J.. 1987. Incidence of recreational use of 3.4- methylenedioxymethamphetamine (MDMA. “Ecstasy:”) on an undergraduate campus. N. Engl. J. Med 317: 542–1543.

    Google Scholar 

  56. Ecstasy: Everything looks wonderful when you’re young and on drugs, l981 Wet Magazine, September–October, p 76.

    Google Scholar 

  57. ca. 1984. (a) General Information; MDMA. (b) Ecstasy: 21st Century Entheogen. The former is directed towards therapists; the latter is strictly promotional in nature.

    Google Scholar 

  58. Adler, J.. 1985 Getting high on “Ecstasy.” Newsweek. April 15. p. 96.

    Google Scholar 

  59. Toufexis. A., 1985. A crackdown on Ecstasy. Time. June 10. p. 64

    Google Scholar 

  60. Dowling, C.G.. 1985. The trouble with Ecstasy. Life Magazine. August, pp. 88 - 94.

    Google Scholar 

  61. Baum. R.M.. 1985 New variety of street drugs poses growing problen. Chem. Eng. News. September 9. pp. 7–16

    Google Scholar 

  62. Grinspoon. L. and Bakalar.JB.., 1985. What is MDMA? Harvard Medical School Mental Health Letter 2(2):8

    Google Scholar 

  63. Gertz. K.R.. 1985. “HugDrug” alert: The agony of Ecstasy. Harper’s Bazaar. November, p. 48.

    Google Scholar 

  64. Gold. M.S.. 1985. Ecstasy. Etc. Alcoholism and Addiction. September-October. p. 11.

    Google Scholar 

  65. Abramson. DM .. 1985 Ecstasy: The new drug underground. New Age, October, pp. 35–40.

    Google Scholar 

  66. Shafer, J.. 1985. MDMA. Psychedelic drug faces regulation. Psychology Today, May. pp. 68–69.

    Google Scholar 

  67. O’Rourkc, P J., I9B5. Tune in. Turn on. Go to the office late on Monday. Rolling Stone. December 19, p. 109.

    Google Scholar 

  68. Trudeau, G.B.. 1985. Doonesbury. August 12–August 24. 1985. Universal Press Syndicate.

    Google Scholar 

  69. Doblin. R.. 1985. MDMA — a multidisciplinary investigation: Reports from the medical, scientific, and regulatory communities. The Earth Metabolic Design Laboratories. Inc., Berkeley. CA.

    Google Scholar 

  70. MDMA. A Multidisciplinary Conference. May 17 and 18. 1986. Institute for Addiction Studies. Meritt Peralta Hospital. Oakland. CA. Psychoactive Drugs 18 (4)

    Google Scholar 

  71. A, 1985 MDMA. NIDA Capsules. Issued by the Press Office of the Naiicnal Institute on Drug Abuse, Rockland. MO. July. 1985. (b) Designer drugs new concern for the drug abuse community. NIDA Notes. December. 1985. pp 2–3.

    Google Scholar 

  72. Schulman, R, 1985. The losing war against “designer drugs.” Business Week. June 24. pp. 101–104.

    Google Scholar 

  73. Smith. DE. Wesson, DR.. and Buffum. J.. 1985. MDMA. “Ecstasy” as a adjunct to psychotherapy and a street drug of abuse. California Society for the Treatment of Alcoholism and Other Drug Dependencies News. 12:1–3.

    Google Scholar 

  74. Nichols, D. E., 1985 MDMA represents a new type of pharmacologic agent and cannot be considered to be either a hallucinogenic agent or an amphetamine-type stimulant. Essay distributed to the DEA and the WHO. in connection with the hearings concerning the scheduling of MDMA.

    Google Scholar 

  75. Nichols, D.E., 1986. Differences between the mechanism of action of MDMA. MBDB. and the classic hallucinogens. Identification of a new therapeutic class, entactogens. J. Psychoactive Drugs 18: 305–313.

    PubMed  CAS  Google Scholar 

  76. Nichols, D E. Hoffman. A.J., Oberlender. R.A., Jacob III. P.. and Shulgin. AT.. 1986. Derivatives of l-(1,3-benzodioxol-5-yl)-2-butanamine: Representatives of a novel therapeutic class J Med. Chem. 29: 2009–2015.

    Google Scholar 

  77. Randolph. WF ., 1984. International drug scheduling; convention on psychotropic substances. stimulant and/or hallucinogenic drugs. Fed. Regis. 49(140):29273–29274

    Google Scholar 

  78. Mullen. F.M., 1984 Schedules of controlled substances. Proposed placement of 3.4- methylenedioxymethamphetamine into Schedule I. Fed. Regis. 49(146):302l0–30211.

    Google Scholar 

  79. Cotton. R. 1984 Letter from Dewey. Ballantine. Bushby. Palmer amp; Wood 1775 Pennsylvania Avenue, N.W.. Washington. D.C. to F.M Mullen Jr.. DEA. September 12. 1984.

    Google Scholar 

  80. Mullen. FM ., 1984. Schedules of controlled substances. Proposed placement of 3,4- methylenedioxymethamphetamine into Schedule I. Hearing Fed. Regis. 49(252):50732–50733

    Google Scholar 

  81. Young. F.L., 1985. Opinion and recommended decision on preliminary issue. Docket No. 84–48. June 1.

    Google Scholar 

  82. Lawn. J.C. 1985 Schedules of controlled substances. Temporary placement of 3.4- methylenedioxymethamphetamine (MDMA) into Schedule I. Fed. Regis 50 (105): 23118–23120.

    Google Scholar 

  83. Young. F.L., 1986. Opinion and recommended ruling, findings of fact, conclusions of law and decision of administrative law judge Docket 84–48. May 22.

    Google Scholar 

  84. Stone. S.E. and Johnson, C A. 1986. Government’s exceptions to the opinion and recommended ruling, findings of fact, conclusions of law and decision of the administrative law judge. Docket 84–48. June 13

    Google Scholar 

  85. Lawn. JC .. 1986, Schedules of controlled substances Extension of temporary control of 3.4-methylenedioxymethamphctaminc (MDMA) in Schedule I Fed. Regis 51(116): 21911–21912.

    Google Scholar 

  86. Lawn, J.C., 1986. Schedules of controlled substances. Scheduling of 3.4-methylenedioxy- methamphetamine (MDMA) into Schedule I of ibe Controlled Substances Act. Fed Regis, 5l (198): 36552–36560.

    Google Scholar 

  87. Kane. J.. 1986 Memorandum and opinion. Case No 86-CR-153 in the United States District Court for the District of Colorado. Pees and McNeill. Defendenis. October 1.

    Google Scholar 

  88. Coffin. Torruella. and Pettin, 1987. United States Court of Appeals for the First Circuit. Lester Grinspoon, Petitioner, vs. Drug Enforcement Administration. Respondent. September 18.

    Google Scholar 

  89. Lawn, J.C.. 1988. Schedules of controlled substances. Deletion of 3.4-methylenedioxymcth- amphetamine (MDMA) from Schedule I of the Controlled Substances Act. Fed. Regis. 53: 2225.

    Google Scholar 

  90. Lawn, J.C.. 1988. Schedule of controlled substances. Scheduling of 3.4-methylenedioxy- methamphctininc (MDMA) into Schedule I of the Controlled Substances Act. Remand. Fed. Regis. 53: 5156.

    Google Scholar 

  91. Harbin. H. 1988. MDMA. Narcotics. Forfeiture, and Money Laundering Update. U.S. Department of Justice, Criminal Division. Winter, pp. 14–19.

    Google Scholar 

  92. Sciden. L.S., 1W5. Report of preliminary results on MDMA. Document entered into evidence Re: MDMA Scheduling Docket No. 844–48. U.S. Department of Justice. Drug Enforcement Administration. October 16.

    Google Scholar 

  93. Griffiths, R.R.. Lamb. R.. and Brady. J. V.. 1985. A preliminary report on the reinforcing cffccts of racenuc 3.4-nKlhylencdioxyrnethamphetamine in the baboon. Document entered into evidence Rc MDMA Scheduling Docket No. 84–48. U.S. Department of Justice. Drug Enforcement Administration. October 16.

    Google Scholar 

  94. Sclilemmer Jr. R.F., Montcll. S.E.. and Davis. J.M. 1986. MDMA induces behavioral clunges in members of primate social colonies. Fed. Proc. 45: 1059 (#5263).

    Google Scholar 

  95. Thompson. D M. Wmsauer. P.J., and Mastropaolo. J.. 1987. Effects of phencydidine. ketamme and MDMA on complex operant behavior in monkeys. Pharmacol. Biochem. Behav. 26: 401–405.

    Google Scholar 

  96. Glennon. R.A.. Little. P.J.. Rosecrans. J.A.. and Youiif. M„ 1987. The effects of MDMA (“Ecstasy”) and its optical isomers on schedule-controlled responding in mice. Pharmacol. Biochem. Behav. 26: 425–426.

    Google Scholar 

  97. Rosecrans. J.A. and Glennon. R.A.. 1987. The effect of MDA and MDMA (“Ecstasy”) isomers in combination with pirenpirone on operant responding in mice. Pharmacol. Biochem. Behav. 28: 39–42.

    Article  PubMed  CAS  Google Scholar 

  98. Kulmala. H.K.. Boja. J.W.. and Schechter. M.D.. 1987. Behavioral suppression following 3.4-methylenedioxyamphetamine. Life Sci. 41: 1425–1429.

    Article  PubMed  CAS  Google Scholar 

  99. Bird. M. and Kornetsky. C.. 1986. Naloxone antagonism of the effects of MDMA “Ecstasy” on rewarding brain stimulation. Pharmacologist 28: 149 (#319).

    Google Scholar 

  100. Hubner. C.B.. Bird. M.. Rassnick. S.. and Kornetsky. C„ 1988. The threshold lowering cffccts of MDMA ( Ecstasy) on brain-stimulating reward. Phychopharmacology 95: 49–51.

    Google Scholar 

  101. Beards ley. P.M.. Balster. R.L.. and Harris. L.S., 1986. Self administration of methylene- dioxymcthamphetamine (MDMA) in rhesus monkeys. Drug and Alc. Depend. 18: 149–157.

    Google Scholar 

  102. Lamb, R.J. and Griffith. R R.. 1987. Self-injection of dl-3.4- methylenedioxymethamphetamine in the baboon Psychopharmacology 91: 268–272.

    Article  PubMed  CAS  Google Scholar 

  103. Braun. U. Shulgin, A.T., and Braun, G., 1980. Prufung auf zentral Aktivitat und Analgesia von N-substituierten Analogen des Amphetamin-Derivates 3,4-Methylenedioxyphenyliso propylamin. Arzneim.-Forsch. 30: 825–830.

    CAS  Google Scholar 

  104. Beaton. J.M.. Benington. F., Christian. S.T.. Monti. J.A.. and Morui. R.D. 1987. Analgesie effects of MDMA and related compounds. Pharmacologist 29: 281 (abstract).

    Google Scholar 

  105. Callahan. P M and Appel. J.B., 1987. Differences m the stimulus properties of 3.4- methylenedioxyamphetamine (MDA) and N-mcthyl-3.4- methylenedioxymethamphetamine (MDMA) in animals trained to discriminate hallucinogens from saline. Soc. Neurosci. Abstr 13 (part 3 ): 1720 (#476.2).

    Google Scholar 

  106. Gold. L.H and Koob, G F. 1988 Methysergide potentiates the hyperactivity produced by MDMA in rats. Pharmacol. Biochem. Behav. 29: 645–648.

    Article  PubMed  CAS  Google Scholar 

  107. Gletmon, R.A. Young, R, Rosecrans, J.A., and Anderson. G.M., 1982. Discriminative stimulus properties of MDA analogs. Biol. Psychiat. 17: 807–814.

    Google Scholar 

  108. Glennon. R A. and Young, R., 1984. Further investigation of the discriminative stimulus propetti« of MDA. Pharmacol. Biochem. Behav. 20: 501–505.

    Google Scholar 

  109. Schechter. M D., 1986. Discriminative profile of MDMA. Pharmcol. Biochem. Behav. 24: 1533–1537.

    Article  Google Scholar 

  110. Oberlender, R and Nichols, D.E., 1988. Drug discrimination studies with MDMA and amphetamine Psychopharmacology. 95: 71–76.

    Article  PubMed  CAS  Google Scholar 

  111. Schechter, M.D, 1987. MDMA as a discriminative stimulus: Isomeric comparisons. Pharmacol. Biochem. Behav. 27: 41–44.

    Article  PubMed  CAS  Google Scholar 

  112. Evans, S M. and Johanson. C.E.. 1986. Discriminative stimulus properties of (+/−)-3,4- methylenedioxymethamphetamine and (+/-)methylenedioxyamphetamine in pigeons. Drug and Alc. Depend 18: 159–164.

    Google Scholar 

  113. Kamien. J.B.. Johanson. C.E.. Schustcr. C R., and Woolverton. W.L.. 1986. The effects of (+/−)methylenedioxymethamphetamine and (+/−)methylenedioxyamphetamine in monkeys trained to discriminate (+) amphetamine from saline. Drug and Alc. Depend. 18: 139–147.

    Google Scholar 

  114. Woolverton, W.L.. Virus. R M.. Katmen. J B. Nencini. P., Johanson, C.E., Seiden. L.S., and Schuster, C.R., 1985. Amer. Coll Neuropsychopharm. Absts., p. 173.

    Google Scholar 

  115. Gibb.J.W., Hanson. GR.. and Johnson. M. 1986 Effects of (+) 3.4- methylenedioxymethamphetamine [(+)MDMA] and (-) 3.4- methylenedioxymethamphetamine [(-)MDMA] on brain dopamine, serotonin, and their biosynthetic enzymes. Soc. Neurosci Absts. 12: 169. 2.

    Google Scholar 

  116. Stone. D.M.. Stahl. D C.. Hanson. GR. and Gibb, J W. 1986 The effects of 3.4- methylenedioxymethamphetamine (MDMA) and 3.4- methylenedioxyamphetamine (MDA) on monoaminergic systems in the rat brain Europ J. Pharmacol. 128: 41–48

    Article  CAS  Google Scholar 

  117. Stone. D.M., Hanson. G R.. and Gibb. J. W. 1987. GABA-transaminase inhibitor protects against methylencdioxymcthamplutamine (MDMA) induced neurotoxicity. Soc. Neurosci. Absts. !3(part 3):#2S1. 3.

    Google Scholar 

  118. Johnson. M.. Bush. L.G., Stone. D.M.. Hanson. GR. and Gibb. J.W. 1987. Effects of adrenalectomy on the 3,4- methylenedioxymethamphetamine -induced decrease of tryptophan hydroxylase activity in the frontal cortex and hippocampus. Soc. Neurosci. Absts. 13(Part 3):#464. 6.

    Google Scholar 

  119. Brady. J.F.. Di Stephano. E.W.. and Cho. A.K., 1986. Spccual and inhibitory interactions of(+/-) 3.4- methylenedioxyamphetamine (MDA) and (+/-) 3.4- methylenedioxymethamphetamine (MDMA) with rat hepatic microsomes. Life Sci. 39: 1457–1464.

    CAS  Google Scholar 

  120. Lim, H.K. and Foltt. R.L.. 1988 Metabolism of 3.4- methylenedioxymethamphetamine (MDMA) in rat. FASEB Abst. 2(5):A-1060 (#4440).

    Google Scholar 

  121. Nichols. D.E.. Lloyd. D.H., Hoffman, A.J.. Nichols. M B.. and Yim. G.K.W.. 1982. Effects of certain hallucinogtc amphetamine analogues on the release of [3H] serotonin from rat brain synaptosoincs. J. Med Chem. 25: 530–535

    Article  PubMed  CAS  Google Scholar 

  122. Levin. J A.. Schmidt. C.J.. and Lovenberg. W.. 1986. Release of [3H] monoamines from superfused rat striatal slices by methvlenedioxymethamphetamine (MDMA). Fed. Proc. 45: 1059 (#5265).

    Google Scholar 

  123. Lyon. R.A. Glennon, R.A.. and Titclcr. M.. 1986. 3.4-Methylenedioxymethamplietamme (MDMA): Stereoselective interactions at brain 5-HT1 and S-HT2 receptors. Psychopharmacology 88: 525–526.

    Google Scholar 

  124. Battaglia. G.. Brooks. B P.. Kulsakdinum. C.. and Dc Souaa. EB.. 1988 Pharmacologic profile of MDMA (3.4- methylenedioxymethamphetamine) it various brain recognition sites. Europ. J. Pharmacol. 149: 159–163.

    Article  CAS  Google Scholar 

  125. Kalix. P.. 1986 A comparison of the effects of some phenethylamines or the release of radioactivity from isolated rat caudate nucleus prelabaled with 3H-dopamine. Arzneim Forsch. 36: 1019–1021.

    CAS  Google Scholar 

  126. Kalix. P.. Yoosif. MY.. and Glennon, R A.. 1988. Differential effects of the enantiomers of methylenedioxymethamphetamine (MDMA) on the release of radioactivity from (3H) dopamine prelabelled rat striatum. Res. Commun Subst Abuse 9: 45–52.

    CAS  Google Scholar 

  127. Battaglia. G.. Kuhar. M.J.. and De Soura. E.B.. 1986 MDA and MDMA (Ecstasy) interactions with brain serotonin receptors and uptake sites. In vtiro studies. Soc Neurosci. Absts. 12: 336. 4.

    Google Scholar 

  128. Johnson. M P.. Hoffman. A.J.. and Nichols. D.E.. 1986. Effects of the mantiomers of MDA. MDMA, and related analogues on [3H] serotonin and [3H] dopamitc release from superfused rat brain slices. Eur. J. Pharmacol. 132: 269–276

    Article  PubMed  CAS  Google Scholar 

  129. Wang. SS.. Ricaurte. GA.. and Peroutka. SJ., 1987 [3H) 3.4-methylcncdioxymctham- phctanune (MDMA) interactions with brain membranes and glass fiber filter paper Eur J. Pharmacol. 138:439–443.

    Article  PubMed  CAS  Google Scholar 

  130. Frye. G. and Matthews. R.. 1986. Effect of 3,4- methylenedioxymethamphetamine (MDMA) on contractile responses in the guinea pig ilium. Pharmacologist 28: 149 (#318).

    Google Scholar 

  131. Ricaurte. G.A.. Bryan. G.. Strauss. L.. Sewlen. L.. and Schuster. C.. 1985 Hallucinogenic amphetamine selectively destroys brain serotonin nerve terminals Science 229: 986–988.

    Google Scholar 

  132. Ingrasci. R.. 1988 Personal communication.

    Google Scholar 

  133. Thornton. M., 1985 DEA will ban hallucinogen known to users as “Ecstasy.” Washington Post. June 1, p. A 1.

    Google Scholar 

  134. Stone, D M.. Hanson. G.R. and Gibb. J.W.. 1987. Differences in the central serotonergic effects of methylenedioxymethamphetamine (MDMA) in mice and rats. Neuropharmacology 26: 1657–1661.

    Article  PubMed  CAS  Google Scholar 

  135. Battaglia. G.. Yeh. S.Y.. and De Souza. E.B.. 1988. MDMA-induced neurotoxicity parameters of degeneration and recovery of brain serotonin neurons. Pharmacol. Biochem. Behav. 29: 269–274.

    Article  PubMed  CAS  Google Scholar 

  136. Logan. B.J.. Laverty. R.. Sanderson. W.D.. and Yee. Y.B.. 1988. Differenas between rats and micein MDMA (methvlenedioxymcthylamphctamtne) neurotoxicity. Eur.J. Pharmacol. 152: 227–234.

    Google Scholar 

  137. Ali. S.F.. Scallet. A.C., Holson. R.R.. Newport. G.D.. and Slikker Jr. W„ 1987. Acute administration of MDMA (Ecstasy): Neurochemical changes persist up to 120 davs in rat brain. Soc. Neurosci. Absts. 13(Part 3 ): 904 (#251.1).

    Google Scholar 

  138. Battaglia. G., Yeh. S.Y.. OHeam. E.. Molliver. M.E.. Kuhar. M.J.. and De Souza. E.B.. 1987. 3,4- Methylenedioxymethamphetamine and 3,4- methylenedioxyamphetamine destroy serotonin terminals in rat brain: Quantification of neuro-degeneration by measurements of [3H] paroxetine-labelled serotonin uptake sites. J. Pharmacol. Exp. Ther. 249: 911–916.

    Google Scholar 

  139. Champney. T.H., Golden, P.T.. and Matthews. R.T., 1986. Reduction ui hypothalamic serotonin levels after acute MDMA administration. Soc. Neurosci. Absts. 12: 101. 6.

    Google Scholar 

  140. Commins, D.I… Vosmer. G.. Virus. R.M., Woolverton. G.R., Schuster. C.R.. and Seiden. L.S., 1987. Biochemical and histological evidence that methylenedioxymethamphetamine (MDMA) is toxic to neurons in rat brain. J. Pharmacol. Exp. Ther. 241: 338–345.

    Google Scholar 

  141. Dc Souza. E.B., Battaglia, H.. Yeh. S.Y., and Kuhar. M.J.. 1986. In vitro anc in vivo effects of MDA and MDMA (Ecstasy) on brain receptors and uptake sites: Evidence for selective neurotoxic actions on serotonin terminals. Am. Coll. Neuropsvchopharmacol.. Dec. 8–12. p. 207.

    Google Scholar 

  142. Fmnigan. K.T.. Ricaurte. G.A.. Ritchie, L.D., Irwin. I.. Peroutka. S.J., and Langston, J.W.. 1988. Orally administered MDMA causes a long-term depletion of serotonin in rat brain. Brain Res. 447: 141 - 144.

    Google Scholar 

  143. Molker, D.J., Robinson. S.E.. and Rosecrans. J.A.. 1987. (+/-) 3,4- methylenedioxymethamphetamine (MDMA) produces long-term reductions in brain 5-hydroxytryptamine in rats. Eur. J. Pharmacol. 138: 265–268.

    Google Scholar 

  144. Yeh. S.Y., Battaglia. G.. O Heam. E.. Mollivar. M.E.. Kuhar. M.J.. and I* Souza. E.B.. 1986. Effect of MDA and MDMA (Ecstasy) on brain monoammergic systems: In vivo studies. Soc. Neurosci. Absts 12:#336. 5.

    Google Scholar 

  145. Ricaurte. G.A.. Finnigan. K F.. Nichols. D.E., DeLanney. L.E.. Irwin. I. and UngttOfl. J.W.. 1987. 3.4- Methylenedioxythylamphetamine (MDE). a novel analogue of MDMA, produces long-lasting depletion of serotonin in the rat brain. Eur. J Pharmacol. 137: 265–268.

    Google Scholar 

  146. Schmidt. C.J.. 1987 Acute administration of methylenedioxymethamphetamine: Comparison with the neurochemical effects on its N-desmethyl and N-ethyl analogs Eur. J Pharmacol. 136: 81–88.

    Article  PubMed  CAS  Google Scholar 

  147. Molliver, M.E.. O’Hearn. E. Battaglu. G., and De Souza. E.B.. 1986. Direct intracerebral administration of MDA and MDMA does not produce serotonin neurotoxicity. Soc. Neurosci. Absts. 12:336.3

    Google Scholar 

  148. Yeh. S.Y. and Hsu. F.L., 1987. Neurotoxicity of metabolites of MDA and MDMA (Ecstasy) in the rat Soc. Neurosci. Absts. 13(Part 3 ): 906 (#251.11).

    Google Scholar 

  149. Bird. M P.. Svensen, C.N.. Knapp. C„ Hrbek. C.C.. Bird. E D. and Kotnetsky. C. 1987 Evidence for dopinergic and not serotonergic mediation of the threshold lowering effects of MDMA on rewarding brain stimulation. Soc Neurosci. Absts 13(Part 3 ): 1323 (#365.13)

    Google Scholar 

  150. Gold, L.H., Hubner. C.B.. and Koob, G.F.. 1987. The role of inesolimbic dopamine in the stimulant action of MDMA. Soc. Neurosci. Absts. 13(Part 3 ): 833 (#234.13).

    Google Scholar 

  151. Trulson. T.J. and Trulson. M.E., 1987. 3.4- Methylenedioxymethamphetamine (MDMA) suppresses serotonergic dorsal raphe neuronal activity, in freely moving cats and in midbrain slices in vitro. Soc. Neurosci. Absts. 13(Part 3):905 (#251.7).

    Google Scholar 

  152. Wilson. M.A.. Ricaurte. G.A.. and Molliver. M.E.. 1987. The psychotropic drug 3,4- methylenedioxyincthamphctaminc (MDMA) destroys serotonergic axons in primate forebrain: Regional and laminar differences in vulnerability. Soc Neurosci Absts. 13(Pan 3 ): 905 (#251.8).

    Google Scholar 

  153. Ricaurte. G A. Forno, L-S-. Wilson. M.A., DeLanney, L.E., Irwin, I., Moliver, M.E., and Langston, J W., 1988. (+/-) Methylenedioxymethamphetamine selectively damages central serotonergic neurons in nonhuman primates. JAMA 260: 51–55.

    Google Scholar 

  154. Ricaurte, G A.. DeLanney, L.E.. Irwin. I., and Langston. J.W., 1988. Toxic effects of MDMA on central serotonergic neurons in the primate: Importance of route and frequency of drug application. Brain Res. 446: 165–169.

    Article  PubMed  CAS  Google Scholar 

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Shulgin, A.T. (1990). History of MDMA. In: Peroutka, S.J. (eds) Ecstasy: The Clinical, Pharmacological and Neurotoxicological Effects of the Drug MDMA. Topics in the Neurosciences, vol 9. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-1485-1_1

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