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Formation of a Novel and Neurotoxic Tetrahydroisoquinoline Derivative, 1,3-Dimethyltetrahydroisoquinoline (1, 3DiMeTIQ), a Condensation Product of Amphetamines and Acetaldehyde in Vivo

  • Yukiko Makino
  • Yoshikazu Tasaki
  • Masaki Kashiwasake
  • Osamu Tachikawa
  • Shigeru Ohta
  • Masaaki Hirobe
Part of the Advances in Behavioral Biology book series (ABBI, volume 38A)

Abstract

d-Amphetamine and alcohol are generally thought to be mutually antagonistic with respect to their pharmacological action. However the toxic effect of d-amphetamines is not appreciably reduced by the concomitant administration of alcohol.1 It is reported that the combined abuse of methamphetamine and alcohol causes a significant increase in psychosomatic disorders than the abuse of methamphetamine only.2 We hypothesized that a novel metabolite of amphetamines may be involved in such disorders and proposed that 1,2,3,4-tetrahydroisoquinoline (TIQ) and 1-methyl-1,2,3,4-tetrahydroisoquinoline (1MeTIQ) are formed by ring cyclization of endogenous phenylethylamine.3–5 In the present study, we examined the possibility that 1,3DiMeTIQ could be formed from exogenous amphetamines, an analog of phenylethylamine, by cyclization with acetaldehyde, a metabolite of ethanol (Fig. 1).

Keywords

Biogenic Amine Condensation Product Behavioral Alteration Electron Impact Mass Spectrum Psychosomatic Disorder 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

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Copyright information

© Plenum Press, New York 1990

Authors and Affiliations

  • Yukiko Makino
    • 1
  • Yoshikazu Tasaki
    • 1
  • Masaki Kashiwasake
    • 1
  • Osamu Tachikawa
    • 1
  • Shigeru Ohta
    • 1
  • Masaaki Hirobe
    • 1
  1. 1.Faculty of Pharmaceutical SciencesUniversity of TokyoHongo, Bunkyo-ku, Tokyo 113Japan

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