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The highly condensed dream element trimethylamin is central to the dream of Irma's injection. After a brief review of the medical literature on timethylamine (TMA), it is suggested that two important meanings of this chemical and its properties lie in its disguised reference to disparaging views of women, as well as to Freud's homosexual connection to Wilhelm Fliess. Freud's misogynistic and homosexual impulses were stimulated by Fliess's recent surgical error committed while operating on Freud's patient Emma Eckstein. Evidence is presented that the collaboration between Freud and Fliess in performing an aggressive act toward a woman was for Freud an enactment of a childhood situation in which he and his nephew John had ganged up on John's sister Pauline. The later relationship between Freud, Jung, and Sabina Spielrein is seen as an additional reenactment of this childhood triangle. An examination of Freud's associations to and analysis of the Irma dream, as well as some of his later relationships with women, indicates that guilt and the wish to make reparation were also prominent themes in Freud's inner life.

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