Hypochondriac or phobic reactions to venereal disease, specifically syphilis, have invited over three centuries of medical reification and nosological reframing. This bibliographic overview establishes that the early specification and psychiatricization of early modern concepts of melancholy and hypochondriasis, imaginary syphilis or syphilophobia, animated the early respective territorializations of venereology, infectiology more broadly, neurology, and mental medicine. Together with mercuriophobia and a wider emergent clinical sensitivity to sexual angst, the diagnosis, while evidently only sporadically made, functioned as a durable soundboard in the confrontation of emergent medical rationale with various confounders and contenders: medically literate and increasingly mobile but possibly deluded patients; charlatans and putative malpractitioners; self-referral laboratory serology (after 1906); and eventually, through psychoanalysis, the patient's unconscious. Requiring medical psychology early on, syphilology became and remained self-conscious and circumspect, attentive to the casualties of overdiagnosis, overtreatment, and iatrogenesis. Finally, patient apprehension led to makeshift forms of "moral treatment," including fear-instilling and placebos.