Designer Hallucinogens

A25-year-old man was brought to the emergency department from a late-night dance club. A friend reported that the patient commonly used designer drugs that he purchased over the Internet. While at the club, he started to vomit and experience visual hallucinations. He had no previous medical history and took no prescription medications. On searching the patient's clothing, medical staff found an empty container that apparently had contained a powder and was labeled “5-methoxy-N,N-diisopropyltryptamine” with the warning “Not Fit for Human Consumption.” On examination, the patient was retching and hallucinating. Blood pressure was 140/90 mm Hg, pulse rate 132 bpm, respiratory rate 24 bpm, and temperature 37.7°C. Pupils were dilated, his lungs were clear, and the abdomen was soft. The remainder of the physical exam was unremarkable. Treatment included intravenous ondansetron for nausea and vomiting and Ativan for sedation. A CT scan of the head was normal. The patient was transferred to the medical intensive care unit. Within five hours of arrival at the hospital, his physical and mental status returned to normal. He admitted taking a substance called “foxy-methoxy,” and said he probably “screwed up the dose.” Hallucinogenic Properties Tryptamines are a class of natural or synthetic compounds, many of which have hallucinogenic properties. (See table.) The most familiar example of a hallucinogenic tryptamine is psilocybin. Recently, synthetic tryptamines have appeared at dance clubs and raves, apparently in an attempt to mimic the effects of the drug ecstasy. In April 2003, the U.S. Drug Enforcement Administration placed two of these compounds - 5-MeO-DIPT and alpha-methyltryptamine (AMT) - into Schedule I of the Controlled Substances Act, creating criminal liability for any unauthorized activity involving their use or distribution. 5-MeO-DIPT has the street names “foxy-methoxy” or just “foxy,” probably because of its chemical structure and reported aphrodisiac properties. Its affects mainly the neurological and gastrointestinal systems, causing hallucinations, mydriasis, blurred vision, irritability, restlessness, dysphoria, nausea, vomiting, and diarrhea. Occasionally the neurological and gastrointestinal manifestations of 5-MeO-DIPT may interact, as in this user's experience described in the book “TIHKAL” (Tryptamines I Have Known and Loved): “I ate a vegetarian burrito four hours earlier. It took an hour for me to turn on. I have never experienced such an increase of the peristalsis process in moving the burrito through my colon, and with each defecation I would become a little more turned on. … As the effects of the material were rather extreme, I never felt as though I was having a psychedelic experience. Maybe because it was all about dealing with body load and discomfort.” (Shulgin & Shulgin, TIHKAL: The Continuation. Transform Press, 1997.) 5-MeO-DIPT acts relatively rapidly, with an onset of 20 minutes. It peaks at about one hour and lasts three to six hours. Effects are dose-dependent, with larger doses causing hallucinations similar to LSD. It often is supplied as a capsule or as a purple tablet with the image of a spider or alien head pressed into it. It has recently appeared as a liquid soaked into a sugar cube or LSD-style blotter paper (U.S. Drug Enforcement Administration, Microgram Bulletin, May 2003). A recent report of 5-MeO-DIPT intoxication (J Analytical Tox 2003;27:313) confirmed the presence of the drug in urine by gas chromatography-mass spectrometry, but unfortunately contained few clinical details.Figure: Structure of Foxy, 5-methoxy-N, N-diisopropyltryptamine, 5-MeO-DOPT.Tryptamines, natural or synthetic compounds, have hallucinogenic properties AMT has effects similar to 5-MeO-DIPT but with a more extended time course. Onset is three to four hours, and duration is 12 to 24 hours. Because it has properties as a monoamine oxidase inhibitor, AMT was studied in the 1960s for use as an antidepressant, but never marketed as such in the United States. A recent abstract described a 21-year-old male college student who presented after ingesting AMT obtained through the Internet. He had inadvertently taken 10 times his usual dose. He had dilated pupils and was described as hyper-vigilant, restless, tremulous, and experiencing visual hallucinations. His symptoms did not begin to resolve until 10 hours after presentation (J Tox Clin Tox 2003;41[5]:746). To date there have been no reported deaths associated with either 5-MeO-DIPT or AMT, although fatalities have been associated with exposure to other designer hallucinogens, including ethyltryptamine (J Forensic Sci 1993;38[3]:721). Another class of chemicals that causes effects similar to MDMA (ecstasy) is the piperazines, including benzylpiperazine (BZP) and trifluoromethylphenylpiperazine (TFMPP). These preparations have appeared as tablets pressed with the image of a fly, crown, heart, butterfly, or bull's head. They also have been sold as capsules containing a light-colored powder (U.S. Drug Enforcement Administration, Drug Intelligence Brief, December 2001). In high doses, piperazines can cause hallucinations, seizures, and respiratory depression. Piperazines are used in industry, and have been available legally through chemical supply houses. Both BZP and TFMTT were reclassified as Schedule I substances in September 2002. Hallucinogenic Tryptamines ▪ Psilocybin (O-phosphoryl-4-hydroxy-N, N-ethyltryptamine) ▪ Psilocyn (4-hydroxy-N, N-dimethyltryptamine) ▪ Bufotenine (5-hydroxy-N, N-dimethyltryptamine) ▪ Alpha-ethyltryptamine (AET) ▪ Diethyltryptamine (DET) ▪ Dimehtyltryptamine (DMT) ▪ Alpha-methyltryptamine (AMT) ▪ 5-methoxy-N, N-dimethyltryptamine (5-MeO-DMT) ▪ 5-methoxy-N, N-diisopropyltryptamine (5-MeO-DIPT) (Foxy, foxy-methoxy) Source: Drug Intelligence Brief, U.S. Drug Enforcement Administration, October 2002.