SOFT 2004 Meeting Abstracts - Society of Forensic Toxicologists

C9
A PROPOSED SCHEME FOR FOXY METABOLISM
JM Wilson*\ F McGeorge l , R Meatherale.
l.Dept of Clinical Pathology and Emergency Medicine, William Beaumont Hospital, Royal Oak, MI USA.
2. St. Boniface General Hospital, Winnipeg, Manitoba CAN.
We report an emergency room admission following an ingestion of 5-Methoxy-N,N-diisopropyItryptamine,
5-MeO-DIPT or FOXY. The subject was a 23 year old Caucasian male presenting 3 hours post ingestion
of a capsule provided by an acquaintance and initially described as "acid". This ingestion was preceded by
intake of 4 beers. Approximately thirty minutes before presentation the subject experienced four episodes
of vomiting followed by tactile hallucinations and paranoia, primarily related to a suspicion of being
poisoned. He denied auditory and visual hallucinations or other neurological symptoms. Vital signs
revealed a temperature of 31 "C, pulse 16 bpm, respirations 18 per min and blood pressure of 135170 mm
Hg. Pupils were midpoint and reactive with normal neurological, motor, reflex, cardiovascular and
gastrointestinal function. Blood and urine chemistry and hematology results were not revealing. Urine
toxicology screening reported presence of 5-MeO-DIPT and suspected metabolites. The subject received
activated charcoal, intravenous fluids, three additional hours of supportive care with resolution of his initial
condition and was discharged without complaints or subsequent readmission.
Urine toxicology testing involved initial screening by ToxiLab® (Varian Inc, Lake Forest CA) followed by
confirmation by electron impact GC/MS. Toxi-A revealed three spots at RF 2.4, 4.6,6.1 (S 1 all blanch, S2
4.6 tan, others faded, S3 all UV absorption, S4 all brown). Extraction for confirmation was preceded by
combination of 2 mL of urine, 0.5 mL of 1 N sodium hydroxide, 500 ng of internal standard (SKF-525-A)
and 5 mL of dichloromethane. Mixing, separation of the organic layer, evaporation under an air stream at
45 "C in a water bath was followed by reconstitution with 25 ilL of ethy I acetate. One ilL of the extract
was injected for GCIMS analysis on a Hewlett Packard 5912A Mass Selective Detector equipped with a 30
m, 0.25 mm id DB-5® (Agilent Technologies, Wilmington DE) capillary gc column with a 0.25 Ilm film
thickness using splitless injection. Oven temperature was initially 120 "C for 3 min, raised to 225°C at 10
"C per min and held for 5 min, followed by a second temperature increase to 300 "C at 15°C per min and a
3 min hold.
Electron impact GCIMS data revealed four chromatographic peaks (RT 15.86, 18.76, 20.13, 21.07) with
molecular ions of 232, 274, 260, and 290 m/z, respectively. These have been tentatively identified, in
chromatographic order, as 5-MeO-NIPT, the N-desalkyl metabolite, 5-MeO-DIPT, the parent substance, 5­
OH-DIPT, the O-desmethyl metabolite, and 5-MeO-DIPT N-oxide, the ring oxidation product of the parent
substance. Identifications were based on comparative spectra with literature sources and, in the case of 5­
OH-DIPT, corroborative CIIMS with 5 % ammonia in methane, and ethylation with ethyl iodidelTMAH.
Assuming that peak heights reflect urine concentrations, the relative magnitude of parent substance and
metabolites were 5-MeO-DIPT>5-0H-DIPT>5-MeO-DIPT N-oxide>5-MeO-NIPT. Detection and
identification of these metabolites permits the characterization of FOXY metabolism as three parallel
oxidative pathways involving each ofthe molecule's non-carbon sites.
Key words: 5-Methoxy-N,N-diisopropyltryptamine, metabolism, FOXY
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