The article was request by 7is.
J. Anal. Tox., 2003, 27, 313-317.pdf (http://www.angelfire.com/scifi2/lego/journals/27.pdf)
(http://www.angelfire.com/scifi2/lego/journals/27.pdf)
No DOI found
Abstract: http://konstanza.ingentaselect.com/vl=4372698/cl=28/nw=1/rpsv/ij/pres/01464760/v27n5/s9/p313 (http://konstanza.ingentaselect.com/vl=4372698/cl=28/nw=1/rpsv/ij/pres/01464760/v27n5/s9/p313)
Case Report
Foxy, a Designer Tryptamine Hallucinogen*
Robert Meatherall1,† and Pankaj Sharma2
1Laboratory Medicine, St. Boniface General Hospital, Winnipeg, Manitoba, Canada and 2Emergency Department, Victoria General Hospital, Winnipeg, Manitoba, Canada
* Presented at the Society of Forensic Toxicologists annual meeting, Detroit, MI, October 2002.
† Author to whom correspondence should be sent: Robert Meatherall, PhD, Laboratory Medicine, St. Boniface General Hospital, 409 Tache Ave., Winnipeg, Manitoba, Canada, R2H 2A6.
Abstract
Foxy is slang for 5-methoxy-N,N-diisopropyltryptamine. It has hallucinogenic properties, similar to other tryptamine compounds, and is mildly euphoric. This case report describes a 21-year-old Caucasian man who ingested a pill called Foxy containing an unknown amount of drug. He was observed in hospital for 2 h, during which time he had mild hallucinations and could not move his limbs. A urine sample was collected approximately 4 h after drug ingestion. The patient was then discharged with no follow up assessment. The 5-methoxy-N,N-diisopropyltryptamine was identified in the urine by gas chromatography-mass spectrometry. Standards prepared from the pure material were used in the identification. Quantitative analysis using the same analytical technique resulted in a urinary concentration of 1.7 µg/mL. Through oxidative deamination, the metabolite, 5-methoxy-indole acetic acid, was formed. It was identified in the urine, and the concentration was determined to be 1.3 µg/mL using gas chromatography-mass spectrometry. Two other compounds were discovered in the urine sample as a result of a routine drug screen. From their mass spectra, they were tentatively identified as 5-methoxy-N-isopropyltryptamine and 5-methoxy-N,Ndiisopropyltryptamine-N'-oxide.
Abstract
Introduction
Foxy, 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT), is an uncommon designer hallucinogen. The structure is shown in Figure 1. It is the diisopropyl analogue of the more familiar hallucinogen 5-methoxy-dimethyltryptamine. The U.S. Drug Enforcement Administration identified (1-6) capsules containing 5-MeO-DIPT obtained in California, Arizona, New York, Washington state, Texas, and Virginia. Further analysis of one of the capsules showed it to contain a 4-mg dose (1). In Canada, Health Protection Branch, Winnipeg was the first to report the seizure of capsules in two separate instances. Clinically, the drug promotes emotional expression, a talkative uninhibited state (7), and visual and auditory sensory distortions (8). No other clinical studies appear in the medical literature. There are no reported pharmacological studies in humans. Some of the drug's physiological properties are also common to the recreational drug methylenedioxymethamphetamine (Ecstasy). Not surprisingly, 5-MeO-DIPT is a club drug (2) and has been substituted for Ecstasy on the street (3).
Case History
A 21-year-old Caucasian man presented to the emergency department about 1.5 h after consuming a pill to get high. He was told the pill was called Foxy; it was sold to him on the street for $10. Within an hour of ingestion, he said he felt "weird". He started seeing unfamiliar symbols on the wall and could not move his limbs. No nausea, pain, or visual deficit were apparent. He denied using any other recreational drugs or alcohol. On examination, he was alert and oriented. His pulse was 106 with a blood pressure of 122/56 mm Hg and a respiration
rate of 20. His pupils were 8 mm, equal, and reactive. Extra ocular movements were intact, and there was no motor sensory deficit. His cardiorespiratory examination was unremarkable. He received only supportive care throughout his hospital stay. The effects wore off 3.5 h after ingestion. He stopped seeing the symbols and could move his limbs normally. A urine sample was collected at 4 h postingestion for a drug screen just before he was discharged from hospital. Blood was not collected because no other laboratory work up was required. There was no investigative follow up.
The patient did not have a documented drug-abuse problem.
Molecule: (https://www.the-hive.ws/forum/faq.pl?Cat=#applet)
DIPT ("n1cc(c2c1cccc2)CCN(C(C)C)C(C)C")
Figure 1. Structure of Foxy, 5-methoxy-N,N-diisopropyltryptamine, 5-MeO-DIPT.
Methods
Authentic 5-MeO-DIPT powder was obtained from Health Protection Branch (Health Canada, Winnipeg, MB, Canada); 5-methoxyindoleacetic acid (5-MeO-IAA) and 5-hydroxyindoleacetic acid (5-HIAA) were obtained from Aldrich (Oakville, ON, Canada). Amphetamines (1000 ng/mL cut-off), barbiturates (200 ng/mL cut-off), cannabinoids (50 ng/mL cut-off), benzoylecgonine (150 ng/mL cut-off), opiates (300 ng/mL cut-off), and phencyclidine (25 ng/mL cut-off) were screened by EMIT II Plus (Dade Behring, Mississauga, ON, Canada). Also, benzodiazepines (100 ng/mL cut-off) were screened by CEDIA (Microgenics, Freemont, CA) using a Hitachi 717 analyzer (Roche Diagnostics, Laval, QC, Canada). LSD (500 pg/mL cut-off) was screened in a separate procedure by ELISA (Immunalysis Corp., Pomona, CA).
Basic and neutral drugs were screened by gas chromatography mass spectrometry (GC-MS) using a modified method of Foerster et al. (9); acidic and neutral drugs were screened by a method developed for barbiturate analysis (10). Alcohols were screened by GC on a 1.83-m Carbopack B column coated with 5% Carbowax 20M (11) supplied by Supelco (Oakville, ON, Canada). Direct injection (12) was used for sample introduction. Positive screening tests were obtained for cannabinoids and opiates. The major urinary metabolite, ?9-carboxy-tetrahydrocannabinol, was confirmed by GC-MS using a modification of the method described by Wimbish and Johnson (13). The opiates were confirmed and quantitated by GC-MS (14). Acetaminophen was detected in both the basic and acidic drug screen and subsequently quantitated by HPLC (15).
Analysis of 5-MeO-DIPT
The urine quantitation of 5-MeO-DIPT was performed by GC-MS. A stock standard was prepared in methanol at 1000 µg/mL and was used to spike urine at 4, 2, 1, 0.5, and 0 µg/mL. One-milliliter aliquots of the standards and case sample were pipetted into 12-mL screw-capped extraction tubes. One microgram of the internal standard, p-chlorodisopyramide (Searle, Mississauga, ON, Canada), was added to each tube. After the addition of 0.8 mL of 1M NaHCO3 (pH 9), 4 mL of methyl-t-butylether, and 2 mL of methylene chloride, the tubes were capped and mixed on a rotating wheel for 15 min. The two phases were separated by centrifugation, and the top solvent layer was transferred to a 5-mL conical tube containing 100 µL of 0.1N HCl. The solvent was dried in a 45°C sand bath under a gentle stream of nitrogen. Acetonitrile (50 µL) was added to the remaining 100 µL of HCl and washed with 250 µL of hexane to remove lipids. The hexane was aspirated to waste. After the addition of 100 µL of 1M NaHCO3 and 2 mL of methylene chloride, the contents were mixed by vortex mixing for 2 min, then centrifuged to separate the phases. The upper aqueous layer was aspirated to waste. The remaining organic solvent was dried with 100 mg of anhydrous sodium sulfate then transferred to a clean 5-mL conical tube. Acetonitrile (100 µL) was added as a keeper solvent before the methylene chloride was evaporated with nitrogen. The acetonitrile was further reduced to 30 µL, of which 1 µL was injected into the GC-MS. The GC-MS was an ITS40 ion trap running Magnum software (Thermoquest Finnigan, San Jose, CA). Separation was performed with a DB-1 (15-m × 0.25-mm, 0.25-µm film thickness) methyl silicone capillary column. A 1-m × 0.52-mm retention gap deactivated with 5% phenyl methyl silicone connected the analytical column to the temperature programmable injector. Helium carrier gas flowed at 45 cm/s. The oven was initially held at 80°C for 1 min, then programmed at 10°C/min to a final temperature of 290°C, where it was held for 5 min. The temperature programmable injector was ramped from 85°C to 290°C at 13°C/min. Electron impact mass spectra were collected in full scan from 44 to 650 amu at 1 scan/s. Mass spectral fit to 5-MeO-DIPT in the case sample was 990 of a possible 1000; the retention time agreed to within 3 s. The quantitation ions for 5-MeO-DIPT and the internal standard p-chlorodisopyramide were the base peak ions, 114 and 229 amu, respectively. Linear regression of the 6 calibration standards between 0 and 4 µg/mL was handled by the Magnum software. The standard curve was linear with a correlation coefficient (r2) of 0.94. By interpolation, the 5-MeO-DIPT concentration was determined to be 1.7 µg/mL. Four months later, repeat analysis of a frozen urine aliquot using freshly prepared urine calibrators resulted in a 5-MeO-DIPT concentration of 1.8 µg/mL.
Analysis of 5-MeO-IAA and 5-HIAA
Methanolic stock standards of each were prepared at a concentration of 1000 µg/mL. Combined dilutions were prepared in drug-free urine at 4, 1, 0.5, 0.1, and 0 µg/mL. The standards and patient sample were assayed using a modification of a method routinely used to quantitate barbiturates (10). Phosphate buffer (pH 6.8) was replaced by 1N HCl in the solvent extraction part of the procedure to enhance the recovery of these two compounds. The extract was dried and ethylated to form derivatives suitable for GC-MS analysis. The retention times of derivatized 5-MeO-IAA, 5-HIAA, and the internal standard tolybarb were 698, 728, and 654 s, respectively. The quantitation ions were the base peak ions 160, 174, and 274 amu. Linear regressions of the calibration standards were used to calculate the patient values. In addition, 10 drug-free urine samples from healthy volunteers were analyzed to establish normal baseline values.
Foxy Methoxy: A New Drug Of Abuse
Susan C. Smolinske, Rahul Rastogi, Stephen Schenkel, Susan C. Smolinske
Int. J. Med. Toxicol. 7(1), 3 (2004) (http://www.ijmt.net/7_1/7_1_3.html)
(http://www.ijmt.net/7_1/7_1_3.html)
Abstract
Background: In 1999, a new synthetic tryptamine, 5-MeO-DIPT, became known as a street drug, with the street name of "Foxy" or "Foxy Methoxy". By February 2003, the DEA reported law enforcement seizures and/or reports of abuse in 12 states. We report a case along with an analysis of poison center data on this new drug of abuse. Case report: A 19-year-old male was brought to the emergency department following ingestion of a larger than his usual dose of Foxy. Upon arrival, he had hallucinations, hypertension, tachycardia, mydriasis, and catalepsy. Symptoms resolved within two hours after administration of lorazepam and he recovered uneventfully. Results: The AAPCC TESS database contained 41 exposures to "Foxy" between April, 2002 and June, 2003; 26 had moderate or major effects, indicating this drug has significant toxic potential. Conclusion: Given the expanding use of this and other club drugs, the spectrum of toxicity from this new agent will continue to be elucidated.
Kudos to Java, who originally found the article.
A foxy intoxication
John M. Wilson, Frank McGeorge, Susan Smolinske and Robert Meatherall
Forensic Science International, Article in Press
DOI:10.1016/j.forsciint.2004.04.017 (http://dx.doi.org/10.1016/j.forsciint.2004.04.017)
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_imgs/pdf.gif)
Abstract
Foxy is the colloquial name for the hallucinogen 5-ethoxy-diisopropyltryptamine (5-MeO-DIPT). A non-fatality involving a 23-year-old Caucasian man who ingested a capsule containing 5-MeO-DIPT is described. He presented to the Emergency Department, not with visual nor auditory hallucinations but with sensory hallucinations, that of formication and paranoia. He was observed and given supportive care for 4 h, then discharged without any known sequelae. Blood and urine were collected for laboratory analyses. Foxy and its metabolites were identified in urine by gas chromatography–mass spectrometry. The concentrations of 5-MeO-DIPT in the serum and urine were 0.14 and 1.6 µg/mL, respectively. The drug undergoes oxidative deamination to form 5-methoxy-indole acetic acid. The urinary concentration of this metabolite was 0.17 µg/mL. Also, the urine contained three other related compounds. Two of them have been described in a previous case of 5-MeO-DIPT ingestion as 5-methoxy-isopropyltryptamine (5-MeO-IPT) and 5-methoxy-diisopropyltryptamine-N?-oxide (5-MeO-DIPT-N?-oxide). The third compound was substantially present in the urine and was tentatively identified as 5-hydroxy-diisopropyltryptamine (5-OH-DIPT). Only the parent drug, 5-MeO-DIPT was detected in the serum sample.