Have A Nice Tryptamine. Brian Waters LA County Coroner CAT San Francisco June, 2006

Transcription

1 Have A Nice Tryptamine Brian Waters LA County Coroner CAT San Francisco June, 2006

2 What s In A Tryptamine? Tryptamine (3-(2-aminoethyl)indole) Monoamine compound Widespread in nature Biosynthesis proceeds from tryptophan C 10 H 12 N 2 Molar Mass g/mol

3 Tryptophan

4 Tryptamine General Structure

5 Tryptamines Found in the Body

6 Monoamine neurotransmitter Believed to regulate mood, sleep, and appetite Serotonin (5-Hydroxytryptamine)

7 Melatonin (5-Methoxy-N-Acetyltryptamine) Hormone found in all living creatures Involved in regulating the sleep-wake cycle

8 Tryptamines Found in Plants & Animals

9 DMT (Dimethyltryptamine) Visual psychedelic Usually smoked or taken orally with a MAO inhibitor Found in the brain Produced by many plants

10 Psilocybin (4-Phosphoryloxy-N,N-dimethyl-tryptamine ) Psychedelic Alkaloid Present in many species of fungi Converted to Psilocin in the body

11 Psilocybin Mushroom

12 5-MeO-DMT (5-Methoxy-Dimethyltryptamine) Naturally occurring in many plants and toad venom Comparable to DMT in effects, although less visual Requires much less dosage than DMT (1/10 to ½)

13 Psychoactive Toad Venom

14 Synthetic Tryptamines

15 5-MeO-DIPT (Foxy) (5-methoxy-N,N-diisopropyltryptamine) Used as a psychedelic Orally active Officially placed into Schedule I in 2004

16 AMT (α-methyltryptamine) Developed as an antidepressant in the 1960s Psychedelic hallucinogen at sufficient dosages Became a Schedule I drug in 2004

17 5-MeO-AMT (5-Methoxy-α-Methyltryptamine)

18 5-MeO-AMT Considered one of the most potent tryptamines Also known as alpha-o, O-DMS, or just alpha Often mistaken for or sold as LSD

19 Presentation Typically available as a powder Often dissolved and used on blotter paper and sugar cubes (hence the confusion with LSD) Also found on candy, gelatin, pressed into tablets or placed in capsules

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21 Usage Typically consumed in mg dosages May be administered by smoking or snorting Effects can be felt within 1 hour of administration Effects generally last hours

22 Users Typically abused by teenagers and young adults Used at raves, nightclubs, and parties along with other club drugs (ecstasy, etc.)

23 Reported Effects Hallucinations Sweating Nausea Diarrhea Vomiting Delusional, psychotic behavior Diminished inhibitions

24 Legality Illegal for human consumption Analog of 5-MeO-DiPT and AMT, both of which are Schedule I drugs under the Controlled Substances Act

25 The Case of the Fallen Angel

26 Case Details 20 year old male Drove up from San Diego with friends to attend a party in Santa Monica En route they stopped and purchased some illegal drugs Arrived at the party between hours

27 Became agitated and began acting erratic at 0600 hours Became more aggressive and was removed from the party by friends Broke free from his friends and ran toward a cliff Began yelling incoherently and walked off of the cliff at about 0800 hours

28 Fell feet landing in a tree Extricated by paramedics and taken to UCLA Medical Center where he expired at 0936 hours due to his injuries Mother and stepfather both stated he had been happy and denied that he would have committed suicide

29 The decedent s mother called many times inquiring about the case, specifically the toxicology She was concerned that the decedent was acting strangely because of something he was given

30 The decedent s mother offered many suggestions as to what drugs he might have been given Butanol Butyl CI 2CI FOXY 5-MEO-AMT

31 Toxicological Analysis

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33 Extraction 2 ml sample size Protein precipitation with 5% Zinc Sulfate Solid phase extraction using UCT Clean- Screen CSDAU206 (6 ml) columns Wash with 0.10 M Sodium Acetate Buffer, 1 M Acetic Acid & Methanol Elute with 78:20:2 Methylene Chloride: Isopropanol: Ammonium Hydroxide solution Blow down to dryness and reconstitute in 50 µl MSTFA; derivitize at 75 F for 40 minutes

34 Analysis Analysis performed on an Agilent GC/MS with an HP-5 Capillary Column at 10 /min, then at 60 /min Monitored ions for 5-MeO-AMT (MSTFA derivitization) were m/z 356, 383, and 159 Elution order: Amphetamine Methamphetamine 5-MeO-AMT Foxy

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36 Quantitation Calibration curves from 0.05 ug/ml to 4.0 ug/ml standards were inconsistent Most likely due to an incompatible Internal Standard Results were reported out as just Present

37 Toxicology Results 5-MeO-AMT Amphetamine Methamphetamine Ethanol GHB Heart Blood Present 0.09 ug/ml ND ND 19 ug/ml* Urine Present 2.0 ug/ml ND ND 2.8 ug/ml* * GHB level consistent with endogenous levels in postmortem specimens

38 Cause of death was from traumatic injuries due to the fall Mode was initially called a suicide, but ultimately classified as undetermined

39 Other Reported Tryptamine Cases Feb 2003 Miami-Dade County Medical Examiner Department reported the first known death related to AMT (Journal of Analytical Toxicology) Summer Spokane County Office of the Medical Examiner reported the death of a 19 y/o female caused by toxic encephalopathy due to 5-MeO- AMT intoxication

40 Future Projects Develop a quantitation method for 5-MeO-AMT with a suitable Internal Standard (possibly using LC/MS/MS) Develop a screening method to detect the most common of the abused tryptamines (AMT, 5-MeO- AMT, 5-MeO-DMT, Foxy, Psilocybin, etc.)

41 Sources Shulgin A, Shulgin A. TIHKAL: The Continuation, Transform Press, Berkeley, CA, U.S. DOJ National Drug Intelligence Center. 5-MeO-AMT Fast Facts, 2004.