Have A Nice Tryptamine

Brian WatersLA County CoronerCAT – San Francisco

June, 2006

What’s In A Tryptamine?

• Tryptamine (3-(2-aminoethyl)indole)•Monoamine compound•Widespread in nature•Biosynthesis proceeds from tryptophan

• C10H12N2

• Molar Mass 160.22 g/mol

Tryptophan

Tryptamine General Structure

Tryptamines Found in the Body

Serotonin(5-Hydroxytryptamine)

• Monoamine neurotransmitter

• Believed to regulate mood, sleep, and appetite

Melatonin (5-Methoxy-N-Acetyltryptamine)• Hormone found in

all living creatures

• Involved in regulating the sleep-wake cycle

Tryptamines Found in Plants & Animals

DMT (Dimethyltryptamine)

• Visual psychedelic• Usually smoked or

taken orally with a MAO inhibitor

• Found in the brain• Produced by

many plants

Psilocybin(4-Phosphoryloxy-N,N-dimethyl-

tryptamine )• Psychedelic

Alkaloid• Present in many

species of fungi• Converted to

Psilocin in the body

Psilocybin Mushroom

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)

Psychoactive Toad Venom

Synthetic Tryptamines

5-MeO-DIPT (Foxy)(5-methoxy-N,N-diisopropyltryptamine)

• Used as a psychedelic

• Orally active• Officially placed

into Schedule I in 2004

AMT(-Methyltryptamine)

• Developed as an antidepressant in the 1960s

• Psychedelic hallucinogen at sufficient dosages

• Became a Schedule I drug in 2004

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

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

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

Usage

• Typically consumed in 2.0 – 4.5 mg dosages

• May be administered by smoking or snorting

• Effects can be felt within 1 hour of administration

• Effects generally last 12-18 hours

Users

• Typically abused by teenagers and young adults

• Used at raves, nightclubs, and parties along with other “club” drugs (ecstasy, etc.)

Reported Effects

• Hallucinations• Sweating• Nausea• Diarrhea• Vomiting• Delusional, psychotic behavior• Diminished inhibitions

Legality

• Illegal for human consumption• Analog of 5-MeO-DiPT and AMT,

both of which are Schedule I drugs under the Controlled Substances Act

The Case of the Fallen Angel

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 1900-2200 hours

• 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

• Fell 80-100 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

• 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

•The decedent’s mother offered many suggestions as to what drugs he might have been given

•Butanol

•Butyl

•CI

•2CI

•FOXY

•5-MEO-AMT

Toxicological Analysis

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

Analysis

• Analysis performed on an Agilent GC/MS with an HP-5 Capillary Column

• 100° - 200° at 10°/min, then 200° - 300° 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

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”

Toxicology Results

Heart Blood

Urine

5-MeO-AMT Present Present

Amphetamine 0.09 ug/ml 2.0 ug/ml

Methamphetamine ND ND

Ethanol ND ND

GHB 19 ug/ml* 2.8 ug/ml*

* GHB level consistent with endogenous levels in postmortem specimens

• Cause of death was from traumatic injuries due to the fall

• Mode was initially called a suicide, but ultimately classified as undetermined

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 2005 - 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”

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.)

Sources

• www.erowid.org• Shulgin A, Shulgin A. TIHKAL: The

Continuation, Transform Press, Berkeley, CA, 1997.

• U.S. DOJ National Drug Intelligence Center. 5-MeO-AMT Fast Facts, 2004.