Ecstasy Designer Drug 2C-E and a Death in Oklahoma

Chemical Structure 2C-E

If you are a parent of a teenager I hope you took chemistry in high school or college because you are going to need it.  The reason you are going to need it is the emergence of designer drugs of abuse.  Designer drugs typically have a parent compound that is chemically modified.  There are two key reasons to modify existing illegal compounds: 1.) the new compound may not be illegal until state and federals laws can be modified and 2.) the new compound may have potent psychoactive effects.

Unfortunately, some effects of the designer drugs may not be so beneficial.  A young adult Oklahoma woman died recently after ingesting a designer drug known as 2C-E.  Additionally, seven young adults at the same party were hospitalized for adverse effects. 

The number and type of designer drugs is pretty extensive.  The parent compounds for some of these designer drugs include marijuana (tetrahydrocannabinol), ecstasy (MDMA), PCP and the opiate drug fentanyl.  2C-E is a designer drug derived from phenethylamine.

Deaths due to ecstasy use are uncommon.  Many deaths in ecstasy users occur in the context of alcohol and other drug use making the specific contribution from ecstasy unclear.  MDMA may contribute to risk of death through seizure, cardiac arrhythmia, hyperthermia or water intoxication.  MDMA may cause inappropriate release of the endogenous hormone ADH (antidiuretic hormone) that can cause low serum sodium, brain edema and death via water intoxication.

Given the acute toxic effects on multiple users of 2C-E in Oklahoma, the potential for toxic contaminants will need to be explored. 2C-E is thought to block the 5-HT2A (serotonin) receptor.  There is some evidence this effect is potentiated in those taking a selective serotonin reuptake inhibitory antidepressant drugs like Prozac.  Some of these designer drugs can be ordered online.  There is essentially no safety data so users are the defacto guinea pigs.  Autopsy results in the Oklahoma death will not be known for weeks.

Here is a listing of the compounds listed by parent compound type from a recent research review that explored the metabolism of these compounds.

2C phenethylamine compounds

(2C-B), 4-bromo-2,5-dimethoxy-beta-phenethylamine

(2C-I), 4-iodo-2,5-dimethoxy-beta-phenethylamine

(2C-D), 2,5-dimethoxy-4-methyl-beta-phenethylamine

(2C-E), 4-ethyl-2,5-dimethoxy-beta-phenethylamine

(2C-T-2), 4-ethylthio-2,5-dimethoxy-beta-phenethylamine and

(2C-T-7) 2,5-dimethoxy-4-propylthio-beta-phenethylamine

Beta-keto designer drugs

 (butylone, bk-MBDB), 2-methylamino-1-(3,4-methylenedioxyphenyl)butan

(ethylone, bk-MDEA), 1-one2-ethylamino-1-(3,4-methylenedioxyphenyl)propan

(methylone, bk-MDMA) 2-methylamino-1-(3,4-methylene notdioxy notphenyl)propan

pyrrolidino notphenones

(MPBP) 4-methyl-pyrrolidinobutyrophenone

(PVP) alpha-pyrrolidinovalerophenone

(PCPr) N (1 phenylcyclohexyl) propanamine

phencyclidine (PCP)-derived drugs

(PCEEA),N-(1-phenylcyclohexyl)-2-ethoxyethanamine

PCMPA), N-(1-phenylcyclohexyl)-3-methoxypropanamine

(PCMEA), (N-(1-phenylcyclohexyl)-2-methoxyethanamine

Tryptamines

(5-MeO-DIPT), 5-methoxy-N,N-diisopropyl nottryptamine

Alpha methylfentanyl

(alpha-MF) alpha-methylfentanyl

(3-MF) 3-methylfentanyl

Cannabis Compounts-K2, Spice

Cannabicyclohexanol

HU-210

JWH-018

JWH-073

Chemical model of the drug 2C-E from Wikipedia Creative Commons authored by sbrools.

Farah R, & Farah R (2008). Ecstasy (3,4-methylenedioxymethamphetamine)-induced inappropriate antidiuretic hormone secretion. Pediatric emergency care, 24 (9), 615-7 PMID: 18797371

Meyer MR, & Maurer HH (2010). Metabolism of designer drugs of abuse: an updated review. Current drug metabolism, 11 (5), 468-82 PMID: 20540700