The Dendrobium Craze, Or What Happens if You Ignore the Obvious Difference Between "A" and "B" - Latest Study: At Best Trace Amounts of "Meth Analog" in DS Craze
|DS Craze was not the only dendobrium containing supplement that disappeared from the market, when "the craze" about meth in dietary supplements broke lose.|
Using what they considered established reference standards and sensitive analytical methods, Cohen et al. found what they thought was N,α-DEPEA at concentrations ranging from 21 to 35 mg per serving in the supplements (Cohen. 2013)
The results from this the study Cohen et al. conducted in 2013 were later officially confirmed by researchers from the Korean Forensic Service who found 0.40 and 0.44% N,α-DEPEA, respectively — the equivalent of roughly 23 mg per serving in their samples of Craze (Lee. 2014).
Now, N,α-DEPEA is only one out of several phenylethylamines aka "PEAs", of which even Cohen et al., whose paper started the whole craze say that the spectrum of PEAs "range[s] from benign compounds found in chocolate to synthetically produced illicit drugs" (Cohen. 2014). In that, minimal structural differences determine, whether we are dealing with a harmless ingredient of chocolate or a methamphetamine analog like N,α-DEPEA with the difference in the chemical structure of the agents being small, in some cases marginal (Lee. 2014).
|Figure 1: Different phenylethylamines (PEAs) with different degrees of structural resemblance |
and different physiological effects (Wahlstom. 2014)
"[...] N,α and N,β isomers have very similar chromatographic characteristics and are difficult to resolve unless the test method being used is optimized to properly separate both isomers" (Wait. 2014)This similarity makes the two DEPEA isomers very difficult to distinguish. More importantly, the existence of the N,β isomer implies that anyone who analyzes dietary supplements for N,α-diethyl phenethylamine runs the risk of generating false positive - yet unfortunately, this is exactly what Cohen et al. (2013) and Lee et al. (2013) and before them Mahmoud A. ElSohly & Waseem Gul (2013) obviously did.
Needless to say that the existence of said structural difference does also imply that the agent won't fit into the corresponding receptor site or interact with the same enzymes N,α-DEPEA and "real" methamphetamies do. Accordingly, the biological activity associated with that compound are certainly different from those of N,α-diethyl phenethylamine.
"As such, the alleged presence of the N,α isomer may actually be the N,β isomer, or a combination of the two.
My previous Craze article is now obviously obsolete | read more.
Unequivocal identifiation of the N,β and N,α isomers is particularly critical since the N,β isomer does not share the same structural similarities that N,α shares with methamphetamine (also alkylated in the α position, not the β position)." (Wait. 2014)
In said paper, the authors, Wahlstrum, Styles and Hägglund present the results of an analysis of two samples of Driven Sports' pre-workout product Craze ("Candy Grape", batch # 1305323 and "Berry Lemonade" batch # 1303298) that was conducted with a new analytical method that can "reliably" identify and quantify the individual amounts of N,α-diethyl phenethylamine (N,α isomer), N,β-diethyl-phenethylamine (N,β isomer), and N,N-diethyl-phenethylamine (N,N isomer) in a sample.
|Table 1: Amounts and relative standard deviations (RSD) for the two samples of |
DS Craze with lot no. 1303298 and 1305323 (Wahlstrom. 2014)
- Cohen, Pieter A., John C. Travis, and Bastiaan J. Venhuis. "A methamphetamine analog (N, α‐diethyl‐phenylethylamine) identified in a mainstream dietary supplement." Drug testing and analysis (2013).
- ElSohly, Mahmoud A., and Waseem Gul. "LC–MS-MS Analysis of Dietary Supplements for N-ethyl-α-ethyl-phenethylamine (ETH), N, N-diethylphenethylamine and Phenethylamine." Journal of analytical toxicology (2013): bkt097.
- Kedia, A. William, et al. "Effects of a Pre-workout Supplement on Lean Mass, Muscular Performance, Subjective Workout Experience and Biomarkers of Safety." International journal of medical sciences 11.2 (2014): 116.
- Lee, Jaesin, et al. "Identification and quantitation of N, α-diethylphenethylamine in preworkout supplements sold via the internet." Forensic Toxicology 32.1 (2014): 148-153.
- Wait, D. "The importance of reliable product chemistry data: A case study." In AHPA Report | The Official Publication of the American Herbal Products Association 29.10 (2014).
- Wahlstrom, R., C. Styles, and G. Hägglund. "Reliable identification and quantification of three diethylphenethylamines in a Dendrobium-based dietary supplement." Analytical Methods 6.19 (2014): 7891-7897.