Dimethylamylamine was reported to have been found in the blood of a runner who died in the London Marathon last year. At inquest it was found to be a contributing factor in her death. What is it and how may it have contributed to death?
The stimulant 4-methyl-2-hexaneamine (1,3-dimethylamylamine, DMAA) was listed on the World Anti-Doping Agency (WADA) banned list in 2009, thus banned for sporting use. DMAA falls under the category ‘S6 – STIMULANTS’ – compounds banned ‘in competition’ (WADA, 2012). This caffeine like stimulant was detected 123 times in drug tests in 2010 (WADA, 2010), the most prevalent compound in the stimulant category. Amongst high profile names who have been banned for DMAA are the South African rugby players Chiliboy Ralepelle and Bjorn Basson (due to contaminated supplements), US sprinter Mike Roberts and former world champion boxer Enzo Maccarinelli.
DMAA is purported to originate from the geranium plant (Pelargonium graveolens), but this is disputed. It has often been included in ingredients lists of supplements as ‘geranamine’ to try and signify a natural origin. There has been one paper that I am aware of which suggests DMAA is found in geranium oil or extracts against a growing number which suggest it is not.
Until August last year DMAA was available without restriction in the UK. The Medicines and Healthcare Products Regulatory Agency (MHRA) ruled that DMAA was an unlicensed medicinal product which needed to be withdrawn immediately. In New Zealand DMAA was sold as a ‘party pill’ until controlled in April last year. In the UK and USA DMAA was often included in supplements meant for taking before working out to give extra energy, with names such as ‘Jack3d’ and ‘OXYElite Pro’. The London Marathon is in April each year, so the supplement used (reported to be Jack3d) would have been legally and readily available at that time.
For several months after the MHRA ruling I was able to buy multiple gram quantities of DMAA over the internet from within the UK, but those sites do not seem to be listing it any more. I was buying it for research purposes not my own use!
The DMAA structure is shown above, along with that of amphetamine. The DMAA effects are said to be somewhere between caffeine and amphetamine in intensity. DMAA is a central nervous system stimulant (similar to contents of khat) leading to increased euphoria, alertness and heart rate. The combination of the stimulant on top of a period of sustained exercise is quite a lot for the heart to take. It was reported that the deceased runner, Claire Squires had undergone investigation for heart problems ( The Guardian). The pathologist in the case thought that DMAA ‘was a contributory factor in her death’.
Prof William McKenna, a specialist in cardiovascular disease from University College London Hospital told the inquest:
“…the toxicology identifying an amphetamine-like substance does suggest its contribution to her [cardiac] arrest, particularly after excessive exercise”
DMAA has previously been linked to deaths in the USA and to 3 cases of brain hemorrhage in New Zealand. The real safety profile of the drug doesn’t seem to have been studied, with doses recommended for workouts varying widely and with little known on pharmacokinetics.
What can we learn from this case?
The use of supplements that have little or no testing behind them is going to be a risk. People who use supplements may not be aware that some products have not been extensively tested for safety. The message would be to be very careful about using supplements. If you are going to use supplements check the labels and if unsure as to a certain ingredient then look it up or ask a GP or pharmacist. The UK Anti Doping Agency have a good website to check out the sporting status of drugs.
What supplement next?
With DMAA banned, what comes next? Another compound seems to be very popular now, called synephrine, extracted from Citrus aurantium or ‘Chinese Bitter Orange’. The structure of synephrine is shown below. Synephrine is a positional isomer of phenylephrine – a common decongestant drug.
[Chemistry: Synephrine shown below has the hydroxy group at the para position whilst phenylephrine is at the meta position.]
Synephrine will also have central nervous system effects as listed above for DMAA.
I am a big user of caffeine, both during exercise and for keeping me awake at my desk. Do you use sports supplements? Will this case alter your behaviour around their use?
Thanks for reading – please feel free to share!
Wada banned list (2012)
WADA Laboratory statistics (2010)
Use of Recreational Drug 1,3-Dimethylethylamine (DMAA) Associated With Cerebral Hemorrhage – P Gee et al 2012. DOI: 10.1016/j.annemergmed.2012.04.008
Please note – I do not have access to my full reference list from home, so will update these in the next few days.