2-aminoisoheptane aka DMHA or Octadrine, a Legit DMAA Successor? Structure, Effects & Sides Suggest: "Maybe"

2-aminoisoheptane aka DMHA or Octadrine, a Legit DMAA Successor? Structure, Effects & Sides Suggest: "Maybe"

cognitive performance DMAA DMHA fat burner health lose fat performance preworkout PWO stimulant stimulants

DMHA is rather a stim than a fat burner. But I guess it will be marketed as both.

If you are following the supplement market closely, you will have seen the first products with a new stimulant on the shelves. 2-aminoisoheptane or DMHA - a supposedly worthy successor to DMAA aka "geranamine" (the stuff in the old Jacked3D) with unquestionable structural similarities to the original banned stimulant and a questionable efficacy and safety profile. With two other non-OTC agents that have been (ab)used to lose body fat for decades, namely ephedrine and clenbuterol, DMHA, which is also called octadrine and correctly labeled "2-amino-6-methylheptane" shares a history as an asthma agent (Monroe. 1947).

DMHA will be banned, when this article is a SV Classic and caffeine again the stim of choice

For Caffeine, Timing Matters! 45 Min or More?

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Aside from the previously cited study by Monroe et al., a study that showed weak, but existing cytoxic effects in cancer cells by Craciunesco et al. from the early 1980s and an old safety study in rodents and guinea pigs by Fellows (1947), which allows us to estimate the "safety range" of the agent at a human equivalent roughly < 400mg (in rodents, the equivalent dose will already trigger tremors and sign. increases in activity), there's unfortunately no scientific evidence to prove that the agent is (a) safe for human consumption and/or (b) even works as it is supposed to.

Whether the active substance in Eskay Oralator inhalants from the 1940s is a legitimate successor to DMAA can thus only be answered based on speculation and information from the first users, as well as the fact that the agent ended up on Rasmussen et al's recently published list of "novel stimulants in supplements" that are supposed ot "substitute for recently successful products based on ephedrine and amphetamine" (Rasmussen. 2015 | see Table 1 #8).

Table 1: Trivial and chemical names of the compounds supplement companies have dug up in articles from the 1940-50s to replace banned substances in their products (Rasmussen. 2015).

So let's look at what we have: The obviously unreliable user feedback is positive and in line with the implications of the fact that DMHA shares the same structural characteristics which allowed DMAA to interact with the trace amine associated receptor 1 and modulate dopamine and norepinephrine by increasing their production and reducing their reuptake.

Figure 1: It is not difficult to see the structural ressamblance of "geranium" or "geranamine" aka "DMAA" (found for ex. in the old "Jack3D") and "octadrine" aka "DMHA" (as it is found in supps like "InfraRed") when you compare the two.

The structural resemblance to DMAA (see Figure 1) is yet not the only thing the two agents with similar acronyms have in common. Another one is the lack of compelling scientific evidence of their efficacy and safety: Just like DMHA now, DMAA had no no real scientific backup when it first appeared on the radar of the average supplement junkie and it still blew many away - in the positive sense of being happy w/ the results,... at least until the stimulant effects wore off and the crash turned the positive into similarly negative feelings.

Remember the craze about tainted charges of DS Craze with more than just dendobrium | read more

Speaking of supplement junkies... in view of the facts that corresponding products are already on the market, we are certainly going to learn relatively soon about the efficacy and safety of this compound from hundreds if not thousand of human guinea pigs on "the boards" (fitness forums).

Don't be one of those guinea pigs that use an untested product of which I am sure it's going to be banned soon based on hearsay only - regardless of what you hear about purported α-2 receptor activity (like yohimbine) or the fact that it supposedly has similar effects as high dose caffeine or DMAA, but without the crash, by the way | Comment!

References:

• Craciunescu, D. G., et al. "Structure-antitumour activity relationships for new platinum complexes." Chemico-biological interactions 42.2 (1982): 153-164.
• Fellows, Edwin J. "The pharmacology of 2-amino-6-methylheptane." Journal of Pharmacology and Experimental Therapeutics 90.4 (1947): 351-358.
• Monroe, Russell R., and Hyman J. Drell. "Oral use of stimulants obtained from inhalers." Journal of the American Medical Association 135.14 (1947): 909-915.
• Rasmussen, Nicolas, and Peter HJ Keizers. "History full circle:‘Novel’sympathomimetics in supplements." Drug Testing and Analysis (2015).
• Thompson, W.F. - Memo, ‘Low CNS Inhaler’, 22 December 1941; R.S. Fox memo, ‘Disposal of Certain Patent Cases’, 22 March 1942; M.T. Rabbitt to Thompson re ‘Chronologic Report on the Study of Normal-Amylmethyl Carbinamine Sulfate’, 7 June 1945. All in the archives of the California Institute of Technology, Gordon Alles papers, box 15, unlabelled folder.

Theanine + Caffeine - A Natural and Powerful Combination to Increase Your Attention and Reaction Speed (+6-10%)

Theanine + Caffeine - A Natural and Powerful Combination to Increase Your Attention and Reaction Speed (+6-10%)

attention caffeine cognition cognitive performance l-theanine performance tea theanine

Tea will naturally contain both theanine and caffeine, but will it work, as well as supplemental theanine and caffeine?

While everybody knows caffeine (see last SV article comparing caffeine to coffee), theanine aka L-γ-glutamylethylamide or N5-ethyl-L-glutamine, an amino acid analogue of the proteinogenic amino acids L-glutamate and L-glutamine, is less well known, but as a recent study shows not less potent when it comes to its effects on cognition and neurophysiological measures of selective attention aka "focus" on a task / object (Kahathuduwa. 2016).

You want to know why the researchers from the Universities of Peradeniya, Kelaniya and the Texas Tech University know that? Let's take a look at what the researchers did and why they conclude that the effects of caffeine & theanine add up.

You can learn more about caffeine at the SuppVersity

For Caffeine, Timing Matters! 45 Min or More?

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In a placebo-controlled, five-way crossover trial in 20 healthy male volunteers, Chanaka N. Kahathuduwa et al. compared the effects of l-theanine (200 mg), caffeine (160 mg), their combination, black tea (one cup) and a placebo (distilled water) on cognitive and neurophysiological measures of attention.

Figure 1: Theanine and caffeine contents of 37 commercial white, green, oolong, black, and pu-erh tea samples were quantified by high-performance is a liquid chromatography-diode array detector (Boros. 2016).

To get practically relevant results, the authors used simple [SVRT] and recognition visual reaction time tests, as well as neurophysiological (event-related potentials [ERPs]) measures of attention and recorded the visual (VEPs) and motor evoked potentials (MEPs) of their subjects after ingesting each of the three treatments.

Mean ± SE amounts of l-theanine in cups (200 ml) of commercially-available teas. Mean amounts of l-theanine (mg/200 ml) are also shown in brackets (Keenan. 2011) | rel. values for matcha tea are in the text.

What else can theanine do for you / how much is in tea? As the authors of a not exactly unbiased 1999 review (Juneja. 1999) conclude, theanine is a "unique amino acid found almost solely in tea plants and the main component responsible for the exotic taste of ‘green’ tea". In the brain, theanine appears to act as an inhibitory neurotransmitter that reduces blood pressure; probably by modulating α-waves, which are associated with relaxation. In humans these effects have been shown to occur 40 min after the oral administration of theanine (50–200 mg), without causing drowsiness, however. It should be obvious that this makes theanine the perfect adjunct to caffeine which is known for making people jittery when consumed in doses large enough to elicit significant ergogenic and/or nootropic effects.

On the left hand side, you can see an overview of the theanine content of various commercial teas; in this context it is also worth pointing out that high grate matcha tea contains ~56% more than std. sencha green tea (for low grade gree tea, it's even more than 100% extra theanine in matcha vs. sencha | Goto. 1996).

Lastly, I would like to point out that theanine is not just the "calming" partner of caffeine, more recent research shows that l-theanine has neuroprotective, nootropic, immune-modulating, anti-fatigue, anti-diabetic and anti-depressant effects that are almost on par with caffeine. If you want to learn more about these, check out Liang's latest review (Liang. 2015)

What they found were statistically significant improvements in recognition visual reaction time (RVRT) in response to by theanine (P = 0.019), caffeine (P = 0.043), and theanine–caffeine combination (P = 0.001), but not by tea (P = 0.429) or placebo (P = 0.822). A result that is in line with previous research by Haskell, et al. form 2008.

Figure 2: Pre- ad post recognition visual reaction time (RVRT) latency and P110 visual evoked potential latencies, a measure of the reaction speed of your brain; abs. values in ms, rel. changes in % above the bars (Kahathuduwa. 2016).

Additive benefits for the combination of caffeine and theanine were observed not just for the recognition visual reaction time, but also for other parameters - including the P300 event-related potential amplitudes, an objective measure brain activity of the subjects that refutes the sometimes heard claim that theanine calm down your brain activity too much. At least in combination with caffeine, it's quite clear that the opposite is the case.

Caffeinated soft drink, coffee or tea, caffeine alone or caffeine + l-theanine what's going to yield the desired afterburner effect for your brain? The answer to this question came out probably less straight forward than you'd expected | learn more

Bottom line: For the authors their observations are evidence enough to prove "that high doses of theanine and caffeine have acute [beneficial effects on] attention" (Kahathuduwa. 2016). The authors do yet also point out that further research is necessary to figure out the dose–response relationship, as well as the time-course of theanine supplementation on objective measures of attention.

What I personally find even more interesting, though, is the fact that the evidence clearly indicates that "theanine and caffeine have additive effects" (Kahathuduwa. 2016)... ok, you probably expected that, in view of the fact that they are natural synergists in tea. Against that background, it appears strange that the scientists found no improvements in attention when they gave their subjects tea. The reason for the lack of effects is yet simple: the amount of theanine and caffeine used in the study are equivalent to the amounts found in 6–10 and 2-4 cups of tea, respectively.

Due to the relatively low theanine content of regular tea, even two cups of green, white or black tea will thus only cut it, if you add extra theanine (and a sprinkle of caffeine) to it | Comment!

References:

• Boros, Klára, Nikoletta Jedlinszki, and Dezső Csupor. "Theanine and Caffeine content of infusions prepared from commercial tea samples." Pharmacognosy Magazine 12.45 (2016): 75.
• Goto T., Yoshida Y., Amano I., Horie H., Foods Food Ingredients J. 170 (1996): 46-51. 
• Juneja, Lekh Raj, et al. "L-theanine—a unique amino acid of green tea and its relaxation effect in humans." Trends in Food Science & Technology 10.6 (1999): 199-204.
• Haskell, Crystal F., et al. "The effects of L-theanine, caffeine and their combination on cognition and mood." Biological psychology 77.2 (2008): 113-122.
• Kahathuduwa, Chanaka N., et al. "Acute effects of theanine, caffeine and theanine–caffeine combination on attention." Nutritional Neuroscience (2016): 1-9.
• Keenan, Emma K., et al. "How much theanine in a cup of tea? Effects of tea type and method of preparation." Food chemistry 125.2 (2011): 588-594.
• Liang, Yue-Rong, et al. "Health Benefits of Theanine in Green Tea: A Review." Tropical Journal of Pharmaceutical Research 14.10 (2015): 1943-1949.