The Complete DMHA Guide; Comparing DMHA to DMAA and Other Monoamines
A Guide To DMHA
(aka 2-Aminoisoheptane, 2-Amino-6-methylheptane, 2-Amino-5-methylheptane)
What is DMHA?
DMHA, Dimethylhexylamine, is a psychoactive, central nervous stimulant that falls in the class known as monoamines; other compounds in this class include1,3-Dimethylamylamine (DMAA), Adderall (Amphetamine), and Crystal Meth (Meth-Amphetamine). While these compounds all vary in potency greatly, they all work in a similar mechanism with just a varying efficiency. They are all considered catecholamine reuptake inhibitors due to their structure that allows them to bind to transporter proteins that are responsible for taking your catecholamine neurotransmitters (dopamine, epinephrine (adrenaline), and nor-epinephrine (nor-adrenaline) out of your synapse to be recycled. Before we go to into depth, lets take a look at DMHA's structure and it's significance.
DMHA Structure and it's Functional Significance
DMHA exists in two different forms, a naturally derived form called 2-amino-5-methylheptane, and a chemically synthesized one called 2-amino-6-methylheptane- these two forms only differing by the location of their methyl group. So looking at the names of these two compounds we can infer a couple things;
- Heptane: "Hept-" tells us that this molecule has 7 carbon chain backbone and the "-ane" let's us know that it is what is known as an alkane- or a chain of single bonded carbons.
- 2-Amino: This indicates that there's an amine group (NH2) on the second carbon. This is what gives the structure it's classification as a monoamine and allows it to work on catecholamine transporter proteins.
- 5 or 6-Methyl: This indicates that there's a methyl (CH3) group located on the 5th or 6th carbon depending on the form being used. Methyl groups are significant in biochemistry because 1. They cause the molecule to become amphiphilic- this means they have both hydrophobic (water fearing) and Hydrophilic (water loving) which helps it become more soluble in lipids and pass through the Blood-Brain-Barrier (BBB) more easily 2. Sterically blocks enzymes from the breaking down the molecule; in this case the methyl group on DMHA blocks Monoamine Oxidase increasing potency by allowing the molecule to remain in its active form longer.
So How Do 2-Amino-5-methylheptane and 2-Amino-6-methylheptane Differ?
As you can see from the diagram above, the difference between the two structures comes from the location of it's methyl-group. In the "5" version the methyl is located on the 5th carbon while in the "6" version it is located on the 6th carbon. If you notice in the 5 version, the methyl group is located 1 carbon closer to the amine group which actually increases it's potency by better sterically blocking monoamine oxidase. This enzyme scans for single amine containing compounds so if a methyl group is closer to the amine, it better "hides" it from detection and allows it to remain active. The 2-amino-5 version is also naturally extracted from Kigela Africana plants, so due to it's potency and where it's derived from we have chosen to include it in our GoldStack pre-workout.
How Do Monoamines Actually Work?Both compounds work similarly as Catecholamine Reuptake Inhibitors, which increase functioning catecholamine levels within your body. Catecholamine’s are neurotransmitters within the body that get their name from their structure (as all these compounds do). They are both monoamines with what is referred to as a catechol, a benzene ring(Black Arrow) with two hydroxyl groups(OH) on two consecutive carbons:
Both these monoamines, DMAA and DMHA, act as reuptake inhibitors for the catecholamines. Reuptake occurs in the synapse of your neurons, when neurotransmitters are absorbed by the plasma membrane of an axon terminal after a neural impulse has been conducted. So if some of the reuptake is inhibited by these compounds binding to and blocking the function of each specific Catecholamine Active Transporter, the concentration of the neurotransmitters outside of your cells are increased. This generates the enhanced effects each catecholamine is responsible for; focus, energy, bronchodilation, etc. However, the structure of each compound is what causes the differences in effectiveness, as DMHA is said to be about 70-80% the strength of DMAA.
Comparing DMHA to DMAA, Adderall, and MethDMAA is an extremely effective stimulant whose structure we’ll compare to a commonly known compound, amphetamine (adderall). Notice both the structures have the suffix “amine” in their name, indicating the presence of a NH2 group which classifies it as a monoamine and allows for the inhibition of reuptake processes mentioned above to be carried out when present. The only difference between the two structures is the fact that amphetamine contains a benzene ring and methyl group(CH3-black arrows) while DMAA only contains methyl groups. While the methyl group functions well in blocking enzymes (in this case mainly monoamine oxidase(MAO))from breaking them down, the bulky benzene ring functions even more effectively. DMAA contains two methyl groups located directly next to the NH2 group on either side, very effectively blocking MOA and increasing potency. As we said though, even though DMAA contains two methyl groups and amphetamine only contains 1, the presence of the benzene ring causes amphetamine to more effectively block the MAO causing increased effects. The most potent monoamine as a stimulant, methamphetamine, contains the same double methyl-group as DMAA, and also with the benzene ring of amphetamine. The presence of the benzene ring also increases the passing of the compound through the blood-brain-barrier, which is important for working on neurotransmitter pathways. Compare this structure of DMAA with 2 methyl groups to the structure of DMHA and you'll understand why DMHA is said to have about 70-80% the strength of DMAA.
Depending on which form you're ingesting, the doses are different due to their potency variations discussed above. For the 2-amino-5-methylheptane version which we use the sweet spot is between 65-75mg while the 2-amino-6-version is upwards of around 150mg for the same effects.
Will DMHA Cause a Positive Drug Test?
While DMHA is by no way an illegal compound or restricted, since it is similar in structure as a monoamine to other controlled substances such as amphetamine, in very rare cases positives for amphetamines can happen. Now this is very rare because 1. DMHA has a very low affinity for the antibodies used to detect amphetamines in your system. They are made to bind to amphetamine not DMHA so it is not likely a positive is registered and 2. DMHA is not needed in high concentrations and since its half life is only 9-11 hours, it typically falls to undetectable levels fast. If you're involved in a profession or sport that involves testing for amphetamines it is best to talk to your authorities. In the case of false positives it can usually be resolved by explaining the cross reactivity of DMHA, but then again this is very rare.
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