
Examining Aniracetam and It’s Metabolites
Aniracetam was the second racetam developed by Dr. Corneliu Giurgea after piracetam. Piracetam, which began it’s life as a cyclic derivative of the primary inhibitory neurotransmitter GABA was modified in the 70’s to create the related racetam, aniracetam. Oddly enough, there are studies that may suggest that aniracetam itself may not specifically be nootropic on it’s own. If this is so then why is it still such a popular nootropic supplement? The answer may lie within the process of aniracetam’s breakdown which results in multiple by-products known as metabolites. It seems that these metabolites may actually be more important as nootropic compounds than the parent compound itself.
In fact it’s the activity of the three primary metabolites of aniracetam that form one of the primary differences in aniracetam’s pharmacokinetic profile as compared to piracetam. Aniracetam is rapidly absorbed in the intestines where 90% of it is bio-available and rapidly metabolized into N-anisoyl-GABA (4-p-anisaminobutyric acid), 2-pyrrolidinone (the chemical backbone structure for all the racetams) and p-anisic acid. Aniracetam and it’s 3 primary metabolites all seem to have some part in it’s overall action, but aniracetam itself may only be responsible for the first phase in a multi-phasic activity that ends shortly after it’s metabolized.
P-anisic acid is the primary resultant metabolite in rat studies, but it’s the N-anisoyl-GABA that seems to be the primary metabolite in humans. 70% of aniracetam metabolizes into n-anisoyl-GABA. 2-pyrollidinone and p-anisic acid will continue to breakdown and produce further metabolites. The rapid metabolism of these compounds has complicated in vitro studies (clinical trials in humans have been running since the 90’s) but it’s the multiphasic effect and multiple metabolites that may be a part of aniracetams benefits that range from increased executive function, anxiolysis (anxiety relief), increased memory, mild psychostimulatory effect and improved cholinergic functions.
Aniracetam has a short half life in addition to ready and swift metabolism. As a result, a dosage of once every 4-6 hours is suggested for optimal nootropic effects. In rats peak plasma is reached in as quick as 20 to 30 minutes after oral administration and it’s half life is only 1.7 – 2.1 hours. In humans, peak plasma is reached in about 2 hours and reach baseline (back to normal) in 6 hours.
N-Anisoyl-GABA
The main metabolite of aniracetam seems to be N-anisoyl-GABA, which is considered primary to it’s nootropic action. N-anisoyl-GABA is actually an analogue of Gamma-amino-butyric acid (GABA) ,which is the primary inhibitory neurotransmitter in the brain. GABA’s primary function is primarily to quiten an overstimulated brain and most anxiolytics, like the benzodiazepine class, act on the GABAergic system in order to offer their anxiety relieving benefit. Though originally piracetam’s effect on the primary excitatory neurotransmitter glutamate seemed to suggest that the racetam’s activity was primarily due to psychostimulatory action due to the glutamergic response, however more recent studies show that the inhibitory effect may be just as important in improving neuronal transmission.
P-Anisic Acid
Another one of the primary metabolites of aniracetam is p-Anisic acid, which is also known as 4-methoxybenzoic acid or draconic acid. P-anisic acid is an isomer of anisic acid. Isomerism is a condition where, since molecules have a three dimensional shape they can have the same chemical formula but a different 3-d structure. Anisic acid itself refers to this specific isomer which is found naturally in anise. P-anisic acid in it’s pure molecular form, is a white crystalline solid that is not soluble in water, but highly soluble in alcohol, ether and ethyl acetate. It is also a common additive in skincare, body care, hair care, sun protection products and anti-aging skin products.
Monoaminergic Effects
Aniracetam has been shown in a recent study “to preferentially increase extracellular levels of dopamine (DA) and serotonin (5-HT) in the prefrontal cortex (PFC), basolateral amygdala and dorsal hippocampus of the mesocorticolimbic system in stroke-prone spontaneously hypertensive rats. This may support the anecdotal evidence of users who have suggested they felt anxiety relief and a mood lift from supplementation of aniracetam. To test whether aniracetam itself was to be primarily implicated, scientists perfused the pre-frontal cortex of rats with p-anisic acid and n-anisoyl-GABA without the initial aniracetam and found that these two metabolites on their own enhanced dopaminergic and 5-HT (serotonergic) activity. The fact that the effects were not only mimicked by the metabolites, but extinguished by haloperidol (an anti-psychotic that works to reduce dopamine activity) led to the theory that the mechanism responsible for improved mood was due to enhancement of dopaminergic signalling through the nicotinic receptors (a subset of the acetylcholine system).
In fact according to the same study, researchers failed to find any effect of aniracetam itself. A direct injection of N-anisoyl-GABA (1 nmol) into the pedunculopontine tegmental nucleus of SHRSP enhanced the release in the nucleus reticularis thalami. Thus, this data shows that aniracetam can facilitate central cholinergic neurotransmission via both metabolites. In other words, aniracetam seems to be active on it’s own prior to metabolism and may not be responsible for the majority of the mood lifting and nootropic effects.
Some anecdotal evidence would suggest that aniracetam is more so a simple short-acting anxiolytic compound. Due to it’s short half life however, the metabolites kick in after 2 hours and it is these compounds that provide the primary cognitive enhancing, nootropic effects. N-anisoyl-GABA, itself, is an AMPAkine (acts on a subreceptor of the glutamergic/excitatory system) which may be largely responsible for the psychostimulatory effect of phase 2.
In fact, although piracetam has some AMPAkine activity, aniracetam and it’s metabolites are much stronger AMPAkines. 2-pyrrolidinone, p-anisic acid and anisamide butyrate all act on the AMPA receptors. 2-pyrrolidinone, the common chemical structure that’s shared by all true racetams enhances calcium ion (Ca2+) permeability of AMPA receptors. In addition to piracetam and aniracetam’s cholinergic activity, the calcium channel activity that improves permeability of neurons is often an overlooked mechanism in the nootropic effect of racetams.
So in the end though some studies may suggest aniracetam to have minimal nootropic activity on it’s own that doesn’t at all mean that adding it to a supplementation regimen will not result in cognitive enhancing benefit, rather the main brain boost may come from by-products of your body breaking down aniracetam into active compounds.
Always remember to safely use supplements. Check with your physician first, especially if you’re on any medications or have any pre-existing illnesses you’re being treated for. After being cleared by your personal care practitioner always observe minimum effective dosing based on the recommended amount. Aniracetam or its metabolites may cause allergic reactions in some individuals.
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