Gabapentin (60142-96-3)

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The precise mechanism of action underlying the anticonvulsant effect of gabapentin is not known. Although Gabapentin is structurally related to, and was designed to mimic GABA , it does not bind to GABA receptors. Gabapentin binds preferentially to neurons in the outer layer of the rat cortex at sites that are distinct from other anticonvulsants. It is likely that gabapentin acts at an intracellular site as the maximal anticonvulsant effect is achieved 2h after an intravenous injection of gabapentin in rats. This occurs after the plasma and interstitial fluid concentrations have peaked and reflects the additional time required for intra-neural transport. Furthermore, its distinct profile of anticonvulsant activity in animal seizure models and its lack of activity at many drug binding sites associated with other antiepileptic drugs indicate that its mechanism of action is different.
The finding that gabapentin can antagonize presynaptic, voltage-gated (voltage-sensitive) calcium channels containing the alpha 2-delta (α2δ) subunit, thereby limiting neurotransmitter release, has focused attention on this mechanism as the action underlying the therapeutic effects of gabapentin in epilepsy and pain. However, gabapentin also increases the synaptic concentration of GABA, enhances GABA responses at non-synaptic sites in neuronal tissues, and reduces the release of mono-amine neurotransmitters. One of the mechanisms implicated in this effect of gabapentin is the reduction of the axon excitability measured as an amplitude change of the presynaptic fibre volley (FV) in the CA1 area of the hippocampus. This is mediated through its binding to presynaptic N-methyl-d-aspartate (NMDA) receptors. Other studies have shown that the effects of gabapentin in alleviating neuropathic pain are mediated by the descending noradrenergic system, resulting in the activation of spinal alpha2-adrenergic receptors. Gabapentin has also been shown to bind and activate the adenosine A1 receptor. The following table gives the possible target receptors for gabapentin.

Target ReceptorAction
Voltage-dependent calcium channel subunit alpha-2/delta-1inhibitor
Voltage-dependent calcium channel subunit alpha-2/delta-2inhibitor
Voltage-dependent N-type calcium channel subunit alpha-1Binhibitor
Adenosine receptor A1agonist
NMDA receptorNot Available
Gamma-aminobutyric acid type B receptor subunit 1Not Available
Gamma-aminobutyric acid type B receptor subunit 2

Not Available

Storage conditions: Preserve in well-closed containers. Store at room temperature

Packaging: : polyethylene nylon plastic bag

CAS Number:  60142-96-3

Formula:  C9H17NO2

Molecular Weight: 171.24 g/mol

Method of Analysis: Based on: USP


Gamma-AminoButyric Acid (GABA) is an inhibitory neurotransmitter that is very widely distributed in the neurons of the cortex. GABA contributes to motor control, vision, and many other cortical functions. Gabapentin was first formed by the addition of a cyclohexyl group to GABA which allowed this form of GABA to cross the blood–brain barrier.
Epilepsy is a disorder characterized by abnormal neuronal discharges and while its causes are many, the fundamental disorder is secondary to abnormal synchronous discharges of a network of neurons. Whether or not a seizure occurs depends upon the balance between excitability and inhibition. The most common excitatory neurotransmitter in the brain, glutamate, has been implicated in both the initiation and propagation of seizures as well as brain damage that can occur following prolonged or repeated seizures. GABA, on the other hand, being the most common inhibitory neurotransmitter, usually suppresses seizure activity. So, Gabapentin was originally developed for the treatment of epilepsy, particularly partial (focal) and mixed seizures. However, presently, gabapentin is widely used to relieve pain. It is recommended as one of a number of first line medications for the treatment of neuropathic pain in diabetic neuropathy, postherpetic neuralgia, and central neuropathic pain. It is also used in hot flashes, and restless legs syndrome. Its other off-label uses include treatment of anxiety disorders, insomnia, and bipolar disorder. Gabapentin is well tolerated in most patients and has a relatively mild side-effect profile. Following oral administration, gabapentin is rapidly absorbed by the L-amino acid transport system and is excreted by the kidneys, unmetabolized. It is not an enzyme-inducing anticonvulsant.