Gabapentin
[CAS# 60142-96-3]

Identification

• Classification: API >> Nervous system medication >> Antiepileptic and anticonvulsant
• Name: Gabapentin
• Synonyms: Gabapentin; Neurontin; 1-(Aminomethyl)cyclohexaneacetic acid
• Molecular Formula: C₉H₁₇NO₂
• Molecular Weight: 171.24
• CAS Registry Number: 60142-96-3
• EC Number: 262-076-3
• SMILES: C1CCC(CC1)(CC(=O)O)CN

Properties

• Density: 1.1$+/-$0.1 g/cm³ Calc.^*
• Melting point: 162 $degree$C (Expl.)
• Boiling point: 314.4$+/-$15.0 $degree$C 760 mmHg (Calc.)^*
• Flash point: 144.0$+/-$20.4 $degree$C (Calc.)^*
• Solubility: DMSO $lessThan$1 mg/mL, Water 34 mg/mL, Ethanol $lessThan$1 mg/mL (Expl.)
• Index of refraction: 1.489 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H315-H319-H335-H360
• Safety Statements: P203-P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Reproductive toxicity	Repr.	1B	H360
Reproductive toxicity	Repr.	2	H361
Carcinogenicity	Carc.	2	H351
Reproductive toxicity	Repr.	1A	H360
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Reproductive toxicity	Lact.	-	H362
Carcinogenicity	Carc.	1B	H350

Discovery and Applications

Gabapentin is a structural analogue of the neurotransmitter gamma-aminobutyric acid (GABA), chemically classified as 1-(aminomethyl)cyclohexaneacetic acid. It was first synthesized in the 1970s and developed as a pharmaceutical compound for its effects on the nervous system. Although structurally related to GABA, gabapentin does not act directly on GABA receptors; instead, it modulates calcium channels in the central nervous system, influencing neurotransmitter release and neuronal excitability.

The molecular structure of gabapentin consists of a cyclohexane ring attached to a carboxymethyl group and a primary amino group. The cyclohexane moiety provides rigidity, while the amino and carboxyl groups confer hydrophilicity and enable the molecule to participate in ionic interactions with target proteins. The compound is water-soluble and forms stable crystalline solids, which facilitates its formulation as oral tablets, capsules, or solutions for pharmaceutical use.

Gabapentin was initially investigated for its anticonvulsant properties. It is widely prescribed for the management of partial seizures in epilepsy, often as adjunctive therapy in combination with other antiepileptic drugs. Its mechanism involves binding to the α₂δ subunit of voltage-gated calcium channels, which reduces excitatory neurotransmitter release in hyperactive neurons and contributes to its anticonvulsant effect.

Beyond epilepsy, gabapentin has applications in the treatment of neuropathic pain. Clinical studies have demonstrated its efficacy in alleviating pain associated with conditions such as postherpetic neuralgia, diabetic neuropathy, and spinal cord injuries. By modulating calcium channel activity in sensory neurons, gabapentin reduces neuronal hyperexcitability, leading to diminished pain perception. It is also explored in some cases for off-label use in anxiety disorders and restless legs syndrome, although its primary approved indications remain epilepsy and neuropathic pain.

Gabapentin is manufactured using synthetic organic chemistry methods, typically involving cyclization of appropriate amino acid precursors followed by functional group modifications to produce the final carboxylated and aminated cyclohexane structure. The synthesis aims to maintain stereochemical integrity, although gabapentin is used as a racemic mixture in most pharmaceutical formulations. The compound’s stability, solubility, and bioavailability make it suitable for oral administration and systemic distribution.

Overall, gabapentin is a widely used pharmaceutical compound with significant therapeutic value in neurology. Its structural features, including the cyclohexane ring and amino acid-like functional groups, allow for modulation of neuronal calcium channels, leading to anticonvulsant and analgesic effects. Its applications in epilepsy and neuropathic pain management have established gabapentin as an important drug in clinical practice.

References

2025. [Therapy strategies for repetitive vocalizations in dementia : A systematic review]. Neuropsychiatrie : Klinik, Diagnostik, Therapie und Rehabilitation : Organ der Gesellschaft Osterreichischer Nervenarzte und Psychiater.
DOI: 10.1007/s40211-024-00511-5

2025. [Evidence-based interventions to treat chronic low back pain: treatment selection for a personalized medicine approach : German version]. Schmerz (Berlin, Germany).
DOI: 10.1007/s00482-024-00798-x

2025. [Opioid prescriptions for insured individuals without cancer in Germany: data from the BARMER]. Schmerz (Berlin, Germany).
DOI: 10.1007/s00482-024-00852-8