GABA vs Gabapentin: what is the difference?
Gabapentin is GABA with a cyclohexane ring built onto its middle carbon, which lets it reach the brain, though it never acts on the GABA receptor itself.
Sources and notes
- The sentence under the titlefrom sourceMoleculeFinder comparison notesThe pair's answer line.
- The two drawingscomputedMoleculeFinder rule (RDKit MCS)Each molecule's own drawing, as its page shows it. The common core, 4 of 12 atoms, is too small to align on.
Side by side
| GABA | Gabapentin | |
|---|---|---|
| Molecular weightCalculated PubChem | 103.12 g/molC4H9NO2 | 171.24 g/molC9H17NO2 |
| Hydrogen-bond donorsCalculated PubChem | 2 | 2 |
| FamilyEditorial MoleculeFinder curated | Neurotransmitters | Anticonvulsants |
| Everyday groupEditorial MoleculeFinder curated | Body | Prescription medicine |
| Chemical groupsCalculated Found by rule (RDKit) | Carboxylic Acids, Amines | Carboxylic Acids, Amines |
| Hazard labelReported ECHA, HSDB via PubChem | Not recorded | Danger |
| The supplier-filed hazard label's signal word, not a statement about ordinary use. | ||
Sources and notes
- Molecular weightcomputedPubChemComputed from the structure; the formula is under each weight.
- Hydrogen-bond donorscomputedPubChemThe hydrogens on nitrogen or oxygen that each molecule can lend to a hydrogen bond, counted from its structure.
- Familyfrom sourceMoleculeFinder curated
- Everyday groupfrom sourceMoleculeFinder curated
- Chemical groupscomputedFound by rule (RDKit)Each group is found in the structure by a chemical pattern.
- Hazard labelfrom sourceECHA, HSDB via PubChem
- ECHAfrom sourceAttributionSource: European Chemicals Agency, echa.europa.eu.
- Identifiersfrom sourcePubChemPubChem CID 119 (GABA) and 3446 (Gabapentin).
In more detail
GABA is the brain's main inhibitory neurotransmitter, a small amino acid of C4H9NO2 at 103.12 that the body makes itself. Gabapentin, C9H17NO2 at 171.24, was designed as GABA with a cyclohexane ring attached to its middle carbon, the idea being a version that could cross from the blood into the brain, which GABA swallowed as a supplement does poorly. The ring worked for that, but the molecule turned out not to act on GABA receptors at all: it binds the alpha-2-delta subunit of voltage-gated calcium channels instead, reducing the release of excitatory neurotransmitters, which is how it treats seizures and nerve pain. GABA is sold as a supplement, gabapentin as a prescription medicine, Neurontin, approved by the FDA in 1993. The name is the only thing the two share in practice: one is the messenger, the other a medicine named after it.
Sources and notes
- The paragraphfrom sourceMoleculeFinder comparison notes
Questions
- What is the difference between GABA and Gabapentin?
- Gabapentin is GABA with a cyclohexane ring built onto its middle carbon, which lets it reach the brain, though it never acts on the GABA receptor itself.
- Is GABA bigger than Gabapentin?
- Gabapentin is the heavier molecule, 171.24 g/mol against 103.12 g/mol for GABA. GABA is C4H9NO2 and Gabapentin is C9H17NO2.
Sources and notes
- The answersfrom sourceMoleculeFinderThe first is the pair's answer line; the others are read off the table above.