G154

Gabapentin

≥98% (HPLC), solid, anticonvulsant

• Synonym(s): 1-(Aminomethyl)-cyclohexaneacetic acid, Neurontin
• Empirical Formula (Hill Notation): C₉H₁₇NO₂
• CAS Number: 60142-96-3
• Molecular Weight: 171.24
• Beilstein: 2359739
• EC Number: 262-076-3
• MDL number: MFCD00865286
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278159
• NACRES: NA.77

Properties

• product name: Gabapentin, solid
• form: solid
• color: off-white
• solubility: H₂O: 10 mg/mL
• SMILES string: NCC1(CC(O)=O)CCCCC1
• InChI: 1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)
• InChI key: UGJMXCAKCUNAIE-UHFFFAOYSA-N
• Gene Information: human ... ADORA1(134) , CACNA1A(773) , CACNA1B(774) , CACNA1C(775) , CACNA1D(776) , CACNA1E(777) , CACNA1F(778) , CACNA1G(8913) , CACNA1H(8912) , CACNA1I(8911) , CACNA1S(779) , CACNA2D1(781) , CACNA2D2(9254) , CACNA2D3(55799) , CACNA2D4(93589) , CACNB1(782) , CACNB2(783) , CACNB3(784) , CACNB4(785) , CACNG1(786) , CACNG2(10369) , CACNG3(10368) , CACNG4(27092) , CACNG5(27091) , CACNG6(59285) , CACNG7(59284) , CACNG8(59283) ; rat ... Cacna1a(25398)

Description

Application

Gabapentin has been used:

• as the α2δ-ligand to examine whether the allyl isothiocyanate (AITC) sensitized thermal aversion assay might be useful as a screening method for the identification of presumptive analgesics
• dissolved in uptake buffer which is used to measure the to measure ASP (trans-4-[4-(Dimethylamino)styryl]-1-methylpyridinium iodide) substrate by organic cation transporter type 2 (OCTN2) using liquid chromatography - mass spectrometry
• used as an analgesic adjuvant for intraperitoneal injections

Biochem/physiol Actions

Anticonvulsant with unknown mechanism of action; crosses the blood brain barrier; increases GABA concentrations in the brain and reduces excitatory amino acid neurotransmission, perhaps through its effects on voltage-gated calcium channels; exhibits antinociceptive, anxiolytic, neuroprotective and anti-epileptic effects.

Gabapentin serves as a ligand for the α2δ subunit of L-type calcium channels.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves