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
• Quality Level: 200
• 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