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G154

Gabapentin

≥98% (HPLC), solid, anticonvulsant

Sinónimos:

1-(Aminomethyl)-cyclohexaneacetic acid, Neurontin

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Fórmula empírica (notación de Hill):
C9H17NO2
Número CAS:
60142-96-3
Peso molecular:
171.24
NACRES:
NA.77
PubChem Substance ID:
24278159
UNSPSC Code:
12352200
EC Number:
262-076-3
MDL number:
MFCD00865286
Beilstein/REAXYS Number:
2359739
Form:
solid
Quality level:
200
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Nombre del producto

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)

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.

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Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificados de análisis (COA)

Lot/Batch Number
0000512520
0000512520
0000512514
0000512514
0000450312

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The impact of advanced opioid drugs and analgesic adjuvants on murine macrophage oxygen burst
Kozlowski M, et al.
Folia Medica Cracoviensia (2017)
Michael F Jarvis et al.
Proceedings of the National Academy of Sciences of the United States of America, 104(20), 8520-8525 (2007-05-08)
Activation of tetrodotoxin-resistant sodium channels contributes to action potential electrogenesis in neurons. Antisense oligonucleotide studies directed against Na(v)1.8 have shown that this channel contributes to experimental inflammatory and neuropathic pain. We report here the discovery of A-803467, a sodium channel
Thomas R Belliotti et al.
Journal of medicinal chemistry, 48(7), 2294-2307 (2005-04-02)
Pregabalin exhibits robust activity in preclinical assays indicative of potential antiepileptic, anxiolytic, and antihyperalgesic clinical efficacy. It binds with high affinity to the alpha(2)-delta subunit of voltage-gated calcium channels and is a substrate of the system L neutral amino acid
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