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Documenti fondamentali

G154

Sigma-Aldrich

Gabapentin

≥98% (HPLC), solid, anticonvulsant

Sinonimo/i:

1-(Aminomethyl)-cyclohexaneacetic acid, Neurontin

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About This Item

Formula empirica (notazione di Hill):
C9H17NO2
Numero CAS:
Peso molecolare:
171.24
Beilstein:
2359739
Numero CE:
Numero MDL:
Codice UNSPSC:
12352200
ID PubChem:
NACRES:
NA.77

Nome del prodotto

Gabapentin, solid

Stato

solid

Livello qualitativo

Colore

off-white

Solubilità

H2O: 10 mg/mL

Stringa SMILE

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)
UGJMXCAKCUNAIE-UHFFFAOYSA-N

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Applicazioni

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

Azioni biochim/fisiol

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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


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Certificati d'analisi (COA)

Lot/Batch Number

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USP

USP

1559618

Pregabalin

Gabapentin impurity B European Pharmacopoeia (EP) Reference Standard

Y0001348

Gabapentin impurity B

The impact of advanced opioid drugs and analgesic adjuvants on murine macrophage oxygen burst
Kozlowski M, et al.
Folia Medica Cracoviensia (2017)
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
M J Field et al.
British journal of pharmacology, 121(8), 1513-1522 (1997-08-01)
1. Gabapentin (neurontin) is a novel antiepileptic agent that binds to the alpha 2 delta subunit of voltage-dependent calcium channels. The only other compound known to possess affinity for this recognition site is the (S)-(+)-enantiomer of 3-isobutylgaba. However, the corresponding
Samuel J Dobson et al.
Antiviral research, 179, 104819-104819 (2020-05-12)
During virus entry, members of the Polyomaviridae transit the endolysosomal network en route to the endoplasmic reticulum (ER), from which degraded capsids escape into the cytoplasm and enter the nucleus. Emerging evidence suggests that viruses require both endosomal acidification and
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

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