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G154

Sigma-Aldrich

Gabapentin

≥98% (HPLC), solid, anticonvulsant

Synonyme(s) :

1-(Aminomethyl)-cyclohexaneacetic acid, Neurontin

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About This Item

Formule empirique (notation de Hill):
C9H17NO2
Numéro CAS:
60142-96-3
Poids moléculaire :
171.24
Numéro Beilstein :
2359739
Numéro CE :
262-076-3
Numéro MDL:
MFCD00865286
Code UNSPSC :
12352200
ID de substance PubChem :
24278159
Nomenclature NACRES :
NA.77

product name

Gabapentin, solid

Forme

solid

Couleur

off-white

Solubilité

H2O: 10 mg/mL

Chaîne SMILES 

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)

Clé InChI

UGJMXCAKCUNAIE-UHFFFAOYSA-N

Informations sur le gène

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)

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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

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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USP

USP

1559618

Pregabalin

Gabapentin-D10 solution 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant®

Supelco

G-017

Gabapentin-D10 solution

Gabapentin-D10 solution 100 μg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant®

Supelco

G-901

Gabapentin-D10 solution

KINK-1 hydrochloride ≥98% (HPLC)

Sigma-Aldrich

SML2098

KINK-1 hydrochloride

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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