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G154

Sigma-Aldrich

Gabapentin

≥98% (HPLC), solid, anticonvulsant

Synonym(s):

1-(Aminomethyl)-cyclohexaneacetic acid, Neurontin

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About This Item

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

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)

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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

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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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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