Gabapentin A compound structurally similar to GABA that binds to voltage-sensitive Ca2+ channels

Gabapentin (CAS 60142-96-3)

Gabapentin | CAS 60142-96-3 is rated 5.0 out of 5 by 1.
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Synonym: Neurontin; Gabarone;1-(Aminomethyl)cyclohexaneacetic Acid; GOE-3450
Application: A compound structurally similar to GABA that binds to voltage-sensitive Ca2+ channels
CAS Number: 60142-96-3
Purity: ≥98%
Molecular Weight: 171.20
Molecular Formula: C9H17NO2
* Refer to Certificate of Analysis for lot specific data (including water content).
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Gabapentin is structurally similar to GABA (sc-203053; γ-aminobutyric acid) and is reported in various research studies to increase GABA concentrations within the brain. Gabapentin is also noted to bind to a novel site on voltage-sensitive Ca2+ channels. Additionally, Gabapentin is reported to demonstrate inhibition of dopamine release from caudate nucleus, prevent neuronal cell death, and is antinociceptive.


References

1. Goa, K.L., et al. 1993. Drugs. 46: 409-427. PMID: 7693432
2. Upton, N. 1994. Trends Pharmacol. Sci. 15: 456-463. PMID: 7886818
3. Gee, N.S., et al. 1996. J. Biol. Chem. 271: 5768-5776. PMID: 8621444
4. Malcangio, M., et al. 1996. Trends Pharmacol. Sci. 17: 457-462. PMID: 9014500
5. Field, M.J., et al. 1997. Br. J. Pharmacol. 121: 1513-1522. PMID: 9283683
6. Taylor, C.P., et al. 1998. Epilepsy Res. 29: 233-249. PMID: 9551785
7. De Sarro, G., et al. 1998. Eur. J. Pharmacol. 349: 179-185. PMID: 9671096
8. Fink, K., et al. 2000. Br. J. Pharmacol. 130: 900-906. PMID: 10864898
9. Timmerman, W., et al. 2000. Eur. J. Pharmacol. 398: 53-57. PMID: 10856447
10. Taylor, M.T., et al. 2000. Neuropharmacology. 39: 1267-1273. PMID: 10760368 11. Shimoyama, M., et al. 2000. Pain. 85: 405-414. PMID: 10781913
12. van de Vusse, A.C., et al. 2004. BMC Neurol. 4: 13. PMID: 15453912
13. Stahl, S.M. 2004. J Clin Psychiatry. 65: 1033-1034. PMID: 15323585
14. Caraceni, A., et al. 2004. J. Clin. Oncol. 22: 2909-2917. PMID: 15254060
15. Hahn, K., et al. 2004. J. Neurol. 251: 1260-1266. PMID: 15503108
16. Schwarz, J.B., et al. 2005. J. Med. Chem. 48: 3026-3035. PMID: 15828841

Physical State :
Solid
Solubility :
Soluble in water (10 mg/mL), PBS pH7.2 (~10 mg/ml), and methanol. Sparingly soluble in ethanol, DMSO, and DMF.
Storage :
Store at room temperature
Melting Point :
161-163° C
Boiling Point :
~314.4° C at 760 mmHg (Predicted)
Density :
~1.1 g/cm3 (Predicted)
Refractive Index :
n20D 1.49 (Predicted)
IC50 :
Voltage-gated calcium channel alpha2/delta subunit 2: IC50 = 140 nM (human); Voltage-gated calcium channel alpha2/delta subunit 1: IC50 = 140 nM (human); Voltage-gated calcium channel alpha2/delta subunit 3: IC50 = 140 nM (human); Voltage-gated calcium channel alpha2/delta-4 subunit: IC50 = 140 nM
pK Values :
pKa: pK1: 3.68, pK2: 10.7
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
GU6496000
PubChem CID :
3446
Merck Index :
14: 4319
MDL Number :
MFCD00865286
EC Number :
262-076-3
Beilstein Registry :
2359739
SMILES :
C1CCC(CC1)(CC(=O)O)CN

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Gabapentin  Product Citations

See how others have used Gabapentin. Click on the entry to view the PubMed entry .

Citations 1 to 2 of 2 total

PMID: # 28420991  Anfuso, CD. et al. 2017. Front Pharmacol. 8: 173.

PMID: # 23751335  Writer, JH. et al. 2013. Sci. Total Environ. 461-462: 519-27.

Citations 1 to 2 of 2 total
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Rated 5 out of 5 by from Hahn et al Hahn et al. (PubMed ID 18528841) used gabapentin, which is structurally similar to GABA, to activate voltage gated calcium channels and was found to be an effective treatment for pain reduction in patients suffering from HIV-associated neuropathies. -SCBT Publication Review
Date published: 2015-03-10
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