Gabapentin free base
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MedKoo CAT#: 317961

CAS#: 60142-96-3 (free base)

Description: Gabapentin is a major inhibitory neurotransmitter that functions by binding to the GABA receptors located in the spinal cord. 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. It is structurally similar to GABA and is reported in various research studies to increase GABA concentrations within the brain.


Chemical Structure

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Gabapentin free base
CAS# 60142-96-3 (free base)

Theoretical Analysis

MedKoo Cat#: 317961
Name: Gabapentin free base
CAS#: 60142-96-3 (free base)
Chemical Formula: C9H17NO2
Exact Mass: 171.12593
Molecular Weight: 171.24
Elemental Analysis: C, 63.13; H, 10.01; N, 8.18; O, 18.69

Price and Availability

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1.0g USD 150.0 Same day
2.0g USD 250.0 Same day
5.0g USD 450.0 2 weeks
10.0g USD 650.0 2 weeks
20.0g USD 950.0 2 weeks
1.0kg USD 2650.0 2 weeks
2.0kg USD 4650.0 2 weeks
5.0kg USD 7650.0 2 weeks
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Related CAS #: 60142-95-2 (HCl)   60142-96-3 (free base)    

Synonym: Gabapentin; Gabapentin; Neurontin; Gabapentine; Aclonium; Convalis; gabapentin; Gabapentin Hexal; Gabapentin Stada;

IUPAC/Chemical Name: 2-[1-(aminomethyl)cyclohexyl]acetic acid

InChi Key: UGJMXCAKCUNAIE-UHFFFAOYSA-N

InChi Code: InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)

SMILES Code: NCC1(CCCCC1)CC(=O)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Certificate of Analysis:

Safety Data Sheet (SDS):

Biological target: Gabapentin is a GABA analogue, used to treat seizures and neuropathic pain.
In vitro activity: It’s found that 10 mM gabapentin reduces the growth of HCT116 cells, which have an active branched-chain amino acid transferase but express very low levels of BCAT1, and presumably rely on the mitochondrial BCAT2 enzyme. Gabapentin did not affect transamination of BCAA to branched-chain keto acids (BCKA) in HCT116 cells, nor the reverse formation of BCAA from BCKA, indicating that the branched-chain amino acid transaminase is not inhibited. Moreover, the growth-inhibitory effect of gabapentin could not be rescued by supplementation with BCKA, and this was not due to the lack of uptake of BCKA, indicating that other effects of gabapentin are important. An untargeted LC-MS analysis of gabapentin-treated cells revealed a marked depletion of branched-chain carnitines. These results demonstrate that gabapentin at high concentrations can inhibit cell proliferation without affecting BCAT1 and may affect mitochondrial BCKA catabolism. Reference: Biochemistry. 2018 Dec 11;57(49):6762-6766. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30427175/
In vivo activity: The antipruritic activity of gabapentin, an anticonvulsant, was studied in a mouse model of allergic itch. In mice sensitized by an extract of the salivary glands of the mosquito (ESGM), an intradermal injection of ESGM elicited scratching and increased peripheral nerve firing. Oral or intradermal administration of gabapentin at the ESGM injection site inhibited ESGM-induced scratching and peripheral nerve firing. However, gabapentin did not affect histamine-induced scratching. The distributions of immunoreactivity to the voltage-dependent calcium channel α2δ-1 subunit, a site of gabapentin action, and the histamine H1 receptor differed in the mouse dorsal root ganglia. The α2δ-1 subunit was mainly found in neurons that were 15-20 µm in diameter, whereas the H1 receptor was mainly in 20-30 µm neurons. In addition, α2δ-1 subunit immunoreactivity co-localized with that of transient receptor potential vanilloid 1 (TRPV1). These results suggest that gabapentin regulates allergic itch by acting on the calcium channel α2δ-1 subunit in peripheral TRPV1-positive neurons. Reference: Eur J Pharmacol. 2018 Aug 15;833:44-49. https://linkinghub.elsevier.com/retrieve/pii/S0014-2999(18)30308-X

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Water 34.0 198.55

Preparing Stock Solutions

The following data is based on the product molecular weight 171.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
In vitro protocol: 1. Grankvist N, Lagerborg KA, Jain M, Nilsson R. Gabapentin Can Suppress Cell Proliferation Independent of the Cytosolic Branched-Chain Amino Acid Transferase 1 (BCAT1). Biochemistry. 2018 Dec 11;57(49):6762-6766. doi: 10.1021/acs.biochem.8b01031. Epub 2018 Nov 26. PMID: 30427175; PMCID: PMC6528808.
In vivo protocol: 1. Akiyama T, Andoh T, Ohtsuka E, Nojima H, Ouchi H, Takahata H, Kuraishi Y. Peripheral gabapentin regulates mosquito allergy-induced itch in mice. Eur J Pharmacol. 2018 Aug 15;833:44-49. doi: 10.1016/j.ejphar.2018.05.037. Epub 2018 May 26. PMID: 29842875. 2. Ceretta APC, de Freitas CM, Schaffer LF, Reinheimer JB, Dotto MM, de Moraes Reis E, Scussel R, Machado-de-Ávila RA, Fachinetto R. Gabapentin reduces haloperidol-induced vacuous chewing movements in mice. Pharmacol Biochem Behav. 2018 Mar;166:21-26. doi: 10.1016/j.pbb.2018.01.003. Epub 2018 Jan 31. PMID: 29374574.

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1: Bastiaens L, Galus J, Mazur C. Abuse of Gabapentin is Associated with Opioid
Addiction. Psychiatr Q. 2016 Feb 18. [Epub ahead of print] PubMed PMID: 26887855.

2: Miranda HF, Noriega V, Prieto J, Zanetta P, Castillo R, Aranda N, Sierralta F.
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6: Bugan I, Karagoz Z, Altun S, Djamgoz MB. Gabapentin, an Analgesic Used Against
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7: Besheer J, Frisbee S, Randall PA, Jaramillo AA, Masciello M. Gabapentin
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Imputation Methodology on Pain Assessment over 24 Hours in a Randomized,
Placebo-Controlled Study of Gabapentin Enacarbil in Patients with Neuropathic
Pain Associated with Postherpetic Neuralgia. Pain Med. 2016 Jan 6. pii: pnv072.
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10: Abe K, Chiba Y, Katsuse O, Hirayasu Y. A Case of Parkinson Disease With Both
Visual Hallucination and Pain Improved by Gabapentin. Clin Neuropharmacol. 2016
Jan-Feb;39(1):55-6. doi: 10.1097/WNF.0000000000000122. PubMed PMID: 26757314.

11: Yang W, McNutt TR, Dudley SA, Kumar R, Starmer HM, Gourin CG, Moore JA, Evans
K, Allen M, Agrawal N, Richmon JD, Chung CH, Quon H. Predictive Factors for
Prophylactic Percutaneous Endoscopic Gastrostomy (PEG) Tube Placement and Use in
Head and Neck Patients Following Intensity-Modulated Radiation Therapy (IMRT)
Treatment: Concordance, Discrepancies, and the Role of Gabapentin. Dysphagia.
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12: Reda HM, Zaitone SA, Moustafa YM. Effect of levetiracetam versus gabapentin
on peripheral neuropathy and sciatic degeneration in streptozotocin-diabetic
mice: Influence on spinal microglia and astrocytes. Eur J Pharmacol. 2016 Jan
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26712375.

13: Papathanasiou T, Juul RV, Heegaard AM, Kreilgaard M, Lund TM.
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26610393.

14: Liow NY, Gimeno H, Lumsden DE, Marianczak J, Kaminska M, Tomlin S, Lin JP.
Gabapentin can significantly improve dystonia severity and quality of life in
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15: Bellows BK, Nelson RE, Oderda GM, LaFleur J. Long-term cost-effectiveness of
initiating treatment for painful diabetic neuropathy with pregabalin, duloxetine,
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16: Mimenza Alvarado A, Aguilar Navarro S. Clinical Trial Assessing the Efficacy
of Gabapentin Plus B Complex (B1/B12) versus Pregabalin for Treating Painful
Diabetic Neuropathy. J Diabetes Res. 2016;2016:4078695. doi:
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17: Lee EG, Lee HJ, Hyun DJ, Min K, Kim DH, Yoon MS. Efficacy of low dose
gabapentin in acute herpes zoster for preventing postherpetic neuralgia: a
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[Epub ahead of print] PubMed PMID: 26799145.

18: Larsen MS, Keizer R, Munro G, Mørk A, Holm R, Savic R, Kreilgaard M.
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19: Ostadhadi S, Kordjazy N, Haj-Mirzaian A, Ameli S, Akhlaghipour G, Dehpour A.
Involvement of NO/cGMP pathway in the antidepressant-like effect of gabapentin in
mouse forced swimming test. Naunyn Schmiedebergs Arch Pharmacol. 2016 Jan 12.
[Epub ahead of print] PubMed PMID: 26753696.

20: Marashi SM, Saeedinia SM, Sadeghi M, Movafegh A, Marashi S. Attenuation of
Hemodynamic Responses to Intubation by Gabapentin in Coronary Artery Bypass
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PubMed PMID: 26749228.