Gabapentin free base | CAS#60142-96-3

MedKoo Cat#: 317961 | Name: Gabapentin free base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

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: 171.1259

Molecular Weight: 171.24

Elemental Analysis: C, 63.13; H, 10.01; N, 8.18; O, 18.69

Price and Availability

Size	Price	Availability
1g	USD 150.00	Ready to ship
2g	USD 250.00	Ready to ship
5g	USD 450.00	2 weeks
10g	USD 750.00	2 weeks

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Related CAS #

60142-95-2 (HCl) 60142-96-3 (free base) 478296-72-9 (enacarbil)

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

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#TCI80820

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

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

	Solvent	mg/mL	mM
Solubility
	Water	34.0	198.55

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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

Formulation protocol:

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.

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. Antinociceptive Interaction of Tramadol with Gabapentin in Experimental Mononeuropathic Pain. Basic Clin Pharmacol Toxicol. 2016 Feb 11. doi: 10.1111/bcpt.12567. [Epub ahead of print] PubMed PMID: 26867125. 3: Mersfelder TL, Nichols WH. Gabapentin: Abuse, Dependence, and Withdrawal. Ann Pharmacother. 2016 Mar;50(3):229-33. doi: 10.1177/1060028015620800. Epub 2015 Dec 31. Review. PubMed PMID: 26721643. 4: Edwards L, DeMeo S, Hornik CD, Cotten CM, Smith PB, Pizoli C, Hauer JM, Bidegain M. Gabapentin Use in the Neonatal Intensive Care Unit. J Pediatr. 2016 Feb;169:310-2. doi: 10.1016/j.jpeds.2015.10.013. Epub 2015 Nov 11. PubMed PMID: 26578075; PubMed Central PMCID: PMC4729593. 5: Hwang SH, Park IJ, Cho YJ, Jeong YM, Kang JM. The efficacy of gabapentin/pregabalin in improving pain after tonsillectomy: A meta-analysis. Laryngoscope. 2016 Feb;126(2):357-66. doi: 10.1002/lary.25636. Epub 2015 Sep 25. PubMed PMID: 26404562. 6: Bugan I, Karagoz Z, Altun S, Djamgoz MB. Gabapentin, an Analgesic Used Against Cancer-Associated Neuropathic Pain: Effects on Prostate Cancer Progression in an In Vivo Rat Model. Basic Clin Pharmacol Toxicol. 2016 Mar;118(3):200-7. doi: 10.1111/bcpt.12484. Epub 2015 Oct 29. PubMed PMID: 26335695. 7: Besheer J, Frisbee S, Randall PA, Jaramillo AA, Masciello M. Gabapentin potentiates sensitivity to the interoceptive effects of alcohol and increases alcohol self-administration in rats. Neuropharmacology. 2016 Feb;101:216-24. doi: 10.1016/j.neuropharm.2015.09.027. Epub 2015 Sep 28. PubMed PMID: 26415538. 8: Gabapentin for HIV-associated Neuropathic Pain: A Review of the Clinical Effectiveness [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2016 Jan 22. Available from http://www.ncbi.nlm.nih.gov/books/NBK343848/ PubMed PMID: 26889527. 9: Calkins AM, Gudin J, Gidal B, Jaros MJ, Kim R, Shang G. Impact of Data 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. [Epub ahead of print] PubMed PMID: 26814307. 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. 2016 Jan 11. [Epub ahead of print] PubMed PMID: 26753929. 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 15;771:162-72. doi: 10.1016/j.ejphar.2015.12.035. Epub 2015 Dec 19. PubMed PMID: 26712375. 13: Papathanasiou T, Juul RV, Heegaard AM, Kreilgaard M, Lund TM. Co-administration of morphine and gabapentin leads to dose dependent synergistic effects in a rat model of postoperative pain. Eur J Pharm Sci. 2016 Jan 20;82:97-105. doi: 10.1016/j.ejps.2015.11.015. Epub 2015 Nov 21. PubMed PMID: 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 children. Eur J Paediatr Neurol. 2016 Jan;20(1):100-7. doi: 10.1016/j.ejpn.2015.09.007. Epub 2015 Sep 28. PubMed PMID: 26455274. 15: Bellows BK, Nelson RE, Oderda GM, LaFleur J. Long-term cost-effectiveness of initiating treatment for painful diabetic neuropathy with pregabalin, duloxetine, gabapentin, or desipramine. Pain. 2016 Jan;157(1):203-13. doi: 10.1097/j.pain.0000000000000350. PubMed PMID: 26397932. 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: 10.1155/2016/4078695. Epub 2016 Jan 17. PubMed PMID: 26885528. 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 prospective controlled study. Dermatol Ther. 2016 Jan 22. doi: 10.1111/dth.12331. [Epub ahead of print] PubMed PMID: 26799145. 18: Larsen MS, Keizer R, Munro G, Mørk A, Holm R, Savic R, Kreilgaard M. Pharmacokinetic/Pharmacodynamic Relationship of Gabapentin in a CFA-induced Inflammatory Hyperalgesia Rat Model. Pharm Res. 2016 Jan 15. [Epub ahead of print] PubMed PMID: 26780452. 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 Surgery: a Randomized Clinical Trial. Acta Med Iran. 2015 Dec;53(12):733-7. 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