Gabapentin HCl
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MedKoo CAT#: 571570

CAS#: 60142-95-2 (HCl)

Description: Gabapentin is an oral medication for add-on therapy in the treatment of partial seizures in adult epilepsy; inhibits dopamine release from rabbit caudate nucleus.


Chemical Structure

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Gabapentin HCl
CAS# 60142-95-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 571570
Name: Gabapentin HCl
CAS#: 60142-95-2 (HCl)
Chemical Formula: C9H18ClNO2
Exact Mass: 171.1259
Molecular Weight: 207.698
Elemental Analysis: C, 52.05; H, 8.74; Cl, 17.07; N, 6.74; O, 15.41

Price and Availability

Size Price Availability Quantity
100.0mg USD 350.0 2 Weeks
500.0mg USD 950.0 2 Weeks
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Related CAS #: 60142-95-2 (HCl)   60142-96-3 (free base)    

Synonym: Gabapentin HCl; Gabapentin hydrochloride

IUPAC/Chemical Name: 1-(Aminomethyl)cyclohexaneacetic acid HCl

InChi Key: XBUDZAQEMFGLEU-UHFFFAOYSA-N

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

SMILES Code: O=C(O)CC1(CN)CCCCC1.[H]Cl

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

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:

Biological target: Gabapentin (Neurontin) is a pharmaceutical drug, specifically a GABA analog.
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 50.0 240.73

Preparing Stock Solutions

The following data is based on the product molecular weight 207.698 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
Formulation 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. 2. 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. 3. 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.
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: Qiu R, Perrino AC Jr, Zurich H, Sukumar N, Dai F, Popescu W. Effect of preoperative gabapentin and acetaminophen on opioid consumption in video-assisted thoracoscopic surgery: a retrospective study. Rom J Anaesth Intensive Care. 2018 Apr;25(1):43-48. doi: 10.21454/rjaic.7518.251.gab. PubMed PMID: 29756062; PubMed Central PMCID: PMC5931182.

2: Sicras-Mainar A, Rejas-Gutiérrez J, Perez-Paramo M, Navarro-Artieda R. Cost of treating peripheral neuropathic pain with pregabalin or gabapentin at therapeutic doses in routine practice. J Comp Eff Res. 2018 May 14. doi: 10.2217/cer-2018-0008. [Epub ahead of print] PubMed PMID: 29754518.

3: Crisologo PA, Monson EK, Atway SA. Gabapentin as an Adjunct to Standard Postoperative Pain Management Protocol in Lower Extremity Surgery. J Foot Ankle Surg. 2018 May 7. pii: S1067-2516(18)30059-0. doi: 10.1053/j.jfas.2018.02.005. [Epub ahead of print] Review. PubMed PMID: 29748103.

4: Brown CS, Bachmann GA, Wan J, Foster DC; Gabapentin (GABA) Study Group. Gabapentin for the Treatment of Vulvodynia: A Randomized Controlled Trial. Obstet Gynecol. 2018 May 7. doi: 10.1097/AOG.0000000000002617. [Epub ahead of print] PubMed PMID: 29742655.

5: Leung JG, Rakocevic DB, Allen ND, Handler EM, Perossa BA, Borreggine KL, Stark AL, Betcher HK, Hosker DK, Minton BA, Braus BR, Dierkhising RA, Philbrick KL. Use of a Gabapentin Protocol for the Management of Alcohol Withdrawal: A Preliminary Experience Expanding From the Consultation-Liaison Psychiatry Service. Psychosomatics. 2018 Mar 21. pii: S0033-3182(18)30138-5. doi: 10.1016/j.psym.2018.03.002. [Epub ahead of print] PubMed PMID: 29735241.

6: Ölçücü MT, Ölçücü N, Ölçücüoğlu E, Ölçücüoğlu EA, Özgök Y. Response to duloxetine and gabapentin combination of a patient who has chronical orchialgia with bilateral tubular ectasia of rete testis and multiple epididymal cysts. Turk J Urol. 2018 May;44(3):274-277. doi: 10.5152/tud.2017.17999. Epub 2017 Mar 7. PubMed PMID: 29733802; PubMed Central PMCID: PMC5937648.

7: Chakrabarty S, Ghosh B, Giri TK, Khanam J. Reverse iontophoretic extraction of gabapentin: a mechanistic study. Curr Drug Deliv. 2018 May 3. doi: 10.2174/1567201815666180503122309. [Epub ahead of print] PubMed PMID: 29732968.

8: Cakici ÖU, Hamidi N, Ürer E, Okulu E, Kayigil O. Efficacy of sertraline and gabapentin in the treatment of urethral pain syndrome: retrospective results of a single institutional cohort. Cent European J Urol. 2018;71(1):78-83. doi: 10.5173/ceju.2018.1574. Epub 2017 Jan 16. PubMed PMID: 29732211; PubMed Central PMCID: PMC5926640.

9: Kendall MC, Castro-Alves LJ. Gabapentin to Prevent Acute Phantom-Limb Pain in Pediatric Patients Undergoing Amputation. J Pain Symptom Manage. 2018 May 2. pii: S0885-3924(18)30227-6. doi: 10.1016/j.jpainsymman.2018.04.010. [Epub ahead of print] PubMed PMID: 29729349.

10: Baxter KJ, Hafling J, Sterner J, Patel AU, Giannopoulos H, Heiss KF, Raval MV. Effectiveness of gabapentin as a postoperative analgesic in children undergoing appendectomy. Pediatr Surg Int. 2018 May 4. doi: 10.1007/s00383-018-4274-9. [Epub ahead of print] PubMed PMID: 29728759.

11: Peckham AM, Fairman KA, Sclar DA. Authors' Reply to: Tomoyuki Kawada's Comment on: "All-Cause and Drug-Related Medical Events Associated with Overuse of Gabapentin and/or Opioid Medications: A Retrospective Cohort Analysis of a Commercially Insured US Population''. Drug Saf. 2018 May 3. doi: 10.1007/s40264-018-0671-1. [Epub ahead of print] PubMed PMID: 29725941.

12: Kawada T. Comment on: "All-Cause and Drug-Related Medical Events Associated with Overuse of Gabapentin and/or Opioid Medications: A Retrospective Cohort Analysis of a Commercially Insured US Population". Drug Saf. 2018 May 3. doi: 10.1007/s40264-018-0670-2. [Epub ahead of print] PubMed PMID: 29725940.

13: Sanders J, Cameron C, Dawes P. Response to "Gabapentin to Prevent Acute Pain after Tonsillectomy". Otolaryngol Head Neck Surg. 2018 May;158(5):963-964. doi: 10.1177/0194599818761874. PubMed PMID: 29714109.

14: Kendall MC, Castro-Alves LJ. Gabapentin to Prevent Acute Pain after Tonsillectomy. Otolaryngol Head Neck Surg. 2018 May;158(5):963. doi: 10.1177/0194599818761873. PubMed PMID: 29714108.

15: King HH. Fibromyalgia Symptoms Reduced by Osteopathic Manipulative Medicine and Gabapentin. J Am Osteopath Assoc. 2018 May 1;118(5):349-350. doi: 10.7556/jaoa.2018.071. PubMed PMID: 29710361.

16: Townsend M, Liou T, Kallogjeri D, Schoer M, Scott-Wittenborn N, Lindburg M, Bottros M, Jackson RS, Nussenbaum B, Piccirillo JF. Effect of Perioperative Gabapentin Use on Postsurgical Pain in Patients Undergoing Head and Neck Mucosal Surgery: A Randomized Clinical Trial. JAMA Otolaryngol Head Neck Surg. 2018 Apr 19. doi: 10.1001/jamaoto.2018.0282. [Epub ahead of print] PubMed PMID: 29710075.

17: Bellessort B, Bachelot A, Grouthier V, De Lombares C, Narboux-Neme N, Garagnani P, Pirazzini C, Astigiano S, Mastracci L, Fontaine A, Alfama G, Duvernois-Berthet E, Levi G. Comparative analysis of molecular signatures suggests the use of gabapentin for the management of endometriosis-associated pain. J Pain Res. 2018 Apr 10;11:715-725. doi: 10.2147/JPR.S163611. eCollection 2018. PubMed PMID: 29692624; PubMed Central PMCID: PMC5903492.

18: Akanuma SI, Yamakoshi A, Sugouchi T, Kubo Y, Hartz AMS, Bauer B, Hosoya KI. Role of l-Type Amino Acid Transporter 1 at the Inner Blood-Retinal Barrier in the Blood-to-Retina Transport of Gabapentin. Mol Pharm. 2018 May 2. doi: 10.1021/acs.molpharmaceut.8b00179. [Epub ahead of print] PubMed PMID: 29688723.

19: Schmidt P, Rao S. Effects of gabapentin, pregabalin and gastroretentive gabapentin on simulated driving, daytime sedation and cognition. Pain Manag. 2018 Apr 19. doi: 10.2217/pmt-2018-0005. [Epub ahead of print] PubMed PMID: 29671676.

20: Staller K, Thurler AH, Reynolds JS, Dimisko LR, McGovern R, Skarbinski KF, Kuo B. Gabapentin Improves Symptoms of Functional Dyspepsia in a Retrospective, Open-label Cohort Study. J Clin Gastroenterol. 2018 Apr 17. doi: 10.1097/MCG.0000000000001034. [Epub ahead of print] PubMed PMID: 29668559.