Gamma-aminobutyric acid | CAS#56-12-2 | endogenous neurotransmitter | GABA receptor agonist

Gamma-aminobutyric acid
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 540147

CAS#: 56-12-2

Description: Gamma-aminobutyric acid is an endogenous neurotransmitter and GABA receptor agonist involved in neuronal excitability, muscle tone, stem cell growth, brain development, and mood. It decrease incidence of anxiety and seizures.

Chemical Structure

Gamma-aminobutyric acid

CAS# 56-12-2

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 540147
Name: Gamma-aminobutyric acid
CAS#: 56-12-2
Chemical Formula: C4H9NO2
Exact Mass: 103.06
Molecular Weight: 103.121
Elemental Analysis: C, 46.59; H, 8.80; N, 13.58; O, 31.03

Price and Availability

Size	Price	Availability
25g	USD 250	2 Weeks
100g	USD 450
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Aminalon; DF 468; DF468; DF-468; Mielogen; Mielomade; Gamma-aminobutyric acid

IUPAC/Chemical Name: 4-aminobutanoic acid

InChi Key: BTCSSZJGUNDROE-UHFFFAOYSA-N

InChi Code: InChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)

SMILES Code: O=C(O)CCCN

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

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	γ-Aminobutyric acid (4-Aminobutyric acid) is a major inhibitory neurotransmitter in the adult mammalian brain, binding to the ionotropic GABA receptors (GABAA receptors) and metabotropic receptors (GABAB) receptors.
In vitro activity:	Consistent with the findings on tyrosinase activity, intracellular melanin staining revealed that α-MSH-treated cells contained higher melanin intensities than untreated cells, whereas GABA (20 mM) potently inhibited the high melanin intensity (Figure 2D). This study also confirmed that GABA inhibited α-MSH-induced MITF and tyrosinase expression in a concentration-dependent manner, at both the transcriptional (Figure 2E) and translational (Figure 2F) levels. These results indicate that GABA inhibits melanogenesis in B16F10 melanoma cells. Reference: Int J Mol Sci. 2021 Jul 31;22(15):8257. https://pubmed.ncbi.nlm.nih.gov/34361022/
In vivo activity:	PO administration of GABA (20 and 200 mg/kg) immediately before refeeding reduced food intake during 0–0.5 h after injection but did not alter locomotor activity in mice (Figure 2D). In the taste aversion test, PO GABA (200 mg/kg) or PO saline did not influence saccharine preference, unlike lithium chloride (Figure 2E). These results suggested that PO GABA administration induced satiation without aversion or locomotor impairment. Reference: Nutrients. 2022 Jun 16;14(12):2492. https://pubmed.ncbi.nlm.nih.gov/35745222/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	Water	30.2	292.42

Preparing Stock Solutions

The following data is based on the product molecular weight 103.12 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:	1. Molagoda IMN, Kavinda MHD, Ryu HW, Choi YH, Jeong JW, Kang S, Kim GY. Gamma-Aminobutyric Acid (GABA) Inhibits α-Melanocyte-Stimulating Hormone-Induced Melanogenesis through GABAA and GABAB Receptors. Int J Mol Sci. 2021 Jul 31;22(15):8257. doi: 10.3390/ijms22158257. PMID: 34361022; PMCID: PMC8347673. 2. Ghani MW, Yi Z, Jiang W, Bin L, Cun LG, Birmany MW, Mei X. γ-Aminobutyric Acid (GABA) Induced in Vitro Differentiation of Rat Pancreatic Ductal Stem Cells into Insulin-Secreting Islet-Like Cell Clusters. Folia Biol (Praha). 2019;65(5-6):246-255. PMID: 32362308. 3. Nakamura U, Nohmi T, Sagane R, Hai J, Ohbayashi K, Miyazaki M, Yamatsu A, Kim M, Iwasaki Y. Dietary Gamma-Aminobutyric Acid (GABA) Induces Satiation by Enhancing the Postprandial Activation of Vagal Afferent Nerves. Nutrients. 2022 Jun 16;14(12):2492. doi: 10.3390/nu14122492. PMID: 35745222; PMCID: PMC9227210. 4. Lee H, Ji SY, Hwangbo H, Kim MY, Kim DH, Park BS, Park JH, Lee BJ, Kim GY, Jeon YJ, Choi YH. Protective Effect of Gamma Aminobutyric Acid against Aggravation of Renal Injury Caused by High Salt Intake in Cisplatin-Induced Nephrotoxicity. Int J Mol Sci. 2022 Jan 3;23(1):502. doi: 10.3390/ijms23010502. PMID: 35008928; PMCID: PMC8745502.
In vitro protocol:	1. Molagoda IMN, Kavinda MHD, Ryu HW, Choi YH, Jeong JW, Kang S, Kim GY. Gamma-Aminobutyric Acid (GABA) Inhibits α-Melanocyte-Stimulating Hormone-Induced Melanogenesis through GABAA and GABAB Receptors. Int J Mol Sci. 2021 Jul 31;22(15):8257. doi: 10.3390/ijms22158257. PMID: 34361022; PMCID: PMC8347673. 2. Ghani MW, Yi Z, Jiang W, Bin L, Cun LG, Birmany MW, Mei X. γ-Aminobutyric Acid (GABA) Induced in Vitro Differentiation of Rat Pancreatic Ductal Stem Cells into Insulin-Secreting Islet-Like Cell Clusters. Folia Biol (Praha). 2019;65(5-6):246-255. PMID: 32362308.
In vivo protocol:	1. Nakamura U, Nohmi T, Sagane R, Hai J, Ohbayashi K, Miyazaki M, Yamatsu A, Kim M, Iwasaki Y. Dietary Gamma-Aminobutyric Acid (GABA) Induces Satiation by Enhancing the Postprandial Activation of Vagal Afferent Nerves. Nutrients. 2022 Jun 16;14(12):2492. doi: 10.3390/nu14122492. PMID: 35745222; PMCID: PMC9227210. 2. Lee H, Ji SY, Hwangbo H, Kim MY, Kim DH, Park BS, Park JH, Lee BJ, Kim GY, Jeon YJ, Choi YH. Protective Effect of Gamma Aminobutyric Acid against Aggravation of Renal Injury Caused by High Salt Intake in Cisplatin-Induced Nephrotoxicity. Int J Mol Sci. 2022 Jan 3;23(1):502. doi: 10.3390/ijms23010502. PMID: 35008928; PMCID: PMC8745502.

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1: Kırımlıoğlu GY, Yazan Y, Erol K, Çengelli Ünel Ç. Gamma-aminobutyric acid loaded halloysite nanotubes and in vitro-in vivo evaluation for brain delivery. Int J Pharm. 2015 Nov 30;495(2):816-26. doi: 10.1016/j.ijpharm.2015.08.087. Epub 2015 Sep 18. PubMed PMID: 26387616.

2: Wang LY, Tong R, Kohane DS. Synthesis and proton NMR spectroscopy of intra-vesicular gamma-aminobutyric acid (GABA). Conf Proc IEEE Eng Med Biol Soc. 2013;2013:1093-5. doi: 10.1109/EMBC.2013.6609695. PubMed PMID: 24109882; PubMed Central PMCID: PMC4717476.

3: Takayama H, Ogawa N, Yamamoto M, Asanuma M, Hirata H, Ota Z. Age-related changes in cerebrospinal fluid gamma-aminobutyric acid concentration. Eur J Clin Chem Clin Biochem. 1992 May;30(5):271-4. PubMed PMID: 1627723.

4: Feuerstein TJ. Commentary: Gabapentin-lactam and gamma-aminobutyric acid/lactam analogs: the enigma of their mechanism of action. Int J Oral Maxillofac Implants. 2013 Sep-Oct;28(5):e239-42. doi: 10.11607/jomi.te03. PubMed PMID: 24066340.

5: Bassett ML, Mullen KD, Scholz B, Fenstermacher JD, Jones EA. Increased brain uptake of gamma-aminobutyric acid in a rabbit model of hepatic encephalopathy. Gastroenterology. 1990 Mar;98(3):747-57. PubMed PMID: 2298374.

6: Harty RF, Boharski MG, Bochna GS, Carr TA, Eagan PE, Rings M, Lassiter DC, Pour MP, Schafer DF, Markin RS. gamma-Aminobutyric acid localization and function as modulator of cholinergic neurotransmission in rat antral mucosal/submucosal fragments. Gastroenterology. 1991 Nov;101(5):1178-86. PubMed PMID: 1936787.

7: Nomura M, Kimoto H, Someya Y, Furukawa S, Suzuki I. Production of gamma-aminobutyric acid by cheese starters during cheese ripening. J Dairy Sci. 1998 Jun;81(6):1486-91. PubMed PMID: 9684157.

8: Kapil V, Green JL, Le Lait MC, Wood DM, Dargan PI. Misuse of the γ-aminobutyric acid analogues baclofen, gabapentin and pregabalin in the UK. Br J Clin Pharmacol. 2014 Jul;78(1):190-1. PubMed PMID: 25083536; PubMed Central PMCID: PMC4168395.

9: Tanganelli S, Ferraro L, Bianchi C, Beani L. Changes in gamma-aminobutyric acid release induced by topical administration of drugs affecting its metabolism and receptors: studies in freely moving guinea pigs with epidural cups. Neurochem Int. 1992 Jul;21(1):15-20. PubMed PMID: 1338898.

10: Yurtdaş Kırımlıoğlu G, Menceloğlu Y, Erol K, Yazan Y. In vitro/in vivo evaluation of gamma-aminobutyric acid-loadedN,N-dimethylacrylamide-based pegylated polymeric nanoparticles for brain delivery to treat epilepsy. J Microencapsul. 2016 Nov;33(7):625-635. Epub 2016 Sep 22. PubMed PMID: 27606701.

11: Zhong M, Meng XB, Li ZJ. Synthesis of gamma-aminobutyric acid analogs based on carbohydrate scaffolds. Carbohydr Res. 2010 Jun 16;345(9):1099-106. doi: 10.1016/j.carres.2010.03.033. Epub 2010 Mar 28. PubMed PMID: 20400064.

12: Banerji S, Habibuddin M, Pal SP. Antiulcer and gastric secretory activity of N-phthaloyl gamma-aminobutyric acid. Eur J Pharmacol. 1992 Aug 25;219(2):211-5. PubMed PMID: 1425950.

13: Matsuzaki M, Hayama T, Kasai H, Ellis-Davies GC. Two-photon uncaging of gamma-aminobutyric acid in intact brain tissue. Nat Chem Biol. 2010 Apr;6(4):255-7. doi: 10.1038/nchembio.321. Epub 2010 Feb 21. PubMed PMID: 20173751; PubMed Central PMCID: PMC4104925.

14: Moroni F, Riggio O, Carlà V, Festuccia V, Ghinelli F, Marino IR, Merli M, Natali L, Pedretti G, Fiaccadori F, et al. Hepatic encephalopathy: lack of changes of gamma-aminobutyric acid content in plasma and cerebrospinal fluid. Hepatology. 1987 Sep-Oct;7(5):816-20. PubMed PMID: 3653849.

15: Emmett MR, Grover HK, Kerr MA. Tandem ring-opening decarboxylation of cyclopropane hemimalonates with sodium azide: a short route to γ-aminobutyric acid esters. J Org Chem. 2012 Aug 3;77(15):6634-7. doi: 10.1021/jo3010606. Epub 2012 Jul 16. PubMed PMID: 22775774.

16: Ishikawa A, Oka H, Hiemori M, Yamashita H, Kimoto M, Kawasaki H, Tsuji H. Development of a method for the determination of gamma-aminobutyric acid in foodstuffs. J Nutr Sci Vitaminol (Tokyo). 2009 Jun;55(3):292-5. PubMed PMID: 19602840.

17: Lin-Michell E, Chweh AY, Swinyard EA. Effect of ethosuximide alone and in combination with gamma-aminobutyric acid receptor agonists on brain gamma-aminobutyric acid concentration, anticonvulsant activity and neurotoxicity in mice. J Pharmacol Exp Ther. 1986 May;237(2):486-9. PubMed PMID: 3009789.

18: Valdizán EM, García AP, Armijo JA. Effects of increasing doses of vigabatrin on platelet gamma-aminobutyric acid-transaminase and brain gamma-aminobutyric acid in rats. Eur J Pharmacol. 1999 Mar 19;369(2):169-73. PubMed PMID: 10206175.

19: Brennan MJ, Cantrill RC, Oldfield M, Krogsgaard-Larsen P. Inhibition of gamma-aminobutyric acid release by gamma-aminobutyric acid agonist drugs. Pharmacology of the gamma-aminobutyric acid autoreceptor. Mol Pharmacol. 1981 Jan;19(1):27-30. PubMed PMID: 6259511.

20: Watt CB, Li T, Lam DM, Wu SM. Interactions between enkephalin and gamma-aminobutyric acid in the larval tiger salamander retina. Brain Res. 1987 Apr 7;408(1-2):258-62. PubMed PMID: 3594214.

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Gamma-aminobutyric acid featured