Homocarnosine is a brain-specific dipeptide of gamma-aminobutyric acid (GABA) and histidine. Homocarnosine is an inhibitory neuromodulator synthesized in neurons from GABA and has anticonvulsant (antiepileptic/antiseizure) effects. Homocarnosine also has antioxidant and anti~inflammatory effects, protects against DNA damage, and inhibits the formation of advanced glycation end products.

Physicochemical Properties

Molecular Formula	C10H16N4O3
Molecular Weight	240.25904
Exact Mass	240.122
CAS #	3650-73-5
Related CAS #	Homocarnosine TFA
PubChem CID	10243361
Appearance	Typically exists as solid at room temperature
Boiling Point	646.9ºC at 760mmHg
Flash Point	345.1ºC
Index of Refraction	1.579
LogP	0.351
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	7
Heavy Atom Count	17
Complexity	272
Defined Atom Stereocenter Count	1
SMILES	NCCCC(NC(CC1=CNC=N1)C(O)=O)=O
InChi Key	CCLQKVKJOGVQLU-QMMMGPOBSA-N
InChi Code	InChI=1S/C10H16N4O3/c11-3-1-2-9(15)14-8(10(16)17)4-7-5-12-6-13-7/h5-6,8H,1-4,11H2,(H,12,13)(H,14,15)(H,16,17)/t8-/m0/s1
Chemical Name	(2S)-2-(4-aminobutanoylamino)-3-(1H-imidazol-5-yl)propanoic acid
Synonyms	NSC 92522; L-Homocarnosine; Homocarnosine
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	Synthesized in a subgroup of GABAergic neurons, homocarnosine is an inhibitory neuromodulator that is a dipeptide of gamma-aminobutyric acid (GABA) and histidine [1]. Similar in structure to carnosine, homocarnosine is a powerful substitute imidazole peptide for skeletal muscle. Gamma-aminobutyric acid (GABA) and histidine make up homocarnosine. It is structurally related to carnosine. The main distinction is that beta-alanine in carnosine has one fewer carbon atom than GABA. Homocarnosine is more resilient to serum carnosinase breakdown than carnosine. As a neuroprotective agent in a range of disorders, homocarnosine is only known to be present in the brain and cerebrospinal fluid. Similar to how carnosine works as an antioxidant, high carnosine also guards against oxidative damage to DNA [2].
References	[1]. Vigabatrin increases human brain homocarnosine and improves seizure control. Ann Neurol. 1998 Dec;44(6):948-52. [2]. Dietary GABA induces endogenous synthesis of a novel imidazole peptide homocarnosine in mouse skeletal muscles. Amino Acids. 2020 May;52(5):743-753.
Additional Infomation	L-homocarnosine is a homocarnosine that has S configuration. It has a role as a human metabolite. It is a homocarnosine, a N-acyl-L-alpha-amino acid, a L-histidine derivative and a dipeptide. It is a tautomer of a L-homocarnosine zwitterion. Homocarnosine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Homocarnosine has been reported in Caenorhabditis elegans with data available.

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	4.1622 mL	20.8108 mL	41.6216 mL
	5 mM	0.8324 mL	4.1622 mL	8.3243 mL
	10 mM	0.4162 mL	2.0811 mL	4.1622 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.