1.0 2020-04-17 18:42:49 UTC 2020-12-07 19:11:05 UTC CDB004846 L-Arginine Arginine or l-arginine, abbreviated Arg or R, is an essential amino acid that is physiologically active in the L-form. In mammals, arginine is formally classified as a semi-essential or conditionally essential amino acid, depending on the developmental stage and health status of the individual. Pre-term infants are unable to effectively synthesize arginine, making it nutritionally essential for them. Adults, however, synthesize arginine from glutamate via citrulline. Arginine is a basic amino acid as its side chain contains a positively charged guanidinium group, which is highly polar, at the end of a hydrophobic¬†aliphatic¬†hydrocarbon chain. With a pKa of 12.48, the guanidinium group is positively charged in neutral, acidic, and even most basic environments. Because of the conjugation between the double bond and the nitrogen lone pairs, the positive charge is delocalized. This group is able to form multiple H-bonds. L-Arginine is an amino acid that has numerous functions in the body. It helps dispose of ammonia, is a precursor of nitric oxide, creatine, L-glutamate, and L-proline, and it can be converted into glucose and glycogen if needed. In large doses, L-arginine also stimulates the release of the hormones, growth hormone and prolactin. Arginine is a known inducer of mTOR (mammalian target of rapamycin) and is responsible for inducing protein synthesis through the mTOR pathway. mTOR inhibition by rapamycin partially reduces arginine-induced protein synthesis (PMID: 20841502). Catabolic disease states such as sepsis, injury, and cancer cause an increase in arginine utilization, which can exceed normal body production, leading to arginine depletion. Arginine also activates AMP kinase (AMPK) which then stimulates skeletal muscle fatty acid oxidation and muscle glucose uptake, thereby increasing insulin secretion by pancreatic beta-cells (PMID: 21311355). Arginine is found in plant and animal proteins, such as dairy products, meat, poultry, fish, and nuts. While many studies suggested that plant based protein-rich foods like soy protein, which contain less arginine, reduced cardiovascular risk compared to arginine rich foods like animal proteins, other studies have found little or null effects (PMID: 20042191). Arginine is one of the amino acids that are known in cannabis plant (PMID: 6991645). L-Arginine is expected to be in Cannabis as all living plants are known to produce and metabolize it. (2S)-2-Amino-5-(carbamimidamido)pentanoic acid (2S)-2-Amino-5-guanidinopentanoic acid (S)-2-Amino-5-guanidinopentanoic acid (S)-2-Amino-5-guanidinovaleric acid Arg Arginine L-(+)-Arginine L-Arg L-Arginin R (2S)-2-Amino-5-(carbamimidamido)pentanoate (2S)-2-Amino-5-guanidinopentanoate (S)-2-Amino-5-guanidinopentanoate (S)-2-Amino-5-guanidinovalerate (S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoate (S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoic acid (S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoate (S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acid 2-Amino-5-guanidinovalerate 2-Amino-5-guanidinovaleric acid 5-[(Aminoiminomethyl)amino]-L-norvaline L-a-Amino-D-guanidinovalerate L-a-Amino-D-guanidinovaleric acid L-alpha-Amino-delta-guanidinovalerate L-alpha-Amino-delta-guanidinovaleric acid N5-(Aminoiminomethyl)-L-ornithine DL-Arginine acetate, monohydrate L-Isomer arginine Monohydrate DL-arginine acetate L Arginine Arginine, L isomer Arginine, L-isomer Hydrochloride, arginine Arginine hydrochloride DL Arginine acetate, monohydrate C6H14N4O2 174.2 174.1117 (2S)-2-amino-5-carbamimidamidopentanoic acid L-arginine 74-79-3 N[C@@H](CCCNC(N)=N)C(O)=O InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m0/s1 ODKSFYDXXFIFQN-BYPYZUCNSA-N belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-alpha-amino acids Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboximidamides Carboxylic acids Fatty acids and conjugates Guanidines Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Aliphatic acyclic compound Amine Amino acid Carbonyl group Carboximidamide Carboxylic acid Fatty acid Guanidine Hydrocarbon derivative L-alpha-amino acid Monocarboxylic acid or derivatives Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Propargyl-type 1,3-dipolar organic compound Common amino acids L-alpha-amino acid arginine glutamine family amino acid proteinogenic amino acid water_solubility 182 mg/mL at 25 °C Human Metabolome Project logp -4.20 HANSCH,C ET AL. (1995) melting_point 222 °C logp -3.49 ALOGPS logs -1.88 ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 2.41 ChemAxon pka_strongest_basic 12.41 ChemAxon iupac (2S)-2-amino-5-carbamimidamidopentanoic acid ChemAxon average_mass 174.2 ChemAxon mono_mass 174.1117 ChemAxon smiles N[C@@H](CCCNC(N)=N)C(O)=O ChemAxon formula C6H14N4O2 ChemAxon inchi InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m0/s1 ChemAxon inchikey ODKSFYDXXFIFQN-BYPYZUCNSA-N ChemAxon polar_surface_area 125.22 ChemAxon refractivity 53.92 ChemAxon polarizability 17.8 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00062 DB00125 FDB002257 6082 6322 16467 C00001340 L-arginine ARG 33707 5502 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Bauchart-Thevret C, Cui L, Wu G, Burrin DG: Arginine-induced stimulation of protein synthesis and survival in IPEC-J2 cells is mediated by mTOR but not nitric oxide. Am J Physiol Endocrinol Metab. 2010 Dec;299(6):E899-909. doi: 10.1152/ajpendo.00068.2010. Epub 2010 Sep 14. 20841502 Linden KC, Wadley GD, Garnham AP, McConell GK: Effect of l-arginine infusion on glucose disposal during exercise in humans. Med Sci Sports Exerc. 2011 Sep;43(9):1626-34. doi: 10.1249/MSS.0b013e318212a317. 21311355 Vega-Lopez S, Matthan NR, Ausman LM, Harding SV, Rideout TC, Ai M, Otokozawa S, Freed A, Kuvin JT, Jones PJ, Schaefer EJ, Lichtenstein AH: Altering dietary lysine:arginine ratio has little effect on cardiovascular risk factors and vascular reactivity in moderately hypercholesterolemic adults. Atherosclerosis. 2010 Jun;210(2):555-62. doi: 10.1016/j.atherosclerosis.2009.12.002. Epub 2009 Dec 5. 20042191