Arginine

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<h1 id="firstHeading" lang="en">Arginine</h1>

<div id="siteSub">From Wikipedia, the free encyclopedia</div>

Arginine (<a href="http://en.wikipedia.org/wiki/Help:IPA_for_English" title="Help:IPA for English">/</a><a href="http://en.wikipedia.org/wiki/Help:IPA_for_English#Key" title="Help:IPA for English">ˈɑrɡɪniːn</a><a href="http://en.wikipedia.org/wiki/Help:IPA_for_English" title="Help:IPA for English">/</a>, abbreviated as Arg or R)<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-1">[1]</a> is an α-<a href="http://en.wikipedia.org/wiki/Amino_acid" title="Amino acid">amino acid</a>. It was first isolated in 1886.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-mayo-2">[2]</a> The <a href="http://en.wikipedia.org/wiki/Optical_isomerism" title="Optical isomerism">L-form</a> is one of the 20 most common natural amino acids. At the level of molecular genetics, in the structure of the messenger ribonucleic acid <a href="http://en.wikipedia.org/wiki/MRNA" title="MRNA">mRNA</a>, CGU, CGC, CGA, CGG, AGA, and AGG, are the triplets of nucleotide bases or <a href="http://en.wikipedia.org/wiki/Codons" title="Codons">codons</a> that code for arginine during protein synthesis. In mammals, arginine is classified as a semiessential or conditionally essential amino acid, depending on the developmental stage and health status of the individual.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-tapiero-3">[3]</a> Preterm infants are unable to synthesize or create arginine internally, making the amino acid nutritionally essential for them.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-4">[4]</a> There are some conditions that put an increased demand on the body for the synthesis of L-arginine, including surgical or other trauma, sepsis and burns.[<a href="http://en.wikipedia.org/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] Arginine was first isolated from a <a href="http://en.wikipedia.org/wiki/Lupin" title="Lupin">lupin</a> seedling extract in 1886 by the Swiss chemist Ernst Schultze.

In general, most people do not need to take arginine supplements because the body usually produces significant amounts in healthy individuals.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-mayo-2">[2]</a>

<h2>Contents</h2>

[<a href="http://en.wikipedia.org/wiki/Arginine#" id="togglelink">hide</a>] </div>

<ul>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Structure">1 Structure</a></li>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Sources">2 Sources</a>

<ul>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Dietary_sources">2.1 Dietary sources</a></li>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Biosynthesis">2.2 Biosynthesis</a></li>

</ul>

</li>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Function">3 Function</a>

<ul>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Proteins">3.1 Proteins</a></li>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Precursor">3.2 Precursor</a></li>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Treatment_of_dentin_hypersensitivity">3.3 Treatment of dentin hypersensitivity</a></li>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Treatment_of_herpes_simplex_virus">3.4 Treatment of herpes simplex virus</a></li>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Possible_increased_risk_of_death_after_supplementation_following_heart_attack">3.5 Possible increased risk of death after supplementation following heart attack</a></li>

</ul>

</li>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Potential_medical_uses">4 Potential medical uses</a>

<ul>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Lung_inflammation_and_asthma">4.1 Lung inflammation and asthma</a></li>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Growth_hormone">4.2 Growth hormone</a></li>

<li><a href="http://en.wikipedia.org/wiki/Arginine#MELAS_syndrome">4.3 MELAS syndrome</a></li>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Sepsis">4.4 Sepsis</a></li>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Malate_salt">4.5 Malate salt</a></li>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Pre-eclampsia">4.6 Pre-eclampsia</a></li>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Hypertension">4.7 Hypertension</a></li>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Erectile_dysfunction">4.8 Erectile dysfunction</a></li>

<li><a href="http://en.wikipedia.org/wiki/Arginine#Anxiety">4.9 Anxiety</a></li>

</ul>

</li>

<li><a href="http://en.wikipedia.org/wiki/Arginine#References">6 References</a></li>

<li><a href="http://en.wikipedia.org/wiki/Arginine#External_links">7 External links</a></li>

</ul>

</div>

<h2>Structure[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=1" title="Edit section: Structure">edit</a>]</h2>

The <a href="http://en.wikipedia.org/wiki/Amino_acid" title="Amino acid">amino acid</a> <a href="http://en.wikipedia.org/wiki/Substituent" title="Substituent">side-chain</a> of arginine consists of a 3-carbon <a href="http://en.wikipedia.org/wiki/Aliphatic" title="Aliphatic">aliphatic</a> straight chain, the distal end of which is capped by a complex <a href="http://en.wikipedia.org/wiki/Guanidine" title="Guanidine">guanidinium</a> group.

<div>

<div>

Delocalization of charge in guanidinium group of L-Arginine</div>

</div>

With a <a href="http://en.wikipedia.org/wiki/Acid_dissociation_constant" title="Acid dissociation constant">pKa</a> of 12.48, the guanidinium group is positively charged in neutral, acidic, and even most basic environments, and thus imparts <a href="http://en.wikipedia.org/wiki/Basic_(chemistry)" title="Basic (chemistry)">basic</a> chemical properties to arginine. Because of the <a href="http://en.wikipedia.org/wiki/Conjugated_system" title="Conjugated system">conjugation</a> between the double bond and the nitrogen lone pairs, the positive charge is delocalized, enabling the formation of multiple <a href="http://en.wikipedia.org/wiki/Hydrogen_bond" title="Hydrogen bond">H-bonds</a>.

<h2>Sources[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=2" title="Edit section: Sources">edit</a>]</h2>

<h3>Dietary sources[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=3" title="Edit section: Dietary sources">edit</a>]</h3>

Arginine is a conditionally nonessential amino acid, meaning that most of the time it can be manufactured by the human body, and does not need to be obtained directly through the diet. The biosynthetic pathway, however, does not produce sufficient arginine, and some must still be consumed through diet. Individuals with poor nutrition or certain physical conditions may be advised to increase their intake of foods containing arginine. Arginine is found in a wide variety of foods, including:<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-5">[5]</a>

<ul>

<li>Animal sources</li>

</ul>

<dl>

<dd>dairy products (e.g., <a href="http://en.wikipedia.org/wiki/Cottage_cheese" title="Cottage cheese">cottage cheese</a>, <a href="http://en.wikipedia.org/wiki/Ricotta" title="Ricotta">ricotta</a>, <a href="http://en.wikipedia.org/wiki/Milk" title="Milk">milk</a>, <a href="http://en.wikipedia.org/wiki/Yogurt" title="Yogurt">yogurt</a>, <a href="http://en.wikipedia.org/wiki/Whey_protein" title="Whey protein">whey protein</a> drinks), <a href="http://en.wikipedia.org/wiki/Beef" title="Beef">beef</a>, <a href="http://en.wikipedia.org/wiki/Pork" title="Pork">pork</a> (e.g., bacon, ham), <a href="http://en.wikipedia.org/wiki/Gelatin" title="Gelatin">gelatin</a> ,<a href="http://en.wikipedia.org/wiki/Poultry" title="Poultry">poultry</a> (e.g. chicken and turkey light meat), <a href="http://en.wikipedia.org/wiki/Wild_game" title="Wild game">wild game</a> (e.g. pheasant, quail), <a href="http://en.wikipedia.org/wiki/Seafood" title="Seafood">seafood</a> (e.g., halibut, lobster, salmon, shrimp, snails, tuna)</dd>

</dl>

<ul>

<li>Plant sources</li>

</ul>

<dl>

<dd><a href="http://en.wikipedia.org/wiki/Wheat_germ" title="Wheat germ">wheat germ</a> and flour, <a href="http://en.wikipedia.org/wiki/Lupins" title="Lupins">lupins</a>, buckwheat, <a href="http://en.wikipedia.org/wiki/Granola" title="Granola">granola</a>, <a href="http://en.wikipedia.org/wiki/Oatmeal" title="Oatmeal">oatmeal</a>, <a href="http://en.wikipedia.org/wiki/Peanut" title="Peanut">peanuts</a>, <a href="http://en.wikipedia.org/wiki/Nut_(fruit)" title="Nut (fruit)">nuts</a> (coconut, pecans, cashews, walnuts, almonds, Brazil nuts, hazelnuts, pinenuts),<a href="http://en.wikipedia.org/wiki/Seeds" title="Seeds">seeds</a> (pumpkin, sesame, sunflower), <a href="http://en.wikipedia.org/wiki/Chickpea" title="Chickpea">chickpeas</a>, cooked <a href="http://en.wikipedia.org/wiki/Soybeans" title="Soybeans">soybeans</a>, <a href="http://en.wikipedia.org/wiki/Phalaris_canariensis" title="Phalaris canariensis">Phalaris canariensis</a> (canaryseed or ALPISTE)</dd>

</dl>

<h3>Biosynthesis[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=4" title="Edit section: Biosynthesis">edit</a>]</h3>

Arginine is synthesized from <a href="http://en.wikipedia.org/wiki/Citrulline" title="Citrulline">citrulline</a> by the sequential action of the cytosolic enzymes <a href="http://en.wikipedia.org/wiki/Argininosuccinate_synthetase" title="Argininosuccinate synthetase">argininosuccinate synthetase</a> (ASS) and <a href="http://en.wikipedia.org/wiki/Argininosuccinate_lyase" title="Argininosuccinate lyase">argininosuccinate lyase</a> (ASL). In terms of energy, this is costly, as the synthesis of each molecule of argininosuccinate requires hydrolysis of <a href="http://en.wikipedia.org/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">adenosine triphosphate</a> (ATP) to <a href="http://en.wikipedia.org/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">adenosine monophosphate</a> (AMP), i.e., two ATP equivalents. In essence, taking an excess of arginine gives more energy by saving ATPs that can be used elsewhere.

Citrulline can be derived from multiple sources:

<ul>

<li>from arginine via <a href="http://en.wikipedia.org/wiki/Nitric_oxide_synthase" title="Nitric oxide synthase">nitric oxide synthase</a> (NOS)</li>

<li>from <a href="http://en.wikipedia.org/wiki/Ornithine" title="Ornithine">ornithine</a> via catabolism of <a href="http://en.wikipedia.org/wiki/Proline" title="Proline">proline</a> or <a href="http://en.wikipedia.org/wiki/Glutamine" title="Glutamine">glutamine</a>/<a href="http://en.wikipedia.org/wiki/Glutamate" title="Glutamate">glutamate</a></li>

<li>from <a href="http://en.wikipedia.org/wiki/Asymmetric_dimethylarginine" title="Asymmetric dimethylarginine">asymmetric dimethylarginine</a> (ADMA) via DDAH</li>

</ul>

The pathways linking arginine, <a href="http://en.wikipedia.org/wiki/Glutamine" title="Glutamine">glutamine</a>, and <a href="http://en.wikipedia.org/wiki/Proline" title="Proline">proline</a> are bidirectional. Thus, the net utilization or production of these amino acids is highly dependent on cell type and developmental stage.

On a whole-body basis, synthesis of arginine occurs principally via the intestinal–renal axis, wherein <a href="http://en.wikipedia.org/wiki/Epithelial_cell" title="Epithelial cell">epithelial cells</a> of the <a href="http://en.wikipedia.org/wiki/Small_intestine" title="Small intestine">small intestine</a>, which produce<a href="http://en.wikipedia.org/wiki/Citrulline" title="Citrulline">citrulline</a> primarily from <a href="http://en.wikipedia.org/wiki/Glutamine" title="Glutamine">glutamine</a> and <a href="http://en.wikipedia.org/wiki/Glutamate" title="Glutamate">glutamate</a>, collaborate with the <a href="http://en.wikipedia.org/wiki/Proximal_tubule_cell" title="Proximal tubule cell">proximal tubule cells</a> of the <a href="http://en.wikipedia.org/wiki/Kidney" title="Kidney">kidney</a>, which extract citrulline from the circulation and convert it to arginine, which is returned to the circulation. As a consequence, impairment of small bowel or renal function can reduce endogenous arginine synthesis, thereby increasing the dietary requirement.

Synthesis of arginine from citrulline also occurs at a low level in many other cells, and cellular capacity for arginine synthesis can be markedly increased under circumstances that also induce <a href="http://en.wikipedia.org/wiki/Nitric_oxide_synthase" title="Nitric oxide synthase">iNOS</a>. Thus, citrulline, a coproduct of the NOS-catalyzed reaction, can be recycled to arginine in a pathway known as the citrulline-NO or arginine-citrulline pathway. This is demonstrated by the fact that, in many cell types, citrulline can substitute for arginine to some degree in supporting NO synthesis. However, recycling is not quantitative because citrulline accumulates along with nitrate and nitrite, the stable end-products of NO, in NO-producing cells.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-6">[6]</a>

<h2>Function[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=5" title="Edit section: Function">edit</a>]</h2>

Arginine plays an important role in cell division, the healing of wounds, removing ammonia from the body, immune function, and the release of hormones.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-tapiero-3">[3]</a><a href="http://en.wikipedia.org/wiki/Arginine#cite_note-stechmiller-7">[7]</a><a href="http://en.wikipedia.org/wiki/Arginine#cite_note-witte-8">[8]</a>

The benefits and functions attributed to oral supplementation of L-arginine include:

<ul>

<li>Precursor for the synthesis of <a href="http://en.wikipedia.org/wiki/Nitric_oxide" title="Nitric oxide">nitric oxide</a> (NO)<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-9">[9]</a> Non-L-arginine derived NO can be generated by the nitrate-nitrite-nitric oxide pathway that is monitored through <a href="http://en.wikipedia.org/wiki/Saliva_testing" title="Saliva testing">saliva testing</a>.</li>

<li>Reduces healing time of injuries (particularly bone)<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-stechmiller-7">[7]</a><a href="http://en.wikipedia.org/wiki/Arginine#cite_note-witte-8">[8]</a></li>

</ul>

<ul>

<li>Quickens repair time of damaged tissue<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-stechmiller-7">[7]</a><a href="http://en.wikipedia.org/wiki/Arginine#cite_note-witte-8">[8]</a></li>

<li>Helps decrease <a href="http://en.wikipedia.org/wiki/Blood_pressure" title="Blood pressure">blood pressure</a> in clinical hypertensive subjects <a href="http://en.wikipedia.org/wiki/Arginine#cite_note-10">[10]</a><a href="http://en.wikipedia.org/wiki/Arginine#cite_note-11">[11]</a><a href="http://en.wikipedia.org/wiki/Arginine#cite_note-Dong_JY.2C_Qin_LQ.2C_Zhang_Z.2C_Zhao_Y.2C_Wang_J.2C_Arigoni_F.2C_Zhang_W.2011_959.E2.80.93965-12">[12]</a> NO-mediated decrease in blood pressure is influenced by both the L-arginine-dependent <a href="http://en.wikipedia.org/wiki/Nitric_oxide_synthase" title="Nitric oxide synthase">nitric oxide synthase</a> pathway and non-L-arginine or alternative pathway through nitrate-rich foods such as beets and spinach.</li>

</ul>

<h3>Proteins[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=6" title="Edit section: Proteins">edit</a>]</h3>

The distributing basics of the moderate structure found in geometry, charge distribution, and ability to form multiple H-bonds make arginine ideal for binding negatively charged groups. For this reason, arginine prefers to be on the outside of the proteins, where it can interact with the polar environment.

Incorporated in proteins, arginine can also be converted to citrulline by PAD enzymes. In addition, arginine can be <a href="http://en.wikipedia.org/wiki/Methylation" title="Methylation">methylated</a> by protein methyltransferases.

<h3>Precursor[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=7" title="Edit section: Precursor">edit</a>]</h3>

Arginine is the immediate precursor of <a href="http://en.wikipedia.org/wiki/Nitric_oxide" title="Nitric oxide">nitric oxide</a> (NO), <a href="http://en.wikipedia.org/wiki/Urea" title="Urea">urea</a>, <a href="http://en.wikipedia.org/wiki/Ornithine" title="Ornithine">ornithine</a>, and <a href="http://en.wikipedia.org/wiki/Agmatine" title="Agmatine">agmatine</a>; is necessary for the synthesis of <a href="http://en.wikipedia.org/wiki/Creatine" title="Creatine">creatine</a>; and can also be used for the synthesis of <a href="http://en.wikipedia.org/wiki/Polyamine" title="Polyamine">polyamines</a> (mainly through ornithine and to a lesser degree through agmatine), <a href="http://en.wikipedia.org/wiki/Citrulline" title="Citrulline">citrulline</a>, and <a href="http://en.wikipedia.org/wiki/Glutamate" title="Glutamate">glutamate</a>. As a precursor of nitric oxide, arginine may have a role in the treatment of some conditions where <a href="http://en.wikipedia.org/wiki/Vasodilation" title="Vasodilation">vasodilation</a> is required.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-tapiero-3">[3]</a>The presence of <a href="http://en.wikipedia.org/wiki/Asymmetric_dimethylarginine" title="Asymmetric dimethylarginine">asymmetric dimethylarginine</a> (ADMA), a close relative, inhibits the nitric oxide reaction; therefore, ADMA is considered a marker for <a href="http://en.wikipedia.org/wiki/Vascular_disease" title="Vascular disease">vascular disease</a>, just as L-arginine is considered a sign of a healthy <a href="http://en.wikipedia.org/wiki/Endothelium" title="Endothelium">endothelium</a>.

<h3>Treatment of dentin hypersensitivity[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=8" title="Edit section: Treatment of dentin hypersensitivity">edit</a>]</h3>

Arginine (8%) in dental products (e.g., <a href="http://en.wikipedia.org/wiki/Toothpaste" title="Toothpaste">toothpaste</a>) provides effective relief from sensitive teeth by depositing a <a href="http://en.wikipedia.org/wiki/Dentin" title="Dentin">dentin</a>-like <a href="http://en.wikipedia.org/wiki/Mineral" title="Mineral">mineral</a>, containing <a href="http://en.wikipedia.org/wiki/Calcium" title="Calcium">calcium</a> and <a href="http://en.wikipedia.org/wiki/Phosphate" title="Phosphate">phosphate</a>, within the dentin tubules and in a protective layer on the dentin surface.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-petrou-13">[13]</a>

<h3>Treatment of herpes simplex virus[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=9" title="Edit section: Treatment of herpes simplex virus">edit</a>]</h3>

An unproven claim is that a low ratio of arginine to <a href="http://en.wikipedia.org/wiki/Lysine" title="Lysine">lysine</a> may be of benefit in the treatment of herpes simplex virus. For more information, refer to <a href="http://en.wikipedia.org/wiki/Herpes#Treatment" title="Herpes">Herpes - Treatment</a> also see journal article.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-14">[14]</a>

<h3>Possible increased risk of death after supplementation following heart attack[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=10" title="Edit section: Possible increased risk of death after supplementation following heart attack">edit</a>]</h3>

A clinical trial found that patients taking an L-arginine supplement following a heart attack found no change in the heart's vascular tone or decrease in the symptoms of <a href="http://en.wikipedia.org/wiki/Congestive_heart_failure" title="Congestive heart failure">congestive heart failure</a> (the heart's ability to pump). In fact, six more patients that were taking L-arginine died than those taking a placebo, resulting in early termination of the study with the recommendation that the supplement not be used by heart attack patients.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-15">[15]</a><a href="http://en.wikipedia.org/wiki/Arginine#cite_note-16">[16]</a> These findings suggest L-arginine is not beneficial post-heart-attack.

<h2>Potential medical uses[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=11" title="Edit section: Potential medical uses">edit</a>]</h2>

<h3>Lung inflammation and asthma[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=12" title="Edit section: Lung inflammation and asthma">edit</a>]</h3>

Inhalation of L-arginine can increase lung inflammation and worsen asthma.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-17">[17]</a>

<h3>Growth hormone[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=13" title="Edit section: Growth hormone">edit</a>]</h3>

Intravenously-administered arginine stimulates the secretion of <a href="http://en.wikipedia.org/wiki/Growth_hormone" title="Growth hormone">growth hormone</a>,<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-alba-roth-18">[18]</a> and is used in growth hormone stimulation tests.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-19">[19]</a> Two studies have found that oral L-arginine supplementation is also effective at increasing resting GH levels. The first study found that oral preparations of L-arginine are effective at increasing growth hormone levels. In fact, the 9-gram dose resulted in mean peak GH levels of 6.4 (+/- 1.3) microg/L versus placebo levels of 2.9 (+/- 0.7).<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-Collier-20">[20]</a> Another study found similar results. It included resting versus exercise and oral L-arginine versus oral placebo. The authors concluded that "Oral arginine alone (7 g) stimulated GH release, but a greater GH response was seen with exercise alone. The combined effect of arginine before exercise attenuates the GH response... GH production: Ex > Arg+Ex > Arg > placebo" suggesting against supplementing with arginine alone prior to exercise if the goal is to raise GH levels, but concurring with the previous study that oral L-arginine increases GH on days free of significant exercise.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-Collier-20">[20]</a> In contrast to these two studies that found increased resting GH due to oral arginine supplementation, a third study did not find increase in resting GH levels from oral supplementation. In that study, oral preparations of L-arginine were ineffective at increasing growth hormone levels despite being effective at increasing plasma levels of L-arginine.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-Forbes-21">[21]</a>

<h3>MELAS syndrome[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=14" title="Edit section: MELAS syndrome">edit</a>]</h3>

Several trials delved into effects of L-arginine in <a href="http://en.wikipedia.org/wiki/Mitochondrial_encephalomyopathy,lactic_acidosis,and_stroke-like_episodes" title="Mitochondrial encephalomyopathy, lactic acidosis, and stroke-like episodes">MELAS syndrome</a>, a <a href="http://en.wikipedia.org/wiki/Mitochondrial_disease" title="Mitochondrial disease">mitochondrial disease</a>.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-pmid16769961-22">[22]</a><a href="http://en.wikipedia.org/wiki/Arginine#cite_note-pmid19198147-23">[23]</a><a href="http://en.wikipedia.org/wiki/Arginine#cite_note-pmid17276739-24">[24]</a><a href="http://en.wikipedia.org/wiki/Arginine#cite_note-pmid19780807-25">[25]</a>

<h3>Sepsis[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=15" title="Edit section: Sepsis">edit</a>]</h3>

Cellular arginine biosynthetic capacity determined by activity of <a href="http://en.wikipedia.org/wiki/Argininosuccinate_synthetase" title="Argininosuccinate synthetase">argininosuccinate synthetase</a> (AS) is induced by the same mediators of <a href="http://en.wikipedia.org/wiki/Septic_shock" title="Septic shock">septic</a> response — <a href="http://en.wikipedia.org/wiki/Endotoxin" title="Endotoxin">endotoxin</a> and <a href="http://en.wikipedia.org/wiki/Cytokine" title="Cytokine">cytokines</a> — that induce <a href="http://en.wikipedia.org/wiki/Nitric_oxide_synthase" title="Nitric oxide synthase">nitric oxide synthase</a> (NOS), the <a href="http://en.wikipedia.org/wiki/Enzyme" title="Enzyme">enzyme</a> responsible for <a href="http://en.wikipedia.org/wiki/Nitric_oxide" title="Nitric oxide">nitric oxide</a> synthesis.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-26">[26]</a>

<h3>Malate salt[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=16" title="Edit section: Malate salt">edit</a>]</h3>

The <a href="http://en.wikipedia.org/wiki/Malate" title="Malate">malate</a> <a href="http://en.wikipedia.org/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a> of arginine can also be used during the treatment of alcoholic hepatitis and advanced cirrhosis.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-27">[27]</a>

<h3>Pre-eclampsia[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=17" title="Edit section: Pre-eclampsia">edit</a>]</h3>

A preliminary study of supplementation with L-arginine and antioxidant vitamins showed that this combination may help to combat abnormally high blood pressure during high-risk pregnancies.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-28">[28]</a>

<h3>Hypertension[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=18" title="Edit section: Hypertension">edit</a>]</h3>

Intravenous infusion of arginine reduces blood pressure in patients with hypertension as well as normal subjects.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-29">[29]</a>

A recent meta-analysis showed that L-arginine reduces blood pressure with pooled estimates of 5.4/2.7 mmHg for SBP/DBP.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-Dong_JY.2C_Qin_LQ.2C_Zhang_Z.2C_Zhao_Y.2C_Wang_J.2C_Arigoni_F.2C_Zhang_W.2011_959.E2.80.93965-12">[12]</a>

<h3>Erectile dysfunction[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=19" title="Edit section: Erectile dysfunction">edit</a>]</h3>

Arginine taken in combination with <a href="http://en.wikipedia.org/wiki/Proanthocyanidin" title="Proanthocyanidin">proanthocyanidins</a><a href="http://en.wikipedia.org/wiki/Arginine#cite_note-30">[30]</a> or glutamic acid and <a href="http://en.wikipedia.org/wiki/Yohimbine" title="Yohimbine">yohimbine</a>,<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-31">[31]</a> has also been used as a treatment for <a href="http://en.wikipedia.org/wiki/Erectile_dysfunction" title="Erectile dysfunction">erectile dysfunction</a>.

<h3>Anxiety[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=20" title="Edit section: Anxiety">edit</a>]</h3>

Dietary supplementation of L-arginine taken in combination with <a href="http://en.wikipedia.org/wiki/L-lysine" title="L-lysine">L-lysine</a> has been shown potentially useful in treating people subjected to high levels of mental stress and <a href="http://en.wikipedia.org/wiki/Anxiety" title="Anxiety">anxiety</a>, in a double-blind, placebo controlled and randomized study, involving 108 Japanese adults. Trait anxiety and state anxiety induced by cognitive stress battery was significantly reduced, and basal levels of the stress hormone <a href="http://en.wikipedia.org/wiki/Cortisol" title="Cortisol">cortisol</a>were decreased. The study was funded by <a href="http://en.wikipedia.org/wiki/Ajinomoto" title="Ajinomoto">Ajinomoto, Co. Inc.</a>, an industrial manufacturer of lysine and arginine.<a href="http://en.wikipedia.org/wiki/Arginine#cite_note-32">[32]</a>

<ul>

<li><a href="http://en.wikipedia.org/wiki/Arginine_glutamate" title="Arginine glutamate">Arginine glutamate</a></li>

<li><a href="http://en.wikipedia.org/wiki/Canavanine" title="Canavanine">Canavanine</a> and <a href="http://en.wikipedia.org/wiki/Canaline" title="Canaline">canaline</a> are toxic <a href="http://en.wikipedia.org/wiki/Analog_(chemistry)" title="Analog (chemistry)">analogs</a> of arginine and ornithine.</li>

</ul>

<h2>References[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=22" title="Edit section: References">edit</a>]</h2>

<div>

<ol>

<li id="cite_note-1"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-1">Jump up^{</a> IUPAC}-IUBMB Joint Commission on Biochemical Nomenclature. <a rel="nofollow" href="http://www.chem.qmul.ac.uk/iupac/AminoAcid/">"Nomenclature and Symbolism for Amino Acids and Peptides"</a>. Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology etc. <a rel="nofollow" href="http://web.archive.org/web/20070529233449/http://www.chem.qmul.ac.uk/iupac/AminoAcid/">Archived</a> from the original on 29 May 2007. Retrieved 2007-05-17.</li>

<li id="cite_note-mayo-2">^ <a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-mayo_2-0">Jump up to:a</a> <a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-mayo_2-1">b</a> <a rel="nofollow" href="http://www.mayoclinic.com/health/l-arginine/NS_patient-arginine">Mayo Clinic</a></li>

<li id="cite_note-tapiero-3">^ <a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-tapiero_3-0">Jump up to:a</a> <a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-tapiero_3-1">b</a> <a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-tapiero_3-2">c</a> Tapiero, H.; et al. (November 2002). "L-Arginine". Biomedicine and Pharmacotherapy 56 (9): 439–445 REVIEW. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/12481980">12481980</a>.</li>

<li id="cite_note-4"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-4">Jump up^{</a> Wu}, G.; et al. (August 2004). "Arginine deficiency in preterm infants: biochemical mechanisms and nutritional implications". Journal of Nutritional Biochemistry 15 (8): 332–451 REVIEW.<a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<a rel="nofollow" href="http://dx.doi.org/10.1016%2Fj.jnutbio.2003.11.010">10.1016/j.jnutbio.2003.11.010</a>. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/15302078">15302078</a>.</li>

<li id="cite_note-5"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-5">Jump up^{</a> }<a rel="nofollow" href="http://www.keysupplements.com/articles/L-Arginine-Supplements-Nitric-Oxide-Scientific-Studies.htm">"L-Arginine Supplements Nitric Oxide Scientific Studies Food Sources"</a>. Retrieved 2007-02-20.</li>

<li id="cite_note-6"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-6">Jump up^{</a>&nbsp};Morris Jr, SM (October 2004). <a rel="nofollow" href="http://www.nutrition.org/cgi/content/full/134/10/2743S">"Enzymes of arginine metabolism."</a>. The Journal of nutrition 134 (10 Suppl): 2743S–2747S. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/15465778">15465778</a>.</li>

<li id="cite_note-stechmiller-7">^ <a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-stechmiller_7-0">Jump up to:a</a> <a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-stechmiller_7-1">b</a> <a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-stechmiller_7-2">c</a> Stechmiller, J.K.; et al. (February 2005). "Arginine supplementation and wound healing". Nutrition in Clinical Practice 20 (13): 52–61 REVIEW. <a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<a rel="nofollow" href="http://dx.doi.org/10.1177%2F011542650502000152">10.1177/011542650502000152</a>. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/16207646">16207646</a>.</li>

<li id="cite_note-witte-8">^ <a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-witte_8-0">Jump up to:a</a> <a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-witte_8-1">b</a> <a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-witte_8-2">c</a> Witte, M.B.; Barbul, A (Nov–Dec 2003). "Arginine physiology and its implication for wound healing".Wound Repair and Regeneration 11 (6): 419–423 REVIEW. <a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<a rel="nofollow" href="http://dx.doi.org/10.1046%2Fj.1524-475X.2003.11605.x">10.1046/j.1524-475X.2003.11605.x</a>.<a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/14617280">14617280</a>.</li>

<li id="cite_note-9"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-9">Jump up^{</a> Andrew}, P.J.; Myer, B. (August 15, 1999). "Enzymatic function of nitric oxide synthases". Cardiovascular Research 43 (3): 521–531 REVIEW. <a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<a rel="nofollow" href="http://dx.doi.org/10.1016%2FS0008-6363%2899%2900115-7">10.1016/S0008-6363(99)00115-7</a>. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/10690324">10690324</a>. <a rel="nofollow" href="http://cardiovascres.oxfordjournals.org/cgi/content/full/43/3/521">[1]</a></li>

<li id="cite_note-10"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-10">Jump up^{</a> Gokce}, N.. (October 2004). "L-Arginine and hypertension". Journal of Nutrition 134 (10 Suppl): 2807S–2811S REVIEW. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/15465790">15465790</a>.</li>

<li id="cite_note-11"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-11">Jump up^{</a> Rajapakse}, N.W.; et al. (December 2008). <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2680209">"Exogenous L-arginine ameliorates angiotensin II-induced hypertension and renal damage in rats"</a>. Hypertension 52 (6): 1084–1090.<a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<a rel="nofollow" href="http://dx.doi.org/10.1161%2FHYPERTENSIONAHA.108.114298">10.1161/HYPERTENSIONAHA.108.114298</a>. <a href="http://en.wikipedia.org/wiki/PubMed_Central" title="PubMed Central">PMC</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2680209">2680209</a>. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/18981330">18981330</a>. Retrieved 2009-11-29. <a rel="nofollow" href="http://hyper.ahajournals.org/cgi/content/full/52/6/1084">[2]</a></li>

<li id="cite_note-Dong_JY.2C_Qin_LQ.2C_Zhang_Z.2C_Zhao_Y.2C_Wang_J.2C_Arigoni_F.2C_Zhang_W.2011_959.E2.80.93965-12">^ <a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-Dong_JY.2C_Qin_LQ.2C_Zhang_Z.2C_Zhao_Y.2C_Wang_J.2C_Arigoni_F.2C_Zhang_W.2011_959.E2.80.93965_12-0">Jump up to:a</a> <a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-Dong_JY.2C_Qin_LQ.2C_Zhang_Z.2C_Zhao_Y.2C_Wang_J.2C_Arigoni_F.2C_Zhang_W._2011_959.E2.80.93965_12-1">b</a> Dong JY, Qin LQ, Zhang Z, Zhao Y, Wang J, Arigoni F, Zhang W. (2011). "Effect of oral L-arginine supplementation on blood pressure: a meta-analysis of randomized, double-blind, placebo-controlled trials".American Heart Journal 162 (6): 959–965. <a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<a rel="nofollow" href="http://dx.doi.org/10.1016%2Fj.ahj.2011.09.012">10.1016/j.ahj.2011.09.012</a>. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/22137067">22137067</a>.</li>

<li id="cite_note-petrou-13"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-petrou_13-0">Jump up^{</a> Petrou}, I.; et al. (2009). "A breakthrough therapy for dentin hypersensitivity: how dental products containing 8% arginine and calcium carbonate work to deliver effective relief of sensitive teeth.". The Journal of Clinical Dentisry 20 (1): 23–31. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/19489189">19489189</a>.</li>

<li id="cite_note-14"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-14">Jump up^{</a>&nbsp};Takeshi Naito, Hiroshi Irie, Kazuko Tsujimoto, Keiko Ikeda, Tsutomu Arakawa, A. Hajime Koyama (April 2009). <a rel="nofollow" href="http://www.spandidos-publications.com/ijmm/article.jsp?article_id=ijmm_23_4_495">"Antiviral effect of arginine against herpes simplex virus type 1"</a>. International Journal of Molecular Medicine (International Journal of Molecular Medicine) 23 (4): 495–499. <a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<a rel="nofollow" href="http://dx.doi.org/10.3892%2Fijmm_00000156">10.3892/ijmm_00000156</a>.<a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/19288025">19288025</a>. Retrieved 2010-10-18.</li>

<li id="cite_note-15"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-15">Jump up^{</a> }<a rel="nofollow" href="http://www.sciencedaily.com/releases/2008/01/080131161759.htm">Medical College of Georgia. "Diabetes Makes It Hard For Blood Vessels To Relax." ScienceDaily 1 February 2008. 1 February 2008</a></li>

<li id="cite_note-16"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-16">Jump up^{</a> Schulman}, SP, Becker, LC, Kass, DA, Champion, HC, Terrin, ML, Forman, S, Ernst, KV, Kelemen, MD et al. (January 2006). <a rel="nofollow" href="http://jama.ama-assn.org/cgi/content/short/295/1/58">"L-arginine therapy in acute myocardial infarction: the Vascular Interaction With Age in Myocardial Infarction (VINTAGE MI) randomized clinical trial."</a>. JAMA: the Journal of the American Medical Association 295 (1): 58–64. <a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<a rel="nofollow" href="http://dx.doi.org/10.1001%2Fjama.295.1.58">10.1001/jama.295.1.58</a>. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/16391217">16391217</a>.</li>

<li id="cite_note-17"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-17">Jump up^{</a>&nbsp};Sapienza MA, Kharitonov SA, Horvath I, Chung KF, Barnes PJ. "Effect of inhaled L-arginine on exhaled nitric oxide in normal and asthmatic subjects." Thorax. 1998 Mar;53(3):172-5.</li>

<li id="cite_note-alba-roth-18"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-alba-roth_18-0">Jump up^{</a> Alba}-Roth J, Müller O, Schopohl J, von Werder K (1988). "Arginine stimulates growth hormone secretion by suppressing endogenous somatostatin secretion". J Clin Endocrinol Metab 67 (6): 1186–9.<a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<a rel="nofollow" href="http://dx.doi.org/10.1210%2Fjcem-67-6-1186">10.1210/jcem-67-6-1186</a>. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/2903866">2903866</a>.</li>

<li id="cite_note-19"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-19">Jump up^{</a> U.S}. National Library of Medicine (September 2009). <a rel="nofollow" href="http://www.nlm.nih.gov/medlineplus/ency/article/003377.htm">Growth hormone stimulation test</a></li>

<li id="cite_note-Collier-20">^ <a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-Collier_20-0">Jump up to:a</a> <a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-Collier_20-1">b</a> Collier, S. R.; Casey, D. P.; Kanaley, J. A. (2005). "Growth hormone responses to varying doses of oral arginine". Growth Hormone & IGF Research 15 (2): 136–139. <a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<a rel="nofollow" href="http://dx.doi.org/10.1016%2Fj.ghir.2004.12.004">10.1016/j.ghir.2004.12.004</a>.<a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/15809017">15809017</a>. <a href="http://en.wikipedia.org/w/index.php?title=Template:Cite_pmid/15809017&action=edit&editintro=Template:Cite_pmid/editintro2">edit</a></li>

<li id="cite_note-Forbes-21"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-Forbes_21-0">Jump up^{</a> Forbes}, SC; Bell, GJ (June 2011). "The acute effects of a low and high dose of oral L-arginine supplementation in young active males at rest.". Applied physiology, nutrition, and metabolism = Physiologie appliquee, nutrition et metabolisme 36 (3): 405–11. <a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<a rel="nofollow" href="http://dx.doi.org/10.1139%2Fh11-035">10.1139/h11-035</a>. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/21574873">21574873</a>.</li>

<li id="cite_note-pmid16769961-22"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-pmid16769961_22-0">Jump up^{</a>&nbsp};Koga Y, Akita Y, Junko N, Yatsuga S, Povalko N, Fukiyama R, Ishii M, Matsuishi T (June 2006). <a rel="nofollow" href="http://www.neurology.org/cgi/pmidlookup?view=long&pmid=16769961">"Endothelial dysfunction in MELAS improved by l-arginine supplementation"</a>. <a href="http://en.wikipedia.org/wiki/Neurology_(journal)" title="Neurology (journal)">Neurology</a> 66 (11): 1766–9.<a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<a rel="nofollow" href="http://dx.doi.org/10.1212%2F01.wnl.0000220197.36849.1e">10.1212/01.wnl.0000220197.36849.1e</a>. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/16769961">16769961</a>.</li>

<li id="cite_note-pmid19198147-23"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-pmid19198147_23-0">Jump up^{</a>&nbsp};Koga Y (November 2008). "[L-arginine therapy on MELAS]". <a href="http://en.wikipedia.org/w/index.php?title=Rinsho_Shinkeigaku&action=edit&redlink=1" title="Rinsho Shinkeigaku (page does not exist)">Rinsho Shinkeigaku</a> (in Japanese) 48 (11): 1010–2. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/19198147">19198147</a>.</li>

<li id="cite_note-pmid17276739-24"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-pmid17276739_24-0">Jump up^{</a>&nbsp};Koga Y, Akita Y, Nishioka J, Yatsuga S, Povalko N, Katayama K, Matsuishi T (2007). <a rel="nofollow" href="http://linkinghub.elsevier.com/retrieve/pii/S1567-7249(06)00227-3">"MELAS and L-arginine therapy"</a>. <a href="http://en.wikipedia.org/wiki/Mitochondrion" title="Mitochondrion">Mitochondrion</a> 7 (1–2): 133–9. <a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<a rel="nofollow" href="http://dx.doi.org/10.1016%2Fj.mito.2006.11.006">10.1016/j.mito.2006.11.006</a>. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/17276739">17276739</a>.</li>

<li id="cite_note-pmid19780807-25"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-pmid19780807_25-0">Jump up^{</a>&nbsp};Finsterer J (November 2009). <a rel="nofollow" href="http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=1351-5101&date=2009&volume=16&issue=11&spage=1178">"Management of mitochondrial stroke-like-episodes"</a>. <a href="http://en.wikipedia.org/w/index.php?title=Eur.J.Neurol.&action=edit&redlink=1" title="Eur. J. Neurol. (page does not exist)">Eur. J. Neurol.</a> 16(11): 1178–84. <a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<a rel="nofollow" href="http://dx.doi.org/10.1111%2Fj.1468-1331.2009.02789.x">10.1111/j.1468-1331.2009.02789.x</a>. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/19780807">19780807</a>.</li>

<li id="cite_note-26"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-26">Jump up^{</a>&nbsp};MORRIS SM (1995). <a rel="nofollow" href="http://toxnet.nlm.nih.gov/">ROLE OF ARGININE SYNTHESIS IN SURGICAL SEPSIS</a>. Crisp Data Base National Institutes Of Health. <a rel="nofollow" href="http://web.archive.org/web/20100226170753/http://toxnet.nlm.nih.gov/">Archived</a> from the original on 26 February 2010. Retrieved 2010-02-22.</li>

<li id="cite_note-27"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-27">Jump up^{</a> Tissot}-Favre A, Brette R (May–June 1970). "Therapeutic effects of arginine malate in alcoholic cirrhosis".Therapie 25 (3): 629–33. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/5431854">5431854</a>.</li>

<li id="cite_note-28"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-28">Jump up^{</a> Vadillo}-Ortega F et al.; Perichart-Perera, O.; Espino, S.; Avila-Vergara, M. A.; Ibarra, I.; Ahued, R.; Godines, M.; Parry, S.; MacOnes, G.; Strauss, J. F. (2011). <a rel="nofollow" href="http://www.bmj.com/content/342/bmj.d2901">"Effect of supplementation during pregnancy with L-arginine and antioxidant vitamins in medical food on pre-eclampsia in high risk population: randomised controlled trial"</a>. British Medical Journal 342: d2901–d2901. <a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<a rel="nofollow" href="http://dx.doi.org/10.1136%2Fbmj.d2901">10.1136/bmj.d2901</a>.</li>

<li id="cite_note-29"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-29">Jump up^{</a> Nakaki}, T., Hishikawa, K., Suzuki, H., Saruta, T., Kato, R. (1990). "L-arginine-induced hypotension". Lancet336 (8716): 696. <a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<a rel="nofollow" href="http://dx.doi.org/10.1016%2F0140-6736%2890%2992196-O">10.1016/0140-6736(90)92196-O</a>. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/1975886">1975886</a>.</li>

<li id="cite_note-30"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-30">Jump up^{</a> Stanislavov}, R., Nikolova, V (2003). "Treatment of Erectile Dysfunction with Pycnogenol and L-arginine".Journal of Sex and Marital Therapy 29 (3): 207–213. <a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<a rel="nofollow" href="http://dx.doi.org/10.1080%2F00926230390155104">10.1080/00926230390155104</a>.<a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/12851125">12851125</a>.</li>

<li id="cite_note-31"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-31">Jump up^{</a> Lebret}, T.; Hervéa, J. M.; Gornyb, P.; Worcelc, M.; Botto, H. (2002). "Efficacy and Safety of a Novel Combination of L-Arginine Glutamate and Yohimbine Hydrochloride: A New Oral Therapy for Erectile Dysfunction". European Urology 41 (6): 608–613. <a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<a rel="nofollow" href="http://dx.doi.org/10.1016%2FS0302-2838%2802%2900175-6">10.1016/S0302-2838(02)00175-6</a>.<a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/12074777">12074777</a>.</li>

<li id="cite_note-32"><a href="http://en.wikipedia.org/wiki/Arginine#cite_ref-32">Jump up^{</a>&nbsp};Smriga M, Ando T, Akutsu M, Furukawa Y, Miwa K, Morinaga Y. (2007). "Oral treatment with L-lysine and L-arginine reduces anxiety and basal cortisol levels in healthy humans". Institute of Life Sciences 28 (2): 85–90.<a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier">PMID</a> <a rel="nofollow" href="http://www.ncbi.nlm.nih.gov/pubmed/17510493">17510493</a>.</li>

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<h2>External links[<a href="http://en.wikipedia.org/w/index.php?title=Arginine&action=edit&section=23" title="Edit section: External links">edit</a>]</h2>

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<td>Wikimedia Commons has media related to<a href="http://commons.wikimedia.org/wiki/Category:arginine" title="commons:Category:arginine">arginine</a>.</td>

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<li><a rel="nofollow" href="http://webbook.nist.gov/cgi/cbook.cgi?ID=C74793&Units=SI&Mask=4#Thermo-Phase">NIST Chemistry Webbook</a></li>

<li><a rel="nofollow" href="http://www.mayoclinic.com/health/l-arginine/NS_patient-arginine">Mayo Clinic discussion of Arginine.</a></li>

<li><a rel="nofollow" href="http://www.nlm.nih.gov/medlineplus/druginfo/natural/patient-arginine.html">National Institute of Health discussion of Arginine.</a></li>

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Arginine

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