| L-グルタミン |
|
|
|
|
別称
2-Amino-4-carbamoylbutanoic acid
|
| 識別情報 |
| 略称 |
Gln, Q |
| CAS登録番号 |
56-85-9 |
| PubChem |
738 |
| ChemSpider |
718 |
| UNII |
0RH81L854J |
| EINECS番号 |
200-292-1 |
| KEGG |
C00303 |
| ChEMBL |
CHEMBL165351 |
| IUPHARリガンド |
723 |
|
|
- InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)
Key: ZDXPYRJPNDTMRX-UHFFFAOYSA-N
InChI=1/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)
Key: ZDXPYRJPNDTMRX-UHFFFAOYAL
|
| 特性[1] |
| 化学式 |
C5H10N2O3 |
| モル質量 |
146.14 g mol−1 |
| 融点 |
185–186 °C（分解）
|
| 水への溶解度 |
可溶 |
| 比旋光度 [α]D |
+6.5º (H2O, c = 2) |
| 特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。 |
グルタミン (glutamine) はアミノ酸の一種で、2-アミノ-4-カルバモイル酪酸（2-アミノ-4-カルバモイルブタン酸）のこと。側鎖にアミドを有し、グルタミン酸のヒドロキシ基をアミノ基に置き換えた構造を持つ。酸加水分解によりグルタミン酸となる。略号は Gln あるいは Q で、2-アミノグルタルアミド酸とも呼ばれる。グルタミンとグルタミン酸の両方を示す3文字略号は Glx、1文字略号は Z である[2]。動物では細胞外液に多い。
極性無電荷側鎖アミノ酸、中性極性側鎖アミノ酸に分類される。蛋白質構成アミノ酸のひとつ。非必須アミノ酸だが、代謝性ストレスなど異化機能の亢進により、体内での生合成量では不足する場合もあり、準必須アミノ酸として扱われる場合もある。
目次
- 1 生化学
- 2 栄養学
- 2.1 利用
- 2.2 消化機能の補助
- 2.3 手術後の回復補助
- 3 出典
- 4 関連項目
- 5 外部リンク
生化学
RNAのコドン CAA および CAG によってコードされる。窒素代謝においても重要であり、窒素固定で生成したアンモニアはグルタミン酸をグルタミンに変換することによって有機化合物として同化される。この変換を行う酵素はグルタミンシンターゼと呼ばれる。グルタミンは多くの化合物の生合成において窒素源として用いられ、これにはプリンやピリミジンなど、他のアミノ酸も含まれる。
生合成
グルタミン酸よりグルタミンシンテターゼ（グルタミン酸アンモニアリガーゼ、EC 6.3.1.2）の作用により合成される。
栄養学
利用
ウェイトリフティングやボディビルディング、および特に老人に多いが、筋肉に痙攣や痛みを起こした場合にサプリメントとして用いられる。主な目的は運動後や日常生活で消費されたアミノ酸の補給である。
グルタミンの過剰消費に関して研究がなされているが、これまでこれといった結論は出ていない。しかしながら、長時間に及ぶ運動やトレーニングの後にはグルタミンを補給することが推奨されているため、適量の摂取は健康に良いとされる。また、これは断食や怪我をしたとき、免疫不全症やがんにかかった場合にグルタミンが勧められる主な理由でもある。
グルタミンを摂取すると免疫細胞が増え、風邪をひきにくくなる。
消化機能の補助
いくつかの研究によってグルタミンの機能と効果が明らかにされており、グルタミンを添加した食餌と腸の機能、すなわち腸管の防御機能、腸細胞の増殖および分化、敗血症への感染率の減少を関連付ける証拠が提出されている。このような「洗浄」効果は腸がグルタミンを他のアミノ酸より速く吸収することに由来すると考えられており、内臓の状態を整えたい時にグルタミンを用いるのが良いとされる理由となっている[3]。
これらの効果はグルタミンを添加したものとしていない食餌をとった後の血漿濃度を比較した結果から発見された。しかし、グルタミンは「洗浄」作用・効果を持つと考えられてはいるが、様々な食品中に異なる濃度で含まれるため、臨床での効果がどの程度得られるかは不明である[3]。
手術後の回復補助
グルタミンには外科手術後の傷の回復期間を短縮する効果があることも知られている。腹腔部を手術した際、患者にグルタミンを含む高カロリー輸液を行うと入院の期間が短縮される。 臨床試験によって、グルタミンの投与を含む療法で処置を行うと窒素バランスが向上し、投与を行わなかった場合に比べ、顆粒球におけるシステイニルロイコトリエンの生成やリンパ球の回復、腸の透過率に向上が見られること、また副作用が無いことが明らかにされている[4]。
出典
- ^ Weast, Robert C., ed. (1981), CRC Handbook of Chemistry and Physics (62nd ed.), Boca Raton, FL: CRC Press, p. C-311, ISBN 0-8493-0462-8 .
- ^ 牛場大蔵監修 『最新医学略語辞典』 橋本信也ほか編集、中央法規出版、1993年12月20日、第2版、p.439。ISBN 4-8058-1149-8。
- ^ a b Boza, J. J.; Dangin, M.; Moennoz, D.; Montigon, F.; Vuichoud, J.; Jarret, A.; Pouteau, E.; Gremaud, G.; Oguey-Araymon, S.; Courtois, D.; Woupeyi, A.; Finot, P. A.; Ballevre, O. (2001). "Free and protein-bound glutamine have identical splanchnic extraction in healthy human volunteers". Am. J. Physiol. Gastrointest Liver Physiol. 281(1): G267-74. PMID 11408280 全文
- ^ Morlion, B. J.; Stehle, P.; Wachtler, P.; Siedhoff, H. P.; Koller, M.; Konig, W.; Furst, P.; Puchstein, C. (1998). "Total parenteral nutrition with glutamine dipeptide after major abdominal surgery". Ann. Surg. 227(2): 302-308. PMID 9488531
関連項目
- 食餌療法
- 消化器
- グルタミン酸
- グルタミン酸ナトリウム
外部リンク
- グルタミン - 「健康食品」の安全性・有効性情報 （国立健康・栄養研究所）
|
タンパク質を構成するアミノ酸 |
|
| 主なトピック |
|
|
|
| 特性 |
|
脂肪族
|
- 分枝鎖アミノ酸 (バリン
- イソロイシン
- ロイシン)
- メチオニン
- アラニン
- プロリン
- グリシン
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|
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芳香族
|
- フェニルアラニン
- チロシン
- トリプトファン
- ヒスチジン
|
|
|
極性なし
|
|
|
|
正電荷 (pKa)
|
- リシン (≈10.8)
- アルギニン (≈12.5)
- ヒスチジン (≈6.1)
|
|
|
負電荷 (pKa)
|
- アスパラギン酸 (≈3.9)
- グルタミン酸 (≈4.1)
- システイン (≈8.3)
- チロシン (≈10.1)
|
|
|
| 分類 |
- 必須アミノ酸
- ケト原性アミノ酸
- 糖原性アミノ酸
- タンパク質を構成しないアミノ酸
|
|
| 主要な生体物質：炭水化物（アルコール、糖タンパク質、配糖体） · 脂質（エイコサノイド · 脂肪酸/脂肪酸の代謝中間体 · リン脂質 · スフィンゴ脂質 · ステロイド） · 核酸（核酸塩基 · ヌクレオチド代謝中間体） · タンパク質（タンパク質を構成するアミノ酸/アミノ酸の代謝中間体） · テトラピロール · ヘムの代謝中間体 |
|
"Gln" redirects here. For other uses, see GLN (disambiguation).
| L-Glutamine |
|
|
|
|
Other names
L-Glutamine
(levo)glutamide
2-Amino-4-carbamoylbutanoic acid
|
| Identifiers |
| Abbreviations |
Gln, Q |
| CAS number |
56-85-9 Y |
| PubChem |
738 |
| ChemSpider |
718 Y |
| UNII |
0RH81L854J Y |
| EC-number |
200-292-1 |
| KEGG |
C00303 Y |
| ChEBI |
CHEBI:28300 Y |
| ChEMBL |
CHEMBL930 N |
| IUPHAR ligand |
723 |
| ATC code |
A16AA03 |
| Jmol-3D images |
Image 1 |
|
|
-
InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10) Y
Key: ZDXPYRJPNDTMRX-UHFFFAOYSA-N Y
InChI=1/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)
Key: ZDXPYRJPNDTMRX-UHFFFAOYAL
|
| Properties[1] |
| Molecular formula |
C5H10N2O3 |
| Molar mass |
146.14 g mol−1 |
| Melting point |
decomposes around 185°C |
| Solubility in water |
soluble |
| Chiral rotation [α]D |
+6.5º (H2O, c = 2) |
| Supplementary data page |
Structure and
properties |
n, εr, etc. |
Thermodynamic
data |
Phase behaviour
Solid, liquid, gas |
| Spectral data |
UV, IR, NMR, MS |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
| N (verify) (what is: Y/N?) |
| Infobox references |
|
|
Glutamine (abbreviated as Gln or Q, and often called L-glutamine) is one of the 20 amino acids encoded by the standard genetic code. It is considered a conditionally essential amino acid.[2] Its side-chain is an amide formed by replacing the side-chain hydroxyl of glutamic acid with an amine functional group, making it the amide of glutamic acid. Its codons are CAA and CAG. In human blood, glutamine is the most abundant free amino acid, with a concentration of about 500–900 µmol/l.[3]
Contents
- 1 Structure
- 2 Functions
- 2.1 Producing and consuming organs
- 2.1.1 Producers
- 2.1.2 Consumers
- 2.2 Examples of use
- 2.2.1 Aiding recovery after surgery
- 3 Nutrition
- 3.1 Occurrences in nature
- 4 See also
- 5 References
- 6 External links
Structure
Glutamine zwitterionic forms at neutral pH: L-glutamine (left) and D-glutamine
Functions
Glutamine plays a role in a variety of biochemical functions:
- Protein synthesis, as any other of the 20 proteinogenic amino acids
- Regulation of acid-base balance in the kidney by producing ammonium[4]
- Cellular energy, as a source, next to glucose[5]
- Nitrogen donation for many anabolic processes, including the synthesis of purines[3]
- Carbon donation, as a source, refilling the citric acid cycle[6]
- Nontoxic transporter of ammonia in the blood circulation
Producing and consuming organs
Producers
Glutamine is synthesized by the enzyme glutamine synthetase from glutamate and ammonia. The most relevant glutamine-producing tissue is the muscle mass, accounting for about 90% of all glutamine synthesized. Glutamine is also released, in small amounts, by the lung and the brain.[7] Although the liver is capable of relevant glutamine synthesis, its role in glutamine metabolism is more regulatory than producing, since the liver takes up large amounts of glutamine derived from the gut.[3]
Consumers
The most eager consumers of glutamine are the cells of intestines,[3] the kidney cells for the acid-base balance, activated immune cells,[8] and many cancer cells.[6] In respect to the last point mentioned, different glutamine analogues, such as DON, Azaserine or Acivicin, are tested as anticancer drugs.
Examples of use
In catabolic states of injury and illness, glutamine becomes conditionally essential (requiring intake from food or supplements).[9] Glutamine has been studied extensively over the past 10–15 years, and has been shown to be useful in treatment of injuries, trauma, burns, and treatment-related side effects of cancer, as well as in wound healing for postoperative patients. Glutamine is also marketed as a supplement used for muscle growth in weightlifting, bodybuilding, endurance, and other sports. Evidence indicates glutamine, when orally loaded, may increase plasma HGH levels by stimulating the anterior pituitary gland.[10] In biological research, L-glutamine is commonly added to the media in cell culture.[11][12] However, the high level of glutamine in the culture media may inhibit other amino acid transport activities.[13]
Aiding recovery after surgery
Glutamine is also known to have various side effects in reducing healing time after operations. Hospital-stay times after abdominal surgery can be reduced by providing parenteral nutrition regimens containing high amounts of glutamine to patients. Clinical trials have revealed patients on supplementation regimens containing glutamine have improved nitrogen balances, generation of cysteinyl-leukotrienes from polymorphonuclear neutrophil granulocytes, and improved lymphocyte recovery and intestinal permeability (in postoperative patients), in comparison to those that have no glutamine within their dietary regimen, all without any side effects.[14]
Nutrition
Occurrences in nature
Glutamine is the most abundant naturally occurring, nonessential amino acid in the human body, and one of the few amino acids that can directly cross the blood–brain barrier.[15] In the body, it is found circulating in the blood, as well as stored in the skeletal muscles. It becomes conditionally essential (requiring intake from food or supplements) in states of illness or injury.[9]
Dietary sources
Dietary sources of L-glutamine include beef, chicken, fish, eggs, milk, dairy products, wheat, cabbage, beets, beans, spinach, and parsley. Small amounts of free L-glutamine are also found in vegetable juices.[9]
See also
References
- ^ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-311. ISBN 0-8493-0462-8. .
- ^ Dietary Reference Intakes: The Essential Guide to Nutrient Requirements, published by the Institute of Medicine's Food and Nutrition Board, currently available online at http://fnic.nal.usda.gov/dietary-guidance/dietary-reference-intakes/dri-reports
- ^ a b c d Brosnan, John T. (June 2003). "Interorgan amino acid transport and its regulation". J. Nutr. 133 (6 Suppl 1): 2068S–2072S. PMID 12771367.
- ^ Hall, John E.; Guyton, Arthur C. (2006). Textbook of medical physiology (11th ed.). St. Louis, Mo: Elsevier Saunders. p. 393. ISBN 0-7216-0240-1.
- ^ Aledo, J. C. (2004). "Glutamine breakdown in rapidly dividing cells: Waste or investment?". BioEssays 26 (7): 778–785. doi:10.1002/bies.20063. PMID 15221859. edit
- ^ a b Yuneva, M.; Zamboni, N.; Oefner, P.; Sachidanandam, R.; Lazebnik, Y. (2007). "Deficiency in glutamine but not glucose induces MYC-dependent apoptosis in human cells". The Journal of Cell Biology 178 (1): 93–105. doi:10.1083/jcb.200703099. PMC 2064426. PMID 17606868. edit
- ^ Newsholme, P.; Lima, M. M. R.; Procopio, J.; Pithon-Curi, T. C.; Doi, S. Q.; Bazotte, R. B.; Curi, R. (2003). "Glutamine and glutamate as vital metabolites". Brazilian Journal of Medical and Biological Research 36 (2): 153–163. doi:10.1590/S0100-879X2003000200002. PMID 12563517. edit
- ^ Newsholme, P. (2001). "Why is L-glutamine metabolism important to cells of the immune system in health, postinjury, surgery or infection?". The Journal of nutrition 131 (9 Suppl): 2515S–2522S; discussion 2522S–4S. PMID 11533304. edit
- ^ a b c "Glutamine". Medical Reference Guide. University of Maryland Medical Center. 2011-05-24. Archived from the original on 2009-12-09. Retrieved 2014-03-03.
- ^ Welbourne, T. C. (1995). "Increased plasma bicarbonate and growth hormone after an oral glutamine load". The American journal of clinical nutrition 61 (5): 1058–1061. PMID 7733028. edit
- ^ Thilly, William G. (1986). Mammalian cell technology. London: Butterworths. p. 110. ISBN 0-409-90029-X. Retrieved 2012-06-22. "13 amino acids in Eagle's popular culture medium...are arginine, cyst(e)ine, glutamine..."
- ^ Yang H, Roth CM, Ierapetritou MG. (2011) Analysis of amino acid supplementation effects on hepatocyte cultures using flux balance analysis, OMICS, A Journal of Integrative Biology, 15(7-8): 449–460.
- ^ Yang H, Ierapetritou MG, Roth CM. (2010) Effects of amino acid transport limitations on cultured hepatocytes, Biophysical Chemistry, 152(1-3):89-98.
- ^ Morlion, B. J.; Stehle, P.; Wachtler, P.; Siedhoff, H. P.; Köller, M.; König, W.; Fürst, P.; Puchstein, C. (1998). "Total Parenteral Nutrition with Glutamine Dipeptide After Major Abdominal Surgery". Annals of Surgery 227 (2): 302–308. doi:10.1097/00000658-199802000-00022. PMC 1191250. PMID 9488531. edit
- ^ Lee, W. J.; Hawkins, R. A.; Viña, J. R.; Peterson, D. R. (1998). "Glutamine transport by the blood-brain barrier: A possible mechanism for nitrogen removal". The American journal of physiology 274 (4 Pt 1): C1101–C1107. PMID 9580550. edit
External links
|
Other alimentary tract and metabolism products (A16)
|
|
| Amino acids and derivatives |
- Levocarnitine
- Ademetionine
- Levoglutamide
- Cysteamine
- Carglumic acid
- Betaine
|
|
| Enzymes |
- Carbohydrate metabolism: sucrase (Sacrosidase)
- alpha-glucosidase (Alglucosidase alfa)
- Glycolipid/sphingolipid: glucocerebrosidase (Alglucerase
- Imiglucerase
- Taliglucerase alfa
- Velaglucerase alfa)
- alpha-galactosidase (Agalsidase alfa
- Agalsidase beta)
- Glycosaminoglycan: iduronidase (Laronidase)
- arylsulfatase B (Galsulfase)
- iduronate-2-sulfatase (Idursulfase)
|
|
Various alimentary tract
and metabolism products |
- Anethole trithione
- Glycerol phenylbutyrate
- Miglustat
- Nitisinone
- Sapropterin
- Sodium phenylbutyrate
- Teduglutide
- Tioctic acid
- Zinc acetate
|
|
|
|
anat (t, g, p)/phys/devp/enzy
|
noco/cong/tumr, sysi/epon
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proc, drug (A2A/2B/3/4/5/6/7/14/16), blte
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|
|
|
|
The 20 common amino acids
|
|
| General topics |
- Protein
- Peptide
- Genetic code
|
|
|
| By properties |
|
Aliphatic
|
- Branched-chain amino acids (Valine
- Isoleucine
- Leucine)
- Methionine
- Alanine
- Proline
- Glycine
|
|
|
Aromatic
|
- Phenylalanine
- Tyrosine
- Tryptophan
- Histidine
|
|
|
Polar, uncharged
|
- Asparagine
- Glutamine
- Serine
- Threonine
|
|
|
Positive charge (pKa)
|
- Lysine (≈10.8)
- Arginine (≈12.5)
- Histidine (≈6.1)
|
|
|
Negative charge (pKa)
|
- Aspartic acid (≈3.9)
- Glutamic acid (≈4.1)
- Cysteine (≈8.3)
- Tyrosine (≈10.1)
|
|
|
| Other classifications |
- Essential amino acid
- Ketogenic amino acid
- Glucogenic amino acid
- Non-proteinogenic amino acid
|
|
- Biochemical families: carbohydrates
- alcohols
- glycoproteins
- glycosides
- lipids
- eicosanoids
- fatty acids / intermediates
- glycerides
- phospholipids
- sphingolipids
- steroids
- nucleic acids
- constituents / intermediates
- proteins
- Amino acids / intermediates
- tetrapyrroles / intermediates
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|
|
Dietary supplements
|
|
| Types |
- Amino acids
- Bodybuilding supplement
- Energy drink
- Energy bar
- Fatty acids
- Herbal Supplements
- Minerals
- Prebiotics
- Probiotics (Lactobacillus
- Bifidobacterium)
- Protein bar
- Vitamins
|
|
Vitamins and
"minerals" (chemical elements) |
- Retinol (Vitamin A)
- B vitamins: Thiamine (B1)
- Riboflavin (B2)
- Niacin (B3)
- Pantothenic acid (B5)
- Pyridoxine (B6)
- Biotin (B7)
- Folic acid (B9)
- Cyanocobalamin (B12)
- Ascorbic acid (Vitamin C)
- Ergocalciferol and Cholecalciferol (Vitamin D)
- Tocopherol (Vitamin E)
- Naphthoquinone (Vitamin K)
- Calcium
- Choline
- Chromium
- Cobalt
- Copper
- Fluorine
- Iodine
- Iron
- Magnesium
- Manganese
- Molybdenum
- Phosphorus
- Potassium
- Selenium
- Sodium
- Sulfur
- Zinc
|
|
| Other common ingredients |
- AAKG
- Carnitine
- Chondroitin sulfate
- Cod liver oil
- Copper gluconate
- Creatine/Creatine supplements
- Dietary fiber
- Echinacea
- Elemental calcium
- Ephedra
- Fish oil
- Folic acid
- Ginseng
- Glucosamine
- Glutamine
- Grape seed extract
- Guarana
- Iron supplements
- Japanese Honeysuckle
- Krill oil
- Lingzhi
- Linseed oil
- Lipoic acid
- Milk thistle
- Melatonin
- Red yeast rice
- Royal jelly
- Saw palmetto
- Spirulina
- St John's wort
- Taurine
- Wheatgrass
- Wolfberry
- Yohimbine
- Zinc gluconate
|
|
| Related articles |
- Codex Alimentarius
- Enzyte
- Hadacol
- Herbal tea
- Nutraceutical
- Multivitamin
- Nutrition
|
|
|
Glutamatergics
|
|
| Ionotropic |
|
AMPA
|
- Agonists: 5-Fluorowillardiine
- AMPA
- Domoic acid
- Quisqualic acid; Positive allosteric modulators: Aniracetam
- Cyclothiazide
- CX-516
- CX-546
- CX-614
- CX-691
- CX-717
- Diazoxide
- HCTZ
- IDRA-21
- LY-392,098
- LY-404,187
- LY-451,395
- LY-451,646
- LY-503,430
- Org 26576
- Oxiracetam
- PEPA
- Piracetam
- Pramiracetam
- S-18986
- Sunifiram
- Unifiram
Antagonists: ATPO
- Barbiturates
- BGG492
- Caroverine
- CNQX
- DNQX
- GYKI-52466
- NBQX
- Perampanel
- Talampanel
- Tezampanel
- Topiramate; Negative allosteric modulators: GYKI-53,655
|
|
|
NMDA
|
- Agonists: Glutamate/active site competitive agonists: Aspartate
- Glutamate
- Homoquinolinic acid
- Ibotenic acid
- NMDA
- Quinolinic acid
- Tetrazolylglycine; Glycine site agonists: ACBD
- ACPC
- ACPD
- Alanine
- CCG
- Cycloserine
- DHPG
- Fluoroalanine
- Glycine
- GLYX-13
- HA-966
- L-687,414
- Milacemide
- NRX-1074
- Sarcosine
- Serine
- Tetrazolylglycine; Polyamine site agonists: Acamprosate
- Spermidine
- Spermine
Antagonists: Competitive antagonists: AP5 (APV)
- AP7
- CGP-37849
- CGP-39551
- CGP-39653
- CGP-40116
- CGS-19755
- CPP
- LY-233,053
- LY-235,959
- LY-274,614
- MDL-100,453
- Midafotel (d-CPPene)
- NPC-12,626
- NPC-17,742
- PBPD
- PEAQX
- Perzinfotel
- PPDA
- SDZ-220581
- Selfotel; Noncompetitive antagonists: ARR-15,896
- Caroverine
- Dexanabinol
- FPL-12495
- FR-115,427
- Hodgkinsine
- Magnesium
- MDL-27,266
- NPS-1506
- Psychotridine
- Zinc; Uncompetitive pore blockers: 2-MDP
- 3-MeO-PCP
- 8A-PDHQ
- Alaproclate
- Amantadine
- Aptiganel
- ARL-12,495
- ARL-15,896-AR
- ARL-16,247
- Budipine
- Delucemine
- Dexoxadrol
- Dextrallorphan
- Dieticyclidine
- Dizocilpine
- Endopsychosin
- Esketamine
- Etoxadrol
- Eticyclidine
- Gacyclidine
- Ibogaine
- Indantadol
- Ketamine
- Ketobemidone
- Lanicemine
- Loperamide
- Memantine
- Methadone (Levomethadone)
- Methorphan (Dextromethorphan
- Levomethorphan)
- Methoxetamine
- Milnacipran
- Morphanol (Dextrorphan
- Levorphanol)
- NEFA
- Neramexane
- Nitromemantine
- Nitrous oxide
- Noribogaine
- Orphenadrine
- PCPr
- Pethidine (meperidine)
- Phencyclamine
- Phencyclidine
- Propoxyphene
- Remacemide
- Rhynchophylline
- Rimantadine
- Rolicyclidine
- Sabeluzole
- Tenocyclidine
- Tiletamine
- Tramadol
- Xenon; Glycine site antagonists: ACEA-1021
- ACEA-1328
- ACC
- Carisoprodol
- CGP-39653
- CKA
- DCKA
- Felbamate
- Gavestinel
- GV-196,771
- Kynurenic acid
- L-689,560
- L-701,324
- Licostinel
- LU-73,068
- MDL-105,519
- Meprobamate
- MRZ 2/576
- PNQX
- ZD-9379; NR2B subunit antagonists: Besonprodil
- CERC-301 (MK-0657)
- CO-101,244 (PD-174,494)
- Eliprodil
- Haloperidol
- Ifenprodil
- Isoxsuprine
- Nylidrin
- Ro8-4304
- Ro25-6981
- Traxoprodil; Polyamine site antagonists: Arcaine
- Co 101676
- Diaminopropane
- Acamprosate
- Diethylenetriamine
- Huperzine A
- Putrescine
- Ro 25-6981; Unclassified/unsorted antagonists: Chloroform
- Diethyl ether
- Diphenidine
- Enflurane
- Ethanol (alcohol)
- Halothane
- Isoflurane
- Methoxyflurane
- Toluene
- Trichloroethane
- Trichloroethanol
- Trichloroethylene
- Xylene
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Kainate
|
- Agonists: 5-Iodowillardiine
- ATPA
- Domoic acid
- Kainic acid
- LY-339,434
- SYM-2081
Antagonists: BGG492
- CNQX
- DNQX
- LY-382,884
- NBQX
- NS102
- Tezampanel
- Topiramate
- UBP-302; Negative allosteric modulators: NS-3763
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| Metabotropic |
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Group I
|
- Agonists: Non-selective: ACPD
- DHPG
- Quisqualic acid; mGlu1-selective: Ro01-6128
- Ro67-4853
- Ro67-7476
- VU-71; mGlu5-selective: ADX-47273
- CDPPB
- CHPG
- DFB
- VU-1545
Antagonists: Non-selective: MCPG
- NPS-2390; mGlu1-selective: BAY 36-7620
- CPCCOEt
- LY-367,385
- LY-456,236; mGlu5-selective: CTEP
- DMeOB
- LY-344,545
- Mavoglurant
- SIB-1757
- SIB-1893; Negative allosteric modulators:
- Basimglurant
- Dipraglurant
- Fenobam
- GRN-529
- MPEP
- MTEP
- Raseglurant
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Group II
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- Agonists: Non-selective: CBiPES
- DCG-IV
- Eglumegad
- LY-379,268
- LY-404,039
- LY-487,379
- MGS-0028; mGlu2-selective: BINA
- LY-566,332
Antagonists: Non-selective: APICA
- EGLU
- HYDIA
- LY-307,452
- LY-341,495
- MCPG
- MGS-0039; mGlu2-selective: PCCG-4
- mGlu3-selective: CECXG; Negative allosteric modulators: Decoglurant
- RO4491533
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Group III
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- Agonists: Non-selective: L-AP4; mGlu4-selective: PHCCC
- VU-001,171
- VU-0155,041; mGlu7-selective: AMN082; mGlu8-selective: DCPG
Antagonists: Non-selective: CPPG
- MAP4
- MSOP
- MPPG
- MTPG
- UBP-1112; mGlu7-selective: MMPIP
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Transporter
inhibitors |
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| Others |
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Precursors
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Cofactors
|
- α-Ketoglutaric acid
- Iron
- Sulfur
- Vitamin B2 (as FAD and FMN)
- Vitamin B3 (as NADPH)
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Others
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- N-Acetylcysteine
- L-Theanine
- Riluzole
- Tianeptine
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GABAergics
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Receptor
ligands |
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GABAA
|
- Agonists: Main site: Bamaluzole
- Gaboxadol
- Ibotenic acid
- Isoguvacine
- Isonipecotic acid
- Muscimol (Amanita muscaria)
- Progabide
- SL 75102
- Thiomuscimol
- Tolgabide; Positive allosteric modulators: Ethanol • isopropanol • 2M2B
- Barbiturates
- Benzodiazepines
- Carbamates
- Chlormezanone
- Clomethiazole
- Etomidate
- Kavalactones (kava)
- Loreclezole
- Metomidate
- Neuroactive steroids
- Nonbenzodiazepines (β-carbolines, cyclopyrrolones, imidazopyridines, pyrazolopyrimidines, etc.)
- Phenols
- Piperidinediones
- Propanidid
- Pyrazolopyridines
- Quinazolinones
- ROD-188
- Skullcap
- Stiripentol
- Valerenic acid (valerian)
Note: See the GABAA receptor PAMs navbox for a full list of GABAA positive allosteric modulators.
- Antagonists: Main site: Bicuculline
- Gabazine
- Pitrazepin
- Quisqualamine; Negative allosteric modulators: 17-Phenylandrostenol (17-PA)
- α5IA
- Bilobalide
- Cicutoxin
- Cyclothiazide
- DMCM
- Flumazenil
- Flurothyl
- Furosemide
- Iomazenil (123I)
- L-655,708
- Oenanthotoxin
- Penicillin
- Pentylenetetrazol
- Picrotoxin
- PWZ-029
- Radequinil
- Ro15-4513
- Sarmazenil
- Suritozole
- Terbequinil
- Thujone
- Thiocolchicoside
- ZK-93426
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GABAB
|
- Agonists: Main site: 1,4-Butanediol
- Baclofen
- GBL
- GHB
- GHV
- GVL
- Lesogaberan
- Phenibut
- Progabide
- SKF-97,541
- Tolgabide; Positive allosteric modulators: BHF-177
- BHFF
- BSPP
- CGP-7930
- GS-39783
Antagonists: Main site: CGP-35348
- Phaclofen
- Saclofen
- SCH-50911
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GABAC
|
- Agonists: Main site: CACA
- CAMP
- GABOB
- N4-Chloroacetylcytosine arabinoside
- Progabide
- Tolgabide
Antagonists: Main site: Bilobalide
- TPMPA
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Reuptake
inhibitors |
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Plasmalemmal
|
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GAT inhibitors
|
- CI-966
- Deramciclane
- EF-1502
- Gabaculine
- Guvacine
- Nipecotic acid
- NNC 05-2090
- SKF-89976A
- SNAP-5114
- Tiagabine
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Enzyme
inhibitors |
|
Anabolism
|
|
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Catabolism
|
|
GABA-T inhibitors
|
- 3-Hydrazinopropionic acid
- Aminooxyacetic acid
- Gabaculine
- Isoniazid
- Phenelzine
- Phenylethylidenehydrazine
- Rosmarinic acid (lemon balm)
- Sodium valproate
- Valnoctamide
- Valproate pivoxil
- Valproate semisodium (divalproex sodium)
- Valproic acid
- Valpromide
- Vigabatrin
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| Others |
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Precursors
|
|
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Cofactors
|
- Vitamin B6 (pyridoxine
- pyridoxamine
- pyridoxal phosphate)
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Others
|
- Hopantenic acid
- Picamilon
- L-Theanine
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