HOME
ListMoto - Glycine


--- Advertisement ---



Foloogical sci For other uses, see Glycine
Glycine
(other). "Gly" redirects here. For the unit of measurement, see light-year.

Glycine[1]

Canonical amino acid form

Zwitterionic form at physiological pH

Names

Preferred IUPAC name

Glycine

Systematic IUPAC name

Aminoethanoic acid

Other names Aminoacetic acid Glycocoll

Identifiers

CAS Number

56-40-6 Y

3D model (JSmol)

Interactive image

Abbreviations Gly, G

ChEBI

CHEBI:15428 Y

ChEMBL

ChEMBL773 Y

ChemSpider

730 Y

DrugBank

DB00145 Y

ECHA InfoCard 100.000.248

EC Number 200-272-2

IUPHAR/BPS

727

KEGG

D00011 Y

PubChem CID

750

UNII

TE7660XO1C Y

InChI

InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5) Y Key: DHMQDGOQFOQNFH-UHFFFAOYSA-N Y

InChI=1/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5) Key: DHMQDGOQFOQNFH-UHFFFAOYAW

SMILES

C(C(=O)O)N

Properties

Chemical formula

C2H5NO2

Molar mass 75.07 g·mol−1

Appearance White solid

Density 1.607 g/cm3

Melting point 233 °C (451 °F; 506 K) (decomposition)

Solubility
Solubility
in water

24.99 g/100 mL (25 °C)[2]

Solubility soluble in pyridine sparingly soluble in ethanol insoluble in ether

Acidity (pKa) 2.34 (carboxyl), 9.6 (amino)[3]

Magnetic susceptibility (χ)

-40.3·10−6 cm3/mol

Pharmacology

ATC code

B05CX03 (WHO)

Hazards

Safety data sheet See: data page

Lethal dose or concentration (LD, LC):

LD50 (median dose)

2600 mg/kg (mouse, oral)

Supplementary data page

Structure and properties

Refractive index
Refractive index
(n), Dielectric constant
Dielectric constant
(εr), etc.

Thermodynamic data

Phase behaviour solid–liquid–gas

Spectral data

UV, IR, NMR, MS

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)

Infobox references

Glycine
Glycine
(symbol Gly or G[4]) (/ˈɡlʌɪsiːn/)[5] is the amino acid that has a single hydrogen atom as its side chain. It is the simplest possible amino acid. The chemical formula of glycine is NH2‐CH2‐COOH. Glycine
Glycine
is one of the proteinogenic amino acids. In the genetic code, all codons starting with GG, namely GGU, GGC, GGA, GGG, code for glycine. Glycine
Glycine
is a colorless, sweet-tasting crystalline solid. It is the only achiral proteinogenic amino acid. It can fit into hydrophilic or hydrophobic environments, due to its minimal side chain of only one hydrogen atom. The acyl radical is glycyl.

Glycine
Glycine
is a white crystalline solid

Contents

1 History and etymology 2 Production 3 Acid-base properties 4 Metabolism

4.1 Biosynthesis 4.2 Degradation

5 Physiological function

5.1 As a biosynthetic intermediate 5.2 As a neurotransmitter

6 Uses

6.1 Animal and human foods 6.2 Cosmetics and miscellaneous applications 6.3 Chemical feedstock 6.4 Laboratory research

7 Presence in space 8 See also 9 References 10 Further reading 11 External links

History and etymology[edit] Glycine
Glycine
was discovered in 1820 by Henri Braconnot
Henri Braconnot
when he hydrolyzed gelatin by boiling it with sulfuric acid.[6] He originally called it "sugar of gelatin",[7] but a student of Liebig showed that it contained Nitrogen, and Berzelius renamed it "glycine".[8] The name comes from the Greek word γλυκύς "sweet tasting"[9] (which is also related to the prefixes glyco- and gluco-, as in glycoprotein and glucose). Another early name for glycine was "glycocoll".[10] Production[edit] Although glycine can be isolated from hydrolyzed protein, this is not used for industrial production, as it can be manufactured more conveniently by chemical synthesis.[11] The two main processes are amination of chloroacetic acid with ammonia, giving glycine and ammonium chloride,[12] and the Strecker amino acid synthesis,[13] which is the main synthetic method in the United States and Japan.[14] About 15 thousand tonnes are produced annually in this way.[15] Glycine
Glycine
is also cogenerated as an impurity in the synthesis of EDTA, arising from reactions of the ammonia coproduct.[16] Acid-base properties[edit]

In aqueous solution, glycine itself is amphoteric: at low pH the molecule can be protonated with a pKa of about 2.4 and at high pH it loses a proton with a pKa of about 9.6 (precise values of pKa depend on temperature and ionic strength). Metabolism[edit] Biosynthesis[edit] Glycine
Glycine
is not essential to the human diet, as it is biosynthesized in the body from the amino acid serine, which is in turn derived from 3-phosphoglycerate, but the metabolic capacity for glycine biosynthesis does not satisfy the need for collagen synthesis.[17] In most organisms, the enzyme serine hydroxymethyltransferase catalyses this transformation via the cofactor pyridoxal phosphate:[18]

serine + tetrahydrofolate → glycine + N5,N10-Methylene tetrahydrofolate + H2O

In the liver of vertebrates, glycine synthesis is catalyzed by glycine synthase (also called glycine cleavage enzyme). This conversion is readily reversible:[18]

CO2 + NH+ 4 + N5,N10-Methylene tetrahydrofolate + NADH
NADH
+ H+ ⇌ Glycine
Glycine
+ tetrahydrofolate + NAD+

Degradation[edit] Glycine
Glycine
is degraded via three pathways. The predominant pathway in animals and plants is the reverse of the glycine synthase pathway mentioned above. In this context, the enzyme system involved is usually called the glycine cleavage system:[18]

Glycine
Glycine
+ tetrahydrofolate + NAD+ ⇌ CO2 + NH+ 4 + N5,N10-Methylene tetrahydrofolate + NADH
NADH
+ H+

In the second pathway, glycine is degraded in two steps. The first step is the reverse of glycine biosynthesis from serine with serine hydroxymethyl transferase. Serine
Serine
is then converted to pyruvate by serine dehydratase.[18] In the third pathway of glycine degradation, glycine is converted to glyoxylate by D-amino acid oxidase. Glyoxylate
Glyoxylate
is then oxidized by hepatic lactate dehydrogenase to oxalate in an NAD+-dependent reaction.[18] The half-life of glycine and its elimination from the body varies significantly based on dose.[19] In one study, the half-life varied between 0.5 and 4.0 hours.[19] Physiological function[edit] The principal function of glycine is as a precursor to proteins. Most proteins incorporate only small quantities of glycine, a notable exception being collagen, which contains about 35% glycine due to its periodically repeated role in the formation of collagen's helix structure in conjunction with hydroxyproline.[18][20] In the genetic code, glycine is coded by all codons starting with GG, namely GGU, GGC, GGA and GGG. As a biosynthetic intermediate[edit] In higher eukaryotes, δ-aminolevulinic acid, the key precursor to porphyrins, is biosynthesized from glycine and succinyl-CoA by the enzyme ALA synthase. Glycine
Glycine
provides the central C2N subunit of all purines.[18] As a neurotransmitter[edit] Glycine
Glycine
is an inhibitory neurotransmitter in the central nervous system, especially in the spinal cord, brainstem, and retina. When glycine receptors are activated, chloride enters the neuron via ionotropic receptors, causing an Inhibitory postsynaptic potential (IPSP). Strychnine
Strychnine
is a strong antagonist at ionotropic glycine receptors, whereas bicuculline is a weak one. Glycine
Glycine
is a required co-agonist along with glutamate for NMDA
NMDA
receptors. In contrast to the inhibitory role of glycine in the spinal cord, this behaviour is facilitated at the (NMDA) glutamatergic receptors which are excitatory.[21] The LD50 of glycine is 7930 mg/kg in rats (oral),[22] and it usually causes death by hyperexcitability. Uses[edit] In the US, glycine is typically sold in two grades: United States Pharmacopeia (“USP”), and technical grade. USP grade sales account for approximately 80 to 85 percent of the U.S. market for glycine. Where the customer’s purity requirements exceed the minimum required under the USP standard, for example for some pharmaceutical applications such as intravenous injections, pharmaceutical grade glycine, often produced to proprietary specifications and typically sold at a premium over USP grade glycine, may be used. Technical grade glycine, which may or may not meet USP grade standards, is sold at a lower price for use in industrial applications; e.g., as an agent in metal complexing and finishing.[23] Animal and human foods[edit] USP glycine has a wide variety of uses, including as an additive in pet food and animal feed, in foods and pharmaceuticals as a sweetener/taste enhancer, or as a component of food supplements and protein drinks. Two glycine molecules in a dipeptide form (Diglycinate) are sometimes used as a way to enhance the absorption of mineral supplementation since, only when bound to a dipeptide, can be absorbed through a different set of transporters.[24] Cosmetics and miscellaneous applications[edit] Glycine
Glycine
serves as a buffering agent in antacids, analgesics, antiperspirants, cosmetics, and toiletries. A variety of industrial and chemical processes use glycine or its derivatives, such as the production of fertilizers and metal complexing agents.[25] Chemical feedstock[edit] Glycine
Glycine
is an intermediate in the synthesis of a variety of chemical products. It is used in the manufacture of the herbicide glyphosate.[26] Laboratory research[edit] Glycine
Glycine
is a significant component of some solutions used in the SDS-PAGE method of protein analysis. It serves as a buffering agent, maintaining pH and preventing sample damage during electrophoresis. Glycine
Glycine
is also used to remove protein-labeling antibodies from Western blot
Western blot
membranes to enable the probing of numerous proteins of interest from SDS-PAGE gel. This allows more data to be drawn from the same specimen, increasing the reliability of the data, reducing the amount of sample processing, and number of samples required. This process is known as stripping. Presence in space[edit] The presence of glycine outside the earth was confirmed in 2009, based on the analysis of samples that had been taken in 2004 by the NASA spacecraft Stardust from comet Wild 2
Wild 2
and subsequently returned to earth. Glycine
Glycine
had previously been identified in the Murchison meteorite in 1970.[27] The discovery of cometary glycine bolstered the theory of panspermia, which claims that the "building blocks" of life are widespread throughout the Universe.[28] In 2016, detection of glycine within Comet 67P/Churyumov-Gerasimenko by the Rosetta spacecraft was announced.[29] The detection of glycine outside the solar system in the interstellar medium has been debated.[30] In 2008, the Max Planck Institute for Radio Astronomy discovered the glycine-like molecule aminoacetonitrile in the Large Molecule
Molecule
Heimat, a giant gas cloud near the galactic center in the constellation Sagittarius.[31] See also[edit]

Trimethylglycine Amino acid
Amino acid
neurotransmitter

References[edit]

^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, ISBN 091191028X , 4386. ^ "Solubilities and densities". Prowl.rockefeller.edu. Retrieved 2013-11-13.  ^ Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959. ^ "Nomenclature and Symbolism for Amino Acids and Peptides". IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived from the original on 9 October 2008. Retrieved 5 March 2018.  ^ https://en.oxforddictionaries.com/definition/glycine ^ R.H.A. Plimmer (1912) [1908]. R.H.A. Plimmer; F.G. Hopkins, eds. The chemical composition of the proteins. Monographs on biochemistry. Part I. Analysis (2nd ed.). London: Longmans, Green and Co. p. 82. Retrieved January 18, 2010.  ^ MacKenzie, Colin (1822). One Thousand Experiments in Chemistry: With Illustrations of Natural Phenomena; and Practical Observations on the Manufacturing and Chemical Processes at Present Pursued in the Successful Cultivation of the Useful Arts ... Sir R. Phillips and Company.  ^ Nye, Mary Jo (1999). Before Big Science: The Pursuit of Modern Chemistry and Physics, 1800-1940. Harvard University Press. ISBN 9780674063822.  ^ "glycine". Oxford Dictionaries. Retrieved 2015-12-06.  ^ Ihde, Aaron J. (1970). The Development of Modern Chemistry. Courier Corporation. ISBN 9780486642352.  ^ Okafor, Nduka (2016-03-09). Modern Industrial Microbiology and Biotechnology. CRC Press. ISBN 9781439843239.  ^ Ingersoll, A. W.; Babcock, S. H. (1932). "Hippuric acid". Organic Syntheses. 12: 40. ; Collective Volume, 2, p. 328  ^ Wiley (2007-12-14). Kirk-Othmer Food and Feed Technology, 2 Volume Set. John Wiley & Sons. ISBN 9780470174487.  ^ " Glycine
Glycine
Conference (prelim)". USITC. Archived from the original on 2012-02-22. Retrieved 2014-06-13. CS1 maint: BOT: original-url status unknown (link) ^ Drauz, Karlheinz; Grayson, Ian; Kleemann, Axel; Krimmer, Hans-Peter; Leuchtenberger, Wolfgang and Weckbecker, Christoph (2007) "Amino Acids" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. doi:10.1002/14356007.a02_057.pub2 ^ Hart, J. Roger (2005) "Ethylenediaminetetraacetic Acid and Related Chelating Agents" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_095 ^ Meléndez-Hevia, E; De Paz-Lugo, P; Cornish-Bowden, A; Cárdenas, M. L. (December 2009). "A weak link in metabolism: the metabolic capacity for glycine biosynthesis does not satisfy the need for collagen synthesis". Journal of biosciences. 34 (6): 853–72. doi:10.1007/s12038-009-0100-9. PMID 20093739.  ^ a b c d e f g Nelson, David L.; Cox, Michael M. (2005), Principles of Biochemistry (4th ed.), New York: W. H. Freeman, pp. 127, 675–77, 844, 854, ISBN 0-7167-4339-6  ^ a b Hahn RG (1993). "Dose-dependent half-life of glycine". Urological Research. 21 (4): 289–291. doi:10.1007/BF00307714. PMID 8212419.  ^ Szpak, Paul (2011). "Fish bone chemistry and ultrastructure: implications for taphonomy and stable isotope analysis". Journal of Archaeological Science. 38 (12): 3358–3372. doi:10.1016/j.jas.2011.07.022.  ^ "Recent development in NMDA
NMDA
receptors". Chinese Medical Journal. 2000.  ^ "Safety (MSDS) data for glycine". The Physical and Theoretical Chemistry Laboratory Oxford University. 2005. Retrieved 2006-11-01.  ^ " Glycine
Glycine
From Japan and Korea" (PDF). U.S. International Trade Commission. January 2008. Retrieved 2014-06-13.  ^ Kurtis, Frank,; Kamal, Patel,; Gregory, Lopez,; Bill, Willis, (2017-08-01). " Glycine
Glycine
Research Analysis". Examine.com.  ^ "Notice of Preliminary Determination of Sales at Less Than Fair Value: Glycine
Glycine
From India" Federal Register 72 (7 November 2007): 62827. ^ Stahl, Shannon S.; Alsters, Paul L. (2016-07-13). Liquid Phase Aerobic Oxidation Catalysis: Industrial Applications and Academic Perspectives. John Wiley & Sons. ISBN 9783527690152.  ^ Kvenvolden, Keith A.; Lawless, James; Pering, Katherine; Peterson, Etta; Flores, Jose; Ponnamperuma, Cyril; Kaplan, Isaac R.; Moore, Carleton (1970). "Evidence for extraterrestrial amino-acids and hydrocarbons in the Murchison meteorite". Nature. 228 (5275): 923–926. Bibcode:1970Natur.228..923K. doi:10.1038/228923a0. PMID 5482102.  ^ Reuters (18 August 2009). "Building block of life found on comet - Thomson Reuters 2009". Retrieved 2009-08-18.  ^ European Space Agency (27 May 2016). "Rosetta's comet contains ingredients for life". Retrieved 2016-06-05.  ^ Snyder LE, Lovas FJ, Hollis JM, et al. (2005). "A rigorous attempt to verify interstellar glycine". Astrophys J. 619 (2): 914–930. arXiv:astro-ph/0410335 . Bibcode:2005ApJ...619..914S. doi:10.1086/426677.  ^ Staff. "Organic Molecule, Amino Acid-Like, Found In Constellation Sagittarius 27 March 2008 - Science Daily". Retrieved 2008-09-16. 

Further reading[edit]

Kuan YJ, Charnley SB, Huang HC, et al. (2003). "Interstellar glycine". Astrophys J. 593 (2): 848–867. Bibcode:2003ApJ...593..848K. doi:10.1086/375637.  Rachel Nowak. " Amino acid
Amino acid
found in deep space - 18 July 2002 - New Scientist". Retrieved 2007-07-01. 

External links[edit]

Wikimedia Commons has media related to Glycine.

Glycine
Glycine
MS Spectrum Glycine
Glycine
at PDRHealth.com Glycine
Glycine
cleavage system Glycine
Glycine
Therapy - A New Direction for Schizophrenia Treatment? "Organic Molecule, Amino Acid-Like, Found In Constellation Sagittarius". ScienceDaily. 27 March 2008.  Guochuan E. Tsai (1 December 2008). "A New Class of Antipsychotic Drugs: Enhancing Neurotransmission Mediated by NMDA
NMDA
Receptors". Psychiatric Times. 25 (14).  ChemSub Online (Glycine). NASA
NASA
scientists have discovered glycine, a fundamental building block of life, in samples of comet Wild 2
Wild 2
returned by NASA's Stardust spacecraft.

v t e

The encoded amino acid

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
Lysine
(≈10.8) Arginine
Arginine
(≈12.5) Histidine
Histidine
(≈6.1)

Negative charge (pKa)

Aspartic acid
Aspartic acid
(≈3.9) Glutamic acid
Glutamic acid
(≈4.1) Cysteine
Cysteine
(≈8.3) Tyrosine
Tyrosine
(≈10.1)

Amino acids
Amino acids
types: Encoded (proteins) Essential Non-proteinogenic Ketogenic Glucogenic Imino acids D-amino acids Dehydroamino acids

v t e

Amino acid
Amino acid
metabolism metabolic intermediates

K→acetyl-CoA

lysine→

Saccharopine Allysine α-Aminoadipic acid α-Ketoadipate Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA

leucine→

β-Hydroxy β-methylbutyric acid β-Hydroxy β-methylbutyryl-CoA Isovaleryl-CoA α-Ketoisocaproic acid β-Ketoisocaproic acid β-Ketoisocaproyl-CoA β-Leucine β-Methylcrotonyl-CoA β-Methylglutaconyl-CoA β-Hydroxy β-methylglutaryl-CoA

tryptophan→alanine→

N'-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

G

G→pyruvate→citrate

glycine→serine→

3-Phosphoglyceric acid

glycine→creatine: Glycocyamine Phosphocreatine Creatinine

G→glutamate→ α-ketoglutarate

histidine→

Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde

proline→

1-Pyrroline-5-carboxylic acid

arginine→

Agmatine Ornithine Citrulline Cadaverine Putrescine

other

cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→ succinyl-CoA

valine→

α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid

isoleucine→

2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA

methionine→

generation of homocysteine: S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine

conversion to cysteine: Cystathionine alpha-Ketobutyric acid+Cysteine

threonine→

α-Ketobutyric acid

propionyl-CoA→

Methylmalonyl-CoA

G→fumarate

phenylalanine→tyrosine→

4-Hydroxyphenylpyruvic acid Homogentisic acid 4-Maleylacetoacetic acid

G→oxaloacetate

see urea cycle

Other

Cysteine
Cysteine
metabolism

Cysteine
Cysteine
sulfinic acid

v t e

Neurotransmitters

Amino acid-derived

Major excitatory/inhibitory systems: Glutamate
Glutamate
system: Agmatine Aspartic acid
Aspartic acid
(aspartate) Cycloserine Glutamic acid
Glutamic acid
(glutamate) Glutathione Glycine GSNO GSSG Kynurenic acid NAA NAAG Proline Serine; GABA system: GABA GABOB GHB; Glycine
Glycine
system: α-Alanine β-Alanine Glycine Hypotaurine Proline Sarcosine Serine Taurine; GHB system: GHB T-HCA (GHC)

Biogenic amines: Monoamines: 6-OHM Dopamine Epinephrine
Epinephrine
(adrenaline) NAS (normelatonin) Norepinephrine
Norepinephrine
(noradrenaline) Serotonin
Serotonin
(5-HT); Trace amines: 3-Iodothyronamine N-Methylphenethylamine N-Methyltryptamine m-Octopamine p-Octopamine Phenylethanolamine Phenethylamine Synephrine Tryptamine m-Tyramine p-Tyramine; Others: Histamine

Neuropeptides: See here instead.

Lipid-derived

Endocannabinoids: 2-AG 2-AGE (noladin ether) 2-ALPI 2-OG AA-5-HT Anandamide
Anandamide
(AEA) DEA LPI NADA NAGly OEA Oleamide PEA RVD-Hpα SEA Virodhamine
Virodhamine
(O-AEA)

Neurosteroids: See here instead.

Nucleobase-derived

Nucleosides: Adenosine
Adenosine
system: Adenosine ADP AMP ATP

Vitamin-derived

Cholinergic system: Acetylcholine

Miscellaneous

Gasotransmitters: Carbon monoxide
Carbon monoxide
(CO) Hydrogen
Hydrogen
sulfide (H2S) Nitric oxide
Nitric oxide
(NO); Candidates: Acetaldehyde Ammonia
Ammonia
(NH3) Carbonyl sulfide
Carbonyl sulfide
(COS) Nitrous oxide
Nitrous oxide
(N2O) Sulfur dioxide
Sulfur dioxide
(SO2)

v t e

Glycine receptor
Glycine receptor
modulators

Receptor (ligands)

GlyR

Agonists: β-Alanine β-ABA (BABA) β-AIBA Caesium D-Alanine D-Serine GABA Glycine Hypotaurine Ivermectin L-Alanine L-Proline L-Serine L-Threonine MDL-27531 Milacemide Picolinic acid Propofol Quisqualamine Sarcosine Taurine

Positive modulators: Alcohols (e.g., brometone, chlorobutanol (chloretone), ethanol (alcohol), tert-butanol (2M2P), tribromoethanol, trichloroethanol, trifluoroethanol) Alkylbenzene sulfonate Anandamide Barbiturates
Barbiturates
(e.g., pentobarbital, sodium thiopental) Chlormethiazole D12-116 Dihydropyridines (e.g., nicardipine) Etomidate Ginseng
Ginseng
constituents (e.g., ginsenosides (e.g., ginsenoside-Rf)) Glutamic acid
Glutamic acid
(glutamate) Ivermectin Ketamine Neuroactive steroids (e.g., alfaxolone, pregnenolone (eltanolone), pregnenolone acetate, minaxolone, ORG-20599) Nitrous oxide Penicillin G Propofol Tamoxifen Tetrahydrocannabinol Triclofos Tropeines (e.g., atropine, bemesetron, cocaine, LY-278584, tropisetron, zatosetron) Volatiles/gases (e.g., chloral hydrate, chloroform, desflurane, diethyl ether (ether), enflurane, halothane, isoflurane, methoxyflurane, sevoflurane, toluene, trichloroethane (methyl chloroform), trichloroethylene) Xenon Zinc

Antagonists: 2-Aminostrychnine 2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol
Gaboxadol
(THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline N-Methylstrychnine N,N-Dimethylmuscimol Nipecotic acid Pitrazepin Pseudostrychnine Quinolines (e.g., 4-hydroxyquinoline, 4-hydroxyquinoline-3-carboxylic acid, 5,7-CIQA, 7-CIQ, 7-TFQ, 7-TFQA) RU-5135 Sinomenine Strychnine Thiocolchicoside Tutin

Negative modulators: Amiloride Benzodiazepines (e.g., bromazepam, clonazepam, diazepam, flunitrazepam, flurazepam) Corymine Cyanotriphenylborate Daidzein Dihydropyridines (e.g., nicardipine, nifedipine, nitrendipine) Furosemide Genistein Ginkgo constituents (e.g., bilobalide, ginkgolides (e.g., ginkgolide A, ginkgolide B, ginkgolide C, ginkgolide J, ginkgolide M)) Imipramine NBQX Neuroactive steroids (e.g., 3α-androsterone sulfate, 3β-androsterone sulfate, deoxycorticosterone, DHEA sulfate, pregnenolone sulfate, progesterone) Opioids (e.g., codeine, dextromethorphan, dextrorphan, levomethadone, levorphanol, morphine, oripavine, pethidine, thebaine) Picrotoxin
Picrotoxin
(i.e., picrotin and picrotoxinin) PMBA Riluzole Tropeines (e.g., bemesetron, LY-278584, tropisetron, zatosetron) Verapamil Zinc

NMDAR

See here instead.

Transporter (blockers)

GlyT1

ACPPB ALX-1393 ALX-5407 (NFPS) AMG-747 ASP2535 Bitopertin
Bitopertin
(RG1678/RO4917838) CP-802079 Ethanol
Ethanol
(alcohol) Glycyldodecylamide GSK1018921 LY-2365109 ORG-24598 ORG-25935
ORG-25935
(SCH-900435) PF-02545920 PF-03463275 PF-04958242 Sarcosine SSR-103,800 SSR-504,734

GlyT2

Amoxapine Ethanol
Ethanol
(alcohol) NAGly Opiranserin (VVZ-149) ORG-25543 VVZ-368

See also Receptor/signaling modulators GABA receptor modulators GABAA receptor positive modulators Ionotropic glutamate receptor
Ionotropic glutamate receptor
modulators

v t e

Ionotropic glutamate receptor
Ionotropic glutamate receptor
modulators

AMPAR

Agonists: Main site agonists: 5-Fluorowillardiine Acromelic acid (acromelate) AMPA BOAA Domoic acid Glutamate Ibotenic acid Proline Quisqualic acid Willardiine; Positive allosteric modulators: Aniracetam Cyclothiazide CX-516 CX-546 CX-614 Farampator
Farampator
(CX-691, ORG-24448) CX-717 CX-1739 CX-1942 Diazoxide Hydrochlorothiazide
Hydrochlorothiazide
(HCTZ) IDRA-21 LY-392098 LY-395153 LY-404187 LY-451646 LY-503430 Mibampator
Mibampator
(LY-451395) Nooglutyl ORG-26576 Oxiracetam PEPA PF-04958242 Piracetam Pramiracetam S-18986 Tulrampator
Tulrampator
(S-47445, CX-1632)

Antagonists: ACEA-1011 ATPO Becampanel Caroverine CNQX Dasolampanel DNQX Fanapanel
Fanapanel
(MPQX) GAMS Kaitocephalin Kynurenic acid Kynurenine Licostinel
Licostinel
(ACEA-1021) NBQX PNQX Selurampanel Tezampanel Theanine Topiramate YM90K Zonampanel; Negative allosteric modulators: Barbiturates
Barbiturates
(e.g., pentobarbital, sodium thiopental) Cyclopropane Enflurane Ethanol
Ethanol
(alcohol) Evans blue GYKI-52466 GYKI-53655 Halothane Irampanel Isoflurane Perampanel Pregnenolone
Pregnenolone
sulfate Sevoflurane Talampanel; Unknown/unsorted antagonists: Minocycline

KAR

Agonists: Main site agonists: 5-Bromowillardiine 5-Iodowillardiine Acromelic acid (acromelate) AMPA ATPA Domoic acid Glutamate Ibotenic acid Kainic acid LY-339434 Proline Quisqualic acid SYM-2081; Positive allosteric modulators: Cyclothiazide Diazoxide Enflurane Halothane Isoflurane

Antagonists: ACEA-1011 CNQX Dasolampanel DNQX GAMS Kaitocephalin Kynurenic acid Licostinel
Licostinel
(ACEA-1021) LY-382884 NBQX NS102 Selurampanel Tezampanel Theanine Topiramate UBP-302; Negative allosteric modulators: Barbiturates
Barbiturates
(e.g., pentobarbital, sodium thiopental) Enflurane Ethanol
Ethanol
(alcohol) Evans blue NS-3763 Pregnenolone
Pregnenolone
sulfate

NMDAR

Agonists: Main site agonists: AMAA Aspartate Glutamate Homocysteic acid
Homocysteic acid
(L-HCA) Homoquinolinic acid Ibotenic acid NMDA Proline Quinolinic acid Tetrazolylglycine Theanine; Glycine
Glycine
site agonists: β-Fluoro-D-alanine ACBD ACC (ACPC) ACPD AK-51 Apimostinel
Apimostinel
(NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687414 L-Alanine L-Serine Milacemide Neboglamine
Neboglamine
(nebostinel) Rapastinel
Rapastinel
(GLYX-13) Sarcosine; Polyamine site agonists: Neomycin Spermidine Spermine; Other positive allosteric modulators: 24S-Hydroxycholesterol DHEA (prasterone) DHEA sulfate
DHEA sulfate
(prasterone sulfate) Epipregnanolone sulfate Pregnenolone
Pregnenolone
sulfate SAGE-201 SAGE-301 SAGE-718

Antagonists: Competitive antagonists: AP5
AP5
(APV) AP7 CGP-37849 CGP-39551 CGP-39653 CGP-40116 CGS-19755 CPP Kaitocephalin LY-233053 LY-235959 LY-274614 MDL-100453 Midafotel
Midafotel
(d-CPPene) NPC-12626 NPC-17742 PBPD PEAQX Perzinfotel PPDA SDZ-220581 Selfotel; Glycine
Glycine
site antagonists: 4-Cl-KYN (AV-101) 5,7-DCKA 7-CKA ACC ACEA-1011 ACEA-1328 Apimostinel
Apimostinel
(NRX-1074) AV-101 Carisoprodol CGP-39653 CNQX D-Cycloserine DNQX Felbamate Gavestinel GV-196771 Harkoseride Kynurenic acid Kynurenine L-689560 L-701324 Licostinel
Licostinel
(ACEA-1021) LU-73068 MDL-105519 Meprobamate MRZ 2/576 PNQX Rapastinel
Rapastinel
(GLYX-13) ZD-9379; Polyamine site antagonists: Arcaine Co 101676 Diaminopropane Diethylenetriamine Huperzine A Putrescine; Uncompetitive pore blockers (mostly dizocilpine site): 2-MDP 3-HO-PCP 3-MeO-PCE 3-MeO-PCMo 3-MeO-PCP 4-MeO-PCP 8A-PDHQ 18-MC α-Endopsychosin Alaproclate Alazocine
Alazocine
(SKF-10047) Amantadine Aptiganel Argiotoxin-636 Arketamine ARL-12495 ARL-15896-AR ARL-16247 Budipine Coronaridine Delucemine
Delucemine
(NPS-1506) Dexoxadrol Dextrallorphan Dextromethadone Dextromethorphan Dextrorphan Dieticyclidine Diphenidine Dizocilpine Ephenidine Esketamine Etoxadrol Eticyclidine Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Levomethadone Levomethorphan Levomilnacipran Levorphanol Loperamide Memantine Methadone Methorphan Methoxetamine Methoxphenidine Milnacipran Morphanol NEFA Neramexane Nitromemantine Noribogaine Norketamine Orphenadrine PCPr PD-137889 Pethidine
Pethidine
(meperidine) Phencyclamine Phencyclidine Propoxyphene Remacemide Rhynchophylline Rimantadine Rolicyclidine Sabeluzole Tabernanthine Tenocyclidine Tiletamine Tramadol; Ifenprodil (NR2B) site antagonists: Besonprodil Buphenine
Buphenine
(nylidrin) CO-101244 (PD-174494) Eliprodil Haloperidol Isoxsuprine Radiprodil (RGH-896) Rislenemdaz
Rislenemdaz
(CERC-301, MK-0657) Ro 8-4304 Ro 25-6981 Safaprodil Traxoprodil
Traxoprodil
(CP-101606); NR2A-selective antagonists: MPX-004 MPX-007 TCN-201 TCN-213; Cations: Hydrogen Magnesium Zinc; Alcohols/volatile anesthetics/related: Benzene Butane Chloroform Cyclopropane Desflurane Diethyl ether Enflurane Ethanol
Ethanol
(alcohol) Halothane Hexanol Isoflurane Methoxyflurane Nitrous oxide Octanol Sevoflurane Toluene Trichloroethane Trichloroethanol Trichloroethylene Urethane Xenon Xylene; Unknown/unsorted antagonists: ARR-15896 Bumetanide Caroverine Conantokin D-αAA Dexanabinol Flufenamic acid Flupirtine FPL-12495 FR-115427 Furosemide Hodgkinsine Ipenoxazone (MLV-6976) MDL-27266 Metaphit Minocycline MPEP Niflumic acid Pentamidine Pentamidine
Pentamidine
isethionate Piretanide Psychotridine Transcrocetin
Transcrocetin
(saffron)

See also: Receptor/signaling modulators Metabotropic glutamate receptor modulators Glutamate
Glutamate
metabolism/transport modulators

v t e

Molecules detected in outer space

Molecules

Diatomic

Aluminium monochloride Aluminium monofluoride Aluminium monoxide Argonium Carbon
Carbon
monophosphide Carbon
Carbon
monosulfide Carbon
Carbon
monoxide Carborundum Cyanogen
Cyanogen
radical Diatomic carbon Fluoromethylidynium Hydrogen
Hydrogen
chloride Hydrogen
Hydrogen
fluoride Hydrogen
Hydrogen
(molecular) Hydroxyl radical Iron(II) oxide Magnesium
Magnesium
monohydride cation Methylidyne radical Nitric oxide Nitrogen
Nitrogen
(molecular) Nitrogen
Nitrogen
monohydride Nitrogen
Nitrogen
sulfide Oxygen
Oxygen
(molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon mononitride Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfur monohydride Sulfur monoxide Titanium oxide

Triatomic

Aluminium hydroxide Aluminium isocyanide Amino radical Carbon
Carbon
dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen
Hydrogen
cyanide (HCN) Hydrogen
Hydrogen
isocyanide (HNC) Hydrogen
Hydrogen
sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium
Magnesium
cyanide Magnesium
Magnesium
isocyanide Methylene radical N2H+ Nitrous oxide Nitroxyl Ozone Phosphaethyne Potassium cyanide Protonated molecular hydrogen Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide Silicon naphthalocyanine Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water

Four atoms

Acetylene Ammonia Cyanic acid Cyanoethynyl Cyclopropynylidyne Formaldehyde Fulminic acid HCCN Hydrogen
Hydrogen
peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methylene amidogen Methyl radical Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thioformaldehyde Tricarbon
Tricarbon
monoxide Tricarbon
Tricarbon
sulfide Thiocyanic acid

Five atoms

Ammonium
Ammonium
ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy
Methoxy
radical Methylenimine Propadienylidene Protonated formaldehyde Protonated formaldehyde Silane Silicon-carbide cluster

Six atoms

Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC4N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene

Seven atoms

Acetaldehyde Acrylonitrile

Vinyl cyanide

Cyanodiacetylene Ethylene
Ethylene
oxide Hexatriynyl radical Methylacetylene Methylamine Methyl isocyanate Vinyl alcohol

Eight atoms

Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Heptatrienyl radical Hexapentaenylidene Methylcyanoacetylene Methyl formate Propenal

Nine atoms

Acetamide Cyanohexatriyne Cyanotriacetylene Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Propionitrile

Ten atoms or more

Acetone Benzene Benzonitrile Buckminsterfullerene
Buckminsterfullerene
(C60 fullerene, buckyball) C70 fullerene Cyanodecapentayne Cyanopentaacetylene Cyanotetra-acetylene Ethylene
Ethylene
glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propanal n-Propyl cyanide Pyrimidine

Deuterated molecules

Ammonia Ammonium
Ammonium
ion Formaldehyde Formyl radical Heavy water Hydrogen
Hydrogen
cyanide Hydrogen
Hydrogen
deuteride Hydrogen
Hydrogen
isocyanide Methylacetylene N2D+ Trihydrogen cation

Unconfirmed

Anthracene Dihydroxyacetone Ethyl methyl ether Glycine Graphene H2NCO+ Linear C5 Naphthalene
Naphthalene
cation Phosphine Pyrene Silylidine

Related

Abiogenesis Astrobiology Astrochemistry Atomic and molecular astrophysics Chemical formula Circumstellar envelope Cosmic dust Cosmic ray Cosmochemistry Diffuse interstellar band Earliest known life forms Extraterrestrial life Extraterrestrial liquid water Forbidden mechanism Helium hydride ion Homochirality Intergalactic dust Interplanetary medium Interstellar medium Photodissociation region Iron–sulfur world theory Kerogen Molecules in stars Nexus for Exoplanet System Science Organic compound Outer space PAH world hypothesis Panspermia Polycyclic aromatic hydrocarbon
Polycyclic aromatic hydrocarbon
(PAH) RNA world hypothesis Spectroscopy Tholin

Book:Chemistry Category:Astrochemistry Category:Molecules Portal:Astrobiology Portal:Astronomy Portal:Chemistry

Authority control

.