Agmatine

Not to be confused with agmatidine or arginine.

Agmatine  Skeletal formula of agmatine

Names
IUPAC name

1-(4-Aminobutyl)guanidine[1]

Identifiers

CAS Number

* 306-60-5 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:17431 Y

ChEMBL |

* ChEMBL58343 Y

ChemSpider |

* 194 Y

ECHA InfoCard | 100.005.626
EC Number |

* 206-187-7

KEGG |

* C00179 Y

MeSH | Agmatine

PubChem CID

* 199

UNII |

* 70J407ZL5Q Y

CompTox Dashboard (EPA)

* DTXSID0040961

InChI

* InChI=1S/C5H14N4/c6-3-1-2-4-9-5(7)8/h1-4,6H2,(H4,7,8,9) Y

Key: QYPPJABKJHAVHS-UHFFFAOYSA-N Y

SMILES

* NCCCCNC(N)=N

Properties

Chemical formula

| C5H14N4
Molar mass | 130.195 g·mol−1
Density | 1.2 g/ml
Melting point | 102 °C (216 °F; 375 K)
Boiling point | 281 °C (538 °F; 554 K)

Solubility in water

| high
log P | −1.423
Basicity (pKb)  | 0.52
Hazards
Flash point | 95.8 °C (204.4 °F; 368.9 K)

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

N verify (what is YN ?)

Infobox references

Chemical compound

Agmatine, also known as 4-aminobutyl-guanidine, was discovered in 1910 by Albrecht Kossel.[2] It is a chemical substance which is naturally created from the amino acid arginine. Agmatine has been shown to exert modulatory action at multiple molecular targets, notably: neurotransmitter systems, ion channels, nitric oxide (NO) synthesis, and polyamine metabolism and this provides bases for further research into potential applications.

## History

[edit]

The term agmatine stems from A- (for amino-) + g- (from guanidine) + -ma- (from ptomaine) + -in (German)/-ine (English) suffix with insertion of -t- apparently for euphony.[3] A year after its discovery, it was found that agmatine could increase blood flow in rabbits;[4] however, the physiological relevance of these findings were questioned given the high concentrations (high μM range) required.[5] In the 1920s, researchers in the diabetes clinic of Oskar Minkowski showed that agmatine can exert mild hypoglycemic effects.[6] In 1994, endogenous agmatine synthesis in mammals was discovered.[7]

## Metabolic pathways

[edit]

Agmatine Metabolic Pathways

Agmatine is a cationic amine formed by decarboxylation of L-arginine by the mitochondrial enzyme arginine decarboxylase (ADC).[8] Agmatine degradation occurs mainly by hydrolysis, catalyzed by agmatinase into urea and putrescine, the diamine precursor of polyamine biosynthesis.[9] An alternative pathway, mainly in peripheral tissues, is by diamine oxidase-catalyzed oxidation into agmatine-aldehyde, which is in turn converted by aldehyde dehydrogenase into guanidinobutyrate and secreted by the kidneys.[10]

## Mechanisms of action

[edit]

Agmatine was found to exert modulatory actions directly and indirectly at multiple key molecular targets underlying cellular control mechanisms of cardinal importance in health and disease. It is considered capable of exerting its modulatory actions simultaneously at multiple targets.[11] The following outline indicates the categories of control mechanisms, and identifies their molecular targets:

* Neurotransmitter receptors and receptor ionophores. Nicotinic, imidazoline I1 and I2, α2-adrenergic, glutamate NMDAr, and serotonin 5-HT2A and 5HT-3 receptors.
* Ion channels. Including: ATP-sensitive K+ channels, voltage-gated Ca2+ channels, and acid-sensing ion channels (ASICs).
* Membrane transporters. Agmatine specific-selective uptake sites, organic cation transporters (mostly OCT2 subtype), extraneuronal monoamine transporters (ENT), polyamine transporters, and mitochondrial agmatine specific-selective transport system.
* Nitric oxide (NO) synthesis modulation. Both differential inhibition and activation of NO synthase (NOS) isoforms is reported.[12][13]
* Polyamine metabolism. Agmatine is a precursor for polyamine synthesis, competitive inhibitor of polyamine transport, inducer of spermidine/spermine acetyltransferase (SSAT), and inducer of antizyme.
* Protein ADP-ribosylation. Inhibition of protein arginine ADP-ribosylation.
* Matrix metalloproteases (MMPs). Indirect down-regulation of the enzymes MMP 2 and 9.
* Advanced glycation end product (AGE) formation. Direct blockade of AGEs formation.
* NADPH oxidase. Activation of the enzyme leading to H2O2 production.[14]

## Food consumption

[edit]

Agmatine sulfate injection can increase food intake with carbohydrate preference in satiated, but not hungry, rats and this effect may be mediated by neuropeptide Y.[15] However, supplementation in rat drinking water results in slight reductions in water intake, body weight, and blood pressure.[16] In addition, force feeding with agmatine leads to a reduction in body weight gain during rat development.[17] It is also found that many fermented foods contain agmatine.[18][19]

## Pharmacokinetics

[edit]

Agmatine is present in small amounts in plant-, animal-, and fish-derived foodstuff and gut microbial production is an added source for agmatine. Oral agmatine is absorbed from the gastrointestinal tract and readily distributed throughout the body.[20] Rapid elimination from non-brain organs of ingested (un-metabolized) agmatine by the kidneys has indicated a blood half life of about 2 hours.[21]

## Research

[edit]

A number of potential medical uses for agmatine have been suggested.[22]

### Cardiovascular

[edit]

Agmatine produces mild reductions in heart rate and blood pressure, apparently by activating both central and peripheral control systems via modulation of several of its molecular targets including: imidazoline receptors subtypes, norepinephrine release and NO production.[23]

### Glucose regulation

[edit]

Agmatine hypoglycemic effects are the result of simultaneous modulation of several molecular mechanisms involved in blood glucose regulation.[11]

### Kidney functions

[edit]

Agmatine has been shown to enhance glomerular filtration rate (GFR) and to exert nephroprotective effects.[24]

### Neurotransmission

[edit]

Agmatine has been discussed as a putative neurotransmitter. It is synthesized in the brain, stored in synaptic vesicles, accumulated by uptake, released by membrane depolarization, and inactivated by agmatinase. Agmatine binds to α2-adrenergic receptor and imidazoline receptor binding sites, and blocks NMDA receptors and other cation ligand-gated channels. However, while agmatine binds to α2-adrenergic receptors, it exerts neither an agonistic nor antagonistic effect on these receptors, lacking any intrinsic activity.[25][26] Short only of identifying specific ("own") post-synaptic receptors, agmatine fulfills Henry Dale's criteria for a neurotransmitter and is hence considered a neuromodulator and co-transmitter. The existence of theoretical agmatinergic-mediated neuronal systems has not yet been demonstrated although the existence of such receptors is implied by its prominence in the mediation of both the central and peripheral nervous systems.[11] Research into agmatine-specific receptors and transmission pathways continues.

Due to its ability to pass through open cationic channels, agmatine has also been used as a surrogate metric of integrated ionic flux into neural tissue upon stimulation.[27] When neural tissue is incubated in agmatine and an external stimulus is applied, only cells with open channels will be filled with agmatine, allowing identification of which cells are sensitive to that stimuli and the degree to which they opened their cationic channels during the stimulation period.

### Opioid liability

[edit]

Systemic agmatine can potentiate opioid analgesia, and prevent tolerance to chronic morphine in laboratory rodents. Since then, cumulative evidence amply shows that agmatine inhibits opioid dependence and relapse in several animal species.[28]

## See also

[edit]

* Agmatine deiminase
* Agmatinase

## References

[edit]

1. ^ "agmatine (CHEBI:17431)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 15 August 2008. Main. Retrieved 11 January 2012.
2. ^ Kossel A (1910). "Über das Agmatin". Zeitschrift für Physiologische Chemie (in German). 66 (3): 257–261\. doi:10.1515/bchm2.1910.66.3.257.257-261&rft.date=1910&rft_id=info:doi/10.1515/bchm2.1910.66.3.257&rft.aulast=Kossel&rft.aufirst=A&rft_id=http://vlp.mpiwg-berlin.mpg.de/references?id=lit18967&rfr_id=info:sid/en.wikipedia.org:Agmatine" class="Z3988">
3. ^ "agmantine". Oxford English Dictionary (Online ed.). Oxford University Press. (Subscription or participating institution membership required.)
4. ^ Engeland R, Kutscher F (1910). "Ueber eine zweite wirksame Secale-base". Z Physiol Chem (in German). 57: 49–65\. doi:10.1515/bchm2.1908.57.1-2.49.49-65&rft.date=1910&rft_id=info:doi/10.1515/bchm2.1908.57.1-2.49&rft.aulast=Engeland&rft.aufirst=R&rft.au=Kutscher,+F&rft_id=https://zenodo.org/record/1627042&rfr_id=info:sid/en.wikipedia.org:Agmatine" class="Z3988">
5. ^ Dale HH, Laidlaw PP (October 1911). "Further observations on the action of beta-iminazolylethylamine". The Journal of Physiology. 43 (2): 182–95\. doi:10.1113/jphysiol.1911.sp001464. PMC 1512691. PMID 16993089.182-95&rft.date=1911-10&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1512691#id-name=PMC&rft_id=info:pmid/16993089&rft_id=info:doi/10.1113/jphysiol.1911.sp001464&rft.aulast=Dale&rft.aufirst=HH&rft.au=Laidlaw,+PP&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1512691&rfr_id=info:sid/en.wikipedia.org:Agmatine" class="Z3988">
6. ^ Frank E, Nothmann M, Wagner A (1926). "über Synthetisch Dargestellte Körper mit Insulinartiger Wirkung Auf den Normalen und Diabetischen Organismus". Klinische Wochenschrift (in German). 5 (45): 2100–2107\. doi:10.1007/BF01736560. S2CID 35090913.2100-2107&rft.date=1926&rft_id=info:doi/10.1007/BF01736560&rft_id=https://api.semanticscholar.org/CorpusID:35090913#id-name=S2CID&rft.aulast=Frank&rft.aufirst=E&rft.au=Nothmann,+M&rft.au=Wagner,+A&rfr_id=info:sid/en.wikipedia.org:Agmatine" class="Z3988">
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8. ^ Molderings GJ, Haenisch B (2012-03-01). "Agmatine (decarboxylated l-arginine): Physiological role and therapeutic potential". Pharmacology & Therapeutics. 133 (3): 351–365\. doi:10.1016/j.pharmthera.2011.12.005. ISSN 0163-7258.351-365&rft.date=2012-03-01&rft_id=info:doi/10.1016/j.pharmthera.2011.12.005&rft.issn=0163-7258&rft.aulast=Molderings&rft.aufirst=Gerhard+J.&rft.au=Haenisch,+Britta&rft_id=https://www.sciencedirect.com/science/article/pii/S0163725811002282&rfr_id=info:sid/en.wikipedia.org:Agmatine" class="Z3988">
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25. ^ Pinthong D, Wright IK, Hanmer C, Millns P, Mason R, Kendall DA, Wilson VG (January 1995). "Agmatine recognizes alpha 2-adrenoceptor binding sites but neither activates nor inhibits alpha 2-adrenoceptors". Naunyn-Schmiedeberg's Archives of Pharmacology. 351 (1): 10–16\. doi:10.1007/BF00169058. ISSN 0028-1298. PMID 7715734. S2CID 20785398.10-16&rft.date=1995-01&rft.issn=0028-1298&rft_id=https://api.semanticscholar.org/CorpusID:20785398#id-name=S2CID&rft_id=info:pmid/7715734&rft_id=info:doi/10.1007/BF00169058&rft.aulast=Pinthong&rft.aufirst=D.&rft.au=Wright,+I.+K.&rft.au=Hanmer,+C.&rft.au=Millns,+P.&rft.au=Mason,+R.&rft.au=Kendall,+D.+A.&rft.au=Wilson,+V.+G.&rft_id=https://pubmed.ncbi.nlm.nih.gov/7715734/&rfr_id=info:sid/en.wikipedia.org:Agmatine" class="Z3988">
26. ^ Pineda J, Ruiz-Ortega JA, Martín-Ruiz R, Ugedo L (1996-11-22). "Agmatine does not have activity at alpha 2-adrenoceptors which modulate the firing rate of locus coeruleus neurones: an electrophysiological study in rat". Neuroscience Letters. 219 (2): 103–106\. doi:10.1016/s0304-3940(96)13180-3. ISSN 0304-3940. PMID 8971790. S2CID 32456961.103-106&rft.date=1996-11-22&rft.issn=0304-3940&rft_id=https://api.semanticscholar.org/CorpusID:32456961#id-name=S2CID&rft_id=info:pmid/8971790&rft_id=info:doi/10.1016/s0304-3940(96)13180-3&rft.aulast=Pineda&rft.aufirst=J.&rft.au=Ruiz-Ortega,+J.+A.&rft.au=Martín-Ruiz,+R.&rft.au=Ugedo,+L.&rft_id=https://pubmed.ncbi.nlm.nih.gov/8971790/&rfr_id=info:sid/en.wikipedia.org:Agmatine" class="Z3988">
27. ^ Marc RE (April 1999). "Mapping glutamatergic drive in the vertebrate retina with a channel-permeant organic cation". The Journal of Comparative Neurology. 407 (1): 47–64\. doi:10.1002/(sici)1096-9861(19990428)407:1<47::aid-cne4>3.0.co;2-0. PMID 10213187. S2CID 15955446.47-64&rft.date=1999-04&rft_id=https://api.semanticscholar.org/CorpusID:15955446#id-name=S2CID&rft_id=info:pmid/10213187&rft_id=info:doi/10.1002/(sici)1096-9861(19990428)407:1<47::aid-cne4>3.0.co;2-0&rft.aulast=Marc&rft.aufirst=RE&rfr_id=info:sid/en.wikipedia.org:Agmatine" class="Z3988">
28. ^ Su RB, Li J, Qin BY (July 2003). "A biphasic opioid function modulator: agmatine". Acta Pharmacologica Sinica. 24 (7): 631–6\. PMID 12852826.631-6&rft.date=2003-07&rft_id=info:pmid/12852826&rft.aulast=Su&rft.aufirst=RB&rft.au=Li,+J&rft.au=Qin,+BY&rft_id=http://www.chinaphar.com/article/view/9162/9833&rfr_id=info:sid/en.wikipedia.org:Agmatine" class="Z3988">

## Further reading

[edit]

* Wilcox G, Fiska A, Haugan F, Svendsen F, Rygh L, Tjolsen A, Hole K (2004). "Central sensitization: The endogenous NMDA antagonist and NOS inhibitor agmatine inhibits spinal long term potentiation (LTP)". The Journal of Pain. 5 (3): S19. doi:10.1016/j.jpain.2004.02.041.

* v
* t
* e

Neurotransmitters

Amino acid-derived|

| Major excitatory /
inhibitory systems|

| Glutamate system|

* Agmatine
* Aspartic acid (aspartate)
* Glutamic acid (glutamate)
* Glutathione
* Glycine
* GSNO
* GSSG
* Kynurenic acid
* NAA
* NAAG
* Proline
* Serine

|

GABA system|

* GABA
* GABOB
* GHB

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 (adrenaline)
* NAS (normelatonin)
* Norepinephrine (noradrenaline)
* 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 (AEA)
* DEA
* LPI
* NADA
* NAGly
* OEA
* Oleamide
* PEA
* RVD-Hpα
* SEA
* Virodhamine (O-AEA)

|

Neurosteroids|

* See here instead.

Nucleobase-derived|

| Nucleosides|

| Adenosine system|

* ADP
* AMP
* ATP

|

Vitamin-derived|

|

Miscellaneous|

| Cholinergic system|

* Acetylcholine

|

Gasotransmitters|

* Carbon monoxide (CO)
* Hydrogen sulfide (H2S)
* Nitric oxide (NO)

|

Candidates|

* Acetaldehyde
* Ammonia (NH3)
* Carbonyl sulfide (COS)
* Nitrous oxide (N2O)
* Sulfur dioxide (SO2)

|

* v
* t
* e

Amino acid metabolism metabolic intermediates

K→acetyl-CoA|

| lysine→|

* Saccharopine
* Allysine
* α-Aminoadipic acid
* 2-Oxoadipic acid
* 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→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
* α-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 metabolism|

* Cysteine sulfinic acid

|

Acetylcholine receptor modulators

* v
* t
* e

Muscarinic acetylcholine receptor modulators

mAChRsTooltip Muscarinic acetylcholine receptors|

| Agonists|

* 77-LH-28-1
* AC-42
* AC-260,584
* Aceclidine
* Acetylcholine
* AF30
* AF150(S)
* AF267B
* Alvameline
* AQRA-741
* Arecoline
* Bethanechol
* Butyrylcholine
* Carbachol
* CDD-0034
* CDD-0078
* CDD-0097
* CDD-0098
* CDD-0102
* Cevimeline
* Choline
* cis-Dioxolane
* Clozapine
* Desmethylclozapine (norclozapine)
* Ethoxysebacylcholine
* Itameline
* LY-593,039
* L-689,660
* LY-2,033,298
* McNA343
* Methacholine
* Milameline
* Muscarine
* NGX-267
* Ocvimeline
* Oxotremorine
* PD-151,832
* Pilocarpine
* RS86
* Sabcomeline
* SDZ 210-086
* Sebacylcholine
* Suberyldicholine
* Talsaclidine
* Tazomeline
* Thiopilocarpine
* Vedaclidine
* VU-0029767
* VU-0090157
* VU-0152099
* VU-0152100
* VU-0238429
* WAY-132,983
* Xanomeline
* YM-796

|

Antagonists|

* 3-Quinuclidinyl benzilate
* 4-DAMP
* Aclidinium bromide (+formoterol)
* Abediterol
* AF-DX 250
* AF-DX 384
* Ambutonium bromide
* Anisodamine
* Anisodine
* Antihistamines (first-generation) (e.g., brompheniramine, buclizine, captodiame, chlorphenamine (chlorpheniramine), cinnarizine, clemastine, cyproheptadine, dimenhydrinate, dimetindene, diphenhydramine, doxylamine, meclizine, mequitazine, perlapine, phenindamine, pheniramine, phenyltoloxamine, promethazine, propiomazine, triprolidine)
* AQ-RA 741
* Atropine
* Atropine methonitrate
* Atypical antipsychotics (e.g., clozapine, fluperlapine, olanzapine (+fluoxetine), rilapine, quetiapine, tenilapine, zotepine)
* Benactyzine
* Benzatropine (benztropine)
* Benzilone
* Benzilylcholine mustard
* Benzydamine
* Bevonium
* BIBN 99
* Biperiden
* Bornaprine
* Camylofin
* CAR-226,086
* CAR-301,060
* CAR-302,196
* CAR-302,282
* CAR-302,368
* CAR-302,537
* CAR-302,668
* Caramiphen
* Cimetropium bromide
* Clidinium bromide
* Cloperastine
* CS-27349
* Cyclobenzaprine
* Cyclopentolate
* Darifenacin
* DAU-5884
* Desfesoterodine
* Dexetimide
* DIBD
* Dicycloverine (dicyclomine)
* Dihexyverine
* Difemerine
* Diphemanil metilsulfate
* Ditran
* Drofenine
* EA-3167
* EA-3443
* EA-3580
* EA-3834
* Emepronium bromide
* Etanautine
* Etybenzatropine (ethybenztropine)
* Fenpiverinium
* Fentonium bromide
* Fesoterodine
* Flavoxate
* Glycopyrronium bromide (+beclometasone/formoterol, +indacaterol, +neostigmine)
* Hexahydrodifenidol
* Hexahydrosiladifenidol
* Hexbutinol
* Hexocyclium
* Himbacine
* HL-031,120
* Homatropine
* Imidafenacin
* Ipratropium bromide (+salbutamol)
* Isopropamide
* J-104,129
* Hyoscyamine
* Mamba toxin 3
* Mamba toxin 7
* Mazaticol
* Mebeverine
* Meladrazine
* Mepenzolate
* Methantheline
* Methoctramine
* Methylatropine
* Methylhomatropine
* Methylscopolamine
* Metixene
* Muscarinic toxin 7
* N-Ethyl-3-piperidyl benzilate
* N-Methyl-3-piperidyl benzilate
* Nefopam
* Octatropine methylbromide (anisotropine methylbromide)
* Orphenadrine
* Otenzepad (AF-DX 116)
* Otilonium bromide
* Oxapium iodide
* Oxitropium bromide
* Oxybutynin
* Oxyphencyclimine
* Oxyphenonium bromide
* PBID
* PD-102,807
* PD-0298029
* Penthienate
* Pethidine
* pFHHSiD
* Phenglutarimide
* Phenyltoloxamine
* Pipenzolate bromide
* Piperidolate
* Pirenzepine
* Piroheptine
* Pizotifen
* Poldine
* Pridinol
* Prifinium bromide
* Procyclidine
* Profenamine (ethopropazine)
* Propantheline bromide
* Propiverine
* Quinidine
* 3-Quinuclidinyl thiochromane-4-carboxylate
* Revefenacin
* Rociverine
* RU-47,213
* SCH-57,790
* SCH-72,788
* SCH-217,443
* Scopolamine (hyoscine)
* Scopolamine butylbromide (hyoscine butylbromide)
* Silahexacyclium
* Sofpironium bromide
* Solifenacin
* SSRIsTooltip Selective serotonin reuptake inhibitors (e.g., femoxetine, paroxetine)
* Telenzepine
* Terodiline
* Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine)
* Tiemonium iodide
* Timepidium bromide
* Tiotropium bromide
* Tiquizium bromide
* Tofenacin
* Tolterodine
* Tricyclic antidepressants (e.g., amitriptyline (+perphenazine), amitriptylinoxide, butriptyline, cidoxepin, clomipramine, desipramine, desmethyldesipramine, dibenzepin, dosulepin (dothiepin), doxepin, imipramine, lofepramine, nitroxazepine, northiaden (desmethyldosulepin), nortriptyline, protriptyline, quinupramine, trimipramine)
* Tridihexethyl
* Trihexyphenidyl
* Trimebutine
* Tripitamine (tripitramine)
* Tropacine
* Tropatepine
* Tropicamide
* Trospium chloride
* Typical antipsychotics (e.g., chlorpromazine, chlorprothixene, cyamemazine (cyamepromazine), loxapine, mesoridazine, thioridazine)
* Umeclidinium bromide (+vilanterol)
* WIN-2299
* Xanomeline
* Zamifenacin

Precursors
(and prodrugs)|

* Acetyl-coA
* Adafenoxate
* Choline (lecithin)
* Citicoline
* Cyprodenate
* Dimethylethanolamine
* Glycerophosphocholine
* Meclofenoxate (centrophenoxine)
* Phosphatidylcholine
* Phosphatidylethanolamine
* Phosphorylcholine
* Pirisudanol

See also
Receptor/signaling modulators
Nicotinic acetylcholine receptor modulators
Acetylcholine metabolism/transport modulators

* v
* t
* e

Nicotinic acetylcholine receptor modulators

nAChRsTooltip Nicotinic acetylcholine receptors|

| Agonists
(and PAMsTooltip positive allosteric modulators)|

* 5-HIAA
* 6-Chloronicotine
* A-84,543
* A-366,833
* A-582,941
* A-867,744
* ABT-202
* ABT-418
* ABT-560
* ABT-894
* Acetylcholine
* Altinicline
* Anabasine
* Anatabine
* Anatoxin-a
* AR-R17779
* Bephenium hydroxynaphthoate
* Butinoline
* Butyrylcholine
* Carbachol
* Choline
* Choline m-bromophenyl ether
* Cotinine
* Cytisine
* Decamethonium
* Desformylflustrabromine
* Dianicline
* Dimethylphenylpiperazinium
* Epibatidine
* Epiboxidine
* Ethanol (alcohol)
* Ethoxysebacylcholine
* EVP-4473
* EVP-6124
* Galantamine
* GTS-21
* Ispronicline
* Ivermectin
* JNJ-39393406
* Levamisole
* Lobeline
* MEM-63,908 (RG-3487)
* Morantel
* Nicotine (tobacco)
* NS-1738
* PHA-543,613
* PHA-709,829
* PNU-120,596
* PNU-282,987
* Pozanicline
* Pyrantel
* Rivanicline
* RJR-2429
* Sazetidine A
* SB-206553
* Sebacylcholine
* SIB-1508Y
* SIB-1553A
* SSR-180,711
* Suberyldicholine
* Suxamethonium (succinylcholine)
* Suxethonium (succinyldicholine)
* TC-1698
* TC-1734
* TC-1827
* TC-2216
* TC-5214
* TC-5619
* TC-6683
* Tebanicline
* Tribendimidine
* Tropisetron
* UB-165
* Varenicline
* WAY-317,538
* XY-4083

|

Antagonists
(and NAMsTooltip negative allosteric modulators)|

* 18-MAC
* 18-MC
* α-Neurotoxins (e.g., α-bungarotoxin, α-cobratoxin, α-conotoxin, many others)
* ABT-126
* Alcuronium
* Allopregnanolone
* Amantadine
* Anatruxonium
* AQW051
* Atracurium
* Barbiturates (e.g., pentobarbital, sodium thiopental)
* BNC-210
* Bungarotoxins (e.g., α-bungarotoxin, κ-bungarotoxin)
* Bupropion
* BW284C51
* BW-A444
* Candocuronium iodide (chandonium iodide)
* Chlorisondamine
* Cisatracurium
* Coclaurine
* Coronaridine
* Curare
* Cyclopropane
* Dacuronium bromide
* Decamethonium
* Dehydronorketamine
* Desflurane
* Dextromethorphan
* Dextropropoxyphene
* Dextrorphan
* Diadonium
* DHβE
* Dihydrochandonium
* Dimethyltubocurarine (metocurine)
* Dioscorine
* Dipyrandium
* Dizocilpine (MK-801)
* Doxacurium
* Encenicline
* Enflurane
* Erythravine
* Esketamine
* Fazadinium
* Gallamine
* Gantacurium chloride
* Halothane
* Hexafluronium
* Hexamethonium (benzohexonium)
* Hydroxybupropion
* Hydroxynorketamine
* Ibogaine
* Isoflurane
* Ketamine
* Kynurenic acid
* Laudanosine
* Laudexium (laudolissin)
* Levacetylmethadol
* Levomethadone
* Malouetine
* ME-18-MC
* Mecamylamine
* Memantine
* Methadone
* Methorphan (racemethorphan)
* Methyllycaconitine
* Metocurine
* Mivacurium
* Morphanol (racemorphan)
* Neramexane
* Nitrous oxide
* Norketamine
* Pancuronium bromide
* Pempidine
* Pentamine
* Pentolinium
* Phencyclidine
* Pipecuronium bromide
* Progesterone
* Promegestone
* Radafaxine
* Rapacuronium bromide
* Reboxetine
* Rocuronium bromide
* Sevoflurane
* Stercuronium iodide
* Surugatoxin
* Thiocolchicoside
* Threohydrobupropion
* Toxiferine
* Tramadol
* Trimetaphan camsilate (trimethaphan camsylate)
* Tropeinium
* Tubocurarine
* Vanoxerine
* Vecuronium bromide
* Xenon

Precursors
(and prodrugs)|

* Acetyl-coA
* Adafenoxate
* Choline (lecithin)
* Citicoline
* Cyprodenate
* Dimethylethanolamine
* Glycerophosphocholine
* Meclofenoxate (centrophenoxine)
* Phosphatidylcholine
* Phosphatidylethanolamine
* Phosphorylcholine
* Pirisudanol

See also
Receptor/signaling modulators
Muscarinic acetylcholine receptor modulators
Acetylcholine metabolism/transport modulators

Glutamate receptor modulators

* v
* t
* e

Ionotropic glutamate receptor modulators

AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor|

* 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 (CX-691, ORG-24448)
* CX-717
* CX-1739
* CX-1942
* Diazoxide
* Hydrochlorothiazide (HCTZ)
* IDRA-21
* LY-392098
* LY-395153
* LY-404187
* LY-451646
* LY-503430
* Mibampator (LY-451395)
* Nooglutyl
* ORG-26576
* Oxiracetam
* PEPA
* Pesampator (BIIB-104, PF-04958242)
* Piracetam
* Pramiracetam
* S-18986
* Tulrampator (S-47445, CX-1632)

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

KARTooltip Kainate receptor|

* 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 (ACEA-1021)
* LY-382884
* NBQX
* NS102
* Selurampanel
* Tezampanel
* Theanine
* Topiramate
* UBP-302; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental)
* Enflurane
* Ethanol (alcohol)
* Evans blue
* NS-3763
* Pregnenolone sulfate

NMDARTooltip N-Methyl-D-aspartate receptor|

* Agonists: Main site agonists: AMAA
* Aspartate
* Glutamate
* Homocysteic acid (L-HCA)
* Homoquinolinic acid
* Ibotenic acid
* NMDA
* Proline
* Quinolinic acid
* Tetrazolylglycine
* Theanine; Glycine site agonists: β-Fluoro-D-alanine
* ACBD
* ACC (ACPC)
* ACPD
* AK-51
* Apimostinel (NRX-1074)
* B6B21
* CCG
* D-Alanine
* D-Cycloserine
* D-Serine
* DHPG
* Dimethylglycine
* Glycine
* HA-966
* L-687,414
* L-Alanine
* L-Serine
* Milacemide
* Neboglamine (nebostinel)
* Rapastinel (GLYX-13)
* Sarcosine; Polyamine site agonists: Neomycin
* Spermidine
* Spermine; Other positive allosteric modulators: 24S-Hydroxycholesterol
* DHEATooltip Dehydroepiandrosterone (prasterone)
* DHEA sulfate (prasterone sulfate)
* Epipregnanolone sulfate
* Plazinemdor
* Pregnenolone sulfate
* SAGE-201
* SAGE-301
* SAGE-718

* Antagonists: Competitive antagonists: AP5 (APV)
* AP7
* CGP-37849
* CGP-39551
* CGP-39653
* CGP-40116
* CGS-19755
* CPP
* Kaitocephalin
* LY-233053
* LY-235959
* LY-274614
* MDL-100453
* Midafotel (d-CPPene)
* NPC-12626
* NPC-17742
* PBPD
* PEAQX
* Perzinfotel
* PPDA
* SDZ-220581
* Selfotel; Glycine site antagonists: 4-Cl-KYN (AV-101)
* 5,7-DCKA
* 7-CKA
* ACC
* ACEA-1011
* ACEA-1328
* 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 (ACEA-1021)
* LU-73068
* MDL-105519
* Meprobamate
* MRZ 2/576
* PNQX
* 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 (SKF-10047)
* Amantadine
* Aptiganel
* Argiotoxin-636
* Arketamine
* ARL-12495
* ARL-15896-AR
* ARL-16247
* Budipine
* Coronaridine
* 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 (meperidine)
* Phencyclamine
* Phencyclidine
* Propoxyphene
* Remacemide
* Rhynchophylline
* Rimantadine
* Rolicyclidine
* Sabeluzole
* Tabernanthine
* Tenocyclidine
* Tiletamine
* Tramadol; Ifenprodil (NR2B) site antagonists:
* Besonprodil
* Buphenine (nylidrin)
* CO-101244 (PD-174494)
* Eliprodil
* Haloperidol
* Isoxsuprine
* Radiprodil (RGH-896)
* Rislenemdaz (CERC-301, MK-0657)
* Ro 8-4304
* Ro 25-6981
* Safaprodil
* 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 (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 isethionate
* Piretanide
* Psychotridine
* Transcrocetin (saffron)

* Unsorted: Allosteric modulators: AGN-241751

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

* v
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* e

Metabotropic glutamate receptor modulators

Group I|

| mGluR1Tooltip Metabotropic glutamate receptor 1|

* Agonists: ACPD
* DHPG
* Glutamate
* Ibotenic acid
* Quisqualic acid
* Ro01-6128
* Ro67-4853
* Ro67-7476
* VU-71
* Theanine

* Antagonists: BAY 36-7620
* CPCCOEt
* Cyclothiazide
* LY-367,385
* LY-456,236
* MCPG
* NPS-2390

|

mGluR5Tooltip Metabotropic glutamate receptor 5|

* Agonists: ACPD
* ADX-47273
* CDPPB
* CHPG
* DFB
* DHPG
* Glutamate
* Ibotenic acid
* Quisqualic acid
* VU-1545; Positive allosteric modulators: LSN2463359

* Antagonists: CTEP
* DMeOB
* LY-344,545
* Mavoglurant
* MCPG
* NPS-2390
* Remeglurant
* SIB-1757
* SIB-1893; Negative allosteric modulators: AZD9272
* Basimglurant
* Dipraglurant
* Fenobam
* GRN-529
* MPEP
* MTEP
* Raseglurant

Group II|

| mGluR2Tooltip Metabotropic glutamate receptor 2|

* Agonists: BINA
* CBiPES
* DCG-IV
* Eglumegad
* Glutamate
* Ibotenic acid
* LY-379,268
* LY-404,039 (pomaglumetad)
* LY-487,379
* LY-566,332
* MGS-0028
* Pomaglumetad methionil (LY-2140023)
* Talaglumetad; Positive allosteric modulators: JNJ-40411813 (ADX-71149)

* Antagonists: APICA
* CECXG
* EGLU
* HYDIA
* LY-307,452
* LY-341,495
* MCPG
* MGS-0039
* PCCG-4; Negative allosteric modulators: Decoglurant
* RO4491533

|

mGluR3Tooltip Metabotropic glutamate receptor 3|

* Agonists: CBiPES
* DCG-IV
* Eglumegad
* Glutamate
* Ibotenic acid
* LY-379,268
* LY-404,039 (pomaglumetad)
* LY-487,379
* MGS-0028
* Pomaglumetad methionil (LY-2140023)
* Talaglumetad

* Antagonists: APICA
* CECXG
* EGLU
* HYDIA
* LY-307,452
* LY-341,495
* MCPG
* MGS-0039; Negative allosteric modulators: Decoglurant
* RO4491533

Group III|

| mGluR4Tooltip Metabotropic glutamate receptor 4|

* Agonists: Glutamate
* L-AP4
* LSP2-9166
* PHCCC
* VU-001,171
* VU-0155,041; Positive allosteric modulators: Foliglurax
* MPEP

* Antagonists: CPPG
* MAP4
* MPPG
* MSOP
* MTPG
* UBP-1112

|

mGluR6Tooltip Metabotropic glutamate receptor 6|

* Agonists: Glutamate
* L-AP4

* Antagonists: CPPG
* MAP4
* MPPG
* MSOP
* MTPG
* UBP-1112

mGluR7Tooltip Metabotropic glutamate receptor 7|

* Agonists: AMN082
* Glutamate
* L-AP4
* LSP2-9166

* Antagonists: CPPG
* MAP4
* MMPIP
* MPPG
* MSOP
* MTPG
* UBP-1112
* XAP044; Negative allosteric modulators: ADX71743

mGluR8Tooltip Metabotropic glutamate receptor 8|

* Agonists: DCPG
* Glutamate
* L-AP4; Positive allosteric modulators: AZ12216052

* Antagonists: CPPG
* MAP4
* MPPG
* MSOP
* MTPG
* UBP-1112

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

* v
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* e

Imidazoline receptor modulators

IRTooltip Imidazoline receptor|

* Agonists: 2-BFI
* 7-Me-Marsanidine
* Agmatine
* Apraclonidine
* BU224
* Clonidine
* Clorgyline
* Harmalas
* LNP-509
* LNP-911
* mCPP
* Moxonidine
* Rilmenidine
* S-23515
* S-23757

* Antagonists: BU99006
* Efaroxan
* Idazoxan

* Unsorted/unknown: CR-4056
* Pargyline

See also: Receptor/signaling modulators
*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[mAChRs]: Muscarinic acetylcholine receptors
*[SSRIs]: Selective serotonin reuptake inhibitors
*[nAChRs]: Nicotinic acetylcholine receptors
*[PAMs]: positive allosteric modulators
*[NAMs]: negative allosteric modulators
*[AMPAR]: α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
*[KAR]: Kainate receptor
*[NMDAR]: N-Methyl-D-aspartate receptor
*[DHEA]: Dehydroepiandrosterone
*[mGluR1]: Metabotropic glutamate receptor 1
*[mGluR5]: Metabotropic glutamate receptor 5
*[mGluR2]: Metabotropic glutamate receptor 2
*[mGluR3]: Metabotropic glutamate receptor 3
*[mGluR4]: Metabotropic glutamate receptor 4
*[mGluR6]: Metabotropic glutamate receptor 6
*[mGluR7]: Metabotropic glutamate receptor 7
*[mGluR8]: Metabotropic glutamate receptor 8
*[IR]: Imidazoline receptor