Tetraethylammonium

Identification

Generic Name

Tetraethylammonium

DrugBank Accession Number

DB08837

Background

Tetraethylammonium is an experimental drug with no approved indication or marketed formulation. The only marketed drug containing tetraethylammonium was a combination drug called Fosglutamina B6, but this drug has now been discontinued. As an experimental agent, tetraethylammonium is used in its salt forms such as tetraethylammonium chloride and tetraethylammonium bromide. Its mechanism of action is still being investigated, but it is known that tetraethylammonium blocks autonomic ganglia, calcium- and voltage- activated potassium channels, and nicotinic acetylcholine receptors. Because of its inhibitory actions at the autonomic ganglia, tetraethylammonium was thought to be a potential therapeutic vasodilator but serious toxic effects were found. The most common use of tetraethylammonium presently is as a pharmacological research agent that blocks selective potassium channels. Structurally, tetraethylammonium is positively charged due to its central quaternary ammonium.

Type

Small Molecule

Groups

Experimental, Investigational

Structure

Similar Structures

Weight: Average: 130.2511
Monoisotopic: 130.159574645
Chemical Formula: C₈H₂₀N

Synonyms

Not Available

External IDs

NSC-102778
NSC-156315

Pharmacology

Indication

Tetraethylammonium is an experimental drug with no approved indication.

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Associated Conditions

Bacterial skin infections

Contraindications & Blackbox Warnings

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Pharmacodynamics

Tetraethylammonium is a vasodilator because it blocks autonomic ganglia and prevents signals carrying vasoconstrictor impulses from proceeding.

Mechanism of action

Tetraethylammonium's mechanism of action is still being investigated, but it is known that it blocks autonomic ganglia, calcium- and voltage- activated potassium channels, and nicotinic acetylcholine receptors.

Target	Actions	Organism
UpH-gated potassium channel KcsA	inhibitor	Streptomyces lividans
UNeuronal acetylcholine receptor subunit alpha-9	agonist inhibitor	Humans
UCalcium-activated potassium channel subunit alpha-1	inhibitor	Mouse
UPotassium voltage-gated channel subfamily A member 1	blocker	Humans

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Tetraethylammonium is eliminated by active renal tubular secretion by the cation transport system.

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Studies in animals and humans have reported cases of serious muscle paralysis, which can lead to respiratory distress and death.

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Bethanechol	The risk or severity of hypotension can be increased when Tetraethylammonium is combined with Bethanechol.
Risdiplam	The serum concentration of Tetraethylammonium can be increased when it is combined with Risdiplam.
Vasopressin	Tetraethylammonium may increase the hypertensive activities of Vasopressin.

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Food Interactions

Not Available

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Tetraethylammonium bromide	0435621Z3N	71-91-0	HWCKGOZZJDHMNC-UHFFFAOYSA-M
Tetraethylammonium chloride	8B82Z83XNN	56-34-8	YMBCJWGVCUEGHA-UHFFFAOYSA-M
Tetraethylammonium hydroxide	RA8VU41B1F	77-98-5	LRGJRHZIDJQFCL-UHFFFAOYSA-M
Tetraethylammonium iodide	5YC77AN7EB	Not Available	UQFSVBXCNGCBBW-UHFFFAOYSA-M
Tetraethylammonium phosphate	CRD3CJW5P4	5574-97-0	Not applicable

Chemical Identifiers

UNII: 5AV7G7EIEE
CAS number: 66-40-0
InChI Key: CBXCPBUEXACCNR-UHFFFAOYSA-N
InChI: InChI=1S/C8H20N/c1-5-9(6-2,7-3)8-4/h5-8H2,1-4H3/q+1
IUPAC Name: tetraethylazanium
SMILES: CC[N+](CC)(CC)CC

References

General References

GRAHAM AJ: Toxic effects in animals and man after tetraethylammonium bromide. Br Med J. 1950 Aug 5;2(4674):321-2. [Article]
O'Neil, Maryadele J. (2013). The Merck Index : An Encyclopedia of Chemicals, Drugs, and Biologicals (15th ed.). Royal Society of Chemistry, The. [ISBN:978-1849736701]
Allen, Loyd V., Jr. (2012). Remington : The Science and Practice of Pharmacy (22nd ed.). Pharmaceutical Press. [ISBN:978-0857110626]

External Links

KEGG Compound: C07512
PubChem Compound: 5413
PubChem Substance: 175427115
ChemSpider: 5220
BindingDB: 50149890
ChEBI: 44296
ChEMBL: CHEMBL9324
ZINC: ZINC000000896981
PDBe Ligand: NET
Wikipedia: Tetraethylammonium

PDB Entries

1a9x / 1bxr / 1c30 / 1c3o / 1ce8 / 1cs0 / 1jdb / 1kee / 1m6v / 1t36

MSDS

Download (37.4 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
2	Terminated	Diagnostic	Hyperlipidemias	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Solution	Topical	1 g

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	360 °C or 680 °F	From MSDS.
water solubility	Soluble in water.	From MSDS.

Predicted Properties

Property	Value	Source
Water Solubility	0.00277 mg/mL	ALOGPS
logP	-1.2	ALOGPS
logP	-2.5	Chemaxon
logS	-4.8	ALOGPS
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	0	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	0 Å²	Chemaxon
Rotatable Bond Count	4	Chemaxon
Refractivity	54.9 m³·mol^-1	Chemaxon
Polarizability	17.32 Å³	Chemaxon
Number of Rings	0	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	-	0.9176
Blood Brain Barrier	+	0.9547
Caco-2 permeable	+	0.7044
P-glycoprotein substrate	Non-substrate	0.6461
P-glycoprotein inhibitor I	Non-inhibitor	0.9865
P-glycoprotein inhibitor II	Non-inhibitor	0.9451
Renal organic cation transporter	Non-inhibitor	0.784
CYP450 2C9 substrate	Non-substrate	0.8448
CYP450 2D6 substrate	Non-substrate	0.812
CYP450 3A4 substrate	Non-substrate	0.6615
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9542
CYP450 2C19 inhibitor	Non-inhibitor	0.9182
CYP450 3A4 inhibitor	Non-inhibitor	0.9806
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.901
Ames test	Non AMES toxic	0.9777
Carcinogenicity	Carcinogens	0.8582
Biodegradation	Not ready biodegradable	0.5794
Rat acute toxicity	2.3409 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9107
hERG inhibition (predictor II)	Non-inhibitor	0.8008

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available

Targets

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Details1. pH-gated potassium channel KcsA

Kind: Protein
Organism: Streptomyces lividans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Voltage-gated potassium channel activity
Specific Function: Acts as a pH-gated potassium ion channel; changing the cytosolic pH from 7 to 4 opens the channel, although it is not clear if this is the physiological stimulus for channel opening. Monovalent cat...
Gene Name: kcsA
Uniprot ID: P0A334
Uniprot Name: pH-gated potassium channel KcsA
Molecular Weight: 17693.465 Da

References

Ahern CA, Eastwood AL, Lester HA, Dougherty DA, Horn R: A cation-pi interaction between extracellular TEA and an aromatic residue in potassium channels. J Gen Physiol. 2006 Dec;128(6):649-57. [Article]
Bisset D, Chung SH: Efficacy of external tetraethylammonium block of the KcsA potassium channel: molecular and Brownian dynamics studies. Biochim Biophys Acta. 2008 Oct;1778(10):2273-82. doi: 10.1016/j.bbamem.2008.05.008. Epub 2008 Jun 3. [Article]

Details2. Neuronal acetylcholine receptor subunit alpha-9

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist
Inhibitor

General Function: Calcium channel activity
Specific Function: Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding induces a conformation change that leads to the opening of an ion-conducting channel across the plasm...
Gene Name: CHRNA9
Uniprot ID: Q9UGM1
Uniprot Name: Neuronal acetylcholine receptor subunit alpha-9
Molecular Weight: 54806.63 Da

References

Akk G, Steinbach JH: Activation and block of mouse muscle-type nicotinic receptors by tetraethylammonium. J Physiol. 2003 Aug 15;551(Pt 1):155-68. Epub 2003 Jun 24. [Article]

Details3. Calcium-activated potassium channel subunit alpha-1

Kind: Protein
Organism: Mouse
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Voltage-gated potassium channel activity
Specific Function: Potassium channel activated by both membrane depolarization or increase in cytosolic Ca(2+) that mediates export of K(+). It is also activated by the concentration of cytosolic Mg(2+). Its activati...
Gene Name: Kcnma1
Uniprot ID: Q08460
Uniprot Name: Calcium-activated potassium channel subunit alpha-1
Molecular Weight: 134394.8 Da

References

Lang DG, Ritchie AK: Tetraethylammonium blockade of apamin-sensitive and insensitive Ca2(+)-activated K+ channels in a pituitary cell line. J Physiol. 1990 Jun;425:117-32. [Article]
Latorre R, Vergara C, Hidalgo C: Reconstitution in planar lipid bilayers of a Ca2+-dependent K+ channel from transverse tubule membranes isolated from rabbit skeletal muscle. Proc Natl Acad Sci U S A. 1982 Feb;79(3):805-9. [Article]

Details4. Potassium voltage-gated channel subfamily A member 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Blocker

General Function: Voltage-gated potassium channel activity
Specific Function: Voltage-gated potassium channel that mediates transmembrane potassium transport in excitable membranes, primarily in the brain and the central nervous system, but also in the kidney (PubMed:1990381...
Gene Name: KCNA1
Uniprot ID: Q09470
Uniprot Name: Potassium voltage-gated channel subfamily A member 1
Molecular Weight: 56465.01 Da

References

Kuzmenkov AI, Vassilevski AA, Kudryashova KS, Nekrasova OV, Peigneur S, Tytgat J, Feofanov AV, Kirpichnikov MP, Grishin EV: Variability of Potassium Channel Blockers in Mesobuthus eupeus Scorpion Venom with Focus on Kv1.1: AN INTEGRATED TRANSCRIPTOMIC AND PROTEOMIC STUDY. J Biol Chem. 2015 May 8;290(19):12195-209. doi: 10.1074/jbc.M115.637611. Epub 2015 Mar 19. [Article]

Transporters

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	158000	N/A	N/A	A31144

Details1. Solute carrier family 22 member 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Secondary active organic cation transmembrane transporter activity
Specific Function: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name: SLC22A1
Uniprot ID: O15245
Uniprot Name: Solute carrier family 22 member 1
Molecular Weight: 61153.345 Da

References

Grundemann D, Liebich G, Kiefer N, Koster S, Schomig E: Selective substrates for non-neuronal monoamine transporters. Mol Pharmacol. 1999 Jul;56(1):1-10. [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	156000	N/A	N/A	A16041

Details2. Solute carrier family 22 member 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Quaternary ammonium group transmembrane transporter activity
Specific Function: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name: SLC22A2
Uniprot ID: O15244
Uniprot Name: Solute carrier family 22 member 2
Molecular Weight: 62579.99 Da

References

Grundemann D, Liebich G, Kiefer N, Koster S, Schomig E: Selective substrates for non-neuronal monoamine transporters. Mol Pharmacol. 1999 Jul;56(1):1-10. [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	10300000	N/A	N/A	A16100

Details3. Solute carrier family 22 member 3

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Toxin transporter activity
Specific Function: Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name: SLC22A3
Uniprot ID: O75751
Uniprot Name: Solute carrier family 22 member 3
Molecular Weight: 61279.485 Da

References

Wu X, Huang W, Ganapathy ME, Wang H, Kekuda R, Conway SJ, Leibach FH, Ganapathy V: Structure, function, and regional distribution of the organic cation transporter OCT3 in the kidney. Am J Physiol Renal Physiol. 2000 Sep;279(3):F449-58. [Article]

Details4. Solute carrier family 22 member 4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Symporter activity
Specific Function: Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
Gene Name: SLC22A4
Uniprot ID: Q9H015
Uniprot Name: Solute carrier family 22 member 4
Molecular Weight: 62154.48 Da

References

Wu X, George RL, Huang W, Wang H, Conway SJ, Leibach FH, Ganapathy V: Structural and functional characteristics and tissue distribution pattern of rat OCTN1, an organic cation transporter, cloned from placenta. Biochim Biophys Acta. 2000 Jun 1;1466(1-2):315-27. [Article]

Details5. Solute carrier family 22 member 5

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Symporter activity
Specific Function: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name: SLC22A5
Uniprot ID: O76082
Uniprot Name: Solute carrier family 22 member 5
Molecular Weight: 62751.08 Da

References

Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [Article]

Details6. Solute carrier family 22 member 8

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Sodium-independent organic anion transmembrane transporter activity
Specific Function: Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name: SLC22A8
Uniprot ID: Q8TCC7
Uniprot Name: Solute carrier family 22 member 8
Molecular Weight: 59855.585 Da

References

Enomoto A, Takeda M, Taki K, Takayama F, Noshiro R, Niwa T, Endou H: Interactions of human organic anion as well as cation transporters with indoxyl sulfate. Eur J Pharmacol. 2003 Apr 11;466(1-2):13-20. [Article]

Details7. Multidrug and toxin extrusion protein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Monovalent cation:proton antiporter activity
Specific Function: Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
Gene Name: SLC47A1
Uniprot ID: Q96FL8
Uniprot Name: Multidrug and toxin extrusion protein 1
Molecular Weight: 61921.585 Da

References

Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K: Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71. doi: 10.1016/j.bcp.2007.04.010. Epub 2007 Apr 13. [Article]
Yonezawa A, Inui K: Importance of the multidrug and toxin extrusion MATE/SLC47A family to pharmacokinetics, pharmacodynamics/toxicodynamics and pharmacogenomics. Br J Pharmacol. 2011 Dec;164(7):1817-25. doi: 10.1111/j.1476-5381.2011.01394.x. [Article]

Drug created at February 21, 2013 00:57 / Updated at January 03, 2023 04:24

Tetraethylammonium

Identification

Structure for Tetraethylammonium (DB08837)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

References

References

References

Transporters

References

References

References

References

References

References

References