TETRAETHYLAMMONIUM

US Previously Marketed

First approved in 1947

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H20N
Molecular Weight	130.2511
Optical Activity	NONE
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

CC[N+](CC)(CC)CC

InChI

InChIKey=CBXCPBUEXACCNR-UHFFFAOYSA-N

InChI=1S/C8H20N/c1-5-9(6-2,7-3)8-4/h5-8H2,1-4H3/q+1

HIDE SMILES / InChI

Molecular Formula	C8H20N
Molecular Weight	130.2511
Charge	1
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18120146 | https://www.ncbi.nlm.nih.gov/pubmed/1698974 | https://www.ncbi.nlm.nih.gov/pubmed/12824448 | DOI: 10.1002/047084289X.rn01547

Tetraethylammonium is an experimental drug with no approved indication or marketed formulation. Tetraethylammonium blocks of apamin-sensitive and insensitive Ca2(+)-activated K+ channels. It is a weak agonist of the nicotinic receptor. Tetraethylammonium produces transient reductions in blood pressure. Tetraethylammonium hydroxide is used as a soluble source of hydroxide ions and in the synthesis of ionic organic compounds.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Nicotinic acetylcholine receptor alpha1/beta1/epsilon/delta 14 Target ID: CHEMBL3137264 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12824448	Modulator 846
Small conductance calcium-activated potassium channel 13 Target ID: CHEMBL2096673 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1698974	Blocker 555	3.1 mM [Kd]
Calcium-activated potassium channel subunit alpha-1 26 Target ID: CHEMBL5505 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1698974	Blocker 555	260.0 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Disease of mental health 12 Sources: http://naikutty.in/medicine-list/72522-fosglutamina-b6-medicine (1971) Omnia medica et therapeutica, v.49, page 52, retrieved from: https://books.google.ru/books?id=hDVCAQAAIAAJ	Palliative		Not Provided 511	Fosglutamina B6 Approved Use Unknown
Hypertension 575 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18120146	Primary		Not Provided 511	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
375 mg 1 times / day single, intravenous Studied dose Dose: 375 mg, 1 times / day Route: intravenous Route: single Dose: 375 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15434379/	healthy, adult Health Status: healthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/15434379/	Other AEs: Paralysis, Drowsiness... Other AEs: Paralysis (14.3%) Drowsiness (14.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/15434379/
41 mg/kg 1 times / day single, intravenous Studied dose Dose: 41 mg/kg, 1 times / day Route: intravenous Route: single Dose: 41 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/	Other AEs: Dysphagia, Dysarthria... Other AEs: Dysphagia (66.7%) Dysarthria (66.7%) Nasal congestion (66.7%) Respiration labored (66.7%) Weakness generalized (100%) Dry mouth (100%) Numbness (100%) Ptosis (100%) Mydriasis (100%) Vasomotor collapse (33.3%) Asthma (33.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/

AEs

AE	Significance	Dose	Population
Drowsiness	14.3%	375 mg 1 times / day single, intravenous Studied dose Dose: 375 mg, 1 times / day Route: intravenous Route: single Dose: 375 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15434379/	healthy, adult Health Status: healthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/15434379/
Paralysis	14.3%	375 mg 1 times / day single, intravenous Studied dose Dose: 375 mg, 1 times / day Route: intravenous Route: single Dose: 375 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15434379/	healthy, adult Health Status: healthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/15434379/
Dry mouth	100%	41 mg/kg 1 times / day single, intravenous Studied dose Dose: 41 mg/kg, 1 times / day Route: intravenous Route: single Dose: 41 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/
Mydriasis	100%	41 mg/kg 1 times / day single, intravenous Studied dose Dose: 41 mg/kg, 1 times / day Route: intravenous Route: single Dose: 41 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/
Numbness	100%	41 mg/kg 1 times / day single, intravenous Studied dose Dose: 41 mg/kg, 1 times / day Route: intravenous Route: single Dose: 41 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/
Ptosis	100%	41 mg/kg 1 times / day single, intravenous Studied dose Dose: 41 mg/kg, 1 times / day Route: intravenous Route: single Dose: 41 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/
Weakness generalized	100%	41 mg/kg 1 times / day single, intravenous Studied dose Dose: 41 mg/kg, 1 times / day Route: intravenous Route: single Dose: 41 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/
Asthma	33.3%	41 mg/kg 1 times / day single, intravenous Studied dose Dose: 41 mg/kg, 1 times / day Route: intravenous Route: single Dose: 41 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/
Vasomotor collapse	33.3%	41 mg/kg 1 times / day single, intravenous Studied dose Dose: 41 mg/kg, 1 times / day Route: intravenous Route: single Dose: 41 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/
Dysarthria	66.7%	41 mg/kg 1 times / day single, intravenous Studied dose Dose: 41 mg/kg, 1 times / day Route: intravenous Route: single Dose: 41 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/
Dysphagia	66.7%	41 mg/kg 1 times / day single, intravenous Studied dose Dose: 41 mg/kg, 1 times / day Route: intravenous Route: single Dose: 41 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/
Nasal congestion	66.7%	41 mg/kg 1 times / day single, intravenous Studied dose Dose: 41 mg/kg, 1 times / day Route: intravenous Route: single Dose: 41 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/
Respiration labored	66.7%	41 mg/kg 1 times / day single, intravenous Studied dose Dose: 41 mg/kg, 1 times / day Route: intravenous Route: single Dose: 41 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Ca2+ activated K+ channel 17 K+ channels 73	OCT1 393

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
Ca2+ activated K+ channel 17	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/21630039/	yes
K+ channels 73	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9316019/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OCT1 393	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/32234672/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/12689355/; https://pubmed.ncbi.nlm.nih.gov/19617705/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:44296	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:44296
ZINC	ZINC000000896981	http://zinc15.docking.org/substances/ZINC000000896981

PubMed

Title	Date	PubMed
Cardiovascular effects of lepadiformine, an alkaloid isolated from the ascidians Clavelina lepadiformis (Müller) and C. moluccensis (Sluiter).	2001-08	11306135
Combined antisense and pharmacological approaches implicate hTASK as an airway O(2) sensing K(+) channel.	2001-07-13	11344164
Shear stress-induced vasodilation in porcine coronary conduit arteries is independent of nitric oxide release.	2001-06	11356613
Verapamil inhibits proliferation of LNCaP human prostate cancer cells influencing K+ channel gating.	2001-06	11353796
Pulmonary vascular response to normoxia and K(Ca) channel activity is developmentally regulated.	2001-06	11350805
Potassium channels regulate tone in rat pulmonary veins.	2001-06	11350792
Regulation of ClC-2 chloride channels in T84 cells by TGF-alpha.	2001-06	11350754
Stretch-dependent potassium channels in murine colonic smooth muscle cells.	2001-05-15	11351024
Oxygen dilation in fetal pulmonary arterioles: role of K(+) channels.	2001-05-15	11341793
p38 activation is required upstream of potassium current enhancement and caspase cleavage in thiol oxidant-induced neuronal apoptosis.	2001-05-15	11331359
A pertussis toxin-sensitive 8-lipoxygenase pathway is activated by a nicotinic acetylcholine receptor in aplysia neurons.	2001-05	11353029
Medium afterhyperpolarization and firing pattern modulation in interneurons of stratum radiatum in the CA3 hippocampal region.	2001-05	11353015
Afterhyperpolarization current in myenteric neurons of the guinea pig duodenum.	2001-05	11353011
Chloride channels regulate HIT cell volume but cannot fully account for swelling-induced insulin secretion.	2001-05	11334443
The properties of ryanodine-sensitive Ca(2+) release in mouse gastric smooth muscle cells.	2001-05	11325802
Mechanism underlying slow kinetics of the OFF gating current in Shaker potassium channel.	2001-05	11325719
Lidocaine selectively blocks abnormal impulses arising from noninactivating Na channels.	2001-05	11317273
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.	2001-05	11306713
Effects of P-glycoprotein on cell volume regulation in mouse proximal tubule.	2001-05	11292625
Flow-dependent K+ secretion in the cortical collecting duct is mediated by a maxi-K channel.	2001-05	11292620
Molecular identification of a TTX-sensitive Ca(2+) current.	2001-05	11287346
Functional receptor-channel coupling compared in contractile and proliferative human vascular smooth muscle.	2001-05	11268004
Mechanisms of tetraethylammonium ion block in the KcsA potassium channel.	2001-04-27	11334890
Flow-induced dilation of human coronary arterioles: important role of Ca(2+)-activated K(+) channels.	2001-04-17	11306529
Distinct K currents result in physiologically distinct cell types in the inferior colliculus of the rat.	2001-04-15	11306638
Photosensitization-induced calcium overload in cardiac cells: direct link to membrane permeabilization and calcium influx.	2001-04	11332038
C-type natriuretic peptide-induced vasodilation is dependent on hyperpolarization in human forearm resistance vessels.	2001-04	11304521
Dopamine-mediated volume transmission in midbrain is regulated by distinct extracellular geometry and uptake.	2001-04	11287497
Mouse taste cells with glialike membrane properties.	2001-04	11287479
Chronic extrinsic denervation after small bowel transplantation in rat jejunum: Effects and adaptation in nitrergic and non-nitrergic neuromuscular inhibitory mechanisms.	2001-04	11283540
Inotrophic effects of the K(+) channel blocker TEA on dystrophic (mdx and dy/dy) mouse diaphragm.	2001-04	11282391
Influence of Ca(2+)-activated K(+) channels on rat renal arteriolar responses to depolarizing agonists.	2001-04	11249849
Modulation of voltage-dependent K+ channel current in vascular smooth muscle cells from rat mesenteric arteries.	2001-03-15	11318099
Temperature-dependent expression of a squid Kv1 channel in Sf9 cells and functional comparison with the native delayed rectifier.	2001-03-15	11318098
Characterization of TASK-4, a novel member of the pH-sensitive, two-pore domain potassium channel family.	2001-03-09	11248242
Tetrabutylammonium: a selective blocker of the somatostatin-activated hyperpolarizing current in mouse AtT-20 corticotrophs.	2001-03	11316266
HNS-32, a novel azulene-1-carboxamidine derivative, inhibits nifedipine-sensitive and -insensitive contraction of the isolated rabbit aorta.	2001-03	11284450
The mechanism of gentisic acid-induced relaxation of the guinea pig isolated trachea: the role of potassium channels and vasoactive intestinal peptide receptors.	2001-03	11262590
Functional characterisation of human TASK-3, an acid-sensitive two-pore domain potassium channel.	2001-03	11249964
The characterisation and uptake of paraquat in cultured baboon kidney proximal tubule cells (bPTC).	2001-02	11327515
20-HETE contributes to myogenic activation of skeletal muscle resistance arteries in Brown Norway and Sprague-Dawley rats.	2001-02	11296852
Large-conductance calcium-activated potassium channels in neonatal rat intracardiac ganglion neurons.	2001-02	11294244
Comparative study of the molecular and functional expression of L-type Ca2+ channels and large-conductance, Ca2+-activated K+ channels in rabbit aorta and vas deferens smooth muscle.	2001-02	11294242
Short term hypercholesterolemia alters N(G)-nitro-L-arginine- and indomethacin-resistant endothelium-dependent relaxation by acetylcholine in rabbit renal artery.	2001-02	11286404
Nitrooxy alkyl apovincaminate activates K+ currents in rat neocortical neurons.	2001-02	11286393
Fusicoccin- and IAA-induced elongation growth share the same pattern of K+ dependence.	2001-02	11283169
Relative significance of the nitric oxide (NO)/cGMP pathway and K+ channel activation in endothelium-dependent vasodilation in the femoral artery of developing piglets.	2001-01	11350260
Changes in neuronal excitability and synaptic function in a chronic model of temporal lobe epilepsy.	2001	11311784
[Spontaneous transient outward currents in smooth muscle cells of the rat tail artery].	2001	11296553
Syntheses of halogenated ethenyl isocyanide chromium complexes as organometallic precursor molecules for ethenyl and ethynyl isocyanides.	2001	11288880

Patents

Sample Use Guides

In Vivo Use Guide

5 min infusion of Tetraethylammonium at 1 mg/min

Route of Administration: Intra-arterial

In Vitro Use Guide

TEA is a weak agonist of the nicotinic receptor. No single-channel clusters were observed at concentrations as high as 5 mM TEA or in the presence of a mutation which selectively increases the efficacy of the receptor. When coapplied with 1 mM carbamylcholine (CCh), TEA decreased the effective opening rate demonstrating that it acts as a competitive antagonist of CCh-mediated activation. Kinetic analysis of currents elicited by CCh and TEA allowed an estimate of receptor affinity for TEA of about 1 mM, while an upper limit of 10 s-1 could be set for the wild-type channel-opening rate constant for receptors activated by TEA alone. At millimolar concentrations, TEA inhibited nicotinic receptor currents by depressing the single-channel amplitude. The effect had an IC50 of 2-3 mM, depending on the conditions of the experiment, and resembled a standard open-channel block.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:06:10 GMT 2025` Edited by `admin` on `Mon Mar 31 21:06:10 GMT 2025`
Record UNII	5AV7G7EIEE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-102778

Preferred Name

English

TETRAETHYLAMMONIUM

Systematic Name

English

TETRAETHYLAMMONIUM ION(1+)

Common Name

English

TETRAETHYLAMMONIUM ION

Common Name

English

TETRYLAMMONIUM

Common Name

English

NSC-156315

Code

English

N,N,N-TRIETHYLETHANAMINIUM

Systematic Name

English

TETRAMON

Common Name

English

AMMONIUM, TETRAETHYL-

Systematic Name

English

ETHANAMINIUM, N,N,N-TRIETHYL-

Systematic Name

English

TETRAETHYLAMMONIUM CATION

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID2045024