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Details

Stereochemistry ACHIRAL
Molecular Formula C8H20N
Molecular Weight 130.2514
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of TETRAETHYLAMMONIUM

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 130.2514
Charge 1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Sources: DOI: 10.1515/zpch-1897-2427

Approval Year

Doses

Doses

DosePopulationAdverse 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:
healthy, adult
Health Status: healthy
Age Group: adult
Sex: M+F
Sources:
Other AEs: Paralysis, Drowsiness...
Other AEs:
Paralysis (14.3%)
Drowsiness (14.3%)
Sources:
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
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:
AEs

AEs

AESignificanceDosePopulation
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:
healthy, adult
Health Status: healthy
Age Group: adult
Sex: M+F
Sources:
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:
healthy, adult
Health Status: healthy
Age Group: adult
Sex: M+F
Sources:
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Tox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
Changes in neuronal excitability and synaptic function in a chronic model of temporal lobe epilepsy.
2001
[Spontaneous transient outward currents in smooth muscle cells of the rat tail artery].
2001
Photosensitization-induced calcium overload in cardiac cells: direct link to membrane permeabilization and calcium influx.
2001 Apr
C-type natriuretic peptide-induced vasodilation is dependent on hyperpolarization in human forearm resistance vessels.
2001 Apr
Dopamine-mediated volume transmission in midbrain is regulated by distinct extracellular geometry and uptake.
2001 Apr
Chronic extrinsic denervation after small bowel transplantation in rat jejunum: Effects and adaptation in nitrergic and non-nitrergic neuromuscular inhibitory mechanisms.
2001 Apr
Inotrophic effects of the K(+) channel blocker TEA on dystrophic (mdx and dy/dy) mouse diaphragm.
2001 Apr
Influence of Ca(2+)-activated K(+) channels on rat renal arteriolar responses to depolarizing agonists.
2001 Apr
Iodide and bromide inhibit Ca(2+) uptake by cardiac sarcoplasmic reticulum.
2001 Apr
Contributions of prostacyclin and nitric oxide to carbon monoxide-induced cerebrovascular dilation in piglets.
2001 Apr
Activation of K+ channels induces apoptosis in vascular smooth muscle cells.
2001 Apr
Distinct K currents result in physiologically distinct cell types in the inferior colliculus of the rat.
2001 Apr 15
Flow-induced dilation of human coronary arterioles: important role of Ca(2+)-activated K(+) channels.
2001 Apr 17
Mechanisms of tetraethylammonium ion block in the KcsA potassium channel.
2001 Apr 27
Cardiovascular effects of lepadiformine, an alkaloid isolated from the ascidians Clavelina lepadiformis (Müller) and C. moluccensis (Sluiter).
2001 Aug
The characterisation and uptake of paraquat in cultured baboon kidney proximal tubule cells (bPTC).
2001 Feb
Large-conductance calcium-activated potassium channels in neonatal rat intracardiac ganglion neurons.
2001 Feb
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 Feb
Short term hypercholesterolemia alters N(G)-nitro-L-arginine- and indomethacin-resistant endothelium-dependent relaxation by acetylcholine in rabbit renal artery.
2001 Feb
Nitrooxy alkyl apovincaminate activates K+ currents in rat neocortical neurons.
2001 Feb
Potentiation of bradykinin by angiotensin-(1-7) on arterioles of spontaneously hypertensive rats studied in vivo.
2001 Feb
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 Jan
Shear stress-induced vasodilation in porcine coronary conduit arteries is independent of nitric oxide release.
2001 Jun
Verapamil inhibits proliferation of LNCaP human prostate cancer cells influencing K+ channel gating.
2001 Jun
Pulmonary vascular response to normoxia and K(Ca) channel activity is developmentally regulated.
2001 Jun
Potassium channels regulate tone in rat pulmonary veins.
2001 Jun
Regulation of ClC-2 chloride channels in T84 cells by TGF-alpha.
2001 Jun
Tetrabutylammonium: a selective blocker of the somatostatin-activated hyperpolarizing current in mouse AtT-20 corticotrophs.
2001 Mar
HNS-32, a novel azulene-1-carboxamidine derivative, inhibits nifedipine-sensitive and -insensitive contraction of the isolated rabbit aorta.
2001 Mar
The mechanism of gentisic acid-induced relaxation of the guinea pig isolated trachea: the role of potassium channels and vasoactive intestinal peptide receptors.
2001 Mar
Functional characterisation of human TASK-3, an acid-sensitive two-pore domain potassium channel.
2001 Mar
Three types of depolarization-activated potassium currents in acutely isolated mouse vestibular neurons.
2001 Mar
Molecular cloning and functional characterization of a novel delayed rectifier potassium channel from channel catfish (Ictalurus punctatus): expression in taste buds.
2001 Mar
Modulation of voltage-dependent K+ channel current in vascular smooth muscle cells from rat mesenteric arteries.
2001 Mar 15
Temperature-dependent expression of a squid Kv1 channel in Sf9 cells and functional comparison with the native delayed rectifier.
2001 Mar 15
Increased inwardly rectifying potassium currents in HEK-293 cells expressing murine transient receptor potential 4.
2001 Mar 15
Characterization of TASK-4, a novel member of the pH-sensitive, two-pore domain potassium channel family.
2001 Mar 9
A pertussis toxin-sensitive 8-lipoxygenase pathway is activated by a nicotinic acetylcholine receptor in aplysia neurons.
2001 May
Medium afterhyperpolarization and firing pattern modulation in interneurons of stratum radiatum in the CA3 hippocampal region.
2001 May
Afterhyperpolarization current in myenteric neurons of the guinea pig duodenum.
2001 May
Chloride channels regulate HIT cell volume but cannot fully account for swelling-induced insulin secretion.
2001 May
The properties of ryanodine-sensitive Ca(2+) release in mouse gastric smooth muscle cells.
2001 May
Mechanism underlying slow kinetics of the OFF gating current in Shaker potassium channel.
2001 May
Lidocaine selectively blocks abnormal impulses arising from noninactivating Na channels.
2001 May
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
2001 May
Effects of P-glycoprotein on cell volume regulation in mouse proximal tubule.
2001 May
Flow-dependent K+ secretion in the cortical collecting duct is mediated by a maxi-K channel.
2001 May
Molecular identification of a TTX-sensitive Ca(2+) current.
2001 May
Functional receptor-channel coupling compared in contractile and proliferative human vascular smooth muscle.
2001 May
Stretch-dependent potassium channels in murine colonic smooth muscle cells.
2001 May 15
Patents

Sample Use Guides

5 min infusion of Tetraethylammonium at 1 mg/min
Route of Administration: Intra-arterial
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 Sat Jun 26 15:10:24 UTC 2021
Edited
by admin
on Sat Jun 26 15:10:24 UTC 2021
Record UNII
5AV7G7EIEE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
NSC-102778
Code English
ETHANAMINIUM, N,N,N-TRIETHYL-
Systematic Name English
TETRAETHYLAMMONIUM CATION
Common Name English
Code System Code Type Description
EPA CompTox
66-40-0
Created by admin on Sat Jun 26 15:10:24 UTC 2021 , Edited by admin on Sat Jun 26 15:10:24 UTC 2021
PRIMARY
FDA UNII
5AV7G7EIEE
Created by admin on Sat Jun 26 15:10:24 UTC 2021 , Edited by admin on Sat Jun 26 15:10:24 UTC 2021
PRIMARY
PUBCHEM
5413
Created by admin on Sat Jun 26 15:10:24 UTC 2021 , Edited by admin on Sat Jun 26 15:10:24 UTC 2021
PRIMARY
CAS
66-40-0
Created by admin on Sat Jun 26 15:10:24 UTC 2021 , Edited by admin on Sat Jun 26 15:10:24 UTC 2021
PRIMARY
DRUG BANK
DB08837
Created by admin on Sat Jun 26 15:10:24 UTC 2021 , Edited by admin on Sat Jun 26 15:10:24 UTC 2021
PRIMARY
WIKIPEDIA
TETRAETHYLAMMONIUM
Created by admin on Sat Jun 26 15:10:24 UTC 2021 , Edited by admin on Sat Jun 26 15:10:24 UTC 2021
PRIMARY
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