U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C8H20N
Molecular Weight 130.2511
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 130.2511
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 (mean)
Studied dose
Dose: 375 mg, 1 times / day
Route: intravenous
Route: single
Dose: 375 mg, 1 times / day
Sources:
healthy, adult
n = 7
Health Status: healthy
Age Group: adult
Sex: M+F
Population Size: 7
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
n = 3
Health Status: unhealthy
Condition: hypertension
Age Group: adult
Population Size: 3
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 (mean)
Studied dose
Dose: 375 mg, 1 times / day
Route: intravenous
Route: single
Dose: 375 mg, 1 times / day
Sources:
healthy, adult
n = 7
Health Status: healthy
Age Group: adult
Sex: M+F
Population Size: 7
Sources:
Paralysis 14.3%
375 mg 1 times / day single, intravenous (mean)
Studied dose
Dose: 375 mg, 1 times / day
Route: intravenous
Route: single
Dose: 375 mg, 1 times / day
Sources:
healthy, adult
n = 7
Health Status: healthy
Age Group: adult
Sex: M+F
Population Size: 7
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
n = 3
Health Status: unhealthy
Condition: hypertension
Age Group: adult
Population Size: 3
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
n = 3
Health Status: unhealthy
Condition: hypertension
Age Group: adult
Population Size: 3
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
n = 3
Health Status: unhealthy
Condition: hypertension
Age Group: adult
Population Size: 3
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
n = 3
Health Status: unhealthy
Condition: hypertension
Age Group: adult
Population Size: 3
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
n = 3
Health Status: unhealthy
Condition: hypertension
Age Group: adult
Population Size: 3
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
n = 3
Health Status: unhealthy
Condition: hypertension
Age Group: adult
Population Size: 3
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
n = 3
Health Status: unhealthy
Condition: hypertension
Age Group: adult
Population Size: 3
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
n = 3
Health Status: unhealthy
Condition: hypertension
Age Group: adult
Population Size: 3
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
n = 3
Health Status: unhealthy
Condition: hypertension
Age Group: adult
Population Size: 3
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
n = 3
Health Status: unhealthy
Condition: hypertension
Age Group: adult
Population Size: 3
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
n = 3
Health Status: unhealthy
Condition: hypertension
Age Group: adult
Population Size: 3
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
Inhibition of aquaporin-1 water permeability by tetraethylammonium: involvement of the loop E pore region.
2000 May
Retigabine, a novel anti-convulsant, enhances activation of KCNQ2/Q3 potassium channels.
2000 Sep
Changes in neuronal excitability and synaptic function in a chronic model of temporal lobe epilepsy.
2001
Syntheses of halogenated ethenyl isocyanide chromium complexes as organometallic precursor molecules for ethenyl and ethynyl isocyanides.
2001
C-type natriuretic peptide-induced vasodilation is dependent on hyperpolarization in human forearm resistance vessels.
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
Distinct K currents result in physiologically distinct cell types in the inferior colliculus of the rat.
2001 Apr 15
Cardiovascular effects of lepadiformine, an alkaloid isolated from the ascidians Clavelina lepadiformis (Müller) and C. moluccensis (Sluiter).
2001 Aug
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
Nitrooxy alkyl apovincaminate activates K+ currents in rat neocortical neurons.
2001 Feb
Fusicoccin- and IAA-induced elongation growth share the same pattern of K+ dependence.
2001 Feb
Angiotensin II relaxes microvessels via the AT(2) receptor and Ca(2+)-activated K(+) (BK(Ca)) channels.
2001 Feb
The effect of proteolytic enzymes on the alpha9-nicotinic receptor-mediated response in isolated frog vestibular hair cells.
2001 Feb
H3 receptor-mediated inhibition of intestinal acetylcholine release: pharmacological characterization of signal transduction pathways.
2001 Feb
Characterization of a novel cationic drug transporter in human retinal pigment epithelial cells.
2001 Feb
Immature neocortical neurons exist as extensive syncitial networks linked by dendrodendritic electrical connections.
2001 Feb
Differential expression of kcnq2 splice variants: implications to m current function during neuronal development.
2001 Feb 15
Mechanisms of hydrogen peroxide-induced relaxation in rabbit mesenteric small artery.
2001 Feb 2
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
Uptake properties of lamivudine (3TC) by a continuous renal epithelial cell line.
2001 Jan
Muscarinic activation of transient inward current and contraction in canine colon circular smooth muscle cells.
2001 Jan
Determination of ambroxol or bromhexine in pharmaceuticals by capillary isotachophoresis.
2001 Jan
Apical uptake of organic cations by human intestinal Caco-2 cells: putative involvement of ASF transporters.
2001 Jan
Transport of [3H]MPP+ in an immortalized rat brain microvessel endothelial cell line (RBE 4).
2001 Jan
Modulation of Ca(2+) signaling by K(+) channels in a hypothalamic neuronal cell line (GT1-1).
2001 Jan
Cloning and function of the rat colonic epithelial K+ channel KVLQT1.
2001 Jan 15
Shear stress-induced vasodilation in porcine coronary conduit arteries is independent of nitric oxide release.
2001 Jun
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
Multiple binding sites for melatonin on Kv1.3.
2001 Mar
Multiple Ca(2+)-dependent modulators mediate alkalosis-induced vasodilation in newborn piglet lungs.
2001 Mar
Characterization of TASK-4, a novel member of the pH-sensitive, two-pore domain potassium channel family.
2001 Mar 9
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
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
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 Dec 16 02:00:14 GMT 2023
Edited
by admin
on Sat Dec 16 02:00:14 GMT 2023
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
DTXSID2045024
Created by admin on Sat Dec 16 02:00:14 GMT 2023 , Edited by admin on Sat Dec 16 02:00:14 GMT 2023
PRIMARY
NSC
102778
Created by admin on Sat Dec 16 02:00:14 GMT 2023 , Edited by admin on Sat Dec 16 02:00:14 GMT 2023
PRIMARY
FDA UNII
5AV7G7EIEE
Created by admin on Sat Dec 16 02:00:14 GMT 2023 , Edited by admin on Sat Dec 16 02:00:14 GMT 2023
PRIMARY
PUBCHEM
5413
Created by admin on Sat Dec 16 02:00:14 GMT 2023 , Edited by admin on Sat Dec 16 02:00:14 GMT 2023
PRIMARY
CAS
66-40-0
Created by admin on Sat Dec 16 02:00:14 GMT 2023 , Edited by admin on Sat Dec 16 02:00:14 GMT 2023
PRIMARY
DRUG BANK
DB08837
Created by admin on Sat Dec 16 02:00:14 GMT 2023 , Edited by admin on Sat Dec 16 02:00:14 GMT 2023
PRIMARY
WIKIPEDIA
TETRAETHYLAMMONIUM
Created by admin on Sat Dec 16 02:00:14 GMT 2023 , Edited by admin on Sat Dec 16 02:00:14 GMT 2023
PRIMARY
NSC
156315
Created by admin on Sat Dec 16 02:00:14 GMT 2023 , Edited by admin on Sat Dec 16 02:00:14 GMT 2023
PRIMARY
CHEBI
44296
Created by admin on Sat Dec 16 02:00:14 GMT 2023 , Edited by admin on Sat Dec 16 02:00:14 GMT 2023
PRIMARY
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