TETRAETHYLAMMONIUM

US Previously Marketed

First approved in 1947

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 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 / 0
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 13 Target ID: CHEMBL3137264 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12824448	Modulator 828
Small conductance calcium-activated potassium channel 12 Target ID: CHEMBL2096673 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1698974	Blocker 537	3.1 mM [Kd]
Calcium-activated potassium channel subunit alpha-1 25 Target ID: CHEMBL5505 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1698974	Blocker 537	260.0 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Disease of mental health 11 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 504	Fosglutamina B6 Approved Use Unknown
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18120146	Primary		Not Provided 504	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/15434379/	healthy, adult n = 7 Health Status: healthy Age Group: adult Sex: M+F Population Size: 7 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 n = 3 Health Status: unhealthy Condition: hypertension Age Group: adult Population Size: 3 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 (mean) 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 n = 7 Health Status: healthy Age Group: adult Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/15434379/
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: https://pubmed.ncbi.nlm.nih.gov/15434379/	healthy, adult n = 7 Health Status: healthy Age Group: adult Sex: M+F Population Size: 7 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 n = 3 Health Status: unhealthy Condition: hypertension Age Group: adult Population Size: 3 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 n = 3 Health Status: unhealthy Condition: hypertension Age Group: adult Population Size: 3 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 n = 3 Health Status: unhealthy Condition: hypertension Age Group: adult Population Size: 3 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 n = 3 Health Status: unhealthy Condition: hypertension Age Group: adult Population Size: 3 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 n = 3 Health Status: unhealthy Condition: hypertension Age Group: adult Population Size: 3 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 n = 3 Health Status: unhealthy Condition: hypertension Age Group: adult Population Size: 3 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 n = 3 Health Status: unhealthy Condition: hypertension Age Group: adult Population Size: 3 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 n = 3 Health Status: unhealthy Condition: hypertension Age Group: adult Population Size: 3 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 n = 3 Health Status: unhealthy Condition: hypertension Age Group: adult Population Size: 3 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 n = 3 Health Status: unhealthy Condition: hypertension Age Group: adult Population Size: 3 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 n = 3 Health Status: unhealthy Condition: hypertension Age Group: adult Population Size: 3 Sources: https://pubmed.ncbi.nlm.nih.gov/20238897/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Ca2+ activated K+ channel 16 K+ channels 70	OCT1 327

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
Ca2+ activated K+ channel 16	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/21630039/	yes
K+ channels 70	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9316019/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OCT1 327	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/32234672/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 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
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
Photosensitization-induced calcium overload in cardiac cells: direct link to membrane permeabilization and calcium influx.	2001 Apr	11332038
C-type natriuretic peptide-induced vasodilation is dependent on hyperpolarization in human forearm resistance vessels.	2001 Apr	11304521
Mouse taste cells with glialike membrane properties.	2001 Apr	11287479
Chronic extrinsic denervation after small bowel transplantation in rat jejunum: Effects and adaptation in nitrergic and non-nitrergic neuromuscular inhibitory mechanisms.	2001 Apr	11283540
Inotrophic effects of the K(+) channel blocker TEA on dystrophic (mdx and dy/dy) mouse diaphragm.	2001 Apr	11282391
Influence of Ca(2+)-activated K(+) channels on rat renal arteriolar responses to depolarizing agonists.	2001 Apr	11249849
Iodide and bromide inhibit Ca(2+) uptake by cardiac sarcoplasmic reticulum.	2001 Apr	11247773
Contributions of prostacyclin and nitric oxide to carbon monoxide-induced cerebrovascular dilation in piglets.	2001 Apr	11247758
Activation of K+ channels induces apoptosis in vascular smooth muscle cells.	2001 Apr	11245614
Distinct K currents result in physiologically distinct cell types in the inferior colliculus of the rat.	2001 Apr 15	11306638
Flow-induced dilation of human coronary arterioles: important role of Ca(2+)-activated K(+) channels.	2001 Apr 17	11306529
Mechanisms of tetraethylammonium ion block in the KcsA potassium channel.	2001 Apr 27	11334890
Cardiovascular effects of lepadiformine, an alkaloid isolated from the ascidians Clavelina lepadiformis (Müller) and C. moluccensis (Sluiter).	2001 Aug	11306135
The characterisation and uptake of paraquat in cultured baboon kidney proximal tubule cells (bPTC).	2001 Feb	11327515
20-HETE contributes to myogenic activation of skeletal muscle resistance arteries in Brown Norway and Sprague-Dawley rats.	2001 Feb	11296852
Large-conductance calcium-activated potassium channels in neonatal rat intracardiac ganglion neurons.	2001 Feb	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 Feb	11294242
Short term hypercholesterolemia alters N(G)-nitro-L-arginine- and indomethacin-resistant endothelium-dependent relaxation by acetylcholine in rabbit renal artery.	2001 Feb	11286404
Nitrooxy alkyl apovincaminate activates K+ currents in rat neocortical neurons.	2001 Feb	11286393
Fusicoccin- and IAA-induced elongation growth share the same pattern of K+ dependence.	2001 Feb	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 Jan	11350260
Combined antisense and pharmacological approaches implicate hTASK as an airway O(2) sensing K(+) channel.	2001 Jul 13	11344164
Shear stress-induced vasodilation in porcine coronary conduit arteries is independent of nitric oxide release.	2001 Jun	11356613
Verapamil inhibits proliferation of LNCaP human prostate cancer cells influencing K+ channel gating.	2001 Jun	11353796
Pulmonary vascular response to normoxia and K(Ca) channel activity is developmentally regulated.	2001 Jun	11350805
Potassium channels regulate tone in rat pulmonary veins.	2001 Jun	11350792
Regulation of ClC-2 chloride channels in T84 cells by TGF-alpha.	2001 Jun	11350754
Tetrabutylammonium: a selective blocker of the somatostatin-activated hyperpolarizing current in mouse AtT-20 corticotrophs.	2001 Mar	11316266
HNS-32, a novel azulene-1-carboxamidine derivative, inhibits nifedipine-sensitive and -insensitive contraction of the isolated rabbit aorta.	2001 Mar	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 Mar	11262590
Functional characterisation of human TASK-3, an acid-sensitive two-pore domain potassium channel.	2001 Mar	11249964
Three types of depolarization-activated potassium currents in acutely isolated mouse vestibular neurons.	2001 Mar	11247971
Molecular cloning and functional characterization of a novel delayed rectifier potassium channel from channel catfish (Ictalurus punctatus): expression in taste buds.	2001 Mar	11238731
Modulation of voltage-dependent K+ channel current in vascular smooth muscle cells from rat mesenteric arteries.	2001 Mar 15	11318099
Temperature-dependent expression of a squid Kv1 channel in Sf9 cells and functional comparison with the native delayed rectifier.	2001 Mar 15	11318098
A pertussis toxin-sensitive 8-lipoxygenase pathway is activated by a nicotinic acetylcholine receptor in aplysia neurons.	2001 May	11353029
Medium afterhyperpolarization and firing pattern modulation in interneurons of stratum radiatum in the CA3 hippocampal region.	2001 May	11353015
Afterhyperpolarization current in myenteric neurons of the guinea pig duodenum.	2001 May	11353011
Chloride channels regulate HIT cell volume but cannot fully account for swelling-induced insulin secretion.	2001 May	11334443
The properties of ryanodine-sensitive Ca(2+) release in mouse gastric smooth muscle cells.	2001 May	11325802
Mechanism underlying slow kinetics of the OFF gating current in Shaker potassium channel.	2001 May	11325719
Lidocaine selectively blocks abnormal impulses arising from noninactivating Na channels.	2001 May	11317273
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.	2001 May	11306713
Molecular identification of a TTX-sensitive Ca(2+) current.	2001 May	11287346
Stretch-dependent potassium channels in murine colonic smooth muscle cells.	2001 May 15	11351024
Oxygen dilation in fetal pulmonary arterioles: role of K(+) channels.	2001 May 15	11341793
p38 activation is required upstream of potassium current enhancement and caspase cleavage in thiol oxidant-induced neuronal apoptosis.	2001 May 15	11331359

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 `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

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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