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
KCNQ5, a novel potassium channel broadly expressed in brain, mediates M-type currents.	2000 Aug 4	10816588
KCNA10: a novel ion channel functionally related to both voltage-gated potassium and CNG cation channels.	2000 Jun	10836990
Retigabine, a novel anti-convulsant, enhances activation of KCNQ2/Q3 potassium channels.	2000 Sep	10953053
[Spontaneous transient outward currents in smooth muscle cells of the rat tail artery].	2001	11296553
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
Iodide and bromide inhibit Ca(2+) uptake by cardiac sarcoplasmic reticulum.	2001 Apr	11247773
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
20-HETE contributes to myogenic activation of skeletal muscle resistance arteries in Brown Norway and Sprague-Dawley rats.	2001 Feb	11296852
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
Potentiation of bradykinin by angiotensin-(1-7) on arterioles of spontaneously hypertensive rats studied in vivo.	2001 Feb	11230360
Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2.	2001 Feb	11160873
Characterization of a novel cationic drug transporter in human retinal pigment epithelial cells.	2001 Feb	11160630
Immature neocortical neurons exist as extensive syncitial networks linked by dendrodendritic electrical connections.	2001 Feb	11160498
Mechanism of prolonged vasorelaxation to ATP in the rat isolated mesenteric arterial bed.	2001 Feb	11159721
Adrenocorticotropic hormone activates an outward current in cultured mouse peritoneal macrophages.	2001 Feb 15	11164906
Differential expression of kcnq2 splice variants: implications to m current function during neuronal development.	2001 Feb 15	11160379
Muscarinic activation of transient inward current and contraction in canine colon circular smooth muscle cells.	2001 Jan	11201499
Determination of ambroxol or bromhexine in pharmaceuticals by capillary isotachophoresis.	2001 Jan	11199221
Apical uptake of organic cations by human intestinal Caco-2 cells: putative involvement of ASF transporters.	2001 Jan	11191835
Transport of [3H]MPP+ in an immortalized rat brain microvessel endothelial cell line (RBE 4).	2001 Jan	11191826
Number of K(Ca) channels underlying spontaneous miniature outward currents (SMOCs) in mudpuppy cardiac neurons.	2001 Jan	11152705
Role of potassium channels in regulation of brain arteriolar tone: comparison of cerebrum versus brain stem.	2001 Jan	11136940
Cold transduction by inhibition of a background potassium conductance in rat primary sensory neurones.	2001 Jan 19	11137755
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
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
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
Modulation of voltage-dependent K+ channel current in vascular smooth muscle cells from rat mesenteric arteries.	2001 Mar 15	11318099
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

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