Tetraethylammonium nitrate

US Previously Marketed

First approved in 1947

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H20N.NO3
Molecular Weight	192.256
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[O-][N+]([O-])=O.CC[N+](CC)(CC)CC

InChI

InChIKey=JTJKNAJRGLQKDZ-UHFFFAOYSA-N

InChI=1S/C8H20N.NO3/c1-5-9(6-2,7-3)8-4;2-1(3)4/h5-8H2,1-4H3;/q+1;-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

Molecular Formula	NO3
Molecular Weight	62.0049
Charge	-1
Count

Stereochemistry	ACHIRAL
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
[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
C-type natriuretic peptide-induced vasodilation is dependent on hyperpolarization in human forearm resistance vessels.	2001 Apr	11304521
Dopamine-mediated volume transmission in midbrain is regulated by distinct extracellular geometry and uptake.	2001 Apr	11287497
Mouse taste cells with glialike membrane properties.	2001 Apr	11287479
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
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
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
Potentiation of bradykinin by angiotensin-(1-7) on arterioles of spontaneously hypertensive rats studied in vivo.	2001 Feb	11230360
H3 receptor-mediated inhibition of intestinal acetylcholine release: pharmacological characterization of signal transduction pathways.	2001 Feb	11219402
Modulation of diaphragm action potentials by K(+) channel blockers.	2001 Feb	11173076
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
Comparison of spontaneous and noradrenaline-evoked non-selective cation channels in rabbit portal vein myocytes.	2001 Feb 1	11158276
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
Mechanisms of hydrogen peroxide-induced relaxation in rabbit mesenteric small artery.	2001 Feb 2	11166293
Involvement of K(ATP) channels in diethylstilbestrol-induced relaxation in rat aorta.	2001 Feb 9	11173069
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
Three types of K(+) currents in murine osteocyte-like cells (MLO-Y4).	2001 Jan	11165940
Activation of potassium conductance by ophiopogonin-D in acutely dissociated rat paratracheal neurones.	2001 Jan	11159695
Tetraethylammonium-induced long-term potentiation in layer V horizontal connections of rat motor cortex.	2001 Jan 26	11154830
Expression and function of colonic epithelial KvLQT1 K+ channels.	2001 Jan-Feb	11153543
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
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
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
Molecular cloning and functional characterization of a novel delayed rectifier potassium channel from channel catfish (Ictalurus punctatus): expression in taste buds.	2001 Mar	11238731
Multiple binding sites for melatonin on Kv1.3.	2001 Mar	11222291
Temperature-dependent expression of a squid Kv1 channel in Sf9 cells and functional comparison with the native delayed rectifier.	2001 Mar 15	11318098
Increased inwardly rectifying potassium currents in HEK-293 cells expressing murine transient receptor potential 4.	2001 Mar 15	11237877
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
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
Effects of P-glycoprotein on cell volume regulation in mouse proximal tubule.	2001 May	11292625
Functional receptor-channel coupling compared in contractile and proliferative human vascular smooth muscle.	2001 May	11268004
Oxygen dilation in fetal pulmonary arterioles: role of K(+) channels.	2001 May 15	11341793

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 12:20:26 GMT 2023` Edited by `admin` on `Sat Dec 16 12:20:26 GMT 2023`
Record UNII	8W6G3DV8T2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Tetraethylammonium nitrate

Systematic Name

English

Ethanaminium, N,N,N-triethyl-, nitrate

Systematic Name

English

Ethanaminium, N,N,N-triethyl-, nitrate (1:1)

Systematic Name

English

NSC-152114

Code

English

Code System Code Type Description

EPA CompTox

DTXSID3062075