Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H20N.Cl |
Molecular Weight | 165.704 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Cl-].CC[N+](CC)(CC)CC
InChI
InChIKey=YMBCJWGVCUEGHA-UHFFFAOYSA-M
InChI=1S/C8H20N.ClH/c1-5-9(6-2,7-3)8-4;/h5-8H2,1-4H3;1H/q+1;/p-1
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 | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3137264 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12824448 |
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Target ID: CHEMBL2096673 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1698974 |
3.1 mM [Kd] | ||
Target ID: CHEMBL5505 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1698974 |
260.0 µM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | Fosglutamina B6 Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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: |
healthy, adult n = 7 Health Status: healthy Age Group: adult Sex: M+F Population Size: 7 Sources: |
Other AEs: Paralysis, Drowsiness... |
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%) Sources: 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%) |
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: |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
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Dopamine-mediated volume transmission in midbrain is regulated by distinct extracellular geometry and uptake. | 2001 Apr |
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Mouse taste cells with glialike membrane properties. | 2001 Apr |
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Chronic extrinsic denervation after small bowel transplantation in rat jejunum: Effects and adaptation in nitrergic and non-nitrergic neuromuscular inhibitory mechanisms. | 2001 Apr |
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Inotrophic effects of the K(+) channel blocker TEA on dystrophic (mdx and dy/dy) mouse diaphragm. | 2001 Apr |
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Influence of Ca(2+)-activated K(+) channels on rat renal arteriolar responses to depolarizing agonists. | 2001 Apr |
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Iodide and bromide inhibit Ca(2+) uptake by cardiac sarcoplasmic reticulum. | 2001 Apr |
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Contributions of prostacyclin and nitric oxide to carbon monoxide-induced cerebrovascular dilation in piglets. | 2001 Apr |
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Activation of K+ channels induces apoptosis in vascular smooth muscle cells. | 2001 Apr |
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Flow-induced dilation of human coronary arterioles: important role of Ca(2+)-activated K(+) channels. | 2001 Apr 17 |
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Mechanisms of tetraethylammonium ion block in the KcsA potassium channel. | 2001 Apr 27 |
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Cardiovascular effects of lepadiformine, an alkaloid isolated from the ascidians Clavelina lepadiformis (Müller) and C. moluccensis (Sluiter). | 2001 Aug |
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The characterisation and uptake of paraquat in cultured baboon kidney proximal tubule cells (bPTC). | 2001 Feb |
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20-HETE contributes to myogenic activation of skeletal muscle resistance arteries in Brown Norway and Sprague-Dawley rats. | 2001 Feb |
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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 |
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Short term hypercholesterolemia alters N(G)-nitro-L-arginine- and indomethacin-resistant endothelium-dependent relaxation by acetylcholine in rabbit renal artery. | 2001 Feb |
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Nitrooxy alkyl apovincaminate activates K+ currents in rat neocortical neurons. | 2001 Feb |
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Fusicoccin- and IAA-induced elongation growth share the same pattern of K+ dependence. | 2001 Feb |
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Potentiation of bradykinin by angiotensin-(1-7) on arterioles of spontaneously hypertensive rats studied in vivo. | 2001 Feb |
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The effect of proteolytic enzymes on the alpha9-nicotinic receptor-mediated response in isolated frog vestibular hair cells. | 2001 Feb |
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Modulation of diaphragm action potentials by K(+) channel blockers. | 2001 Feb |
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Selective inhibition of amine oxidases differently potentiate the hypophagic effect of benzylamine in mice. | 2001 Feb 9 |
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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 |
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Muscarinic activation of transient inward current and contraction in canine colon circular smooth muscle cells. | 2001 Jan |
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Cloning and function of the rat colonic epithelial K+ channel KVLQT1. | 2001 Jan 15 |
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Combined antisense and pharmacological approaches implicate hTASK as an airway O(2) sensing K(+) channel. | 2001 Jul 13 |
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Shear stress-induced vasodilation in porcine coronary conduit arteries is independent of nitric oxide release. | 2001 Jun |
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Verapamil inhibits proliferation of LNCaP human prostate cancer cells influencing K+ channel gating. | 2001 Jun |
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Pulmonary vascular response to normoxia and K(Ca) channel activity is developmentally regulated. | 2001 Jun |
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Potassium channels regulate tone in rat pulmonary veins. | 2001 Jun |
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Regulation of ClC-2 chloride channels in T84 cells by TGF-alpha. | 2001 Jun |
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HNS-32, a novel azulene-1-carboxamidine derivative, inhibits nifedipine-sensitive and -insensitive contraction of the isolated rabbit aorta. | 2001 Mar |
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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 |
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Three types of depolarization-activated potassium currents in acutely isolated mouse vestibular neurons. | 2001 Mar |
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Molecular cloning and functional characterization of a novel delayed rectifier potassium channel from channel catfish (Ictalurus punctatus): expression in taste buds. | 2001 Mar |
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Multiple binding sites for melatonin on Kv1.3. | 2001 Mar |
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Modulation of voltage-dependent K+ channel current in vascular smooth muscle cells from rat mesenteric arteries. | 2001 Mar 15 |
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Temperature-dependent expression of a squid Kv1 channel in Sf9 cells and functional comparison with the native delayed rectifier. | 2001 Mar 15 |
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Increased inwardly rectifying potassium currents in HEK-293 cells expressing murine transient receptor potential 4. | 2001 Mar 15 |
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Characterization of TASK-4, a novel member of the pH-sensitive, two-pore domain potassium channel family. | 2001 Mar 9 |
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A pertussis toxin-sensitive 8-lipoxygenase pathway is activated by a nicotinic acetylcholine receptor in aplysia neurons. | 2001 May |
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Medium afterhyperpolarization and firing pattern modulation in interneurons of stratum radiatum in the CA3 hippocampal region. | 2001 May |
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Afterhyperpolarization current in myenteric neurons of the guinea pig duodenum. | 2001 May |
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The properties of ryanodine-sensitive Ca(2+) release in mouse gastric smooth muscle cells. | 2001 May |
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Mechanism underlying slow kinetics of the OFF gating current in Shaker potassium channel. | 2001 May |
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Effects of P-glycoprotein on cell volume regulation in mouse proximal tubule. | 2001 May |
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Molecular identification of a TTX-sensitive Ca(2+) current. | 2001 May |
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Functional receptor-channel coupling compared in contractile and proliferative human vascular smooth muscle. | 2001 May |
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Stretch-dependent potassium channels in murine colonic smooth muscle cells. | 2001 May 15 |
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Oxygen dilation in fetal pulmonary arterioles: role of K(+) channels. | 2001 May 15 |
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p38 activation is required upstream of potassium current enhancement and caspase cleavage in thiol oxidant-induced neuronal apoptosis. | 2001 May 15 |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT00166166
5 min infusion of Tetraethylammonium at 1 mg/min
Route of Administration:
Intra-arterial
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12824448
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.
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5946
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8B82Z83XNN
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m10615
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DTXSID6041137
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CHEMBL9324
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78161
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TETRAETHYLAMMONIUM CHLORIDE
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DBSALT000174
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200-267-5
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56-34-8
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ACTIVE MOIETY
SUBSTANCE RECORD