n,n'-dodecane-1,12-diyl-bis-3-picolinium dibromide profile

N,N'-dodecane-1,12-diyl-bis-3-picolinium dibromide: may selectively block nicotinic acetylcholine receptors involved in regulating dopamine release; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	9983961
CHEMBL ID	54331
SCHEMBL ID	3587002
MeSH ID	M0502506

Synonym
n,n'-dodecylbis-picolinium bromide
CHEMBL54331 ,
SCHEMBL3587002
1,1'-(1,12-dodecanediyl)bis[3-methylpyridinium] dibromide
525596-66-1
bpiddb
AKOS024457487
n,n'-dodecane-1,12-diyl-bis-3-picolinium dibromide
1,1'-(dodecane-1,12-diyl)bis(3-methylpyridin-1-ium) bromide
MS-29545
3-methyl-1-[12-(3-methylpyridin-1-ium-1-yl)dodecyl]pyridin-1-ium;dibromide
CS-0029158
HY-107674
EX-A7742

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Neuronal acetylcholine receptor subunit beta-3	Rattus norvegicus (Norway rat)	IC50 (µMol)	0.0020	0.0020	0.0268	0.1000	AID429984
Neuronal acetylcholine receptor subunit alpha-6	Rattus norvegicus (Norway rat)	IC50 (µMol)	0.0020	0.0020	0.6904	6.0000	AID429984
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (24)

Assay ID	Title	Year	Journal	Article
AID459525	Antagonist activity at nicotinic acetylcholine receptor in rat striatal slices assessed as inhibition of S-(-)-nicotine-induced [3H]dopamine release relative to control	2010	Bioorganic & medicinal chemistry letters, Feb-15, Volume: 20, Issue:4	Novel bis-2,2,6,6-tetramethylpiperidine (bis-TMP) and bis-mecamylamine antagonists at neuronal nicotinic receptors mediating nicotine-evoked dopamine release.
AID146623	Inhibition of [3H]nicotine binding to Nicotinic acetylcholine receptor alpha4-beta2 in rat brain membranes	2004	Bioorganic & medicinal chemistry letters, Apr-19, Volume: 14, Issue:8	Subtype-selective nicotinic receptor antagonists: potential as tobacco use cessation agents.
AID349218	Inhibition of nAChR-mediated nicotine-evoked [3H]DA release in superfused rat striatal slices	2008	Bioorganic & medicinal chemistry letters, Nov-01, Volume: 18, Issue:21	Tetrakis-azaaromatic quaternary ammonium salts: novel subtype-selective antagonists at neuronal nicotinic receptors that mediate nicotine-evoked dopamine release.
AID303825	Antagonist activity at nAChR in rat striatal slices assessed as inhibition of nicotine-evoked [3H]dopamine release at 100 uM	2007	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 17, Issue:24	Tris-azaaromatic quaternary ammonium salts: Novel templates as antagonists at nicotinic receptors mediating nicotine-evoked dopamine release.
AID552607	Antagonist activity at alpha6 nAChR in rat striatum assessed as inhibition of nicotine-induced [3H]dopamine release relative to nicotine	2011	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 21, Issue:1	Novel bis-, tris-, and tetrakis-tertiary amino analogs as antagonists at neuronal nicotinic receptors that mediate nicotine-evoked dopamine release.
AID552606	Antagonist activity at alpha6 nAChR in rat striatum assessed as inhibition of nicotine-induced [3H]dopamine release	2011	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 21, Issue:1	Novel bis-, tris-, and tetrakis-tertiary amino analogs as antagonists at neuronal nicotinic receptors that mediate nicotine-evoked dopamine release.
AID483710	Binding affinity to blood-brain barrier choline transporter in rat brain assessed as inhibition of [3H]choline uptake	2010	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11	Bis-azaaromatic quaternary ammonium salts as ligands for the blood-brain barrier choline transporter.
AID146468	Binding affinity for nicotinic acetylcholine receptor alpha4-beta2 was evaluated by its ability to inhibit [3H]NIC binding to rat brain membranes	2002	Bioorganic & medicinal chemistry letters, Nov-04, Volume: 12, Issue:21	bis-Azaaromatic quaternary ammonium analogues: ligands for alpha4beta2* and alpha7* subtypes of neuronal nicotinic receptors.
AID349216	Displacement of [3H]methyllycaconitine from alpha7 nAChR in rat brain membrane	2008	Bioorganic & medicinal chemistry letters, Nov-01, Volume: 18, Issue:21	Tetrakis-azaaromatic quaternary ammonium salts: novel subtype-selective antagonists at neuronal nicotinic receptors that mediate nicotine-evoked dopamine release.
AID304343	Displacement of [3H]MLA from alpha-7 nAChR expressed in rat brain membrane at 100 uM	2007	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 17, Issue:24	Bis-azaaromatic quaternary ammonium salts as antagonists at nicotinic receptors mediating nicotine-evoked dopamine release: An investigation of binding conformation.
AID304344	Antagonist activity at nAChR in rat striatal slices assessed as inhibition of nicotine-evoked [3H]dopamine release at 100 uM	2007	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 17, Issue:24	Bis-azaaromatic quaternary ammonium salts as antagonists at nicotinic receptors mediating nicotine-evoked dopamine release: An investigation of binding conformation.
AID429982	Antagonist activity at nAChR in Sprague-Dawley rat striatal slices assessed as inhibition of S(-)-nicotine-evoked [3H]dopamine overflow at 100 uM by liquid scintillation counting	2009	Bioorganic & medicinal chemistry, Jul-01, Volume: 17, Issue:13	QSAR study on maximal inhibition (Imax) of quaternary ammonium antagonists for S-(-)-nicotine-evoked dopamine release from dopaminergic nerve terminals in rat striatum.
AID304342	Displacement of [3H]NIC from alpha-4-beta-2 nAChR expressed in rat brain membrane at 100 uM	2007	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 17, Issue:24	Bis-azaaromatic quaternary ammonium salts as antagonists at nicotinic receptors mediating nicotine-evoked dopamine release: An investigation of binding conformation.
AID459524	Antagonist activity at nicotinic acetylcholine receptor in rat striatal slices assessed as inhibition of S-(-)-nicotine-induced [3H]dopamine release	2010	Bioorganic & medicinal chemistry letters, Feb-15, Volume: 20, Issue:4	Novel bis-2,2,6,6-tetramethylpiperidine (bis-TMP) and bis-mecamylamine antagonists at neuronal nicotinic receptors mediating nicotine-evoked dopamine release.
AID180290	Inhibitory activity against nAChR mediated nicotine-evoked [3H]DA overflow using rat striatal slices	2004	Bioorganic & medicinal chemistry letters, Apr-19, Volume: 14, Issue:8	Subtype-selective nicotinic receptor antagonists: potential as tobacco use cessation agents.
AID146934	Binding affinity nicotinic acetylcholine receptor alpha-7 was evaluated by its ability to inhibit [3H]methyllycaconitine ([3H]-MLA) binding to rat brain membranes	2002	Bioorganic & medicinal chemistry letters, Nov-04, Volume: 12, Issue:21	bis-Azaaromatic quaternary ammonium analogues: ligands for alpha4beta2* and alpha7* subtypes of neuronal nicotinic receptors.
AID552605	Antagonist activity at alpha6 nAChR in rat striatum assessed as inhibition of nicotine-induced [3H]dopamine release at 100 nM relative to control	2011	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 21, Issue:1	Novel bis-, tris-, and tetrakis-tertiary amino analogs as antagonists at neuronal nicotinic receptors that mediate nicotine-evoked dopamine release.
AID456869	Inhibition of nAChR-mediated nicotine-induced [3H]dopamine release	2010	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 20, Issue:3	Predictive screening model for potential vector-mediated transport of cationic substrates at the blood-brain barrier choline transporter.
AID303826	Antagonist activity at nAChR in rat striatal slices assessed as inhibition of nicotine-evoked [3H]dopamine release	2007	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 17, Issue:24	Tris-azaaromatic quaternary ammonium salts: Novel templates as antagonists at nicotinic receptors mediating nicotine-evoked dopamine release.
AID459523	Antagonist activity at nicotinic acetylcholine receptor in rat striatal slices assessed as inhibition of S-(-)-nicotine-induced [3H]dopamine release at 100 nM relative to control	2010	Bioorganic & medicinal chemistry letters, Feb-15, Volume: 20, Issue:4	Novel bis-2,2,6,6-tetramethylpiperidine (bis-TMP) and bis-mecamylamine antagonists at neuronal nicotinic receptors mediating nicotine-evoked dopamine release.
AID349214	Displacement of [3H]nicotine from alpha4beta2 nAChR in rat brain membrane	2008	Bioorganic & medicinal chemistry letters, Nov-01, Volume: 18, Issue:21	Tetrakis-azaaromatic quaternary ammonium salts: novel subtype-selective antagonists at neuronal nicotinic receptors that mediate nicotine-evoked dopamine release.
AID146955	Inhibition of [3H]-MLA binding to Nicotinic acetylcholine receptor alpha-7 in rat brain membranes; NA= Not active	2004	Bioorganic & medicinal chemistry letters, Apr-19, Volume: 14, Issue:8	Subtype-selective nicotinic receptor antagonists: potential as tobacco use cessation agents.
AID429984	Antagonist activity at nAChR-alpha-6-beta-2 in Sprague-Dawley rat striatal slices assessed as inhibition of nicotine-evoked [3H]dopamine uptake by liquid beta-scintillation spectrometry	2009	Bioorganic & medicinal chemistry, Jul-01, Volume: 17, Issue:13	QSAR study on maximal inhibition (Imax) of quaternary ammonium antagonists for S-(-)-nicotine-evoked dopamine release from dopaminergic nerve terminals in rat striatum.
AID344669	Binding affinity to blood-brain barrier choline transporter in rat brain assessed as inhibition of [3H]choline uptake	2008	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 18, Issue:20	bis-Pyridinium cyclophanes: novel ligands with high affinity for the blood-brain barrier choline transporter.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	17 (70.83)	29.6817
2010's	7 (29.17)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (4.17%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	23 (95.83%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
choline [no description available]	2.74	3	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
bupropion Bupropion: A propiophenone-derived antidepressant and antismoking agent that inhibits the uptake of DOPAMINE.. bupropion : An aromatic ketone that is propiophenone carrying a tert-butylamino group at position 2 and a chloro substituent at position 3 on the phenyl ring.	2.05	1	aromatic ketone; monochlorobenzenes; secondary amino compound	antidepressant; environmental contaminant; xenobiotic
3,4-dihydroxyphenylacetic acid 3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.	2.04	1	catechols; dihydroxyphenylacetic acid	human metabolite
amphetamine Amphetamine: A powerful central nervous system stimulant and sympathomimetic. Amphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulation of release of monamines, and inhibiting monoamine oxidase. Amphetamine is also a drug of abuse and a psychotomimetic. The l- and the d,l-forms are included here. The l-form has less central nervous system activity but stronger cardiovascular effects. The d-form is DEXTROAMPHETAMINE.. 1-phenylpropan-2-amine : A primary amine that is isopropylamine in which a hydrogen attached to one of the methyl groups has been replaced by a phenyl group.. amphetamine : A racemate comprising equimolar amounts of (R)-amphetamine (also known as levamphetamine or levoamphetamine) and (S)-amphetamine (also known as dexamfetamine or dextroamphetamine.	2.03	1	primary amine
mecamylamine Mecamylamine: A nicotinic antagonist that is well absorbed from the gastrointestinal tract and crosses the blood-brain barrier. Mecamylamine has been used as a ganglionic blocker in treating hypertension, but, like most ganglionic blockers, is more often used now as a research tool.	2.96	4	primary aliphatic amine
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	2.03	1	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	2.48	2	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
quinuclidines Quinuclidines: A class of organic compounds which contain two rings that share a pair of bridgehead carbon atoms and contains an amine group.	2.1	1	quinuclidines; saturated organic heterobicyclic parent
decamethonium dibromide [no description available]	2.01	1
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	3.64	9	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
hexamethonium chloride [no description available]	2.01	1
methyllycaconitine methyllycaconitine: natural toxin from seeds of Delphinium brownii; parasympathomimetic and mild nicotine antagonist; antagonist of alpha-conotoxin-MII sensitive presynaptic nicotinic receptors; potent insecticide; RN refers to (1alpha,4(S),6beta,14alpha,16beta)-isomer	2.05	1
varenicline Varenicline: A benzazepine derivative that functions as an ALPHA4-BETA2 NICOTINIC RECEPTOR partial agonist. It is used for SMOKING CESSATION.. varenicline : An organic heterotetracyclic compound that acts as a partial agonist for nicotinic cholinergic receptors and is used (in the form of its tartate salt) as an aid to giving up smoking.	2.48	2
sazetidine-a sazetidine-A: a ligand that desensitizes alpha4beta2 nicotinic acetylcholine receptors without activating them; structure in first source	2.11	1
aconitine Aconitine: A C19 norditerpenoid alkaloid (DITERPENES) from the root of ACONITUM; DELPHINIUM and larkspurs. It activates VOLTAGE-GATED SODIUM CHANNELS. It has been used to induce ARRHYTHMIAS in experimental animals and it has anti-inflammatory and anti-neuralgic properties.. aconitine : A diterpenoid that is 20-ethyl-3alpha,13,15alpha-trihydroxy-1alpha,6alpha,16beta-trimethoxy-4-(methoxymethyl)aconitane-8,14alpha-diol having acetate and benzoate groups at the 8- and 14-positions respectively.	2.05	1

Condition	Relationship Strength	Studies
Smoking Cessation Discontinuing the habit of SMOKING.	2.44	2
Nicotine Addiction [description not available]	3.37	2
Tobacco Use Disorder Tobacco used to the detriment of a person's health or social functioning. Tobacco dependence is included.	3.37	2
Recrudescence [description not available]	2.96	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.03	1

n,n'-dodecane-1,12-diyl-bis-3-picolinium dibromide

Description

Cross-References

Synonyms (14)

Protein Targets (2)

Inhibition Measurements

Bioassays (24)

Research

Studies (24)

Market Indicators

Research Demand Index: 11.04

Study Types

n,n'-dodecane-1,12-diyl-bis-3-picolinium dibromide

Description

Cross-References

Synonyms (14)

Protein Targets (2)

Inhibition Measurements

Bioassays (24)

Research

Studies (24)

Market Indicators

Research Demand Index: 11.04

Study Types

Related Drugs (15)

Related Conditions (5)