lobelane profile

lobelane: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	10470490
CHEMBL ID	333465
SCHEMBL ID	13845051
MeSH ID	M0535094

Synonym
bdbm50080827
(2r,6s)-1-methyl-2,6-diphenethyl-piperidine
cis-n-methyl-2,6-diphenethylpiperidine
(2s,6r)-1-methyl-2,6-diphenethyl-piperidine
CHEMBL333465 ,
lobelane
SCHEMBL13845051
DTXSID601212781
rel-(2r,6s)-1-methyl-2,6-bis(2-phenylethyl)piperidine
530-51-8
(2r,6s)-1-methyl-2,6-bis(2-phenylethyl)piperidine

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Neuronal acetylcholine receptor subunit alpha-4	Rattus norvegicus (Norway rat)	Ki	14.9000	0.0000	0.1234	5.5000	AID239695
Neuronal acetylcholine receptor subunit beta-2	Rattus norvegicus (Norway rat)	Ki	14.9000	0.0000	0.1082	5.5000	AID239695
Synaptic vesicular amine transporter	Rattus norvegicus (Norway rat)	Ki	2.1582	0.0010	1.3009	6.2600	AID1079719; AID1079720; AID1233246; AID1295286; AID1372167; AID239724; AID254469; AID254488; AID254489; AID778856
Synaptic vesicular amine transporter	Homo sapiens (human)	Ki	0.9700	0.0053	0.8324	2.7600	AID459752
Neuronal acetylcholine receptor subunit alpha-7	Rattus norvegicus (Norway rat)	Ki	26.0000	0.0000	0.7307	8.0000	AID239688
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
response to amphetamine	Synaptic vesicular amine transporter	Homo sapiens (human)
serotonin secretion by mast cell	Synaptic vesicular amine transporter	Homo sapiens (human)
histamine secretion by mast cell	Synaptic vesicular amine transporter	Homo sapiens (human)
neurotransmitter transport	Synaptic vesicular amine transporter	Homo sapiens (human)
chemical synaptic transmission	Synaptic vesicular amine transporter	Homo sapiens (human)
locomotory behavior	Synaptic vesicular amine transporter	Homo sapiens (human)
response to toxic substance	Synaptic vesicular amine transporter	Homo sapiens (human)
post-embryonic development	Synaptic vesicular amine transporter	Homo sapiens (human)
monoamine transport	Synaptic vesicular amine transporter	Homo sapiens (human)
dopamine transport	Synaptic vesicular amine transporter	Homo sapiens (human)
sequestering of neurotransmitter	Synaptic vesicular amine transporter	Homo sapiens (human)
serotonin uptake	Synaptic vesicular amine transporter	Homo sapiens (human)
histamine uptake	Synaptic vesicular amine transporter	Homo sapiens (human)
neurotransmitter loading into synaptic vesicle	Synaptic vesicular amine transporter	Homo sapiens (human)
somato-dendritic dopamine secretion	Synaptic vesicular amine transporter	Homo sapiens (human)
proton transmembrane transport	Synaptic vesicular amine transporter	Homo sapiens (human)
negative regulation of reactive oxygen species biosynthetic process	Synaptic vesicular amine transporter	Homo sapiens (human)
aminergic neurotransmitter loading into synaptic vesicle	Synaptic vesicular amine transporter	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
protein binding	Synaptic vesicular amine transporter	Homo sapiens (human)
monoamine transmembrane transporter activity	Synaptic vesicular amine transporter	Homo sapiens (human)
monoamine:proton antiporter activity	Synaptic vesicular amine transporter	Homo sapiens (human)
serotonin:sodium:chloride symporter activity	Synaptic vesicular amine transporter	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
centrosome	Synaptic vesicular amine transporter	Homo sapiens (human)
plasma membrane	Synaptic vesicular amine transporter	Homo sapiens (human)
synaptic vesicle	Synaptic vesicular amine transporter	Homo sapiens (human)
membrane	Synaptic vesicular amine transporter	Homo sapiens (human)
axon	Synaptic vesicular amine transporter	Homo sapiens (human)
dendrite	Synaptic vesicular amine transporter	Homo sapiens (human)
secretory granule membrane	Synaptic vesicular amine transporter	Homo sapiens (human)
synaptic vesicle membrane	Synaptic vesicular amine transporter	Homo sapiens (human)
intracellular membrane-bounded organelle	Synaptic vesicular amine transporter	Homo sapiens (human)
clathrin-sculpted monoamine transport vesicle membrane	Synaptic vesicular amine transporter	Homo sapiens (human)
dopaminergic synapse	Synaptic vesicular amine transporter	Homo sapiens (human)
terminal bouton	Synaptic vesicular amine transporter	Homo sapiens (human)
synaptic vesicle membrane	Synaptic vesicular amine transporter	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (28)

Assay ID	Title	Year	Journal	Article
AID440782	Displacement of [3H]DTBZ from VMAT2 dihydrotetrabenazine binding site in rat brain synaptic vesicle by scintillation counting	2009	Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23	Pyrrolidine analogues of lobelane: relationship of affinity for the dihydrotetrabenazine binding site with function of the vesicular monoamine transporter 2 (VMAT2).
AID239695	Inhibition of 3 nM [3H]NIC binding to Nicotinic acetylcholine receptor alpha4-beta2 of rat striatal membranes	2005	Journal of medicinal chemistry, Aug-25, Volume: 48, Issue:17	Defunctionalized lobeline analogues: structure-activity of novel ligands for the vesicular monoamine transporter.
AID1295288	Inhibition of SERT in rat striatal synaptosomes assessed as reduction of [3H]5-HT uptake preincubated for 5 mins followed by [3H]5-HT addition measured after 10 mins by liquid scintillation spectrometric method	2016	Bioorganic & medicinal chemistry letters, 05-15, Volume: 26, Issue:10	Lobelane analogues containing 4-hydroxy and 4-(2-fluoroethoxy) aromatic substituents: Potent and selective inhibitors of [(3)H]dopamine uptake at the vesicular monoamine transporter-2.
AID254489	Inhibition constant against [3H]methyllycaconitine binding to vesicular monoamine transporter-2 of rat brain membranes	2005	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 15, Issue:20	Synthesis and evaluation of a series of tropane analogues as novel vesicular monoamine transporter-2 ligands.
AID243421	Ratio of Ki for Nicotinic acetylcholine receptor alpha4-beta2 and Vesicular Monoamine Transporter (VAMT2)	2005	Journal of medicinal chemistry, Aug-25, Volume: 48, Issue:17	Defunctionalized lobeline analogues: structure-activity of novel ligands for the vesicular monoamine transporter.
AID1372169	Selectivity for rat VMAT2 receptor over rat serotonin transporter	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	Fluoroethoxy-1,4-diphenethylpiperidine and piperazine derivatives: Potent and selective inhibitors of [
AID778856	Inhibition of VMAT2-mediated [3H]-dopamine uptake in rat striata isolated synaptic vesicles by liquid scintillation spectroscopy	2013	Bioorganic & medicinal chemistry, Nov-01, Volume: 21, Issue:21	Synthesis and evaluation of novel azetidine analogs as potent inhibitors of vesicular [3H]dopamine uptake.
AID459752	Binding affinity to VMAT2 receptor	2010	Bioorganic & medicinal chemistry, Jan-15, Volume: 18, Issue:2	Lobeline esters as novel ligands for neuronal nicotinic acetylcholine receptors and neurotransmitter transporters.
AID410427	Displacement of [3H]dihydrotetrabenazine from vesicular monoamine transporter-2 in rat brain synaptosome	2008	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 18, Issue:24	Synthesis and evaluation of a series of homologues of lobelane at the vesicular monoamine transporter-2.
AID440784	Ratio of Ki for displacement of [3H]DTBZ from VMAT2 dihydrotetrabenazine binding site in rat brain synaptic vesicle to Ki for inhibition of [3H]dopamine uptake at VMAT2 in rat brain synaptic vesicle	2009	Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23	Pyrrolidine analogues of lobelane: relationship of affinity for the dihydrotetrabenazine binding site with function of the vesicular monoamine transporter 2 (VMAT2).
AID1079720	Inhibition of [3H]DTBZ binding to VMAT2 in rat synaptic vesicle membranes	2013	MedChemComm, Mar, Volume: 4, Issue:3	Exploring the effect of
AID145655	Evaluated for its binding affinity towards Nicotinic acetylcholine receptor in rat brain homogenate	1999	Journal of medicinal chemistry, Sep-09, Volume: 42, Issue:18	Lobeline: structure-affinity investigation of nicotinic acetylcholinergic receptor binding.
AID1233246	Displacement of [3H]DTBZ from VMAT2 in rat whole brain by liquid scintillation spectrometry	2015	Bioorganic & medicinal chemistry letters, Jul-01, Volume: 25, Issue:13	Quinolyl analogues of norlobelane: novel potent inhibitors of [(3)H]dihydrotetrabenazine binding and [(3)H]dopamine uptake at the vesicular monoamine transporter-2.
AID254469	Inhibition constant against [3H]nicotine binding to vesicular monoamine transporter-2 of rat brain membranes	2005	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 15, Issue:20	Synthesis and evaluation of a series of tropane analogues as novel vesicular monoamine transporter-2 ligands.
AID1233247	Inhibition of VMAT2-mediated [3H]DA uptake in rat brain synaptic vesicles by liquid scintillation spectrometry	2015	Bioorganic & medicinal chemistry letters, Jul-01, Volume: 25, Issue:13	Quinolyl analogues of norlobelane: novel potent inhibitors of [(3)H]dihydrotetrabenazine binding and [(3)H]dopamine uptake at the vesicular monoamine transporter-2.
AID1304307	Selectivity ratio of IC50 for Sprague-Dawley rat DA transporter to IC50 for Sprague-Dawley rat VMAT2	2016	Bioorganic & medicinal chemistry letters, 07-01, Volume: 26, Issue:13	1,4-Diphenalkylpiperidines: A new scaffold for the design of potent inhibitors of the vesicular monoamine transporter-2.
AID440783	Inhibition of [3H]dopamine uptake at VMAT2 in rat brain synaptic vesicle by liquid scintillation spectroscopy	2009	Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23	Pyrrolidine analogues of lobelane: relationship of affinity for the dihydrotetrabenazine binding site with function of the vesicular monoamine transporter 2 (VMAT2).
AID1233249	Ratio of Ki for displacement of [3H]DTBZ from VMAT2 in rat whole brain to Ki for inhibition of VMAT2-mediated [3H]DA uptake in rat brain synaptic vesicles	2015	Bioorganic & medicinal chemistry letters, Jul-01, Volume: 25, Issue:13	Quinolyl analogues of norlobelane: novel potent inhibitors of [(3)H]dihydrotetrabenazine binding and [(3)H]dopamine uptake at the vesicular monoamine transporter-2.
AID1372170	Selectivity for rat VMAT2 receptor over human ERG channel	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	Fluoroethoxy-1,4-diphenethylpiperidine and piperazine derivatives: Potent and selective inhibitors of [
AID254488	Inhibition constant against [3H]dihydrotetrabenazine binding to vesicular monoamine transporter-2 of rat synaptic vesicle membranes	2005	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 15, Issue:20	Synthesis and evaluation of a series of tropane analogues as novel vesicular monoamine transporter-2 ligands.
AID239724	Inhibition of 5 nM [3H]DTBZ binding to Vesicular Monoamine Transporter (VAMT2) of rat vesicle membranes	2005	Journal of medicinal chemistry, Aug-25, Volume: 48, Issue:17	Defunctionalized lobeline analogues: structure-activity of novel ligands for the vesicular monoamine transporter.
AID1295287	Inhibition of DAT in rat striatal synaptosomes assessed as reduction of [3H]dopamine uptake preincubated for 5 mins followed by [3H]dopamine addition measured after 10 mins by liquid scintillation spectrometric method	2016	Bioorganic & medicinal chemistry letters, 05-15, Volume: 26, Issue:10	Lobelane analogues containing 4-hydroxy and 4-(2-fluoroethoxy) aromatic substituents: Potent and selective inhibitors of [(3)H]dopamine uptake at the vesicular monoamine transporter-2.
AID239688	Inhibition of 3 nM [3H]-MLA binding to Nicotinic acetylcholine receptor alpha7 of rat brain membranes	2005	Journal of medicinal chemistry, Aug-25, Volume: 48, Issue:17	Defunctionalized lobeline analogues: structure-activity of novel ligands for the vesicular monoamine transporter.
AID1295286	Inhibition of VMAT2 in rat striatal synaptic vesicle assessed as reduction of [3H]dopamine uptake after 8 mins by liquid scintillation spectrometric method	2016	Bioorganic & medicinal chemistry letters, 05-15, Volume: 26, Issue:10	Lobelane analogues containing 4-hydroxy and 4-(2-fluoroethoxy) aromatic substituents: Potent and selective inhibitors of [(3)H]dopamine uptake at the vesicular monoamine transporter-2.
AID1372167	Inhibition of [3H]dopamine uptake at VMAT2 in rat synaptic vesicles after 8 mins by liquid scintillation spectrometry	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	Fluoroethoxy-1,4-diphenethylpiperidine and piperazine derivatives: Potent and selective inhibitors of [
AID1372168	Selectivity for rat VMAT2 receptor over rat dopamine transporter	2017	Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24	Fluoroethoxy-1,4-diphenethylpiperidine and piperazine derivatives: Potent and selective inhibitors of [
AID243420	Ratio of Ki for Nicotinic acetylcholine receptor alpha-7 and Vesicular monoamine transporter (VAMT2)	2005	Journal of medicinal chemistry, Aug-25, Volume: 48, Issue:17	Defunctionalized lobeline analogues: structure-activity of novel ligands for the vesicular monoamine transporter.
AID1079719	Inhibition of [3H]DA uptake at VMAT2 in rat striatal synaptic vesicles	2013	MedChemComm, Mar, Volume: 4, Issue:3	Exploring the effect of
[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	1 (5.88)	18.2507
2000's	5 (29.41)	29.6817
2010's	11 (64.71)	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 (5.88%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	16 (94.12%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
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.	2.05	1	catechols; dihydroxyphenylacetic acid	human metabolite
fluoxetine Fluoxetine: The first highly specific serotonin uptake inhibitor. It is used as an antidepressant and often has a more acceptable side-effects profile than traditional antidepressants.. fluoxetine : A racemate comprising equimolar amounts of (R)- and (S)-fluoxetine. A selective serotonin reuptake inhibitor (SSRI), it is used (generally as the hydrochloride salt) for the treatment of depression (and the depressive phase of bipolar disorder), bullimia nervosa, and obsessive-compulsive disorder.. N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine : An aromatic ether consisting of 4-trifluoromethylphenol in which the hydrogen of the phenolic hydroxy group is replaced by a 3-(methylamino)-1-phenylpropyl group.	2.05	1	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound
vanoxerine vanoxerine: structure given in first source. vanoxerine : An N-alkylpiperazine that consists of piperazine bearing 2-bis(4-fluorophenyl)methoxy]ethyl and 3-phenylpropyl groups at positions 1 and 4 respectively. Potent, competitive inhibitor of dopamine uptake (Ki = 1 nM for inhibition of striatal dopamine uptake). Has > 100-fold lower affinity for the noradrenalin and 5-HT uptake carriers. Also a potent sigma ligand (IC50 = 48 nM). Centrally active following systemic administration.	2.05	1	ether; N-alkylpiperazine; organofluorine compound; tertiary amino compound	dopamine uptake inhibitor
tetrabenazine 9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one : A benzoquinolizine that is 1,2,3,4,4a,9,10,10a-octahydrophenanthrene in which the carbon at position 10a is replaced by a nitrogen and which is substituted by an isobutyl group at position 2, an oxo group at position 3, and methoxy groups at positions 6 and 7.	7.46	2	benzoquinolizine; cyclic ketone; tertiary amino compound
piperidine [no description available]	2.04	1	azacycloalkane; piperidines; saturated organic heteromonocyclic parent; secondary amine	base; catalyst; human metabolite; non-polar solvent; plant metabolite; protic solvent; reagent
azetidine [no description available]	2.08	1	azacycloalkane; azetidines; saturated organic heteromonocyclic parent
methamphetamine Methamphetamine: A central nervous system stimulant and sympathomimetic with actions and uses similar to DEXTROAMPHETAMINE. The smokable form is a drug of abuse and is referred to as crank, crystal, crystal meth, ice, and speed.. methamphetamine : A member of the class of amphetamines in which the amino group of (S)-amphetamine carries a methyl substituent.	9.27	5	amphetamines; secondary amine	central nervous system stimulant; environmental contaminant; neurotoxin; psychotropic drug; xenobiotic
pyrrolidine [no description available]	7.05	1	azacycloalkane; pyrrolidines; saturated organic heteromonocyclic parent
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.	2.05	1	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
lobeline (-)-lobeline : An optically active piperidine alkaloid having a 2-oxo-2-phenylethyl substituent at the 2-position and a 2-hydroxy-2-phenylethyl group at the 6-position.	3.29	6	aromatic ketone; piperidine alkaloid; tertiary amine	nicotinic acetylcholine receptor agonist
dihydrotetrabenazine dihydrotetrabenazine: RN given refers to cpd without isomeric designation	7.05	1	isoquinolines
lobeline [no description available]	2.46	2
lobeline Lobeline: An alkaloid that has actions similar to NICOTINE on nicotinic cholinergic receptors but is less potent. It has been proposed for a variety of therapeutic uses including in respiratory disorders, peripheral vascular disorders, insomnia, and smoking cessation.	4.87	10
piperidines Piperidines: A family of hexahydropyridines.	2.48	2

Condition	Relationship Strength	Studies
Amphetamine Abuse [description not available]	3.69	3
Amphetamine-Related Disorders Disorders related or resulting from use of amphetamines.	3.69	3
Chemical Dependence [description not available]	2.05	1
Substance-Related Disorders Disorders related to substance use or abuse.	2.05	1

lobelane

Description

Cross-References

Synonyms (11)

Protein Targets (5)

Inhibition Measurements

Biological Processes (18)

Molecular Functions (4)

Ceullar Components (12)

Bioassays (28)

Research

Studies (17)

Market Indicators

Research Demand Index: 17.58

Study Types

lobelane

Description

Cross-References

Synonyms (11)

Protein Targets (5)

Inhibition Measurements

Biological Processes (18)

Molecular Functions (4)

Ceullar Components (12)

Bioassays (28)

Research

Studies (17)

Market Indicators

Research Demand Index: 17.58

Study Types

Related Drugs (14)

Related Conditions (4)