Drug Details

General Information of the Drug (ID: DR6343)
Name
Lobeline
Synonyms
lobeline; alpha-Lobeline; (-)-Lobeline; Lobnico; Lobelin; 8,10-Diphenyllobelionol; Lobelina; Lobelinum; 90-69-7; Inflatine; UNII-D0P25S3P81; 2-(6-(2-Hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenylethanone; 2-{(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl}-1-phenylethanone; CHEMBL122270; CHEBI:48723; 2-(6-(beta-Hydroxyphenethyl)-1-methyl-2-piperidyl)acetophenone; D0P25S3P81; NCGC00024378-05; Alpha-Lobeline HCl; Lobeline [INN:BAN]; Lobelinum [INN-Latin]; Lobelina [INN-Spanish]; SR-01000075960; Lobeline A; Lobeline (INN); L0B; EINECS 202-012-3; BRN 0091533; Prestwick0_000585; Prestwick1_000585; Prestwick2_000585; Prestwick3_000585; DSSTox_CID_3219; DSSTox_RID_76929; DSSTox_GSID_23219; Lopac0_000698; BSPBio_000430; 5-21-12-00627 (Beilstein Handbook Reference); Ethanone, 2-(6-(2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenyl-, (2R-(2alpha,6alpha(S*)))-; SCHEMBL290803; SPBio_002649; BPBio1_000474; ZINC1624; DTXSID3023219; Tox21_110900; BDBM50080818; AKOS024278800; CCG-204783; DB05137; NSC 757421; SDCCGSBI-0050676.P002; 2-((2R,6S)-6-((S)-2-hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethan-1-one; CAS-90-69-7; NCGC00024378-06; NCGC00024378-07; NCGC00024378-08; NCGC00024378-09; NCGC00024378-10; NCGC00024378-14; AB00489926; C07475; D02364; Q421905; SR-01000075960-5; BRD-K66206289-003-03-1; BRD-K66206289-003-09-8; UNII-73BJ3LA259 component MXYUKLILVYORSK-HBMCJLEFSA-N
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Molecular Type
Small molecule
Disease Unspecific substance use disorder [ICD-11: 6C4Z] Phase 2 [1]
Structure
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2D MOL

3D MOL

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Formula
C22H27NO2
PubChem CID
101616
Canonical SMILES
CN1C(CCCC1CC(=O)C2=CC=CC=C2)CC(C3=CC=CC=C3)O
InChI
1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
InChIKey
MXYUKLILVYORSK-HBMCJLEFSA-N
CAS Number
CAS 90-69-7
ChEBI ID
CHEBI:48723
TTD Drug ID
D01IVE
DrugBank ID
DB05137
Target and Pathway
Target(s) Synaptic vesicle amine transporter (SLC18A2)  Molecule Info  [2]
KEGG Pathway Synaptic vesicle cycle Click to Show/Hide
2 Serotonergic synapse
3 Dopaminergic synapse
4 Parkinson's disease
5 Cocaine addiction
6 Amphetamine addiction
7 Alcoholism
Panther Pathway Adrenaline and noradrenaline biosynthesis Click to Show/Hide
2 5HT1 type receptor mediated signaling pathway
3 5HT2 type receptor mediated signaling pathway
4 5HT3 type receptor mediated signaling pathway
5 5HT4 type receptor mediated signaling pathway
6 Dopamine receptor mediated signaling pathway
7 Nicotine pharmacodynamics pathway
8 CCKR signaling map ST
Reactome Norepinephrine Neurotransmitter Release Cycle Click to Show/Hide
2 Na+/Cl- dependent neurotransmitter transporters
WikiPathways Dopaminergic Neurogenesis Click to Show/Hide
2 Synaptic Vesicle Pathway
3 Neurotransmitter Release Cycle
4 Nicotine Activity on Dopaminergic Neurons
References
Reference 1 Effects of VMAT2 inhibitors lobeline and GZ-793A on methamphetamine-induced changes in dopamine release, metabolism and synthesis in vivo. J Neurochem. 2013 Oct;127(2):187-98.
Reference 2 Design, synthesis and interaction at the vesicular monoamine transporter-2 of lobeline analogs: potential pharmacotherapies for the treatment of psychostimulant abuse. Curr Top Med Chem. 2011;11(9):1103-27.