Tìm theo
Lobeline
Thuốc Gốc
Small Molecule
CAS: 90-69-7
CTHH: C22H27NO2
PTK: 337.4553
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. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C22H27NO2
Phân tử khối
337.4553
Monoisotopic mass
337.204179113
InChI
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
InChI Key
InChIKey=MXYUKLILVYORSK-HBMCJLEFSA-N
IUPAC Name
2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethan-1-one
Traditional IUPAC Name
(-)-lobeline
SMILES
CN1[C@H](C[C@H](O)C2=CC=CC=C2)CCC[C@@H]1CC(=O)C1=CC=CC=C1
Độ tan chảy
130.5 °C
Độ hòa tan
2.98e-02 g/l
logP
3.78
logS
-4
pKa (strongest acidic)
14.42
pKa (Strongest Basic)
8.77
PSA
40.54 Å2
Refractivity
101.51 m3·mol-1
Polarizability
39.27 Å3
Rotatable Bond Count
6
H Bond Acceptor Count
3
H Bond Donor Count
1
Physiological Charge
1
Number of Rings
3
Bioavailability
1
Rule of Five
true
Ghose Filter
true
MDDR-Like Rule
true
Cơ Chế Tác Dụng : 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. [PubChem] Lobeline inhibits nicotine-evoked dopamine release and [3H]nicotine binding, thus acting as a potent antagonist at both alpha3beta2(*) and alpha4beta2(*) neuronal nicotinic receptor subtypes. However, lobeline does not release dopamine from its presynaptic terminal, but appears to induce the metabolism of dopamine intraneuronally. Reevaluation of the mechanism by which lobeline alters dopamine function reveals that its primary mechanism is inhibition of dopamine uptake and promotion of dopamine release from the storage vesicles within the presynaptic terminal, via an interaction with the tetrabenazine-binding site on the vesicular monoamine transporter (VMAT2). Thus, lobeline appears to perturb the fundamental mechanisms of dopamine storage and release. Based on its neurochemical mechanism, the ability of lobeline to functionally antagonize the neurochemical and behavioral effects of the psychostimulants amphetamine and methamphetamine was examined. Lobeline was found to inhibit the amphetamine-induced release of dopamine in vitro, and amphetamine-induced hyperactivity, drug discrimination, and self-administration.
Chỉ Định : Investigated for use/treatment in addictions.
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB05137
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=101616
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=10232144
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07475
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D02364
ChemSpider
http://www.chemspider.com/Chemical-Structure.91814.html
Wikipedia
http://en.wikipedia.org/wiki/Lobeline
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