α-Lobeline Hydrochcloride

Names

[ CAS No. ]:
134-63-4

[ Name ]:
α-Lobeline Hydrochcloride

[Synonym ]:
Ethanone, 2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methyl-2-piperidinyl]-1-phenyl-, hydrochloride (1:1)
2-[6-(2-Hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl]-1-phenylethanone hydrochloride (1:1)
Lobelin hydrochloride
Lobeline hydrochloride
EINECS 205-150-2
2-{(2R,6S)-6-[(2S)-2-Hydroxy-2-phenylethyl]-1-methyl-2-piperidinyl}-1-phenylethanone hydrochloride
2-{(2R,6S)-6-[(2S)-2-Hydroxy-2-phenylethyl]-1-methyl-2-piperidinyl}-1-phenylethanone hydrochloride (1:1)
MFCD00082455
Ethanone, 2-((2R,6S)-6-((2S)-2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenyl-, hydrochloride
Ethanone, 2-[6-(2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl]-1-phenyl-, hydrochloride (1:1)
2-{(2R,6S)-6-[(2S)-2-Hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl}-1-phenylethanone hydrochloride (1:1)
2-{(2R,6S)-6-[(2S)-2-Hydroxy-2-phenylethyl]-1-methyl-2-piperidinyl}-1-phenylethanonhydrochlorid
α-Lobeline hydrochloride
(-)-Lobeline hydrochloride
2-{(2R,6S)-6-[(2S)-2-Hydroxy-2-phényléthyl]-1-méthyl-2-pipéridinyl}-1-phényléthanone chlorhydrate
2-(6-(2-Hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethanone hydrochloride
Lobeline (hydrochloride)

Biological Activity

[Description]:

Lobeline hydrochloride, a nicotinic receptor agonist, acting as a potent antagonist at both α3β2 and α4β2 neuronal nicotinic receptor subtypes.

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> nAChR

Signaling Pathways >> Neuronal Signaling >> nAChR

Research Areas >> Neurological Disease

Natural Products >> Alkaloid

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
485.6ºC at 760mmHg

[ Melting Point ]:
183-185 °C (dec.)(lit.)

[ Molecular Formula ]:
C₂₂H₂₈ClNO₂

[ Molecular Weight ]:
373.916

[ Flash Point ]:
247.5ºC

[ Exact Mass ]:
373.180847

[ PSA ]:
40.54000

[ LogP ]:
4.97590

[ Vapour Pressure ]:
3.02E-11mmHg at 25°C

[ Index of Refraction ]:
-57.5 ° (C=1, H2O)

[ Storage condition ]:
Store at RT

[ Water Solubility ]:
H2O: 25 mg/mL

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OJ8490100

CHEMICAL NAME :: Lobeline, hydrochloride

CAS REGISTRY NUMBER :: 134-63-4

LAST UPDATED :: 198706

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C22-H27-N-O2.Cl-H

MOLECULAR WEIGHT :: 373.96

WISWESSER LINE NOTATION :: T6NTJ A1 B1YQR& F1VR &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 39900 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,913,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 87500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,913,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7800 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,913,1982

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 150 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - convulsions or effect on seizure threshold

REFERENCE :: AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 163,279,1931

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301 + H331

[ Precautionary Statements ]:
P261-P301 + P310-P311

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T:Toxic;

[ Risk Phrases ]:
R23/25

[ Safety Phrases ]:
S36/37/39-S45

[ RIDADR ]:
UN 1544 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
OJ8490100

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Enhancing perception of contaminated food through acid-mediated modulation of taste neuron responses.

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Natural foods contain not only nutrients, but also nonnutritious and potentially harmful chemicals. Thus, animals need to evaluate food content in order to make adequate feeding decisions.Here, we inv...

Chemical genetics reveals a complex functional ground state of neural stem cells.

Nat. Chem. Biol. 3(5) , 268-273, (2007)

The identification of self-renewing and multipotent neural stem cells (NSCs) in the mammalian brain holds promise for the treatment of neurological diseases and has yielded new insight into brain canc...

The effects of lobeline on nicotine withdrawal-induced depression-like behavior in mice.

Psychopharmacol. Ser. 231(15) , 2989-98, (2014)

Evidence suggests that neuronal nicotinic acetylcholine receptor (nAChR) ligand lobeline has antidepressant-like properties.The present study investigated the effects of lobeline on nicotine withdrawa...