(-)-Lobeline

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Names

[ CAS No. ]:
90-69-7

[ Name ]:
(-)-Lobeline

[Synonym ]:
[2R-[2a,6a(S*)]]-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
2-{(2R,6S)-6-[(2S)-2-Hydroxy-2-phenylethyl]-1-methyl-2-piperidinyl}-1-phenylethanone
Ethanone, 2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methyl-2-piperidinyl]-1-phenyl-
lobeline
Lobron
Bantron
Inflatine
2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone
Zoolobelin
Lobelina

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
485.6±15.0 °C at 760 mmHg

[ Melting Point ]:
130-131°

[ Molecular Formula ]:
C22H27NO2

[ Molecular Weight ]:
337.455

[ Flash Point ]:
247.5±20.4 °C

[ Exact Mass ]:
337.204193

[ PSA ]:
40.54000

[ LogP ]:
3.61

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.563

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
OJ8480000
CHEMICAL NAME :
Lobeline
CAS REGISTRY NUMBER :
90-69-7
BEILSTEIN REFERENCE NO. :
0091533
LAST UPDATED :
199612
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C22-H27-N-O2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
80 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) 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: 132,63,1928
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
43500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
STRAAA Strahlentherapie. (Urban & Schwarzenberg, Postfach 202440, D-8000 Munich 2, Fed. Rep. Ger.) V.1- 1912- Volume(issue)/page/year: 127,245,1965
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
100 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) 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: 132,63,1928
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
6300 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 103,146,1955
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
35 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 4(1),34,1941
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
10 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 31,43,1927

Safety Information

[ Hazard Codes ]:
T

[ Risk Phrases ]:
23/24/25

[ Safety Phrases ]:
36/37/39-45

[ RIDADR ]:
UN 1544

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • α-Lobeline Hydrochcloride
  • N-Methoxy-N-methylbenzamide
  • 4-Phenyl-1-butene-4-one
  • 1-phenyl-3-buten-1-ol
  • (αR)-α-(2-propenyl)benzenemethanol
  • (1R,3S)-2-oxiranyl-1-phenyl-ethanol
  • (4S,6R)-4-iodomethyl-6-phenyl[1,3]dioxan-2-one
  • tert-butyl [(1R)-1-phenylbut-3-enyl] carbonate

DownStream

Related Compounds

  • (cis:trans)-(-)-lobeline
  • (-)-Lobeline hydrochloride
  • lobeline
  • LOBELINE SULFATE
  • Lobeline sulfate
  • Lobeline Hydrochloride
  • 4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
  • 1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
  • 2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
  • 1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
  • 2-(1,3-Benzodioxol-5-yl)-6-nitroquinoline
  • (4-Methyl-tetrahydro-furan-2-yl)-methanol
  • N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
  • 4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
  • tert-Butyl-DL-alanine
  • 2-(benzo[d]thiazol-2-yl(methyl)amino)-N-(3-(methylsulfonamido)phenyl)acetamide