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Related CAS#:
90-69-7 1070913-26-6
134-63-4 10122-32-4
18210-71-4 134-64-5
63990-84-1 1125824-45-4

90-69-7

90-69-7 structure
90-69-7 structure
  • Name: (-)-Lobeline
  • Chemical Name: (-)-lobeline
  • CAS Number: 90-69-7
  • Molecular Formula: C22H27NO2
  • Molecular Weight: 337.455
  • Catalog: API Nervous system medication Central stimulant
  • Create Date: 2018-06-05 08:00:00
  • Modify Date: 2024-01-02 16:45:36
  • Lobeline (α-Lobeline; L-Lobeline), a lipophilic alkaloidal, is a nicotinic receptor agonist. Lobeline inhibits d-methamphetamine self-administration with no dopaminergic toxicity. Lobeline rescues d-amphetamine abuse induced addictive effect. Lobeline increases dopamine (DA) release by inhibiting DA uptake into synaptic vesicles, and altering presynaptic DA storage[1][2][3].
Name (-)-lobeline
Synonyms [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
Description Lobeline (α-Lobeline; L-Lobeline), a lipophilic alkaloidal, is a nicotinic receptor agonist. Lobeline inhibits d-methamphetamine self-administration with no dopaminergic toxicity. Lobeline rescues d-amphetamine abuse induced addictive effect. Lobeline increases dopamine (DA) release by inhibiting DA uptake into synaptic vesicles, and altering presynaptic DA storage[1][2][3].
Related Catalog
In Vitro Lobeline (0.1-100 μM) 诱导 [3H]DA 溢出呈非钙依赖性[1]。 Lobeline 抑制 [3H]DA 被突触小体 (IC50=80 μM) 和囊泡 (IC50=0.88 μM) 摄取[1]。 Lobeline (0.1-1μM; 1 h) 抑制 1 μM d-methamphetamine 诱导的纹状体切片释放多巴胺[2]。
In Vivo Lobeline (0.3-3.0 mg/kg; 皮下注射; 单剂量) 降低模型大鼠 d-methamphetamine 的自我给药能力[3]。 Lobeline (3 mg/kg; 皮下注射; 7 个周期，共 7 次) 以非竞争性的方式特别降低大鼠对 d-methamphetamine 的反应，并增加耐受性发展[3]。 Animal Model: Sprague-Dawley rats (200-250 g)[3] Dosage: 0.3 mg/kg, 1.0 mg/kg, and 3.0 mg/kg for acute administration; 3 mg/kg for chronic administration Administration: Subcutaneous injection; 15 min prior to measurement, or every 15 min for 7 sessions; separated by 2 intervening maintenance days of d-methamphetamine (0.05 mg/kg/infusion) self-administration Result: Decreased d-methamphetamine Self-Administration.
References

[1]. Teng L, et al. Lobeline and nicotine evoke [3H]overflow from rat striatal slices preloaded with [3H]dopamine: differential inhibition of synaptosomal and vesicular [3H]dopamine uptake. J Pharmacol Exp Ther. 1997 Mar;280(3):1432-44.  

[2]. Miller DK, et al. Lobeline inhibits the neurochemical and behavioral effects of amphetamine. J Pharmacol Exp Ther. 2001 Mar;296(3):1023-34.  

[3]. Harrod SB, et al. Lobeline attenuates d-methamphetamine self-administration in rats. J Pharmacol Exp Ther. 2001 Jul;298(1):172-9.  

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

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
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)

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