CAS 90-69-7|(-)-Lobeline
Introduction：Basic information about CAS 90-69-7|(-)-Lobeline, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | (-)-Lobeline | ||
|---|---|---|---|
| CAS Number | 90-69-7 | Molecular Weight | 337.455 |
| Density | 1.1±0.1 g/cm3 | Boiling Point | 485.6±15.0 °C at 760 mmHg |
| Molecular Formula | C22H27NO2 | Melting Point | 130-131° |
| MSDS | / | Flash Point | 247.5±20.4 °C |
Names
| Name | (-)-lobeline |
|---|---|
| Synonym | More Synonyms |
(-)-Lobeline BiologicalActivity
| 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 | Signaling Pathways >>Membrane Transporter/Ion Channel >>nAChRSignaling Pathways >>Neuronal Signaling >>nAChRSignaling Pathways >>Neuronal Signaling >>Dopamine TransporterResearch Areas >>Neurological Disease |
| 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. |
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 |
| InChIKey | MXYUKLILVYORSK-HKBOAZHASA-N |
| SMILES | CN1C(CC(=O)c2ccccc2)CCCC1CC(O)c1ccccc1 |
Toxicological Information
CHEMICAL IDENTIFICATION |
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) |
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 |
