2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethan-1-one hydrochloride

• ChemBase ID: 110145
• Molecular Formular: C22H28ClNO2
• Molecular Mass: 373.91622
• Monoisotopic Mass: 373.18085682
• SMILES: Cl.CN1[C@@H](CCC[C@@H]1CC(=O)c1ccccc1)C[C@H](O)c1ccccc1
• Canonical SMILES: O[C@H](c1ccccc1)C[C@@H]1CCC[C@@H](N1C)CC(=O)c1ccccc1.Cl
• InChI: InChI=1S/C22H27NO2.ClH/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;1H/t19-,20+,21-;/m0./s1
• InChIKey: MKMYPTLXLWOUSO-NFQNBQCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethan-1-one hydrochloride
• IUPAC Traditional name: (-)-lobeline hydrochloride
• Synonyms: α-Lobeline hydrochloride; L-Lobeline hydrochloride; (-)-Lobeline hydrochloride; LOBELINE HCl; α-Lobeline hydrochloride; 2-[6-(2-Hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl]-1-phenylethanone hydrochloride; (-)-Lobeline hydrochloride; α-洛贝林 盐酸盐; L-洛贝林 盐酸盐; (-)-洛贝林 盐酸盐; 2-[6-(2-羟基-2-苯乙基)-1-甲基-2-呱啶基]-1-苯乙酮 盐酸盐; (-)-洛贝林 盐酸盐; α-洛贝林 盐酸盐

Database IDs

• CAS Number: 134-63-4
• EC Number: 205-150-2
• MDL Number: MFCD00082455
• Beilstein Number: 3920196
• PubChem SID: 24882261; 162096366; 24848513
• PubChem CID: 101615

CALCULATED PROPERTIES

• Acid pKa: 14.422222
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.7126789
• LogD (pH = 7.4): 2.3968606
• Log P: 3.7834027
• Molar Refractivity: 101.5121 cm^3
• Polarizability: 39.833355 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble25 mg/mL
• Apperance: white to off-white powder
• Melting Point: 178-180 °C; 183-185 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -56.8°, c = 2 in H2O; [α]20/D -57±2°, c = 2% in H2O

Safety Information

• RTECS: OJ8490100
• European Hazard Symbols: Toxic (T)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 23/25
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H331
• GHS Precautionary statements: P261-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 3

Pharmacology Properties

• Gene Information: human ... SLC18A2(6571)

Product Information

• Purity: ≥98.0% (AT); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C22H27NO2 · HCl

DETAILS

MP Biomedicals - 05213904

MP Biomedicals Rare Chemical collection

Sigma Aldrich - L4376

Biochem/physiol Actions
高亲和性神经元烟碱型乙酰胆碱受体激动剂；呼吸兴奋剂。通过与囊泡单胺转运体 (VMAT2) 的四苯喹嗪结合位点相互作用来抑制多巴胺的突触积累。阻断安非他明诱导的多巴胺释放。

Sigma Aldrich - 141879

Packaging
1 g in glass bottle

Sigma Aldrich - 62630

Biochem/physiol Actions
Agonist at high-affinity neuronal nicotinic acetylcholine receptors; respiratory stimulant. Inhibits synaptosomal accumulation of dopamine by interaction with the tetrabenazine binding site of the vesicular monoamine transporter (VMAT2). Blocks amphetamine-induced dopamine release.