5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride

• ChemBase ID: 155051
• Molecular Formular: C14H16Cl2N2
• Molecular Mass: 283.19624
• Monoisotopic Mass: 282.06905388
• SMILES: Cc1c(c2cc(ccc2[nH]1)Cl)C1=CCNCC1.Cl
• Canonical SMILES: Clc1ccc2c(c1)c(C1=CCNCC1)c([nH]2)C.Cl
• InChI: InChI=1S/C14H15ClN2.ClH/c1-9-14(10-4-6-16-7-5-10)12-8-11(15)2-3-13(12)17-9;/h2-4,8,16-17H,5-7H2,1H3;1H
• InChIKey: WWSNDUWIZDYGIQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride
• IUPAC Traditional name: 5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride
• Synonyms: 5-Chloro-2-methyl-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-Indole hydrochloride; EMD-386088; EMD386088

Database IDs

• CAS Number: 1171123-46-8
• MDL Number: MFCD09038557
• PubChem SID: 162249189
• PubChem CID: 56972198

CALCULATED PROPERTIES

• Acid pKa: 16.276197
• H Acceptors: 1
• H Donor: 2
• LogD (pH = 5.5): -0.31130007
• LogD (pH = 7.4): 0.73810595
• Log P: 2.86974
• Molar Refractivity: 73.216 cm^3
• Polarizability: 29.031305 Å^3
• Polar Surface Area: 27.82 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥16 mg/mL
• Apperance: yellow powder

Safety Information

• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C14H15ClN2 · HCl

DETAILS

Sigma Aldrich - SML0139

Biochem/physiol Actions
EMD-386088 is a potent serotonin 5-HT6-specific agonist. The IC50 for competition of LSD from 5-HT6 expressed in HEK cells is 7.4 nM, and the EC50 for stimulating cAMP production is 1 nM. EMD-386088 is inactive against other HT receptors except 5-HT3 (IC50 = 34 nM).