6-[(2-phenylethyl)(propyl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol hydrochloride

• ChemBase ID: 155212
• Molecular Formular: C21H28ClNO
• Molecular Mass: 345.90612
• Monoisotopic Mass: 345.1859422
• SMILES: CCCN(CCc1ccccc1)C1CCc2c(cccc2O)C1.Cl
• Canonical SMILES: CCCN(C1CCc2c(C1)cccc2O)CCc1ccccc1.Cl
• InChI: InChI=1S/C21H27NO.ClH/c1-2-14-22(15-13-17-7-4-3-5-8-17)19-11-12-20-18(16-19)9-6-10-21(20)23;/h3-10,19,23H,2,11-16H2,1H3;1H
• InChIKey: XWLCIDLCEZAOEY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-[(2-phenylethyl)(propyl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol hydrochloride
• IUPAC Traditional name: 6-[(2-phenylethyl)(propyl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol hydrochloride
• Synonyms: (±)-2-(N-Phenethyl-N-propyl)amino-5-hydroxytetralin hydrochloride; N-0434; (±)-PPHT hydrochloride

Database IDs

• CAS Number: 71787-90-1
• MDL Number: MFCD00055157
• PubChem SID: 24277925; 162249350
• PubChem CID: 11957671

CALCULATED PROPERTIES

• Acid pKa: 10.036638
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.8441389
• LogD (pH = 7.4): 2.263015
• Log P: 4.4010587
• Molar Refractivity: 97.5576 cm^3
• Polarizability: 37.727222 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL; H2O: ≥2 mg/mL
• Apperance: off-white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H27NO · HCl

DETAILS

Sigma Aldrich - P105

Biochem/physiol Actions
Potent D2 dopamine receptor agonist.
A series of new dopamine (DA) receptor agonists, of the 2-aminotetralin group, i.e. N-0434, N-0437 and N-0734 were investigated in both in vivo and in vitro pharmacological test systems. In vivo, the reversal of the gamma-butyrolactone-induced increase in rat central DOPA biosynthesis rate was taken as a measure of presynaptic activity. The homovanillic acid (HVA) decrease, after intraperitoneal and after oral administration of the drugs was also taken as a measure of presynaptic activity. Postsynaptic activity was measured in two behavioural models, i.e. reserpine reversal and stereotypy induction. The effects of (±)-PPHT (N-0434) these drugs on noradrenaline and dopamine turnover (alpha-MpT method) were studied in addition. The results indicate that all three compounds N-0434 ((±)-PPHT), N-0437 and N-0734 are potent and selective DA agonists that lack significant alpha 2 activity.