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P105

Sigma-Aldrich

(±)-PPHT hydrochloride

≥98% (HPLC), solid

Synonym(s):

(±)-2-(N-Phenethyl-N-propyl)amino-5-hydroxytetralin hydrochloride, N-0434

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About This Item

Empirical Formula (Hill Notation):
C21H27NO · HCl
CAS Number:
71787-90-1
Molecular Weight:
345.91
MDL number:
MFCD00055157
UNSPSC Code:
12352200
PubChem Substance ID:
24277925

Assay

≥98% (HPLC)

form

solid

color

off-white

solubility

DMSO: ≥10 mg/mL
H2O: ≥2 mg/mL

SMILES string

Cl[H].CCCN(CCc1ccccc1)C2CCc3c(O)cccc3C2

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

InChI key

XWLCIDLCEZAOEY-UHFFFAOYSA-N

Gene Information

human ... DRD1(1812) , DRD2(1813) , DRD3(1814) , DRD4(1815) , DRD5(1816)

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Biochem/physiol Actions

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.
Potent D2 dopamine receptor agonist.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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M P Seiler et al.
Journal of medicinal chemistry, 29(6), 912-917 (1986-06-01)
5-Hydroxy-2-aminotetralin derivatives in which one N-alkyl substituent carries a functional group have been prepared and their dopaminergic activities compared with those of 5-hydroxy-2-(di-n-propylamino)tetralin (5-OH-DPAT) and known ergolines. Several members of the series demonstrated high affinities in dopamine (DA) receptor binding
M A Ariano et al.
Brain research, 547(2), 208-222 (1991-05-03)
Selective dopamine receptor ligands, (R,S)-5-(4'-aminophenyl)-8-chloro-2,3,4, 5-tetrahydro-3-methyl-[1H]-3-benzazepin-7-ol, the 4'-amino derivative of the high affinity D1 receptor antagonist SCH 23390, the high affinity D2 receptor antagonist N-(p-aminophenethyl)-spiperone or NAPS, and the D2 selective agonist, 2-(N-phenethyl-N-propyl)-amino-5-hydroxytetralin or PPHT were chemically coupled to the
F J Bosker et al.
European journal of pharmacology, 163(2-3), 319-326 (1989-04-25)
Partial purification of the dopamine D-2 receptor from bovine striatum, solubilized in the presence of 1% digitonin, was obtained by chromatography on wheat germ lectin agarose. The preparation was purified approximately 10-fold. The stability of the receptor preparation was considerably
A Mao et al.
Life sciences, 59(21), PL317-PL324 (1996-01-01)
The concentrations of endogenous ligands generally remain in a bounded range around a basal level, a manifestation of control. The dopaminergic system is an excellent example of a control system in which a negative feedback signal is associated with receptor
T P Burris et al.
Neuroendocrinology, 54(2), 175-183 (1991-08-01)
The ability of low concentrations of dopamine (DA) to stimulate the secretion of prolactin (PRL) was examined in perifused or monolayer cultures of anterior pituitary cells. In cultures perifused with media containing 100 nM DA, changing the DA concentration to
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