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U108

S(−)-UH-301 hydrochloride

solid

Synonym(s):

S(−)-5-Fluoro-8-hydroxy-2-dipropylamino-1,2,3,4-tetrahydronaphthalene hydrochloride, S(−)-5-Fluoro-8-hydroxy-DPAT hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C16H24FNO · HCl
CAS Number:
127126-22-1
Molecular Weight:
301.83
UNSPSC Code:
12352200
PubChem Substance ID:
24278820
MDL number:
MFCD00210226
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assay

≥98% (HPLC)

form

solid

color

white

solubility

H2O: >20 mg/mL, ethanol: soluble

SMILES string

Cl[H].CCCN(CCC)[C@H]1CCc2c(F)ccc(O)c2C1

InChI

1S/C16H24FNO.ClH/c1-3-9-18(10-4-2)12-5-6-13-14(11-12)16(19)8-7-15(13)17;/h7-8,12,19H,3-6,9-11H2,1-2H3;1H/t12-;/m0./s1

InChI key

FKUVCCNCUAFKAH-YDALLXLXSA-N

Gene Information

human ... HTR1A(3350)

Biochem/physiol Actions

Potent, selective 5-HT1A serotonin receptor antagonist; D2/D3 dopamine receptor agonist.

Preparation Note

S(-)-UH-301 hydrochloride is soluble in water (>20 mg/ml) and ethanol.

Disclaimer

hygroscopic, photosensitive

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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L Björk et al.
European journal of pharmacology, 199(3), 367-370 (1991-07-09)
The 5-HT1A-receptor antagonist (S)-UH-301 (S)-5-fluoro-8-hydroxy-2- (dipropylamino)tetralin) completely antagonized the hypotension and bradycardia induced by (R) = 8-OH DPAT [R)-8-hydroxy-2- (dipropylamino)tetralin) in conscious rats. (S)-UH-301 alone induced a weak hypertension, which might be due to its 5-HT1A-receptor antagonistic properties. (R)-UH-301 induced
S E Hillver et al.
Chirality, 8(8), 531-544 (1996-01-01)
The (S)-enantiomer of 5-fluoro-8-hydroxy-2-(dipropylamino) tetralin [(S)-2a; (S)-UH301] was the first reported 5-HT1A receptor antagonist. We now give a full account on the synthetic effort leading to the preparation of the racemate and the enantiomers of 2a. The crystal and molecular
S Ahlenius et al.
European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology, 9(1-2), 15-19 (1999-03-19)
The receptor-mediated control of brain monoamine synthesis was used to examine the in vivo intrinsic efficacy of the 5-HT1A receptor antagonists NAD-299, S(-)-UH-301 and WAY-100,635. The rate of monoamine synthesis was estimated by measuring the accumulation of DOPA and 5-HTP
L Björk et al.
The Journal of pharmacology and experimental therapeutics, 258(1), 58-65 (1991-07-01)
The selective 5-hydroxytryptamine (5-HT1A) receptor agonist 8-hydroxy-2-(dipropylamino)tetralin (8-OH-DPAT) induces a large number of pharmacological effects. In the present study we demonstrate that a novel 8-OH-DPAT analog, (S)-5-fluoro-8-hydroxy-2-(dipropylamino)tetralin [(S)-UH-301], is able to antagonize completely the following (R)-8-OH-DPAT-induced effects in the rat:
L Arborelius et al.
Naunyn-Schmiedeberg's archives of pharmacology, 347(4), 353-362 (1993-04-01)
The effects of the selective 5-HT1A receptor agonist (R)-8-hydroxy-2(di-n-propylamino)tetralin [(R)-8-OH-DPAT] and the novel 5-HT1A antagonist (S)-5-fluoro-8-hydroxy-2-(dipropylamino)-tetralin [(S)-UH-301] were studied with regard to the firing pattern of single mesencephalic dopamine (DA) neurons with extracellular recording techniques in chloral hydrate anesthetized male

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