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H8520

Sigma-Aldrich

(±)-8-Hydroxy-2-(dipropylamino)tetralin hydrobromide

≥98%

Synonym(s):

(±)-2-Dipropylamino-8-hydroxy-1,2,3,4-tetrahydronaphthalene, (±)-8-Hydroxy-2-(dipropylamino)tetralin, (±)-8-OH-DPAT

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About This Item

Empirical Formula (Hill Notation):
C16H25NO · HBr
CAS Number:
87394-87-4
Molecular Weight:
328.29
MDL number:
MFCD00055158
UNSPSC Code:
12352100
PubChem Substance ID:
57654276
NACRES:
NA.22

Quality Level

100

Assay

≥98%

SMILES string

Br[H].CCCN(CCC)C1CCc2cccc(O)c2C1

InChI

1S/C16H25NO.BrH/c1-3-10-17(11-4-2)14-9-8-13-6-5-7-16(18)15(13)12-14;/h5-7,14,18H,3-4,8-12H2,1-2H3;1H

InChI key

BATPBOZTBNNDLN-UHFFFAOYSA-N

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Application

(±)-8-Hydroxy-2-(dipropylamino)tetralin hydrobromide is a potent and selective 5-hydroxytryptamine (5HT1A)-receptor agonist which is generally used as the standard in pharmacological studies.

Biochem/physiol Actions

Selective 5-HT1 agonist with high affinity for subtype 5-HT1A receptor.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Arylpiperazine agonists of the serotonin 5-HT 1A receptor preferentially activate cAMP signaling versus recruitment of β-arrestin-2.
Stroth N, et al.
Bioorganic & Medicinal Chemistry, 23(15), 4824-4830 (2015)
Laifu Li et al.
eLife, 10 (2021-06-04)
Consolation is a common response to the distress of others in humans and some social animals, but the neural mechanisms underlying this behavior are not well characterized. By using socially monogamous mandarin voles, we found that optogenetic or chemogenetic inhibition
8-Hydroxy-2-(dipropylamino) tetralin, a new centrally acting 5-hydroxytryptamine receptor agonist.
Arvidsson L E, et al.
Journal of Medicinal Chemistry, 24(8), 921-923 (1981)
S J Peroutka
Journal of neurochemistry, 47(2), 529-540 (1986-08-01)
Drug interactions with 5-HT1 (5-hydroxytryptamine type 1) binding site subtypes were analyzed in rat frontal cortex. 8-Hydroxy-N,N-dipropyl-2-aminotetralin (8-OH-DPAT) displays high affinity (Ki 3.3 +/- 1 nM) for 29 +/- 3% of total [3H]5-HT binding in rat frontal cortex and low
Improved preparation, chromatographic separation and X-ray crystallographic determination of the absolute configuration of the enantiomers of 8-hydroxy-2-(dipropylamino) tetralin (8-OH DPAT).
Karlsson A, et al.
Acta Chemica Scandinavica, 42, 231-236 (1988)
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