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H140

Sigma-Aldrich

(R)-(+)-8-Hydroxy-DPAT hydrobromide

≥98% (HPLC), solid

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Synonym(s):
(R)-(+)-2-Dipropylamino-8-hydroxy-1,2,3,4-tetrahydronaphthalene hydrobromide, (R)-(+)-8-Hydroxy-2-(dipropylamino)tetralin hydrobromide
Empirical Formula (Hill Notation):
C16H25NO · HBr
CAS Number:
78095-19-9
Molecular Weight:
328.29
MDL number:
MFCD00153810
UNSPSC Code:
12352200
PubChem Substance ID:
24278480
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

optical activity

[α]25/D +68.2°, c = 1 in methanol(lit.)

storage condition

desiccated
protect from light

color

white to off-white

solubility

H2O: >10 mg/mL at ±60 °C (with sonication)

SMILES string

Br.CCCN(CCC)[C@@H]1CCc2cccc(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/t14-;/m1./s1

InChI key

BATPBOZTBNNDLN-PFEQFJNWSA-N

Gene Information

human ... HTR1A(3350)

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Application

(R)-(+)-8-Hydroxy-DPAT hydrobromide has been used as a 5-HT1A agonist:
  • in mice to test the activity of the serotonin receptor
  • to test its effect on zebrafish melanocyte migration and survival
  • to stimulate hippocampal neurons

Biochem/physiol Actions

(R)-(+)-8-Hydroxy-DPAT administration reduces aggressive behavior. It decreases food intake by modifying the sensitivity of 5-HT1A receptor during food deprivation.
(R)-(+)-8-Hydroxy-DPAT is a full 5-HT1A serotonin receptor agonist; active enantiomer of (±)-8-hydroxy-DPAT.

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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Masatoshi Nagano et al.
Scientific reports, 8(1), 13675-13675 (2018-09-14)
Disturbance of neurotransmitters and neuromodulators is thought to underlie the pathophysiology of autism spectrum disorder (ASD). Studies of 15q dup mouse models of ASD with human 15q11-13 duplication have revealed that restoring serotonin (5-HT) levels can partially reverse ASD-related symptoms
Jan Brosda et al.
ACS chemical neuroscience, 6(7), 1176-1185 (2015-03-18)
Brain serotonin (5-HT) is involved in the control of food intake. The ingestive effects of 5-HT are mediated by various receptor subtypes, among others the 5-HT1A receptor. While the involvement of presynaptic 5-HT1A receptors is regarded as certain, the role
Mice do not habituate to metabolism cage housing-a three week study of male BALB/c mice
Kalliokoski O, et al.
PLoS ONE, 8(3), 1176-1185 (2013)
Sietse F de Boer et al.
European journal of pharmacology, 526(1-3), 125-139 (2005-11-29)
More than any other brain neurotransmitter system, the indolamine serotonin (5-HT) has been linked to aggression in a wide and diverse range of species, including humans. The nature of this linkage, however, is not simple and it has proven difficult
L Björk et al.
Journal of medicinal chemistry, 32(4), 779-783 (1989-04-01)
The enantiomers of the N,N-dimethylamino (1), N,N-diethylamino (2), and N,N-dibutylamino (4) derivatives of 8-hydroxy-2-(dipropylamino)tetralin (8-OH DPAT; 3) have been synthesized. The compounds have been tested for activity at central 5-hydroxytryptamine and dopamine receptors by use of biochemical and behavioral tests
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