U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C16H25NO.BrH
Molecular Weight 328.288
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 8-HYDROXY-2-DIPROPYLAMINOTETRALIN HYDROBROMIDE

SMILES

Br.CCCN(CCC)C1CCC2=CC=CC(O)=C2C1

InChI

InChIKey=BATPBOZTBNNDLN-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C16H25NO
Molecular Weight 247.3758
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

8-Hyroxy-2-Dipropylaminotetralin Hydrobromide (8-OH-DPAT) is a chemical predominantly used in research settings. It is widely regarded as the first identified complete agonist of the 5-HT1a receptor, for which it has a Ki = 3.18 nM. 8-OH-DPAT also acts as an agonist of the 5-HT7 receptor, and as a substrate of the Sodium dependent serotonin transporter (SERT). Although it has never progressed to human clinical trials 8-OH-DPAT has been studied in animal models for a number of conditions both for its own potential and as a benchmark for other compounds.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.2 nM [Ki]
466.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Traumatically brain injured rats were given a single intraperitoneal dose of 8-OH-DPAT (0.1, 0.5, or 1.0 mg/kg) 15 minutes after controlled cortical impact. Motor and cognitive functions were tested on post operative days 1-5 and 14 -18 respectively. Hippocampal cell survival and cortical lesion volume were recorded at 4 weeks. It was observed that 0.5 mg/kg of 8-OH-DPAT conferred neuroprotective effects by attenuating spatial acquisition deficits and reducing hippocampal CA(3) cell loss.
Route of Administration: Intraperitoneal
In Vitro Use Guide
Monkey kidney cells (cos-7) were grown and transiently transfected with the vector for the human 5-HT7 receptor. Cells were incubated for 30 minutes at 37 degree Celsius with 5 nM [3H] 5-HT and 7 different concentrations of 8-OH-DPAT. A Ki value of 466 nM was recorded for 8-OH-DPAT.
Substance Class Chemical
Record UNII
G8TFV2F5CP
Record Status Validated (UNII)
Record Version