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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
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
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

University of Uppsala
1
Curator's Comment: Arvidsson LE, Hacksell U, Nilsson JL, Hjorth S, Carlsson A, Lindberg P, Sanchez D, Wikstrom H.

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 1.2 nM [Ki]
5-hydroxytryptamine receptor 7
15
Target ID: P34969
Gene ID: 3363.0
Gene Symbol: HTR7
Target Organism: Homo sapiens (Human)
Agonist
2678
 466.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
8-Hydroxy-2-(di-n-propylamino)tetralin, a new centrally acting 5-hydroxytryptamine receptor agonist.
1981 Aug
Cardiovascular response to 8-hydroxy-2-(di-n-propylamino) tetralin (8-OH-DPAT) in the rat: site of action and pharmacological analysis.
1987 Mar
Evidence for postsynaptic mediation of the hypothermic effect of 5-HT1A receptor activation.
1992 Jul
Mediation of the antidepressant-like effect of 8-OH-DPAT in mice by postsynaptic 5-HT1A receptors.
1993 Mar
Cloning of a novel human serotonin receptor (5-HT7) positively linked to adenylate cyclase.
1993 Nov 5
Protective effects of the 5-HT1A receptor agonist 8-hydroxy-2-(di-n-propylamino)tetralin against traumatic brain injury-induced cognitive deficits and neuropathology in adult male rats.
2002 Nov 29
5-hydroxytryptamine1A (5-HT1A) receptor agonists: A decade of empirical evidence supports their use as an efficacious therapeutic strategy for brain trauma.
2016 Jun 1
Patents

Patents

20100168121
1
7071194
1
9125900
1

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
Created
by admin
on Sat Dec 16 08:49:23 GMT 2023
Edited
by admin
on Sat Dec 16 08:49:23 GMT 2023
Record UNII
G8TFV2F5CP
Record Status Validated (UNII)
Record Version
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Name Type Language
8-HYDROXY-2-DIPROPYLAMINOTETRALIN HYDROBROMIDE
Systematic Name English
8-HYDROXY-2-DIPROPYLAMINOTETRALIN HYDROBROMIDE, (±)-
Systematic Name English
(±)-8-OH-DPAT-HBR
Common Name English
1-NAPHTHALENOL, 7-(DIPROPYLAMINO)-5,6,7,8-TETRAHYDRO-, HYDROBROMIDE (1:1)
Systematic Name English
8-HYDROXY-DPAT HYDROBROMIDE
Common Name English
2-DIPROPYLAMINO-8-HYDROXY-1,2,3,4-TETRAHYDRONAPHTHALENE HYDROBROMIDE
Systematic Name English
8-HYDROXY(N,N-DIPROPYL-2-AMINO)TETRALIN HYDROBROMIDE
Systematic Name English
Code System Code Type Description
FDA UNII
G8TFV2F5CP
Created by admin on Sat Dec 16 08:49:23 GMT 2023 , Edited by admin on Sat Dec 16 08:49:23 GMT 2023
PRIMARY
CAS
76135-31-4
Created by admin on Sat Dec 16 08:49:23 GMT 2023 , Edited by admin on Sat Dec 16 08:49:23 GMT 2023
PRIMARY
PUBCHEM
6917794
Created by admin on Sat Dec 16 08:49:23 GMT 2023 , Edited by admin on Sat Dec 16 08:49:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID80896822
Created by admin on Sat Dec 16 08:49:23 GMT 2023 , Edited by admin on Sat Dec 16 08:49:23 GMT 2023
PRIMARY
NIH
NCATS
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