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
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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6460101
Curator's Comment: Arvidsson LE, Hacksell U, Nilsson JL, Hjorth S, Carlsson A, Lindberg P, Sanchez D, Wikstrom H.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26612522 |
1.2 nM [Ki] | ||
Target ID: P34969 Gene ID: 3363.0 Gene Symbol: HTR7 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8226867 |
466.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
8-Hydroxy-2-(di-n-propylamino)tetralin, a new centrally acting 5-hydroxytryptamine receptor agonist. | 1981 Aug |
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Cardiovascular response to 8-hydroxy-2-(di-n-propylamino) tetralin (8-OH-DPAT) in the rat: site of action and pharmacological analysis. | 1987 Mar |
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Evidence for postsynaptic mediation of the hypothermic effect of 5-HT1A receptor activation. | 1992 Jul |
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Mediation of the antidepressant-like effect of 8-OH-DPAT in mice by postsynaptic 5-HT1A receptors. | 1993 Mar |
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Cloning of a novel human serotonin receptor (5-HT7) positively linked to adenylate cyclase. | 1993 Nov 5 |
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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 |
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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
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12429377
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8226867
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.
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SUBSTANCE RECORD