5-OH-DPAT
 | |
| Names | |
|---|---|
| IUPAC name
5-Hydroxy-N,N-dipropyl-2-aminotetralin | |
| Systematic IUPAC name
6-(Dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-ol[1] | |
| Identifiers | |
68593-96-4  | |
| 3D model (Jmol) | Interactive image Interactive image Interactive image |
| Abbreviations | 5-OH-DPAT |
| ChEMBL | ChEMBL273273 |
| ChemSpider | 9474597 (S)  150564 |
| MeSH | 5-Hydroxy-2-N,N-dipropylaminotetralin |
| PubChem | 11299620 (S) 12280580 (R) 172267 |
| |
| |
| Properties | |
| C16H25NO | |
| Molar mass | 247.38 g·mol−1 |
| log P | 3.55 |
| Acidity (pKa) | 10.543 |
| Basicity (pKb) | 3.454 |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
5-OH-DPAT is a synthetic compound that acts as a dopamine receptor agonist with selectivity for the D2 receptor and D3 receptor subtypes.[2][3] Only the (S)-enantiomer is active as an agonist, with the (R)-enantiomer being a weak antagonist at D2 receptors.[4] Radiolabelled 11C-5-OH-DPAT is used as an agonist radioligand for mapping the distribution and function of D2 and D3 receptors in the brain,[5][6] and the drug is also being studied in the treatment of Parkinson's disease.[7]
See also
References
- ↑ "5-hydroxy-2-N,N-dipropylaminotetralin - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
- ↑ Seiler MP, Stoll AP, Closse A, Frick W, Jaton A, Vigouret JM (June 1986). "Structure-activity relationships of dopaminergic 5-hydroxy-2-aminotetralin derivatives with functionalized N-alkyl substituents". Journal of Medicinal Chemistry. 29 (6): 912–7. doi:10.1021/jm00156a007. PMID 3712381.
- ↑ Johansson AM, Nilsson JL, Karlén A, Hacksell U, Svensson K, Carlsson A, Kenne L, Sundell S (July 1987). "C3-methylated 5-hydroxy-2-(dipropylamino)tetralins: conformational and steric parameters of importance for central dopamine receptor activation". Journal of Medicinal Chemistry. 30 (7): 1135–44. doi:10.1021/jm00390a004. PMID 3599021.
- ↑ Karlsson A, Björk L, Pettersson C, Andén NE, Hacksell U (1990). "(R)- and (S)-5-hydroxy-2-(dipropylamino)tetralin (5-OH DPAT): assessment of optical purities and dopaminergic activities". Chirality. 2 (2): 90–5. doi:10.1002/chir.530020206. PMID 1976017.
- ↑ Mukherjee J, Narayanan TK, Christian BT, Shi B, Dunigan KA, Mantil J (July 2000). "In vitro and in vivo evaluation of the binding of the dopamine D2 receptor agonist (11)C-(R,S)-5-hydroxy-2-(di-n-propylamino)tetralin in rodents and nonhuman primate". Synapse (New York, N.Y.). 37 (1): 64–70. doi:10.1002/(SICI)1098-2396(200007)37:1<64::AID-SYN7>3.0.CO;2-F. PMID 10842352.
- ↑ Leung K (2006). "(R,S)-2-(N-Propyl-N-1'-[11C]-propyl)amino-5-hydroxytetralin.". Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US). PMID 20641325.
- ↑ Ackaert OW, Graan JD, Shi S, Vreeken R, Della Pasqua OE, Dijkstra D, Westerink BH, Danhof M, Bouwstra JA (January 2011). "The pharmacokinetics and pharmacological effect of (S)-5-OH-DPAT following controlled delivery with transdermal iontophoresis". Journal of Pharmaceutical Sciences. 100 (7): 2996–3009. doi:10.1002/jps.22492. PMID 21283984.
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