IUPAC name
Systematic IUPAC name
68593-96-4 N
3D model (Jmol) Interactive image
Interactive image
Interactive image
Abbreviations 5-OH-DPAT
ChemSpider 9474597 (S) YesY
150564 YesY
MeSH 5-Hydroxy-2-N,N-dipropylaminotetralin
PubChem 11299620 (S)
12280580 (R)
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).
N verify (what is YesYN ?)
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


  1. "5-hydroxy-2-N,N-dipropylaminotetralin - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. 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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