5-OH-DPAT is a synthetic compound that acts as a dopamine receptor agonist with selectivity for the D2 receptor and D3 receptor subtypes.[1][2] Only the (S)-enantiomer is active as an agonist, with the (R)-enantiomer being a weak antagonist at D2 receptors.[3] 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,[4][5] and the drug is also being studied in the treatment of Parkinson's disease.[6][needs update]

5-OH-DPAT
Stereo, Kekulé, skeletal formula of (S)-5-OH-DPAT
Names
Preferred IUPAC name
(6S)-6-(Dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-ol
Identifiers
3D model (JSmol)
Abbreviations 5-OH-DPAT
ChEMBL
ChemSpider
MeSH 5-Hydroxy-2-N,N-dipropylaminotetralin
  • InChI=1S/C16H25NO/c1-3-10-17(11-4-2)14-8-9-15-13(12-14)6-5-7-16(15)18/h5-7,14,18H,3-4,8-12H2,1-2H3/t14-/m0/s1 checkY
    Key: MDBWEQVKJDMEMK-AWEZNQCLSA-N checkY
  • Oc1cccc2c1CC[C@H](N(CCC)CCC)C2
  • CCCN(CCC)C1CCc2c(O)cccc2C1
  • CCCN(CCC)C1CCC2=C(O)C=CC=C2C1
Properties
C16H25NO
Molar mass 247.382 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).
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See alsoEdit

ReferencesEdit

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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. S2CID 43878278.
  5. ^ 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.
  6. ^ 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.