:5-OH-DPAT

{{Short description|Dopamine receptor agonist compound}}

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 456504309

| ImageFile = 5-OH-DPAT Structure.svg

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageSize = 244

| ImageName = Stereo, Kekulé, skeletal formula of (S)-5-OH-DPAT

| PIN = (6S)-6-(Dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-ol

|Section1={{Chembox Identifiers

| Abbreviations = 5-OH-DPAT

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 68593-96-4

| PubChem2 = 172267

| PubChem1 = 12280580

| PubChem1_Comment = (R)

| PubChem = 11299620

| PubChem_Comment = (S)

| ChemSpiderID1 = 150564

| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 9474597

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID_Comment = (S)

| MeSHName = 5-Hydroxy-2-N,N-dipropylaminotetralin

| ChEMBL = 273273

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| SMILES = Oc1cccc2c1CC[C@H](N(CCC)CCC)C2

| SMILES1 = CCCN(CCC)C1CCc2c(O)cccc2C1

| SMILES2 = CCCN(CCC)C1CCC2=C(O)C=CC=C2C1

| StdInChI = 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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = MDBWEQVKJDMEMK-AWEZNQCLSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

}}

|Section2={{Chembox Properties

| C=16 | H=25 | N=1 | O=1

| LogP = 3.55

| pKa = 10.543

| pKb = 3.454

}}

}}

5-OH-DPAT is a synthetic compound that acts as a dopamine receptor agonist with selectivity for the D₂ receptor and D₃ receptor subtypes.{{cite journal |vauthors =Seiler MP, Stoll AP, Closse A, Frick W, Jaton A, Vigouret JM |title=Structure-activity relationships of dopaminergic 5-hydroxy-2-aminotetralin derivatives with functionalized N-alkyl substituents |journal=Journal of Medicinal Chemistry |volume=29 |issue=6 |pages=912–7 |date=June 1986 |pmid=3712381 |doi= 10.1021/jm00156a007}}{{cite journal |vauthors =Johansson AM, Nilsson JL, Karlén A, Hacksell U, Svensson K, Carlsson A, Kenne L, Sundell S |title=C3-methylated 5-hydroxy-2-(dipropylamino)tetralins: conformational and steric parameters of importance for central dopamine receptor activation |journal=Journal of Medicinal Chemistry |volume=30 |issue=7 |pages=1135–44 |date=July 1987 |pmid=3599021 |doi= 10.1021/jm00390a004}} Only the (S)-enantiomer is active as an agonist, with the (R)-enantiomer being a weak antagonist at D₂ receptors.{{cite journal |vauthors =Karlsson A, Björk L, Pettersson C, Andén NE, Hacksell U |title=(R)- and (S)-5-hydroxy-2-(dipropylamino)tetralin (5-OH DPAT): assessment of optical purities and dopaminergic activities |journal=Chirality |volume=2 |issue=2 |pages=90–5 |year=1990 |pmid=1976017 |doi=10.1002/chir.530020206 }} 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,{{cite journal |vauthors =Mukherjee J, Narayanan TK, Christian BT, Shi B, Dunigan KA, Mantil J |title=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 |journal=Synapse (New York, N.Y.) |volume=37 |issue=1 |pages=64–70 |date=July 2000 |pmid=10842352 |doi=10.1002/(SICI)1098-2396(200007)37:1<64::AID-SYN7>3.0.CO;2-F |s2cid=43878278 |doi-access=free }}{{cite journal |vauthors =Leung K |title=(R,S)-2-(N-Propyl-N-1'-[11C]-propyl)amino-5-hydroxytetralin. |journal=Molecular Imaging and Contrast Agent Database |year=2006 |pmid=20641325 }} and the drug is also being studied in the treatment of Parkinson's disease.{{cite journal |vauthors =Ackaert OW, Graan JD, Shi S, Vreeken R, Della Pasqua OE, Dijkstra D, Westerink BH, Danhof M, Bouwstra JA |title=The pharmacokinetics and pharmacological effect of (S)-5-OH-DPAT following controlled delivery with transdermal iontophoresis |journal=Journal of Pharmaceutical Sciences |volume= 100|issue= 7|pages= 2996–3009|date=January 2011 |pmid=21283984 |doi=10.1002/jps.22492 }}{{Needs update|date=April 2019}}