5-OH-DPAT

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
CAS Number	68593-96-4 ;
3D model (JSmol)	Interactive image; Interactive image; Interactive image;
Abbreviations	5-OH-DPAT
ChEMBL	ChEMBL273273 ;
ChemSpider	9474597 (S) ; 150564 ;
MeSH	5-Hydroxy-2-N,N-dipropylaminotetralin
PubChem CID	11299620 (S); 12280580 (R); 172267;
	InChI 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 Key: MDBWEQVKJDMEMK-AWEZNQCLSA-N ;
	SMILES Oc1cccc2c1CC[C@H](N(CCC)CCC)C2; CCCN(CCC)C1CCc2c(O)cccc2C1; CCCN(CCC)C1CCC2=C(O)C=CC=C2C1;
Properties
Chemical formula	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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	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]

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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[1] "5-hydroxy-2-N,N-dipropylaminotetralin - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.

[pmid3712381-2] 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.

[pmid3599021-3] 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.

[pmid1976017-4] 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.

[pmid10842352-5] 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.

[pmid20641325-6] 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.

[pmid21283984-7] 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.

5-OH-DPAT

See also

References