doxanthrine

{{short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 449581815

| IUPAC_name = (6aS,12bR)-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline-2,3-diol

| image = Doxanthrine Structure.svg

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| metabolism =

| elimination_half-life =

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 916572-45-7

| ATC_prefix = none

| ATC_suffix =

| PubChem = 15981509

| ChemSpiderID = 13112900

| ChEMBL = 387250

| C=16 | H=15 | N=1 | O=3

| smiles = c1ccc2c(c1)CN[C@H]3[C@H]2c4cc(c(cc4OC3)O)O

| StdInChI = 1S/C16H15NO3/c18-13-5-11-15(6-14(13)19)20-8-12-16(11)10-4-2-1-3-9(10)7-17-12/h1-6,12,16-19H,7-8H2/t12-,16-/m1/s1

| StdInChIKey = QDUNOUQOKOYLCH-MLGOLLRUSA-N

}}

Doxanthrine is a synthetic compound which is a potent and selective full agonist for the dopamine D₁ receptor.{{cite journal |vauthors=Cueva JP, Giorgioni G, Grubbs RA, Chemel BR, Watts VJ, Nichols DE |title=trans-2,3-dihydroxy-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline: synthesis, resolution, and preliminary pharmacological characterization of a new dopamine D1 receptor full agonist |journal=Journal of Medicinal Chemistry |volume=49 |issue=23 |pages=6848–57 |date=November 2006 |pmid=17154515 |doi=10.1021/jm0604979 }}{{cite journal |vauthors=Przybyla JA, Cueva JP, Chemel BR, Hsu KJ, Riese DJ, McCorvy JD, Chester JA, Nichols DE, Watts VJ |title=Comparison of the enantiomers of (±)-doxanthrine, a high efficacy full dopamine D1 receptor agonist, and a reversal of enantioselectivity at D1 versus alpha2C adrenergic receptors |journal=European Neuropsychopharmacology |volume=19 |issue=2 |pages=138–46 |date=February 2009 |pmid=19028082 |doi=10.1016/j.euroneuro.2008.10.002 |pmc=2636714}} Doxanthrine has been shown to be orally active in producing contralateral rotation in the 6-hydroxydopamine rat model of Parkinson's disease.{{cite journal |vauthors=McCorvey JD, Watts VJ, Nichols DE |date=July 2012 |title= Comparison of the D1 dopamine full agonists, dihydrexidine and doxanthrine, in the 6-OHDA rat model of Parkinson's disease |journal=Psychopharmacology |volume=222 |pages=81–87 |doi=10.1007/s00213-011-2625-5 |pmid=22222862 |issue=1|s2cid=7641172 }}