ACD/Labs08132110272D

 20 22  0  0  1  0  0  0  0  0  1 V2000
   18.4526  -14.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6044  -15.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3007  -15.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6044  -16.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3008  -16.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4526  -17.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7562  -14.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9081  -15.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7562  -17.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9080  -16.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7564  -13.3602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9083  -12.6953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0599  -14.6904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0601  -13.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6045  -14.0251    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.0598  -16.0204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.2117  -15.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3635  -14.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5153  -15.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1489  -14.6904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  2  4  2  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  6  2  0  0  0  0
  2  7  1  0  0  0  0
  4  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
  7  8  1  0  0  0  0
 11 12  1  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 14  1  0  0  0  0
  7 15  1  6  0  0  0
  8 16  1  1  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 20  1  0  0  0  0
M  END
> <ID>
CHEBI:177372

> <NAME>
naxagolide

> <DEFINITION>
An organic heterotricyclic compound that is (4aR,10bR)-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazine substituted by propyl and hydroxy groups at positions 4 and 9, respectively. It is a potent dopamine D2-receptor agonist and its hydrochloride salt was under clinical development by Merck & Co as a potential antiparkinsonian agent (now discontinued).

> <STAR>
3

> <SYNONYM>
PHNO; nazagolide; dopazinol; (4aR-trans)-3,4,4a,5,6,10b-hexahydro-4-propyl-2H-naphth[1,2-b]-1,4-oxazin-9-ol; (+)-PHNO; (+)-4-propyl-9-hydroxynaphthoxazine

> <IUPAC_NAME>
(4aR,10bR)-4-propyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazin-9-ol

> <INN>
naxagolidum; naxagolide; naxagolide; naxagolida

> <FORMULA>
C15H21NO2

> <MASS>
247.338

> <MONOISOTOPIC_MASS>
247.15723

> <CHARGE>
0

> <SMILES>
[H][C@@]12CCC3=C(C=C(O)C=C3)[C@@]1([H])OCCN2CCC

> <INCHI>
InChI=1S/C15H21NO2/c1-2-7-16-8-9-18-15-13-10-12(17)5-3-11(13)4-6-14(15)16/h3,5,10,14-15,17H,2,4,6-9H2,1H3/t14-,15-/m1/s1

> <INCHIKEY>
JCSREICEMHWFAY-HUUCEWRRSA-N

> <CAS_REGISTRY_NUMBER>
88058-88-2

> <CHEMIDPLUS>
88058-88-2

> <PUBMED_CITATION>
10956195; 11105937; 15646539; 15943487; 1681090; 1840645; 19635669; 2140595; 24325578; 2904649; 3758188; 6433000; 8078498; 8301582

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