Odapipam

Odapipam (INNTooltip International Nonproprietary Name; developmental code names NNC 01-0756, NNC-756, NO-756) is a selective D₁ receptor antagonist of the benzazepine group which was investigated as a potential antipsychotic but was never marketed.^[1][2]

Other namesNNC 01-0756; NNC-01-0756; NNC-010756; NNC010756; NNC01-0756; NNC-756; NNC756; NNC 0756; NNC0756; NO-756; NO756

Drug classDopamine D₁ receptor antagonist

CAS Number

• 131796-63-9

PubChem CID

• 132421

Quick facts Clinical data, Other names ...

Odapipam

Clinical data
Other names	NNC 01-0756; NNC-01-0756; NNC-010756; NNC010756; NNC01-0756; NNC-756; NNC756; NNC 0756; NNC0756; NO-756; NO756
Drug class	Dopamine D1 receptor antagonist
Identifiers
IUPAC name (5S)-8-chloro-5-(2,3-dihydro-1-benzofuran-7-yl)-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol
CAS Number	131796-63-9
PubChem CID	132421
ChemSpider	116932
UNII	847PQF7ZN6
ChEMBL	ChEMBL2106649
CompTox Dashboard (EPA)	DTXSID50157210
Chemical and physical data
Formula	C19H20ClNO2
Molar mass	329.82 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN1CCC2=CC(=C(C=C2[C@H](C1)C3=CC=CC4=C3OCC4)O)Cl
InChI InChI=1S/C19H20ClNO2/c1-21-7-5-13-9-17(20)18(22)10-15(13)16(11-21)14-4-2-3-12-6-8-23-19(12)14/h2-4,9-10,16,22H,5-8,11H2,1H3/t16-/m1/s1 Key:SKMVRXPBCSTNKE-MRXNPFEDSA-N

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It has more than 5,000-fold selectivity for the dopamine D₁ receptor (K_i = 0.17 nM) over the dopamine D₂ receptor (K_i = 942 nM).^[3] Its affinities for other dopamine receptors, such as the dopamine D₅ receptor, were not reported.^[3][4] In addition to the dopamine D₁ receptor, odapipam showed relatively high affinity for the serotonin 5-HT₂ receptor (K_i = 4.5 nM; 26-fold lower than for the D₁ receptor).^[4]

The drug was first described in the scientific literature by 1988.^[4][5]