Odapipam

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;

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.¹²

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.³⁴ 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 1988.⁴⁵

References

Shen WW (1999). "A history of antipsychotic drug development". Compr Psychiatry. 40 (6): 407–414. doi:10.1016/s0010-440x(99)90082-2. PMID 10579370.
Seamans JK, Yang CR (September 2004). "The principal features and mechanisms of dopamine modulation in the prefrontal cortex". Prog Neurobiol. 74 (1): 1–58. doi:10.1016/j.pneurobio.2004.05.006. PMID 15381316.
Neumann J, Hofmann B, Dhein S, Gergs U (March 2023). "Role of Dopamine in the Heart in Health and Disease". Int J Mol Sci. 24 (5): 5042. doi:10.3390/ijms24055042. PMC 10003060. PMID 36902474.
Andersen PH, Grønvald FC, Hohlweg R, Hansen LB, Guddal E, Braestrup C, Nielsen EB (August 1992). "NNC-112, NNC-687 and NNC-756, new selective and highly potent dopamine D1 receptor antagonists". Eur J Pharmacol. 219 (1): 45–52. doi:10.1016/0014-2999(92)90578-r. PMID 1397049.
Waddington JL (January 1989). "Functional interactions between D-1 and D-2 dopamine receptor systems: their role in the regulation of psychomotor behaviour, putative mechanisms, and clinical relevance". J Psychopharmacol. 3 (2): 54–63. doi:10.1177/026988118900300202. PMID 22156499.

[Shen1999-1] Shen WW (1999). "A history of antipsychotic drug development". Compr Psychiatry. 40 (6): 407–414. doi:10.1016/s0010-440x(99)90082-2. PMID 10579370.

[SeamansYang2004-2] Seamans JK, Yang CR (September 2004). "The principal features and mechanisms of dopamine modulation in the prefrontal cortex". Prog Neurobiol. 74 (1): 1–58. doi:10.1016/j.pneurobio.2004.05.006. PMID 15381316.

[NeumannHofmannDhein2023-3] Neumann J, Hofmann B, Dhein S, Gergs U (March 2023). "Role of Dopamine in the Heart in Health and Disease". Int J Mol Sci. 24 (5): 5042. doi:10.3390/ijms24055042. PMC 10003060. PMID 36902474.

[AndersenGrønvaldHohlweg1992-4] Andersen PH, Grønvald FC, Hohlweg R, Hansen LB, Guddal E, Braestrup C, Nielsen EB (August 1992). "NNC-112, NNC-687 and NNC-756, new selective and highly potent dopamine D1 receptor antagonists". Eur J Pharmacol. 219 (1): 45–52. doi:10.1016/0014-2999(92)90578-r. PMID 1397049.

[Waddington1989-5] Waddington JL (January 1989). "Functional interactions between D-1 and D-2 dopamine receptor systems: their role in the regulation of psychomotor behaviour, putative mechanisms, and clinical relevance". J Psychopharmacol. 3 (2): 54–63. doi:10.1177/026988118900300202. PMID 22156499.

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References