SKF-39315

SKF-39315
Clinical data
Other names	SKF39315; SKF-39315A; SK&F-39315A
Identifiers
	IUPAC name 2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol;
CAS Number	138355-28-9;
PubChem CID	10058098;
ChemSpider	8233652;
ChEMBL	ChEMBL57873;
Chemical and physical data
Formula	C10H13NO2
Molar mass	179.219 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CNCCC2=CC(=C(C=C21)O)O;
	InChI InChI=1S/C10H13NO2/c12-9-5-7-1-3-11-4-2-8(7)6-10(9)13/h5-6,11-13H,1-4H2; Key:LPJMTSQTVDKBCO-UHFFFAOYSA-N;

SKF-39315 is a monoamine receptor modulator of the 3-benzazepine family.^[1] It is a cyclized phenethylamine analogue of the neurotransmitter dopamine.^[1] The drug shows affinities (K_i) of 12 nM for the dopamine D₂ receptor and 5,200 nM for the dopamine D₁ receptor.^[1] It also has direct and indirect adrenergic actions.^[1] The 1-phenyl derivative of SKF-39315 is SKF-38393, which has reversed activities at dopamine receptors compared to SKF-39315 and acts as a selective dopamine D₁-like receptor agonist.^[1] SKF-39315 was first described in the scientific literature by at least 1988.^[1]

References

1 2 3 4 5 6 Kebabian JW (1988). "The D-1 dopamine receptor". Central D1 Dopamine Receptors. Advances in Experimental Medicine and Biology. Vol. 235. pp. 19–31. doi:10.1007/978-1-4899-2723-1_2. ISBN 978-1-4899-2725-5. PMID 2976251. Incorporation of a phenyl group in the one position of this ring system marked increases the selectivity of the molecule towards the 0-1 receptor [compare SKF 39315 with SKF 38393] (Figure 3). Weinstock et al. (1985) comment that the incorporation of the phenyl group into the benzazepine nucleus also removes "almost all of the direct and indirect adrenergic effects" from SKF 39315. [...] Figure 3. Phenyl group increases the selectivity of benzazepines towards the D-1 receptor.