SKF-82,958

SKF-82,958 is a synthetic compound of the benzazepine class that acts as a D₁/D₅ receptor full agonist.^[1][2] SKF-82,958 and similar D₁-like-selective full agonists like SKF-81,297 and 6-Br-APB produce characteristic anorectic effects, hyperactivity and self-administration in animals, with a similar but not identical profile to that of dopaminergic stimulants such as amphetamine.^{[3][4][5][6][7][8][9][10][11]} SKF-82,958 was also subsequently found to act as an agonist of ERα with negligible activity at ERβ, making it a subtype-selective estrogen.^[12][13]

SKF-82,958

Identifiers
IUPAC name 3-allyl-6-chloro-1-phenyl-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol
CAS Number	80751-65-1
PubChem CID	1225
ChemSpider	1188
UNII	7W60FE897Q
ChEMBL	ChEMBL317741
CompTox Dashboard (EPA)	DTXSID70894837
Chemical and physical data
Formula	C19H20ClNO2
Molar mass	329.82 g·mol−1
3D model (JSmol)	Interactive image
SMILES C=CCN1CCC2=C(C(=C(C=C2C(C1)C3=CC=CC=C3)O)O)Cl

References

1. Pfeiffer FR, Wilson JW, Weinstock J, Kuo GY, Chambers PA, Holden KG, et al. (April 1982). "Dopaminergic activity of substituted 6-chloro-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines". Journal of Medicinal Chemistry. 25 (4): 352–358. doi:10.1021/jm00346a005. PMID 7069713.
2. Wang JQ, McGinty JF (May 1997). "The full D1 dopamine receptor agonist SKF-82958 induces neuropeptide mRNA in the normosensitive striatum of rats: regulation of D1/D2 interactions by muscarinic receptors". The Journal of Pharmacology and Experimental Therapeutics. 281 (2): 972–982. PMID 9152408.
3. Terry P, Katz JL (1992). "Differential antagonism of the effects of dopamine D1-receptor agonists on feeding behavior in the rat". Psychopharmacology. 109 (4): 403–409. doi:10.1007/BF02247715. PMID 1365854. S2CID 12871227.
4. Self DW, Stein L (June 1992). "The D1 agonists SKF 82958 and SKF 77434 are self-administered by rats". Brain Research. 582 (2): 349–352. doi:10.1016/0006-8993(92)90155-3. PMID 1356585. S2CID 9410802.
5. Rosenzweig-Lipson S, Hesterberg P, Bergman J (September 1994). "Observational studies of dopamine D1 and D2 agonists in squirrel monkeys". Psychopharmacology. 116 (1): 9–18. doi:10.1007/BF02244865. PMID 7862937. S2CID 24204026.
6. Kalivas PW, Duffy P (July 1995). "D1 receptors modulate glutamate transmission in the ventral tegmental area". The Journal of Neuroscience. 15 (7 Pt 2): 5379–5388. doi:10.1523/JNEUROSCI.15-07-05379.1995. PMC 6577867. PMID 7623160.
7. Weed MR, Woolverton WL (December 1995). "The reinforcing effects of dopamine D1 receptor agonists in rhesus monkeys". The Journal of Pharmacology and Experimental Therapeutics. 275 (3): 1367–1374. PMID 8531104.
8. Weed MR, Paul IA, Dwoskin LP, Moore SE, Woolverton WL (October 1997). "The relationship between reinforcing effects and in vitro effects of D1 agonists in monkeys". The Journal of Pharmacology and Experimental Therapeutics. 283 (1): 29–38. PMID 9336305.
9. Abrahams BS, Rutherford JD, Mallet PE, Beninger RJ (February 1998). "Place conditioning with the dopamine D1-like receptor agonist SKF 82958 but not SKF 81297 or SKF 77434". European Journal of Pharmacology. 343 (2–3): 111–118. doi:10.1016/S0014-2999(97)01531-8. PMID 9570457.
10. Tidey JW, Bergman J (June 1998). "Drug discrimination in methamphetamine-trained monkeys: agonist and antagonist effects of dopaminergic drugs". The Journal of Pharmacology and Experimental Therapeutics. 285 (3): 1163–1174. PMID 9618419.
11. Berridge KC, Aldridge JW (September 2000). "Super-stereotypy I: enhancement of a complex movement sequence by systemic dopamine D1 agonists". Synapse. 37 (3): 194–204. doi:10.1002/1098-2396(20000901)37:3<194::AID-SYN3>3.0.CO;2-A. hdl:2027.42/34987. PMID 10881041. S2CID 13215977.
12. Walters MR, Dutertre M, Smith CL (January 2002). "SKF-82958 is a subtype-selective estrogen receptor-alpha (ERalpha ) agonist that induces functional interactions between ERalpha and AP-1". The Journal of Biological Chemistry. 277 (3): 1669–1679. doi:10.1074/jbc.M109320200. PMID 11700319.
13. King AG (2002). Estrogen induces uterine angiogenesis through the expression of vascular endothelial growth factor (Ph.D. thesis). University of Wisconsin--Madison. p. 21.