SKF-82,958

Overview

SKF-82,958 is a synthetic compound of the 3-benzazepine family that acts as a dopamine D₁ and D₅ receptor full agonist. 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. 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.[1–13] WP

Drug class

Dopamine D1-like receptor agonist WP

From the Wikipedia article's infobox.

Chemistry

Formula

C19H20ClNO2 PC

CAS number

80751-65-1 PC

Molar mass (g/mol)

329.8 PC

IUPAC name (computed by PubChem)

9-chloro-5-phenyl-3-prop-2-enyl-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol PC

SMILES

C=CCN1CCC2=C(C(=C(C=C2C(C1)C3=CC=CC=C3)O)O)Cl PC

InChIKey

HJWHHQIVUHOBQN-UHFFFAOYSA-N PC

PubChem CID

1225

IUPAC name

3-allyl-6-chloro-1-phenyl-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol WP

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Pfeiffer FR, Wilson JW, Weinstock J, Kuo GY, Chambers PA, Holden KG, Hahn RA, Wardell JR, Tobia AJ, Setler PE, Sarau HM. Dopaminergic activity of substituted 6-chloro-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines. Journal of Medicinal Chemistry. April 1982. doi:10.1021/jm00346a005 · PMID 7069713
2. Journal / agency Wang JQ, McGinty JF. 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. May 1997. doi:10.1016/S0022-3565(24)36678-9 · PMID 9152408
3. Journal / agency Terry P, Katz JL. Differential antagonism of the effects of dopamine D1-receptor agonists on feeding behavior in the rat. Psychopharmacology. 1992. doi:10.1007/BF02247715 · PMID 1365854
4. Journal / agency Self DW, Stein L. The D1 agonists SKF 82958 and SKF 77434 are self-administered by rats. Brain Research. June 1992. doi:10.1016/0006-8993(92)90155-3 · PMID 1356585
5. Journal / agency Rosenzweig-Lipson S, Hesterberg P, Bergman J. Observational studies of dopamine D1 and D2 agonists in squirrel monkeys. Psychopharmacology. September 1994. doi:10.1007/BF02244865 · PMID 7862937
6. Journal / agency Kalivas PW, Duffy P. D1 receptors modulate glutamate transmission in the ventral tegmental area. The Journal of Neuroscience. July 1995. doi:10.1523/JNEUROSCI.15-07-05379.1995 · PMID 7623160 · PMC6577867
7. Journal / agency Weed MR, Woolverton WL. The reinforcing effects of dopamine D1 receptor agonists in rhesus monkeys. The Journal of Pharmacology and Experimental Therapeutics. December 1995. doi:10.1016/S0022-3565(25)12193-9 · PMID 8531104
8. Journal / agency Weed MR, Paul IA, Dwoskin LP, Moore SE, Woolverton WL. The relationship between reinforcing effects and in vitro effects of D1 agonists in monkeys. The Journal of Pharmacology and Experimental Therapeutics. October 1997. doi:10.1016/S0022-3565(24)36981-2 · PMID 9336305
9. Journal / agency Abrahams BS, Rutherford JD, Mallet PE, Beninger RJ. Place conditioning with the dopamine D1-like receptor agonist SKF 82958 but not SKF 81297 or SKF 77434. European Journal of Pharmacology. February 1998. doi:10.1016/S0014-2999(97)01531-8 · PMID 9570457
10. Journal / agency Tidey JW, Bergman J. Drug discrimination in methamphetamine-trained monkeys: agonist and antagonist effects of dopaminergic drugs. The Journal of Pharmacology and Experimental Therapeutics. June 1998. doi:10.1016/S0022-3565(24)37511-1 · PMID 9618419
11. Journal / agency Berridge KC, Aldridge JW. Super-stereotypy I: enhancement of a complex movement sequence by systemic dopamine D1 agonists. Synapse. September 2000. doi:10.1002/1098-2396(20000901)37:3<194::AID-SYN3>3.0.CO;2-A · PMID 10881041
12. Journal / agency Walters MR, Dutertre M, Smith CL. 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. January 2002. doi:10.1074/jbc.M109320200 · PMID 11700319
13. Other King AG. Estrogen induces uterine angiogenesis through the expression of vascular endothelial growth factor. 2002

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