SKF-10047 Basic information
Product Name:SKF-10047
Synonyms:[2S-(2ALPHA, 6ALPHA, 11R*)]-1,2,3,4,5,6-HEXAHYDRO-6,11-DIMETHYL-3(2-PROPENYL)-2,6-METHANO-3-BENZAZOCIN-8-OL HYDROCHLORIDE;[2S-(2A,6A,11R*)]-1,2,3,4,5,6-HEXAHYDRO-6,11-DIMETHYL-3-(2-PROPENYL)-2,6-METHANO-3-BENZAZOCIN-8-OL HYDROCHLORIDE;(+)-NANM HYDROCHLORIDE;(+)-N-ALLYLNORMETAZOCINE HYDROCHLORIDE;(+)-N-ALLYNORMETAZOCINE HYDROCHLORIDE;SKF-10047;(+)-SKF 10047 HYDROCHLORIDE;(+)-NANM hydrochloride, SKF-10047, [2S-(2α, 6α,11R*)]-1,2,3,4,5,6-Hexahydro-6,11-dimethyl-3-(2-propenyl)-2,6-methano-3-benzazocin-8-ol hydrochloride
Product Categories:Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:133005-41-1.mol
SKF-10047 Structure
SKF-10047 Chemical Properties
Melting point 201-203 °C
storage temp. room temp
solubility H2O: soluble
form solid
color white
optical activity[α]21/D +90.6°, c = 1 in ethanol(lit.)
Safety Information
WGK Germany 3
MSDS Information
SigmaAldrich English
SKF-10047 Usage And Synthesis
UsesNormetazocine analogue as opioid antagonist.
Biological Activityskf 10047 hydrochloride is a prototypical σ1 receptor agonist. behaviorally active in animal models of memory and stress. it has been fully demonstrated that σ binding sites are distinct from phencyclidine binding sites on the nmda receptor-ion channel complex, which has investigated extensively the functional role of σ receptors in the central nervous system [1,2].
Biochem/physiol ActionsSelective σ1 receptor agonist.
in vitrothe effects of the stereoisomers of n-allylnormetazocine (skf-10,047) were compared in rats on the hippocampal cholinergic functions. a putative σ1 receptor agonist, (+)-skf-10,047, increased hippocampal extracellular acetylcholine level as well as anti-amnesic effect against scopolamine-induced memory dysfunctions in rats. haloperidol, a putative σ1 receptor antagonist reversed these phenomena which were not produced by (-)-skf-10,047. such stereoselectivity and antagonism imply σ1 receptors involved in these (+)-skf-10,047-stimulated hippocampal cholinergic functions [2].
in vivo(+)-skf-10,047 and dextromethorphan, being co-administered with phenytoin (10 mg/kg, an anticonvulsant drug), decreased conditioned fear stress with low doses (4 and 20 mg/kg, respectively). the effects were antagonized by the σ receptor antagonists, ne-100 and bmy-14802. furthermore, the effects of (+)-skf-10,047 or dextromethorphan plus phenytoin were inhibited by the dopamine d1 receptor antagonist (sch 23390) and the dopamine d2 receptor antagonist ((-)-sulpiride), and they were also decreased by 6-hydroxydopamine-induced lesions of dopaminergic neurons. the ameliorating effects of (+)-skf-10,047 and dextromethorphan on condition of fear stress using high doses (5 and 30 mg/kg, respectively) were also inhibited by both the dopamine receptor antagonists [3].
references[1] walker jm, bowen wd, walker fo, matsumoto rr, de costa b, rice kc. sigma receptors: biology and function. pharmacol rev. 1990 dec;42(4):355-402.
[2] matsuno k, senda t, kobayashi t, mita s. involvement of sigma 1 receptor in (+)-n-allylnormetazocine-stimulated hippocampal cholinergic functions in rats. brain res. 1995 sep 4; 690 (2): 200-6.
[3]. kamei h, kameyama t, nabeshima t. (+)-skf-10,047 and dextromethorphan ameliorate conditioned fear stress via dopaminergic systems linked to phenytoin-regulated sigma 1 sites. eur j pharmacol. 1996 aug 8;309(2):149-58.
SKF-10047 Preparation Products And Raw materials
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