Basic information Safety Supplier Related

SKF-10047

Basic information Safety Supplier Related

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
CAS:
133005-41-1
MF:
C17H24ClNO
MW:
293.83
Product Categories:
  • Chiral Reagents
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
133005-41-1.mol
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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.)
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Safety Information

WGK Germany 
3

MSDS

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SKF-10047 Usage And Synthesis

Uses

Normetazocine analogue as opioid antagonist.

Biological Activity

skf 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 Actions

Selective σ1 receptor agonist.

in vitro

the 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.

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