SKF-10047
- CAS No.
- 133005-41-1
- Chemical Name:
- SKF-10047
- Synonyms
- D-NANM;SKF-10047;(+)-NANM HYDROCHLORIDE;(+)-N-Allylnormetazocine;(+)-SKF 10047 HYDROCHLORIDE;(+)-SK&F 10047 hydrochloride;(+)-N-ALLYNORMETAZOCINE HYDROCHLORIDE;(+)-N-ALLYLNORMETAZOCINE HYDROCHLORIDE;(+)-N-Allyl-N-norMetazocine hydrochloride;(2S,6S,11S)-3-Allyl-1,2,3,4,5,6-hexahydro-6,11-dimethyl-2,6-methano-3-benzazocine-8-ol
- CBNumber:
- CB9139600
- Molecular Formula:
- C17H24ClNO
- Molecular Weight:
- 293.83
- MDL Number:
- MFCD00078552
- MOL File:
- 133005-41-1.mol
| 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.) |
| FDA UNII | J9S5L9NLC3 |
SKF-10047 Chemical Properties,Uses,Production
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].
storage
Desiccate at +4°C
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.