| Identification | Back Directory | [Name]
SKF-10047 | [CAS]
133005-41-1 | [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
[2S,11S,(+)]-1,2,3,4,5,6-Hexahydro-6,11-dimethyl-3-(2-propenyl)-2β,6β-methano-3-benzazocin-8-ol
(2S,6S,11S)-1,2,3,4,5,6-Hexahydro-6,11-dimethyl-3-(2-propenyl)-2,6-methano-3-benzazocin-8-ol hydrochloride
(2S,6S,11S)-1,2,3,4,5,6-Hexahydro-6,11-diMethyl-3-(2-propen-1-yl)-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
[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
(+)-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 | [Molecular Formula]
C17H24ClNO | [MDL Number]
MFCD00078552 | [MOL File]
133005-41-1.mol | [Molecular Weight]
293.83 |
| Chemical Properties | Back Directory | [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.) |
| Hazard Information | Back Directory | [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. |
|