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A114

Sigma-Aldrich

(+)-N-Allylnormetazocine hydrochloride

≥98% (HPLC)

Synonym(s):

(+)-NANM hydrochloride, SKF-10047, SKF10047, [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

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About This Item

Empirical Formula (Hill Notation):
C17H23NO · HCl
CAS Number:
133005-41-1
Molecular Weight:
293.83
MDL number:
MFCD00078552
UNSPSC Code:
12352200
PubChem Substance ID:
24278250
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

optical activity

[α]21/D +90.6°, c = 1 in ethanol(lit.)

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

storage condition

desiccated

color

white

solubility

H2O: >10 mg/mL

storage temp.

room temp

SMILES string

Cl[H].C[C@@H]1[C@@H]2Cc3ccc(O)cc3[C@@]1(C)CCN2CC=C

InChI

1S/C17H23NO.ClH/c1-4-8-18-9-7-17(3)12(2)16(18)10-13-5-6-14(19)11-15(13)17;/h4-6,11-12,16,19H,1,7-10H2,2-3H3;1H/t12-,16+,17+;/m1./s1

InChI key

ZTGMHFIGNYXMJV-XSCGHNKWSA-N

Gene Information

human ... OPRS1(10280)

Biochem/physiol Actions

Selective σ1 receptor agonist.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Parham Gharagozlou et al.
BMC pharmacology, 6, 3-3 (2006-01-26)
The aim of the present study was to describe the activity of a set of opioid drugs, including partial agonists, in a human embryonic kidney cell system stably expressing only the mouse kappa-opioid receptors. Receptor activation was assessed by measuring
S Shimazu et al.
European journal of pharmacology, 388(2), 139-146 (2000-02-10)
We investigated the potential neuroprotective effects of several sigma receptor ligands in organotypic midbrain slice cultures as an excitotoxicity model system. When challenged with 100-microM N-methyl-D-aspartate (NMDA) for 24 h, dopaminergic neurons in midbrain slice cultures degenerated, and this was
Y Itzhak
Life sciences, 42(7), 745-752 (1988-01-01)
The pharmacological specificity of representative psychotomimetic agents such as phencyclidine (PCP) analogs, opiate benzomorphans and several antipsychotic agents was assessed for the sigma and PCP binding sites. In a series of binding experiments, in rat brain membranes, sigma and PCP
Mohamed S Amer et al.
British journal of pharmacology, 168(6), 1445-1455 (2012-11-06)
The Sigma-1 receptor (Sig1R) impacts on calcium ion signalling and has a plethora of ligands. This study investigated Sig1R and its ligands in relation to endogenous calcium events of endothelial cells and transient receptor potential (TRP) channels. Intracellular calcium and
C Bucolo et al.
The Journal of pharmacology and experimental therapeutics, 289(3), 1362-1369 (1999-05-21)
In this study, we examined the presence of sigma1 and sigma2 sites in the rabbit iris-ciliary body by receptor binding and investigated their effects on intraocular pressure (IOP) in albino rabbits. The iris-ciliary body has binding sites for the sigma1-site
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