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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

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.

Storage Class Code

11 - Combustible Solids

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
R A Wilke et al.
The Journal of biological chemistry, 274(26), 18387-18392 (1999-06-22)
Recent work has indicated that sigma receptor ligands can modulate potassium channels. However, the only sigma receptor characterized at the molecular level has a novel structure unlike any other receptor known to modulate ion channels. This 26-kDa protein has a
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
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