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Merck
CN

A0552

(−)-N-Allylnormetazocine hydrochloride

Synonym(s):

(−)-NANM, (−)-SKF-10047, (2α,6α)-1,2,3,4,5,6-Hexahydro-6,11-dimethyl-3-(2-propenyl)-2,6-methano-3-benzazocin-8-ol

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About This Item

Empirical Formula (Hill Notation):
C17H23NO · HCl
CAS Number:
14198-28-8
Molecular Weight:
293.83
UNSPSC Code:
41116107
PubChem Substance ID:
329770618
MDL number:
MFCD00078553

Key Documents

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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+;/m0./s1

SMILES string

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

InChI key

ZTGMHFIGNYXMJV-YGCKJKTASA-N

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

format

neat

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
099F4001

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K T Brady et al.
Science (New York, N.Y.), 215(4529), 178-180 (1982-01-08)
(+/-)-N-Allylnormetazocine is a benzomorphan opioid with psychotomimetic effects. The pure stereoisomers of this compound, as well as the racemic mixture, were compared to phencyclidine for their behavioral effects on squirrel monkeys and rats trained to discriminate phencyclidine from saline. Dose-response
Felix J Kim et al.
Biochemical and biophysical research communications, 426(2), 177-182 (2012-08-29)
Treatment with sigma1 receptor (Sigma1) ligands can inhibit cell proliferation in vitro and tumor growth in vivo. However, the cellular pathways engaged in response to Sigma1 ligand treatment that contribute to these outcomes remain largely undefined. Here, we show that
Christopher P Palmer et al.
Cancer research, 67(23), 11166-11175 (2007-12-07)
Lipid rafts are membrane platforms that spatially organize molecules for specific signaling pathways that regulate various cellular functions. Cholesterol is critical for liquid-ordered raft formation by serving as a spacer between the hydrocarbon chains of sphingolipids, and alterations in the
Yukio Ago et al.
Psychopharmacology, 217(3), 377-386 (2011-04-14)
Fluvoxamine, a selective serotonin (5-HT) reuptake inhibitor (SSRI) and an agonist for the σ(1) receptors, increases extracellular monoamines in the prefrontal cortex, but it is not known whether the σ(1) receptor is involved in the neurochemical effect of fluvoxamine. In
Laurent Monassier et al.
The Journal of pharmacology and experimental therapeutics, 322(1), 341-350 (2007-04-27)
The sigma(2)-receptor agonist, ifenprodil, was suggested as an inhibitor of G protein-coupled inwardly rectifying potassium channels. Nevertheless, an analysis of the role of sigma(2) receptors in cardiac electrophysiology has never been done. This work aims i) to identify the roles
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