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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
Mitsuo Tanabe
Neuropharmacology, 53(3), 406-414 (2007-07-17)
Using whole-cell voltage-clamp recordings, hyperpolarization-activated cation currents (Ih) were elicited with hyperpolarizing voltage jumps in CA1 pyramidal neurons of rat hippocampal slices, and the effects of phencyclidine (PCP) and some sigma ligands on Ih were studied. PCP concentration-dependently (0.1-100 microM)
Nobuaki Egashira et al.
European journal of pharmacology, 563(1-3), 149-154 (2007-03-14)
In the present study, we examined the involvement of the sigma1 receptor in the inhibitory effect of the selective serotonin reuptake inhibitor (SSRI) fluvoxamine, compared with that of paroxetine, on marble-burying behavior, which is an animal model of obsessive-compulsive disorder.
J Kitanaka et al.
Psychopharmacology, 203(4), 781-792 (2008-12-05)
The effects of sigma receptor antagonists on methamphetamine (METH)-induced stereotypy have not been examined. We examined the effects of sigma antagonists on METH-induced stereotypy in mice. The administration of METH (10 mg/kg) to male ddY mice induced stereotyped behavior consisting
José Francisco Navarro et al.
Psicothema, 24(3), 427-430 (2012-07-04)
Recently, sigma-1 receptor modulators have been considered drugs with an interesting therapeutic potential for the treatment of anxiety. However, there is no clear information in preclinical studies about the possible effects of sigma-1 ligands on anxiety in experimental animal models.
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