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C147

Sigma-Aldrich

(+)-Cyclazocine

solid

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About This Item

Empirical Formula (Hill Notation):
C18H25NO
CAS Number:
3572-80-3
Molecular Weight:
271.40
EC Number:
222-689-9
UNSPSC Code:
12352200
PubChem Substance ID:
24277963

form

solid

optical activity

[α]23/D +119.3°, c = 1.0 in ethanol(lit.)

color

white

solubility

0.1 M HCl: soluble
0.1 M NaOH: insoluble
H2O: insoluble
ethanol: soluble

storage temp.

2-8°C

SMILES string

C[C@H]1[C@H]2Cc3ccc(O)cc3[C@]1(C)CCN2CC4CC4

Gene Information

human ... OPRK1(4986) , OPRS1(10280)
rat ... Oprm1(25601)

Biochem/physiol Actions

σ receptor agonist that is also an agonist at κ opioid receptors and an antagonist at μ opioid receptors.

Caution

Photosensitive

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
097H47114

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T Kobayashi et al.
British journal of pharmacology, 119(1), 73-80 (1996-09-01)
1. Taking advantage of the functional coupling of the opioid receptors with the G-protein-activated K+ (GIRK) channel, we investigated the effects of sigma (sigma) ligands of various structural and pharmacological classes, (+)-N-allylnormetazocine ((+)-SKF10047) and (+)-cyclazocine, (+)-3-(3-hydroxyphenyl)-N-(1-propyl)piperidine ((+)-3PPP), 1,3-di-(2-tolyl)guanidine (DTG), carbetapentane
Frank D King et al.
Organic & biomolecular chemistry, 9(5), 1547-1554 (2011-01-15)
The triflic acid-mediated endocyclic N-acyliminium ion cyclisation provides a facile synthesis of (di)-benzazocinones. On reduction of the 10-phenyl derivative, an unusually non-polar tertiary alkylamine was obtained.
Abil E Aliev et al.
The journal of physical chemistry. A, 116(3), 1093-1109 (2011-12-30)
The potential of an approach combining nuclear magnetic resonance (NMR) spectroscopy, molecular dynamics (MD) simulations, and quantum mechanical (QM) calculations for full structural characterizations in solution is assessed using cyclic organic compounds, namely, benzazocinone derivatives 1-3 with fused five- and
Wallace B Pickworth et al.
Pharmacology, biochemistry, and behavior, 77(4), 711-715 (2004-04-22)
The effects of cyclazocine and hydromorphone on spontaneous and laboratory cigarette smoking were compared in a double-blind, placebo-controlled, crossover study. Participants (seven men, one woman) received oral doses of placebo, cyclazocine (0.2, 0.4, and 0.8 mg) and hydromorphone (5 and
Mark P Wentland et al.
Bioorganic & medicinal chemistry letters, 13(11), 1911-1914 (2003-05-17)
High affinity binding for mu and kappa opioid receptors has been observed in analogues of cyclazocine, ethylketocyclazocine and naltrexone where the prototypic (of opiates) phenolic OH group was replaced with a formamide (-NHCHO) group. For the 8-formamide analogue of cyclazocine
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