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Product Details
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109555-87-5 Name |
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Name |
1H-Indol-3-yl(1-naphthyl)methanone |
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Synonym |
Ketone indol-3-yl 1-naphthyl;1H-Indol-3-yl-1-naphthalenylmethanone;Indol-3-yl 1-Naphthyl Ketone;Methanone, 1H-indol-3-yl-1-naphthalenyl-;(1H-indol-3-yl)(naphthalene-1-yl)Methanone;3-(1-naphthylcarbonyl)indole;1'-Naphthoyl Indole;3-(1-Naphthoyl)indole |
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109555-87-5 Chemical & Physical Properties |
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Melting point |
236ºC |
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Boiling point |
512.2±23.0 °C at 760 mmHg |
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Density |
1.3±0.1 g/cm3 |
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Molecular Formula |
C19H13NO |
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Molecular Weight |
271.313 |
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Flash Point |
264.0±30.0 °C |
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PSA |
32.86000 |
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LogP |
4.34 |
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Exact Mass |
271.099701 |
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Vapour Pressure |
0.0±1.3 mmHg at 25°C |
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Index of Refraction |
1.738 |
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109555-87-5 Uses |
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Metabolite of JWH-018 (P283650). |
3-(1-Naphthoyl)indole is a synthetic cannabinoid receptor agonist that has been used in scientific research. It is a non-selective agonist of the cannabinoid receptor, which can activate CB1 and CB2 receptors in the central and peripheral nervous systems, resulting in cannabimimetic effects such as hyperalgesia and sedation.
InChI:InChI=1/C19H13NO/c21-19(17-12-20-18-11-4-3-9-15(17)18)16-10-5-7-13-6-1-2-8-14(13)16/h1-12,20H
In order to obtain novel pharmacological tools and to investigate a multitargeting analgesic strategy, the CB1 and CB2 cannabinoid receptor agonist JWH-018 was conjugated with the opiate analgesic oxycodone or with an enkephalin related tetrapeptide. The opioid and cannabinoid pharmacophores were coupled via spacers of different length and chemical structure. These results support the strategy of multitargeting G-protein coupled receptors to develop lead compounds with antinociceptive properties.
To identify good biomarker candidates, the metabolism of synthetic cannabinoids must be studied and reference standards need to be acquired. Studies on the metabolism of synthetic cannabinoids containing a terminally fluorinated pentyl side chain have shown that hydroxylation can occur at the four position of the side chain. This makes the 4-hydroxy-5-fluoropentyl side-chain metabolite a good urinary biomarker for proving intake of the corresponding parent drug, as this compound cannot be formed from its nonfluorinated analogue. Here, a concise synthetic route to the 4-hydroxy-5-fluoropentyl side-chain metabolites of the synthetic cannabinoids STS-135, MAM-2201, AM-2201, and XLR-11 is reported.
Synthetic cannabinoids (SCs) are a significant public health concern given their widespread use and severe effects associated with intoxication. However, there is a paucity of controlled human studies investigating the behavioral and physiological effects and pharmacokinetics of these compounds. Designing a reliable method to administer consistent, concentration-dependent synthetic cannabinoids is an integral component of controlled study of these compounds. Optimal conditions to detect metabolites in human plasma as a function of storage temperature (?4 °C to ?80 °C) and time (24 h - 1 month) were also determined. Analyses verified that the method utilized to develop SC cigarettes yielded consistent, concentration-dependent products within 25% of the expected concentrations. JWH-018, JWH-073 and metabolites in spiked plasma were stable under the time and temperature conditions; concentrations were within ±20% of target values. These studies provide techniques and methods to conduct controlled investigations of the dose-dependent effects of first generation SCs to begin understanding risks associated with use. This article is part of the Special Issue entitled ‘Designer Drugs and Legal Highs.’
indole
naphthalene-1-carbonic acid chloride
(1H-indol-3-yl)(naphthalene-1-yl)methanone
| Conditions | Yield |
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With diethylaluminium chloride; In toluene; at 0 - 20 ℃; for 24h;
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93% |
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indole; With methylmagnesium bromide; In diethyl ether; at 20 ℃; for 2h; Inert atmosphere;
naphthalene-1-carbonic acid chloride; In diethyl ether; at 0 - 20 ℃; for 2h;
With ammonium chloride; In diethyl ether; at 20 ℃;
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91% |
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indole; With diethylaluminium chloride; In dichloromethane; toluene; at 0 ℃; for 0.5h;
naphthalene-1-carbonic acid chloride; In dichloromethane; toluene; at 0 ℃; for 16h;
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70% |
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With zirconium(IV) chloride; In 1,2-dichloro-ethane; at 30 ℃; for 20h; Inert atmosphere;
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64% |
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With MeMgX; In diethyl ether;
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With methylmagnesium bromide; ammonium chloride;
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With aluminum oxide; In neat (no solvent); at 100 ℃; for 0.133333h; Microwave irradiation; Green chemistry;
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With methylmagnesium bromide; ammonium chloride;
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indole; With ethylmagnesium bromide; In diethyl ether; at 0 - 20 ℃; for 0.5h;
naphthalene-1-carbonic acid chloride; In diethyl ether; at 20 ℃; for 1.5h;
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0.25 g |
indole
ethyl 2-(1-naphthyl)acetate
(1H-indol-3-yl)(naphthalene-1-yl)methanone
| Conditions | Yield |
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With potassium tert-butylate; copper diacetate; dimethyl sulfoxide; at 110 ℃; for 24h; regioselective reaction;
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67% |
indole
N-acetylindole
1-naphthalenecarbothioamide
N-(trifluoroacetyl)indole
[1-[(1-methyl-2-piperidinyl)methyl]-1H-indol-3-yl]-1-naphthalenylmethanone
1-pentyl-3-(1-naphthoyl)indole
(2-methyl-1H-indol-3-yl)(naphthalen-1-yl) methanone
4-(3-(1-naphthoyl)-2-methyl-1H-indol-1-yl)butanoic acid
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