Names | |
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Preferred IUPAC name 4-Phenylpiperidine | |
Identifiers | |
3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.011.130 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C11H15N | |
Molar mass | 161.248 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
4-Phenylpiperidine is a chemical compound. It features a benzene ring bound to a piperidine ring.
4-Phenylpiperidine is the base structure for a variety of opioids, such as pethidine (meperidine), ketobemidone, alvimopan, loperamide, and diphenoxylate.
The Misuse of Drugs Act 1977, the Misuse of Drugs Act 1984, Misuse of Drugs Act 2015 and the Criminal Justice Act 2010 are the acts of the Oireachtas regulating drugs in Ireland. The acts define the penalties for unlawful production, possession and supply of drugs.
The Controlled Drugs and Substances Act is Canada's federal drug control statute. Passed in 1996 under Prime Minister Jean Chrétien's government, it repeals the Narcotic Control Act and Parts III and IV of the Food and Drugs Act, and establishes eight Schedules of controlled substances and two Classes of precursors. It provides that "The Governor in Council may, by order, amend any of Schedules I to VIII by adding to them or deleting from them any item or portion of an item, where the Governor in Council deems the amendment to be necessary in the public interest."
The Demjanov rearrangement is the chemical reaction of primary amines with nitrous acid to give rearranged alcohols. It involves substitution by a hydroxyl group with a possible ring expansion. It is named after the Russian chemist Nikolai Jakovlevich Demjanov , who first reported it in 1903.
Droxypropine is a cough suppressant of the phenylpiperidine class.
Pethidinic acid is a 4-phenylpiperidine derivative that is both a metabolite of and a precursor to pethidine (meperidine). It is scheduled by UN Single Convention on Narcotic Drugs. It is a Schedule II Narcotic controlled substance in the United States and has an ACSCN of 9234. The 2014 annual manufacturing quota was 6 grams.
Etoxeridine is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine (meperidine).
Furethidine is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine (meperidine), but with around 25x higher potency. According to another source, Furethidine is 500/30 = 16.7 x the potency of pethidine.
Pheneridine is a 4-phenylpiperidine derivative that is related to the opioid analgesic drug pethidine (meperidine).
Oxpheneridine is a 4-phenylpiperidine derivative that is related to the opioid analgesic drug pethidine (meperidine).
Picenadol (LY-97435) is a 4-phenylpiperidine derivative that is an opioid analgesic drug developed by Eli Lilly in the 1970s.
Phenylpiperidines are chemical compounds with a phenyl moiety directly attached to piperidine. Of particular interest are a variety of derivatives of 4-phenylpiperidine, which have pharmacological effects including morphine-like activity or other central nervous system effects.
Tedatioxetine is an experimental antidepressant that was discovered by scientists at Lundbeck; in 2007 Lundbeck and Takeda entered into a partnership that included tedatioxetine but was focused on another, more advanced Lundbeck drug candidate, vortioxetine.
4-Phenylazepane, also known as phenazepane, is a chemical compound.
OSU-6162 (PNU-96391) is a compound which acts as a partial agonist at both dopamine D2 receptors and 5-HT2A receptors. It acts as a dopamine stabilizer in a similar manner to the closely related drug pridopidine, and has antipsychotic, anti-addictive and anti-Parkinsonian effects in animal studies. Both enantiomers show similar activity but with different ratios of effects, with the (S) enantiomer (–)-OSU-6162 that is more commonly used in research, having higher binding affinity to D2 but is a weaker partial agonist at 5-HT2A, while the (R) enantiomer (+)-OSU-6162 has higher efficacy at 5-HT2A but lower D2 affinity.
2-Methyl-3-phenylpiperidine is an intermediate in the preparation of 3-aminopiperidine substance P antagonists.
LY-255582 is a phenylpiperidine non-selective opioid antagonist. It has been shown to reduce ethanol consumption in experiments carried out on rats. It has also been shown to reduce food and water consumption in rats.
Peripherally acting μ-opioid receptor antagonists (PAMORAs) are a class of chemical compounds that are used to reverse adverse effects caused by opioids interacting with receptors outside the central nervous system (CNS), mainly those located in the gastrointestinal tract. PAMORAs are designed to specifically inhibit certain opioid receptors in the gastrointestinal tract and with limited ability to cross the blood–brain barrier. Therefore, PAMORAs do not affect the analgesic effects of opioids within the central nervous system.
LS-115509 is an opioid analgesic related to the 4-phenylpiperidine family. It is comparable to drugs such as prodine and pheneridine, but is distinguished by the presence of an ether group and furan ring at the piperidine 4-position, which are not found in other drugs of this class. In animal studies, it has around 2-3x the potency of morphine depending on what assay is used. Like prodine, it has two stereocenters and four possible enantiomers, but the activity of these has not been tested separately.
LY-88329 is an opioid receptor ligand related to medicines such as pethidine. It has high affinity to the μ-opioid receptor, but unlike structurally related drugs such as 3-methylfentanyl and OPPPP, LY-88329 is a potent opioid antagonist. In animal studies it blocks the effects of morphine and has anorectic action.
Diamocaine is a local anesthetic that was developed by Janssen Pharmaceuticals in the 1970s. It is a 4-phenylpiperidine derivative, structurally related to opioid drugs such as piminodine and antipsychotics such as haloperidol, but in this series only local anesthetics were produced.