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Benzomorphan
Benzomorphan is a chemical compound that is the base for a series of drugs which variably act on the opioid kappa and sigma receptors, including the following compounds: * 5,9-DEHB * 8-CAC * Alazocine * Anazocine * Bremazocine * Butinazocine * Carbazocine * Cogazocine * Cyclazocine * Dezocine * Eptazocine * Etazocine * Ethylketocyclazocine * Fluorophen * Gemazocine * Ibazocine * Ketazocine * Metazocine * Moxazocine * Pentazocine * Phenazocine * Quadazocine * Thiazocine * Tonazocine * Volazocine * Zenazocine Some of these agents are used as analgesics, including pentazocine, phenazocine, dezocine, and eptazocine. See also * Benzazocine * Azocine * Morphinan Morphinan is the prototype chemical structure of a large chemical class of psychoactive drugs, consisting of opiate analgesics, cough suppressants, and dissociative hallucinogens, among others. Structure Morphinan has a phenanthrene cor ... References Benzomorphans {{organic-compoun ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Alazocine
Alazocine (developmental code name -10047), also known more commonly as ''N''-allylnormetazocine (NANM), is a synthetic opioid analgesic of the benzomorphan family related to metazocine, which was never marketed. In addition to its opioid activity, the drug is a sigma receptor agonist, and has been used widely in scientific research in studies of this receptor. Alazocine is described as a potent analgesic, psychotomimetic or hallucinogen, and opioid antagonist. Moreover, one of its enantiomers was the first compound that was found to selectively label the σ1 receptor, and led to the discovery and characterization of the receptor. Pharmacology Pharmacodynamics Alazocine shows stereoselectivity in its pharmacodynamics. The (–)-enantiomer is a non-selective and high- affinity ligand of the μ-, κ-, and δ-opioid receptors (Ki = 3.0, 4.7, and 15 nM in guinea pig brain membranes) with very low affinity for the sigma σ1 receptor (Ki = 1,800–4,657 nM in guinea ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Metazocine
Metazocine is an opioid analgesic related to pentazocine. While metazocine has significant analgesic effects, mediated through a mixed agonist–antagonist action at the mu opioid receptor, its clinical use is limited by dysphoric and hallucinogenic effects which are most likely caused by activity at kappa opioid receptors (where it is a high-efficacy agonist) and/or sigma receptors. Metazocine is in Schedule II of the Controlled Substances Act 1970 of the United States as a Narcotic with ACSCN 9240 with a 19 gram aggregate manufacturing quota as of 2014. The free base conversion ratio for salts includes 0.81 for the hydrochloride and 0.74 for the hydrobromide. It is listed under the Single Convention for the Control of Narcotic Substances 1961 and is controlled in most countries in the same fashion as is morphine. Syntheses The prototype benzomorphan, metazocine (6), can be obtained from a variation of the morphinan synthesis. Thus, reaction of the Grignard reagent from ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phenazocine
Phenazocine (brand names Prinadol, Narphen) is an opioid analgesic drug, which is related to pentazocine and has a similar profile of effects. Effects of phenazocine include analgesia and euphoria, also may include dysphoria and hallucinations at high doses, most likely due to action at κ-opioid and σ receptors. Phenazocine appears to be a much stronger analgesic with fewer side effects than pentazocine, probably due to a more favorable μ/κ binding ratio. Phenazocine is a much more potent analgesic than pentazocine and other drugs in the benzomorphan series, most probably due to the presence of an ''N''-phenethyl substitution, which is known to boost μ-opioid activity in many classes of opioid analgesics. Also, it does not cause spasm of the sphincter of Oddi, making it more suitable than morphine for the treatment of biliary or pancreatic pain. Regarding the two enantiomers of phenazocine, (''R'')-phenazocine has twenty times the potency of morphine as an analgesic, whi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Gemazocine
Gemazocine (R-15,497), also known as cyclogemine, is a non-selective opioid antagonist of the benzomorphan class. It may have partial agonist properties at some of the opioid receptors, such as at the kappa receptor (as it induces dysphoric effects in humans), but seems to be generally antagonistic An antagonist is a character in a story who is presented as the chief foe of the protagonist. Etymology The English word antagonist comes from the Greek ἀνταγωνιστής – ''antagonistēs'', "opponent, competitor, villain, enemy, ri ... in its actions. References Benzomorphans Kappa-opioid receptor agonists Mu-opioid receptor antagonists {{nervous-system-drug-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Fluorophen
Fluorophen, or fluorofen, is a fluorinated analogue of phenazocine, an opioid drug of the benzomorphan group, which was developed as a radioligand for the purpose of labeling opioid receptors during PET scans (with 18F). Unlike most other benzomorphan derivatives, fluorophen acts as a full agonist of the opioid receptors with preferential affinity for the μ-opioid receptor (approximately 6x that of morphine), similar but slightly lower affinity for the δ-opioid receptor (equipotent to D-Ala2, D-Leu5nkephalin">small>D-Ala2, D-Leu5nkephalin), and very low affinity for the κ-opioid receptor The κ-opioid receptor or kappa opioid receptor, abbreviated KOR or KOP, is a G protein-coupled receptor that in humans is encoded by the ''OPRK1'' gene. The KOR is coupled to the G protein Gi/G0 and is one of four related receptors that bind op .... References Benzomorphans Opioids Fluoroarenes Phenols {{Nervous-system-drug-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclazocine
Cyclazocine is a mixed opioid agonist/ antagonist related to dezocine, pentazocine and phenazocine. This family of opioid drugs is called the benzomorphans or benzazocines. It is a KOR agonist and MOR partial agonist, and also has high affinity for the DOR. Use Research into the use of cyclazocine for the treatment of bipolar patients with depression was undertaken by Fink and colleagues (1970). It showed that 8 out of 10 patients experienced moderate improvement. Research during the 1960s and 1970s into the possible use of cyclazocine for management of pain, and later for assisting treatment of narcotic addiction was severely hampered by the drug's psychotomimetic, dysphoric, and hallucinatory effects. The dysphoric/ anxiety inducing effects of the drug correlate with increasing dosage and would likely reduce the risk of abuse in the same manner as other opioids which preferentially act on the KOR versus the DOR and MOR, although the side-effect threshold is often lower t ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Etazocine
Etazocine (NIH-7856) is an opioid analgesic of the benzomorphan family which was never marketed. It acts as a partial agonist of the opioid receptors, with mixed agonist and antagonist effects. In animal studies, it was shown to induce analgesia, dependency, and respiratory depression, with overall effects similar to those of morphine, but with substantially reduced potency in comparison. See also * Benzomorphan Benzomorphan is a chemical compound that is the base for a series of drugs which variably act on the opioid kappa and sigma receptors, including the following compounds: * 5,9-DEHB * 8-CAC * Alazocine * Anazocine * Bremazocine * Butinazocine ... References {{Opioidergics Phenols Analgesics Benzomorphans Opioids ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pentazocine
Pentazocine, sold under the brand name Talwin among others, is a painkiller used to treat moderate to severe pain. It is believed to work by activating (agonizing) κ-opioid receptors (KOR) and μ-opioid receptors (MOR). As such it is called an opioid as it delivers its effects on pain by interacting with the opioid receptors. It shares many of the side effects of other opioids like constipation, nausea, itching, drowsiness and respiratory depression, but unlike most other opioids it fairly frequently causes hallucinations, nightmares and delusions. It is also, unlike most other opioids, subject to a ceiling effect, which is when at a certain dose (which differs from person-to-person) no more pain relief, or side effects, is obtained by increasing the dose any further. Chemically it is classed as a benzomorphan and it comes in two enantiomers, which are molecules that are exact (non-superimposable) mirror images of one another. It was patented in 1960 and approved for medical ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ketazocine
Ketazocine (INN), also known as ketocyclazocine, is a benzomorphan derivative used in opioid receptor research. Ketazocine, for which the receptor is named, is an exogenous opioid that binds to the κ opioid receptor. Activation of this receptor is known to cause sleepiness, a decrease in pain sensation and (potentially) dysphoria, paranoia, and hallucinations. It also causes an increase in urine production because it inhibits the release of vasopressin. (Vasopressin is an endogenous substance that assists in regulating fluid and electrolyte balance in the body and decreases the amount of water released into the urine.) Unlike other opioids, substances that only bind to the κ receptor theoretically do not depress the respiratory system. The crystal structure of ketazocine was determined in 1983. See also * Benzomorphan * Ethylketazocine Ethylketazocine (WIN-35,197-2), is an opioid drug of the benzomorphan family which has been used extensively in scientific research in t ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Dezocine
Dezocine, sold under the brand name Dalgan, is an atypical opioid analgesia, analgesic which is used in the treatment of pain. It is used by intravenous infusion and intramuscular injection. Dezocine is an opioid receptor receptor modulator, modulator, acting as a partial agonist of the μ-opioid receptor, μ- and κ-opioid receptors. It has a similar profile of effects to related opioids acting at the μ-opioid receptor, including analgesia and euphoria. Unlike other opioids acting at the κ-opioid receptor however, dezocine does not produce side effects such as dysphoria or hallucinations at any therapeutically used dose. Dezocine was first synthesized in 1970. It was introduced for medical use in the United States in 1986 but was not marketed in other countries. Dezocine was discontinued in the United States in 2011 with no official reason given. However, it has become one of the most widely used analgesics in China. In light of the opioid epidemic, dezocine has seen a resurge ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Moxazocine
Moxazocine (BL-4566) is an opioid analgesic of the benzomorphan family which was never marketed. It acts as a partial agonist or mixed agonist/ antagonist of the opioid receptors and binds preferentially to the κ-opioid receptor. Despite its failure to reach the market, clinical studies demonstrated moxazocine to be approximately 10x as potent by weight as morphine as an analgesic. Synthesis Reduction of the carbonyl group in oxygenated benzomorphan 1 affords the corresponding alcohol (2). This intermediate is then N-demethylated by means of BrCN. Acylation with cyclopropylcarbonyl chloride gives the amide (3). The alcohol is then converted to the ether by treatment with MeI and base (4). Treatment with LiAlH4 serves to reduce the amide function. Cleavage of the phenolic ether by one of the standard schemes affords moxazocine (6). See also * Benzomorphan Benzomorphan is a chemical compound that is the base for a series of drugs which variably act on the opioid kappa a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Bremazocine
Bremazocine is a κ-opioid receptor agonist related to pentazocine. It has potent and long-lasting analgesic An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ... and diuretic effects. It has 200 times the activity of morphine, but appears to have no addictive properties and does not depress breathing. The crystal structure of bremazocine was determined in 1984 See also * Benzomorphan References Synthetic opioids Phenols Benzomorphans Kappa-opioid receptor agonists Tertiary alcohols Cyclopropanes {{analgesic-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
