Which opioid along with Subutex makes up the two best known of the thevinol, orvinol, or bridged oripavine derivatives?
5da4e7ef35561da94fbea96442faa480
Bentley compounds The Bentley compounds are a class of semi-synthetic opioids that were first synthesized by K. W. Bentley by Diels-Alder reaction of thebaine with various dienophiles. The compounds are also known as thevinols, orvinols, or bridged oripavine derivatives, due to the characteristic 6,14-"endo"-etheno- bridge and substitution at the 7α position. Buprenorphine and etorphine are perhaps the best known of the family, which was the first series of extremely potent μ-opioid agonists, with some compounds in the series having over many thousands of times the analgesic potency of morphine.
3d28e24d56915d8df8b13fd62e359c09
Buprenorphine Buprenorphine, sold under the brand name Subutex, among others, is an opioid used to treat opioid addiction, moderate acute pain and moderate chronic pain. The combination buprenorphine/naloxone is also used for opioid addiction.
358ae61faea680bfcbe41e4f13a3cadb
Methylnaltrexone Methylnaltrexone (MNTX, brand name Relistor), used in form of methylnaltrexone bromide (INN, USAN, BAN), is one of the newer agents of peripherally acting μ-opioid antagonists that act to reverse some of the side effects of opioid drugs such as constipation without affecting analgesia or precipitating withdrawals. Because MNTX is a quaternary ammonium cation, it cannot cross the blood–brain barrier, and so has antagonist effects throughout the body, counteracting effects such as itching and constipation, but without affecting opioid effects in the brain such as analgesia. However, since a significant fraction (up to 60%) of opioid analgesia can be mediated by opioid receptors on peripheral sensory neurons, particularly in inflammatory conditions such as arthritis, traumatic or surgical pain, MNTX may increase pain under such circumstances.
1051e3efbec32d161f3925b38ff55f66
Substituted amphetamine Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents. The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. Examples of substituted amphetamines are amphetamine (itself), methamphetamine, ephedrine, cathinone, phentermine, mephentermine, bupropion, methoxyphenamine, selegiline, amfepramone, pyrovalerone, MDMA (ecstasy), and DOM (STP).
7b2b02fd5406f66914d5d5e6e30eeabe
2,3-Methylenedioxyamphetamine 2,3-Methylenedioxyamphetamine (2,3-MDA) or ORTHO-MDA is an amphetamine derivative which is mentioned in PIHKAL as a fairly potent and long-lasting stimulant drug, but with little or none of the entactogenic effects associated with its better-known structural isomer MDA.
ffa28377cc4058ea6592edc840a8a073
3,14-Diacetyloxymorphone 3,14-Diacetyloxymorphone is an opioid analgesic which has never been marketed. It is an acetyl derivative of oxymorphone. It is related to other acetylated morphone derivatives, including 3,6-diacetyloxymorphone, 3,8,14-triacetyloxymorphone, 3,6,8,14-tetraacetyloxymorphone, noroxymorphone analogs of all or most of the above, and 3,6,14-triacetyloxymorphone, a derivative of oxymorphone whose structure-activity relationship suggests is 800% the potency of the parent drug versus 250% for 3,14-diacetyoxymorphone. Both were developed in Austria in the 1920s along with other derivatives of the strong dihydromorphinones and these drugs are generated by reacting oxymorphone with either acetic anhydride or acetyl chloride at various temperatures in the 80-160 °C for several hours; 3,6,14-triacetyloxymorphone may be more easily made when a catalylst is used but elevated pressure or reaction "in vacuo" or under a nitrogen or noble gas atmosphere is not required. Each of the acetyl esters of oxymorphone has a hydromorphone analogue, and these were all developed around the same time (1915-1930) in Austria and Germany.
3647e57c8da90f46e9f92dcb0dde41d8
14-Cinnamoyloxycodeinone 14-Cinnamoyloxycodeinone is the most potent example in a series of opiate analgesic drugs discovered in the 1960s, with > ×100 times the potency of morphine. It is a derivative of hydroxycodeinone , being the 14-cinnamate ester. In another paper, Buckett assigns the potency as 177 with a range (depending on animal and test) of ×101 - ×310. It may be of interest to researchers that the allyl group in this compound and in allylprodine overlay very closely.
297ed869c45350b8e33a7d4f8029ea25
Salvinorin B methoxymethyl ether Salvinorin B methoxymethyl ether (2-"O"-methoxymethylsalvinorin B) is a semi-synthetic analogue of the natural product salvinorin A which is used in scientific research. It has a longer duration of action of around 2–3 hours, compared to less than 30 minutes for salvinorin A, and has increased affinity and potency at the κ-opioid receptor. Like the related compound herkinorin, salvinorin B methoxymethyl ether is made from salvinorin B, which is most conveniently made from salvinorin A by deacetylation, as while both salvinorin A and salvinorin B are found in the plant "Salvia divinorum", salvinorin A is present in larger quantities.
543e3fa25391a57fe30363853bfa2b72
Pulvinone Pulvinone, an organic compound belonging to the esters, lactones, alcohols and butenolides classes, is a yellow crystalline solid. Although the pulvinone is not a natural product, several naturally occurring hydroxylated derivatives are known. These hydroxylated pulvinones are produced by fungal species, such as the in Europe common Larch Bolete ("Boletus elegans", also known as "Suillus grevillei"), or by moulds such as "Aspergillus Terreus".
9bc94527a28ed8661ab9f1590685c0d0
4-Fluoropethidine 4-Fluoropethidine is a drug that is a derivative of pethidine (meperidine), which combines pethidine's opioid analgesic effects with increased monoamine reuptake inhibition. It is around 50% less potent than pethidine as an opioid analgesic, but conversely is 50% more potent as a dopamine reuptake inhibitor, with other derivatives such as the 4-iodo and 3,4-dichloro analogues being even more potent dopamine reuptake inhibitors again. However none of these compounds substitute for cocaine or produce stimulant effects in animals, suggesting that they still act primarily as opioid analgesic drugs in practice. Its action and degree of relation to pethidine means that it may be controlled in those countries which have laws about controlled-substance analogues; it is not itself listed in the Controlled Substances Act 1970.
b097abedd423bb6f1a26807a0e518109
Methadone Methadone, sold under the brand name Dolophine, among others, is an opioid used to treat pain and as maintenance therapy or to help with tapering in people with opioid dependence. Detoxification using methadone can either be done relatively rapidly in less than a month or gradually over as long as six months. While a single dose has a rapid effect, maximum effect can take five days of use. The effects last about six hours after a single dose. After long term use, in people with normal liver function, effects last 8 to 36 hours. Methadone is usually taken by mouth and rarely by injection into a muscle or vein.
93955a4bb1b882d4e781b825af042509
Desocodeine Desocodeine is a semi-synthetic opioid which is the penultimate intermediate in the manufacture of desomorphine from codeine.
81155e7fe7cd56656cc5c48a5715d527
Nicodicodeine Nicodicodeine is an opioid developed as a cough suppressant and analgesic. Synthesized in 1904, it is not commonly used, but has activity similar to other opioids. Nicodicodeine is metabolised in the liver by demethylation to produce 6-nicotinoyldihydromorphine, and subsequently further metabolised to dihydromorphine. Since the final active metabolite is the slightly stronger opiate dihydromorphine rather than morphine, nicodicodeine can be expected to be marginally more potent and longer acting than nicocodeine. Side effects are similar to those of other opioids and include itching, nausea and respiratory depression.
59cee3d604a9959e49a2b64e8abdc823
Apomorphine Apomorphine (brand names Apokyn, Ixense, Spontane, Uprima) is a type of aporphine having activity as a non-selective dopamine agonist which activates both D-like and, to an order of magnitude lesser extent, D-like receptors. It also acts as an antagonist of 5-HT and α-adrenergic receptors with high affinity. The compound is historically a morphine decomposition product by boiling with concentrated acid, hence the -"morphine" suffix. Apomorphine does not actually contain morphine or its skeleton, nor does it bind to opioid receptors. The "apo"- prefix relates to it being a morphine derivative ("[comes] from morphine").
4a9e46214e22f7f82e85d9c9c381bd32
Naloxegol Naloxegol (INN; PEGylated naloxol; trade names Movantik and Moventig) is a peripherally-selective opioid antagonist developed by AstraZeneca, licensed from Nektar Therapeutics, for the treatment of opioid-induced constipation. It was approved in 2014 in adult patients with chronic, non-cancer pain. Doses of 25 mg were found safe and well tolerated for 52 weeks. When given concomitantly with opioid analgesics, naloxegol reduced constipation-related side effects, while maintaining comparable levels of analgesia.
840b527ad973000f44d451fd4c26a9a8
Nalmexone Nalmexone (INN) (code names EN-1620A, UM-592), or nalmexone hydrochloride (USAN), is a semisynthetic, opioid partial agonist or mixed agonist-antagonist with both analgesic and narcotic antagonist properties that was never marketed. In clinical studies it was found to have comparable analgesic efficacy to morphine, though with several-fold reduced potency. In addition, nalmexone's side effects, the most common of which were sleepiness and sweating, were reported to be similar to those of morphine, albeit with a noticeably higher degree of incidence.
70408ecb10ba903769ceb290cb93a470
Ciprefadol Ciprefadol is an opioid analgesic that is an isoquinoline derivative most closely related to cyclazocine and picenadol, with a number of other related compounds known. Ciprefadol is a mixed agonist–antagonist at μ-opioid receptors and can partly block the effects of morphine at low doses, though at higher doses it acts more like a full agonist. It is also a potent κ-opioid agonist, unlike the corresponding N-methyl and N-phenethyl derivatives which are reasonably μ-selective agonists.
29e367a72ad685342cfdc8265397be1c
Phenampromide Phenampromide is an opioid analgesic from the ampromide family of drugs, related to other drugs such as propiram and diampromide. It was invented in the 1960s by American Cyanamid Co.
ad755ac96ec0945bd6ade22518fe7332
4'-Methyl-α-pyrrolidinohexiophenone 4'-Methyl-α-pyrrolidinohexiophenone or MPHP is a stimulant compound which has been reported as a novel designer drug. It is closely related to pyrovalerone, being simply its chain-lengthened homologue. In the pyrrolidinophenone series, stimulant activity is maintained so long as the positions of the aryl, ketone and pyrrolidinyl groups are held constant, while the alkyl backbone can be varied anywhere between three and as many as seven carbons, with highest potency usually seen with the pentyl or isohexyl backbone, and a variety of substituents are tolerated on the aromatic ring.
d51f5bd2d3daca3b25bb9929f4ca49ae
1,3-Benzodioxolyl-N-ethylbutanamine Ethylbenzodioxolylbutanamine (EBDB; Ethyl-J) is a lesser-known entactogen, stimulant, and psychedelic. It is the "N"-ethyl analogue of benzodioxylbutanamine (BDB; "J"), and also the α-ethyl analogue of methylenedioxyethylamphetamine (MDEA; "Eve").
a97ca0cf7aa18416485708cb67b4ae2a
Myrophine Myrophine (Myristylbenzylmorphine) is an opiate analogue that was developed in 1952. It is a derivative of morphine.
3d8787b0ef48caa1a3b416846bc318be
Acetylmethadol Acetylmethadol, also known as methadyl acetate, is a synthetic opioid analgesic. It is a racemic mixture of alphacetylmethadol (α-acetylmethadol) and betacetylmethadol (β-acetylmethadol), which are in turn racemic mixtures of levacetylmethadol (LAAM; -α-acetylmethadol) and -α-acetylmethadol and -β-acetylmethadol and -β-acetylmethadol, respectively. Hence, acetylmethadol has four possible optical isomers. All of these isomers have been shown to partially or fully substitute for the discriminative stimulus effects of heroin in rats, and thus it can be inferred that, in addition to LAAM which is used clinically as such, they are all likely to be active opioid analgesics in humans.