Semisynthetic opioids

Oxycodone, sold under the brand names Endone and OxyContin (which is the extended-release form) among others, is a semi-synthetic opioid used medically for the treatment of moderate to severe pain. It is a highly addictive and commonly abused drug. It is usually taken orally, and is available in immediate-release and controlled-release formulations. Onset of pain relief typically begins within fifteen minutes and lasts for up to six hours with the immediate-release formulation. In the United Kingdom, it is available by injection. Combination products are also available with paracetamol (acetam

Hydrocodone, also known as dihydrocodeinone, is a semi-synthetic opioid used to treat pain and as a cough suppressant. It is taken by mouth. Typically, it is dispensed as the combination acetaminophen/hydrocodone or ibuprofen/hydrocodone for pain severe enough to require an opioid and in combination with homatropine methylbromide to relieve cough. It is also available by itself in a long-acting form sold under the brand name Zohydro ER, among others, to treat severe pain of a prolonged duration. Hydrocodone is a controlled drug: in the United States, it is classified as a Schedule II Controlle

Desomorphine (or in some formulations known as Krokodil) is a semi-synthetic opioid commercialized by Roche, with powerful, fast-acting effects, such as sedation and analgesia. It was first discovered and patented in Germany by a German team working for Knoll in 1920 but was not generally recognized. It was later synthesized in 1932 by American chemist Lyndon Frederick Small. Small also successfully patented it in 1934 in the United States. Desomorphine was used in Germany, Austria, and Switzerland under the brand name Permonid and was described as having a fast onset and a short duration of a

Dihydrocodeine is a semi-synthetic opioid analgesic prescribed for pain or severe dyspnea, or as an antitussive, either alone or compounded with paracetamol (acetaminophen) (as in co-dydramol) or aspirin. It was developed in Germany in 1908 and first marketed in 1911.

Hydrocodone/paracetamol (also known as hydrocodone/acetaminophen) is the combination of the pain medications hydrocodone (an opioid) and paracetamol (acetaminophen). It is used to treat moderate to severe pain. It is taken by mouth. Recreational use is common in the United States.

Ethylmorphine (also known as codethyline, dionine, and ethyl morphine) is an opioid analgesic and antitussive.

Nalbuphine, sold under the brand names Nubain among others, is an opioid analgesic which is used in the treatment of pain. It is given by injection into a vein, muscle, or fat.

Etorphine (M99) is a semi-synthetic opioid possessing an analgesic potency approximately 1,000–3,000 times that of morphine. It was first prepared in 1960 from oripavine, which does not generally occur in opium poppy extract but rather the related plants Papaver orientale and Papaver bracteatum. It was reproduced in 1963 by a research group at MacFarlan Smith in Edinburgh, led by Kenneth Bentley. It can be produced from thebaine.

Pholcodine is an opioid cough suppressant (antitussive). It helps suppress unproductive coughs and also has a mild sedative effect, but has little or no analgesic effects. It is also known as morpholinylethylmorphine and homocodeine.

Nalorphine (; also known as '''N-allylnormorphine; brand names Lethidrone and Nalline''') is a mixed opioid agonist–antagonist with opioid antagonist and analgesic properties. It was introduced in 1954 and was used as an antidote to reverse opioid overdose and in a challenge test to determine opioid dependence.

Dihydromorphine (Paramorfan, Paramorphan) is a semi-synthetic opioid structurally related to and derived from morphine. The 7,8-double bond in morphine is reduced to a single bond to get dihydromorphine. Dihydromorphine is a moderately strong analgesic and is used clinically in the treatment of pain and also is an active metabolite of the analgesic opioid drug dihydrocodeine. Dihydromorphine occurs in trace quantities in assays of opium on occasion, as does dihydrocodeine, dihydrothebaine, tetrahydrothebaine, etc. The process for manufacturing dihydromorphine from morphine for pharmaceutical u

Acetorphine is a potent opioid analgesic, up to 8700 times stronger than morphine by weight. It is a derivative of the more well-known opioid etorphine, which is used as a very potent veterinary painkiller and anesthetic medication, primarily for the sedation of large animals such as elephants, giraffes and rhinos.

Buprenorphine/naloxone, sold under the brand name Suboxone among others, is a fixed-dose combination medication that includes buprenorphine and naloxone. It is used to treat opioid use disorder, and reduces the mortality of opioid use disorder by 50% (by reducing the risk of overdose on full-agonist opioids such as heroin or fentanyl). It relieves cravings to use and withdrawal symptoms. Buprenorphine/naloxone is available for use in two different forms, under the tongue or in the cheek.

Nicocodeine (Lyopect, Tusscodin) is an opioid analgesic and cough suppressant, an ester of codeine closely related to dihydrocodeine and the codeine analogue of nicomorphine. It is not commonly used in most countries, but has activity similar to other opiates. Nicocodeine and nicomorphine were synthesized in 1904, and introduced in 1957 by Lannacher Heilmittel of Austria. Nicocodeine is metabolised in the liver by demethylation to produce nicomorphine, also known as 6-nicotinoylmorphine, and subsequently further metabolised to morphine. Side effects are similar to those of other opiates and in

Levomethorphan (LVM) (INN, BAN) is an opioid analgesic of the morphinan family that has never been marketed. It is the L-stereoisomer of racemethorphan (methorphan). The effects of the two isomers of racemethorphan are quite different, with dextromethorphan (DXM) being an antitussive at low doses and a hallucinogen at much higher doses. Levomethorphan is about five times stronger than morphine.

Nicodicodine 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. Nicodicodine 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, nicodicodine 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 r

Methylnaltrexone (MNTX, brand name Relistor), used in form of methylnaltrexone bromide (INN, USAN, BAN), is a medication that acts as a peripherally acting μ-opioid receptor antagonist that acts to reverse some of the side effects of opioid drugs such as constipation without significantly affecting pain relief 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 pain r

Nicomorphine (Vilan, Subellan, Gevilan, MorZet) is the 3,6-dinicotinate ester of morphine. It is a strong opioid agonist analgesic two to three times as potent as morphine with a side effect profile similar to that of dihydromorphine, morphine, and diamorphine.

Benzylmorphine (Peronine) is a semi-synthetic opioid narcotic introduced to the international market in 1896 and that of the United States very shortly thereafter. It is much like codeine, containing a benzyl group attached to the morphine molecule just as the methyl group creates codeine and the ethyl group creates ethylmorphine or dionine (used as a generic name for that drug just as peronine is for benzylmorphine). It is about 90% as strong as codeine by weight.

Thebacon (INN; pronounced ), or dihydrocodeinone enol acetate, is a semisynthetic opioid that is similar to hydrocodone and is most commonly synthesised from thebaine. Thebacon was invented in Germany in 1924, four years after the first synthesis of hydrocodone. Thebacon is a derivative of acetyldihydrocodeine, where only the 6–7 double bond is saturated. Thebacon is marketed as its hydrochloride salt under the trade name Acedicon, and as its bitartrate under Diacodin and other trade names. The hydrochloride salt has a free base conversion ratio of 0.846. Other salts used in research and other

Codeinone is an isoquinolone alkaloid found in the opium poppy. As an analgesic, it is one-third the potency of codeine. It is an important intermediate in the production of hydrocodone–a painkiller about three-quarters the potency of morphine–as well as of oxycodone, though the latter can also be synthesized from thebaine.

Acetyldihydrocodeine is an opiate derivative discovered in Germany in 1914 and was used as a cough suppressant and analgesic. It is not commonly used, but has activity similar to other opiates. Acetyldihydrocodeine is a very close relative derivative of thebacon, where only the 6-7 bond is unsaturated. Acetyldihydrocodeine can be described as the 6-acetyl derivative of dihydrocodeine and is metabolised in the liver by demethylation and deacetylation to produce dihydromorphine.

Metopon (5-methylhydromorphone, CAS number 124-92-5) is an opioid analogue that is a methylated derivative of hydromorphone which was invented in 1929 as an analgesic.

6-Monoacetylmorphine (6-MAM, 6-acetylmorphine, or 6-AM) is an opioid and also one of three active metabolites of heroin (diacetylmorphine), the others being morphine and the much less active 3-monoacetylmorphine (3-MAM).

Morphinone is an opioid that is the intermediate when morphine is being converted to hydromorphone (trade name Dilaudid).

Diprenorphine (brand name Revivon; former developmental code name M5050), also known as diprenorfin, is a non-selective, high-affinity, weak partial agonist of the μ- (MOR), κ- (KOR), and δ-opioid receptor (DOR) (with equal affinity) which is used in veterinary medicine as an opioid antagonist. It is used to reverse the effects of super-potent opioid analgesics such as etorphine and carfentanil that are used for tranquilizing large animals. The drug is not approved for use in humans.

Dihydroetorphine was developed by K. W. Bentley at McFarlan-Smith in the 1960s and is a potent opioid analgesic used mainly in China. It is a derivative of the better-known opioid etorphine, a very potent veterinary painkiller and anesthetic medication used primarily for the sedation of large animals such as elephants, giraffes, and rhinos.

Nalfurafine (INN, USAN; brand name Remitch; former developmental code names TRK-820, AC-820, MT-9938) is an antipruritic (anti-itch drug) that is marketed in Japan for the treatment of uremic pruritus in individuals with chronic kidney disease undergoing hemodialysis. It activates the κ-opioid receptor (KOR) and is potent, selective, and centrally active. It was the first selective KOR agonist approved for clinical use. It has also been dubiously referred to as the "first non-narcotic opioid drug" in history.

Naloxazone is an irreversible μ-opioid receptor antagonist which is selective for the μ1 receptor subtype. Naloxazone produces very long lasting antagonist effects as it forms a covalent bond to the active site of the μ-opioid receptor, thus making it impossible for the molecule to unbind and blocking the receptor permanently until the receptor is recycled by endocytosis.

Drotebanol (Oxymethebanol) is a morphinan derivative that acts as an opioid agonist. It was invented by Sankyo Company in Japan during the 1970s. It is synthesised from thebaine.

Methyldesorphine is an opioid analgesic. First synthesized in Germany in 1940 and patented in the US in 1952, it has a high potential for abuse as with any potent opioid agonist, and is sometimes found along with desomorphine as a component of the home-made opioid mixture known as "Krokodil" used in Russia and the neighboring former Soviet republics. It is approximately 15 times more potent than morphine as an analgesic, but if the 6-7 bond is saturated, the β isomer is some 50 times more potent than morphine.

Hydromorphinol (RAM-320, 14-hydroxydihydromorphine), is an opiate analogue that is a derivative of morphine, where the 14-position has been hydroxylated and the 7,8- double bond saturated. It has similar effects to morphine such as sedation, analgesia and respiratory depression, but is twice as potent as morphine and has a steeper dose-response curve and longer half-life. It is used in medicine as the bitartrate salt (free base conversion ratio 0.643, molecular weight 471.5) and hydrochloride (free base conversion ratio 0.770, molecular weight 393.9)

Herkinorin is an opioid analgesic that is an analogue of the natural product salvinorin A. It was discovered in 2005 during structure-activity relationship studies into neoclerodane diterpenes, the family of chemical compounds of which salvinorin A is a member.

Codoxime (Codossima) is an opiate analogue that is a derivative of hydrocodone, where the 6-ketone group has been replaced by carboxymethyloxime. It has primarily antitussive effects and was found to have moderate potential to cause dependence in animal studies.

Diacetyldihydromorphine (also known as Paralaudin, dihydroheroin, acetylmorphinol) is a potent opiate derivative developed in Germany in 1928 which is rarely used in some countries for the treatment of severe pain such as that caused by terminal cancer, as another form of diacetylmorphine (also commonly known as Heroin). Diacetyldihydromorphine is fast-acting and longer-lasting than diamorphine, with a duration of action of around 4–7 hours.

Methyldihydromorphine is a semi-synthetic opioid originally developed in Germany in 1936, controlled under both domestic law and UN conventions because of its possible potential for abuse. Methyldihydromorphine is related to heterocodeine and is not a synonym for dihydrocodeine or dihydroheterocodeine (6-methoxydihydromorphine).

Myrophine (Myristylbenzylmorphine) is an opiate analogue that was developed in 1952. It is a derivative of morphine.

Oxymorphazone is an opioid analgesic drug related to oxymorphone. Oxymorphazone is a potent and long acting μ-opioid agonist which binds irreversibly to the receptor, forming a covalent bond which prevents it from detaching once bound. This gives it an unusual pharmacological profile, and while oxymorphazone is only around half the potency of oxymorphone, with higher doses the analgesic effect becomes extremely long lasting, with a duration of up to 48 hours when administered intraventricularly. However, tolerance to analgesia develops rapidly with repeated doses, as chronically activated opio

Azidomorphine is an opiate analogue that is a derivative of morphine, where the 7,8 double bond has been saturated and the 6-hydroxy group has been replaced by an azide group.

Nalmexone (INN; also known as nalmexone hydrochloride (USAN) or by the development codes EN-1620A and UM-592) 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.

7-PET is an opioid analgesic drug that has 300 times the potency of morphine by weight. It was discovered by K.W. Bentley and is related to the more well known oripavine derivative etorphine, which is used as a veterinary painkiller and anesthetic medication for the sedation of large animals such as elephants, giraffes, and rhinos. 7-PET itself has a 3-O-methyl ether which reduces potency, but the 3-OH derivative is around 2200 times more potent than morphine, almost the same potency as etorphine as a μ agonist, and unexpectedly the 3-hydrogen compound is also around the same potency of 2000 t

Xorphanol (INN; also known as xorphanol mesylate (USAN); developmental codes TR-5379 or TR-5379M) is an opioid analgesic of the morphinan family that was never marketed.

Eseroline is a drug which acts as an opioid agonist. It is a metabolite of the acetylcholinesterase inhibitor physostigmine but unlike physostigmine, the acetylcholinesterase inhibition produced by eseroline is weak and easily reversible, and it produces fairly potent analgesic effects mediated through the μ-opioid receptor. This mixture of activities gives eseroline an unusual pharmacological profile, although its uses are limited by side effects such as respiratory depression and neurotoxicity.

Naltrindole is a highly potent, highly selective delta opioid receptor antagonist used in biomedical research. In May 2012 a paper was published in Nature with the structure of naltrindole in complex with the mouse δ-opioid G-protein coupled receptor, solved by X-ray crystallography.

Oxycodone/naloxone, sold under the brand name Targin among others, is a combination pain medication available as modified-release tablets administered by mouth.

2,4-Dinitrophenylmorphine is an analog of morphine in which a hydroxyl group is substituted with a dinitro phenoxy group.

1-Iodomorphine is a semi-synthetic narcotic analgesic formed by halogenation of the 1 position on the morphine carbon skeleton. Halogenated morphine derivatives were first synthesised in Germany, Austria/Austria-Hungary, the United Kingdom and the United States in the period 1890 to 1930. Use of this drug increased after 1945 for the below-mentioned research. It is a research chemical which is often prepared in the laboratory when it is needed.

Naltriben is a potent and selective antagonist for the delta opioid receptor, which is used in scientific research. It has similar effects to the more widely used δ antagonist naltrindole, but with different binding affinity for the δ1 and δ2 subtypes, which makes it useful for distinguishing the subtype selectivity of drugs acting at the δ receptors. It also acts as a κ-opioid agonist at high doses.

chemical compound

Dibenzoylmorphine is an opioid analogue that is a derivative of morphine. It was developed in the early 1900s after first having been synthesised in 1875 in the UK by the CR Alders Wright organisation at Bayer, along with various other esters of morphine. It was never used medically, instead being widely sold as one of the first "designer drugs" for around five years following the introduction of the first international restrictions on the sale of heroin in 1925. It is described as being virtually identical to heroin and morphine in its effects, and consequently was itself banned international