Butorphanol is a morphinan-type synthetic agonist–antagonist opioid analgesic developed by Bristol-Myers. Butorphanol is most closely structurally related to levorphanol. Butorphanol is available as the tartrate salt in injectable, tablet, and intranasal spray formulations. The tablet form is only used in dogs, cats and horses due to low bioavailability in humans.
Levorphanol is an opioid medication used to treat moderate to severe pain. It is the levorotatory enantiomer of the compound racemorphan. Its dextrorotatory counterpart is dextrorphan.
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 dissociative hallucinogen at much higher doses. Levomethorphan is about five times stronger than morphine.
Methorphan comes in two isomeric forms, each with differing pharmacology and effects:
Metopon is an opioid analogue that is a methylated derivative of hydromorphone which was invented in 1929 as an analgesic.
Hydroxypethidine (Bemidone) is an opioid analgesic that is an analogue of the more commonly used pethidine (meperidine). Hydroxypethidine is slightly more potent than meperidine as an analgesic, 1.5x meperidine in potency, and it also has NMDA antagonist properties like its close relative ketobemidone.
Normethadone, also known as desmethylmethadone or phenyldimazone, is a synthetic opioid analgesic and antitussive agent. Normethadone is listed under the Single Convention on Narcotic Drugs 1961 and is a Schedule I Narcotic controlled substance in the United States, with a DEA ACSCN of 9635 and an annual manufacturing quota of 2 grams. It has an effective span of action for about 14 days, and is 12 to 20 times stronger than morphine. The salts in use are the hydrobromide, hydrochloride (0.890), methyliodide (0.675), oxalate (0.766), picrate (0.563), and the 2,6-ditertbutylnapthalindisulphonate (0.480).
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 and/or sigma receptors.
Diampromide is an opioid analgesic from the ampromide family of drugs, related to other drugs such as propiram and phenampromide. It was invented in the 1960s by American Cyanamid, and can be described as a ring-opened analogue of fentanyl.
Proheptazine is an opioid analgesic related to pethidine. It was invented in the 1960s.
Levophenacylmorphan is a morphinan derivative that acts as an opioid agonist. It has potent analgesic effects and is around 10x more potent than morphine. Adverse effects associated with its use are those of the opioids as a whole, including pruritus, nausea, respiratory depression, euphoria and development of tolerance and dependence to its effects.
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.
Hydromorphinol, 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 and hydrochloride
Normorphine is an opiate analogue, the N-demethylated derivative of morphine, that was first described in the 1950s when a large group of N-substituted morphine analogues were characterized for activity. The compound has relatively little opioid activity in its own right, but is a useful intermediate which can be used to produce both opioid antagonists such as nalorphine, and also potent opioid agonists such as N-phenethylnormorphine. with its formation from morphine catalyzed by the liver enzymes CYP3A4 and CYP2C8.
Norcodeine is an opiate analogue that is the N-demethylated derivative of codeine. It has relatively little opioid activity in its own right, but is formed as a metabolite of codeine following ingestion.
Racemoramide, or simply moramide, is an opioid analgesic and a racemic mixture of the substances dextromoramide and levomoramide, two enantiomers of a chiral molecule.
Racemorphan, or morphanol, is the racemic mixture of the two stereoisomers of 17-methylmorphinan-3-ol, each with differing pharmacology and effects:
Isomethadone (INN, BAN; trade name Liden; also known as isoamidone) is a synthetic opioid analgesic and antitussive related to methadone that was used formerly as a pharmaceutical drug but is now no longer marketed. Isomethadone was used as both an analgesic and antitussive. It binds to and activates both the μ- and δ-opioid receptors, with the (S)-isomer being the more potent of the two enantiomers. Isomethadone is a Schedule II controlled substance in the United States, with an ACSCN of 9226 and a 2014 aggregate manufacturing quota of 5 g. The salts in use are the hydrobromide (HBr, free base conversion ratio 0.793), hydrochloride (HCl, 0.894), and HCl monohydrate (0.850). Isomethadone is also regulated internationally as a Schedule I controlled substance under the United Nations Single Convention on Narcotic Drugs of 1961.
3-Hydroxymorphinan (3-HM), or morphinan-3-ol, is a psychoactive drug of the morphinan family. It is the racemic counterpart to norlevorphanol.
Noracymethadol (INN) is a synthetic opioid analgesic related to methadone that was never marketed. In a clinical trial of postpartum patients it was reported to produce analgesia comparable to that of morphine but with less nausea, dizziness, and drowsiness. Other side effects included salivation, ataxia, and respiratory depression that was reversible by naloxone. Similarly to many of its analogues, noracymethadol is a Schedule I controlled substance in the United States with an ACSCN of 9633 and 2013 annual manufacturing quota of 12 grammes. and is also controlled internationally under the United Nations Single Convention on Narcotic Drugs of 1961. The salts known are the gluconate and hydrochloride (0.903).
