Dextromoramide is a powerful opioid analgesic approximately three times more potent than morphine but shorter acting. It is subject to drug prohibition regimes, both internationally through UN treaties and by the criminal law of individual nations, and is usually prescribed only in the Netherlands.
Methorphan comes in two isomeric forms, each with differing pharmacology and effects:
Phenoperidine, is an opioid analgesic which is structurally related to pethidine and is used clinically as a general anesthetic.
Piritramide(R-3365, trade names Dipidolor, Piridolan, Pirium and others) is a synthetic opioid analgesic that is marketed in certain European countries including: Austria, Belgium, Czech Republic, Slovenia, Germany and the Netherlands. It comes in free form, is about 0.75x times as potent as morphine and is given parenterally for the treatment of severe pain. Nausea, vomiting, respiratory depression and constipation are believed to be less frequent with piritramide than with morphine, and it produces more rapid-onset analgesia when compared to morphine and pethidine. After intravenous administration the onset of analgesia is as little as 1–2 minutes, which may be related to its great lipophilicity. The analgesic and sedative effects of piritramide are believed to be potentiated with phenothiazines and its emetic (nausea/vomiting-inducing) effects are suppressed. The volume of distribution is 0.7-1 L/kg after a single dose, 4.7-6 L/kg after steady-state concentrations are achieved and up to 11.1 L/kg after prolonged dosing.
Bezitramide is an opioid analgesic. Bezitramide itself is a prodrug which is readily hydrolyzed in the gastrointestinal tract to its active metabolite, despropionyl-bezitramide. Bezitramide was discovered at Janssen Pharmaceutica in 1961. It is most commonly marketed under the trade name Burgodin.
Metopon is an opioid analogue that is a methylated derivative of hydromorphone which was invented in 1929 as an analgesic.
Tilidine, sold under the brand name Valoron among others, is a synthetic opioid analgesic, used mainly in Belgium, Bulgaria, Germany, Albania, Luxembourg, South Africa, and Switzerland for the treatment of moderate to severe pain, both acute and chronic. Its onset of pain relief after oral administration is about 10–15 minutes and peak relief from pain occurs about 25–50 minutes after administration.
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.
Prodine is an opioid analgesic that is an analog of pethidine (meperidine). It was developed in Germany in the late 1940s.
Allylprodine is an opioid analgesic that is an analog of prodine. It was discovered by Hoffman-La Roche in 1957 during research into the related drug pethidine. Derivatives were tested to prove the theory that phenolic and non-phenolic opioids bind at different sites of the opiate receptor.
Trimeperidine is an opioid analgesic that is an analogue of prodine. It was developed in the early 1950s in the USSR during research into the related drug pethidine.
Piminodine (Alvodine) is an opioid analgesic that is an analogue of pethidine (meperidine). It was used in medicine briefly during the 1960s and 70s, but has largely fallen out of clinical use. It was used particularly for obstetric analgesia and in dental procedures and, like pethidine, could be combined with hydroxyzine to intensify the effects. The duration of action is 2–4 hours; 7.5–10 mg via the subcutaneous route is the most common starting dose, being equal to 80–100 mg of pethidine, 40–60 mg of alphaprodine and 10 mg of morphine. Oral formulations were also available.
Phenazocine is an opioid analgesic drug, which is related to pentazocine and has a similar profile of effects.
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. Although never given a general release, it was research found that 60 mg of phenampromide is equivalent to about 50 mg of codeine. Tests on its two enantiomers showed that all of the analgesic effects were caused by the (S)-isomer. Introduction of a phenyl group to the 4-position of the piperidine-ring produces a drug 60-fold more potent than morphine. The most potent reported derivative is 4-hydroxy-4-phenyl phenapromide which displays analgesic activity some x150 greater than morphine.
IC-26 is an analogue of the opioid analgesic methadone, where the carbonyl group has been replaced by the bioisosteric sulfone group.
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.
Racemoramide, or simply moramide, is an opioid analgesic and a racemic mixture of the substances dextromoramide and levomoramide, two enantiomers of a chiral molecule.
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.
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).
Desmethylmoramide (INN) is an opioid analgesic related to dextromoramide that was synthesized and characterized in the late 1950s but was never marketed.
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