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| Formula | C20H26N2O |
| Molar mass | 310.441 g·mol−1 |
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Anilopam (INN; PR 786-723) is an opioid analgesic of the benzazepine class which was developed by Pentwell in the 1960s [1] but was never marketed. [2] [3]
Metenolone, or methenolone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as metenolone acetate and metenolone enanthate. Metenolone esters are used mainly in the treatment of anemia due to bone marrow failure. Metenolone acetate is taken by mouth, while metenolone enanthate is given by injection into muscle.
Clorgiline (INN), or clorgyline (BAN), is a monoamine oxidase inhibitor (MAOI) structurally related to pargyline which is described as an antidepressant. Specifically, it is an irreversible and selective inhibitor of monoamine oxidase A (MAO-A). Clorgiline was never marketed, but it has found use in scientific research. It has been found to bind with high affinity to the σ1 receptor (Ki = 3.2 nM) and with very high affinity to the I2 imidazoline receptor (Ki = 40 pM).
Butriptyline, sold under the brand name Evadyne among others, is a tricyclic antidepressant (TCA) that has been used in the United Kingdom and several other European countries for the treatment of depression but appears to no longer be marketed. Along with trimipramine, iprindole, and amoxapine, it has been described as an "atypical" or "second-generation" TCA due to its relatively late introduction and atypical pharmacology. It was very little-used compared to other TCAs, with the number of prescriptions dispensed only in the thousands.
Pipamperone, sold under the brand name Dipiperon, is a typical antipsychotic of the butyrophenone family used in the treatment of schizophrenia and as a sleep aid for depression. It is or has been marketed under brand names including Dipiperon, Dipiperal, Piperonil, Piperonyl, and Propitan. Pipamperone was discovered at Janssen Pharmaceutica in 1961, and entered clinical trials in the United States in 1963.
Gepefrine, also known as 3-hydroxyamphetamine or α-methyl-meta-tyramine and sold under the brand names Pressionorm and Wintonin, is a sympathomimetic medication used as an antihypotensive agent which has been marketed in Germany.
Norfenefrine, also known as meta-octopamine or norphenylephrine and sold under the brand name Novadral among others, is a sympathomimetic medication which is used in the treatment of hypotension. Along with its structural isomer p-octopamine and the tyramines, norfenefrine is a naturally occurring endogenous trace amine and plays a role as a minor neurotransmitter in the brain.
Etafedrine, sold under the brand name Nethaprin among others and also known as N-ethylephedrine, is a sympathomimetic agent used as a bronchodilator to treat asthma. It was previously commercially available as both the free base and as the hydrochloride salt from Sanofi-Aventis but is now no longer marketed.
Delmadinone (INN) is a steroidal progestin which was never marketed. An acylated derivative, delmadinone acetate, is used in veterinary medicine.
Methallenestril, also known as methallenoestril and as methallenestrol, as well as Horeau's acid, is a synthetic nonsteroidal estrogen and a derivative of allenolic acid and allenestrol that was formerly used to treat menstrual issues but is now no longer marketed. It is a seco-analogue of bisdehydrodoisynolic acid, and although methallenestril is potently estrogenic in rats, in humans it is only weakly so in comparison. Vallestril was a brand of methallenestril issued by G. D. Searle & Company in the 1950s. Methallenestril is taken by mouth. By the oral route, a dose of 25 mg methallenestril is approximately equivalent to 1 mg diethylstilbestrol, 4 mg dienestrol, 20 mg hexestrol, 25 mg estrone, 2.5 mg conjugated estrogens, and 0.05 mg ethinylestradiol.
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.
Butinoline (Azulone) is an anticholinergic drug used as an antispasmodic.
Thiotetrabarbital is a drug which is a short-acting barbiturate derivative that is used as an anesthetic. It has been used in veterinary medicine.
Nalmexone 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.
Levofenfluramine (INN), or (−)-3-trifluoromethyl-N-ethylamphetamine, also known as (−)-fenfluramine or (R)-fenfluramine, is a drug of the amphetamine family that, itself (i.e., in enantiopure form), was never marketed. It is the levorotatory enantiomer of fenfluramine, the racemic form of the compound, whereas the dextrorotatory enantiomer is dexfenfluramine. Both fenfluramine and dexfenfluramine are anorectic agents that have been used clinically in the treatment of obesity (and hence, levofenfluramine has been as well since it is a component of fenfluramine). However, they have since been discontinued due to reports of causing cardiovascular conditions such as valvular heart disease and pulmonary hypertension, adverse effects that are likely to be caused by excessive stimulation of 5-HT2B receptors expressed on heart valves.
Plomestane is a steroidal, irreversible aromatase inhibitor which was under development by Marion Merrell Dow/Hoechst Marion Russell as an antineoplastic agent for the treatment of breast cancer. It was found to be effective in preclinical studies and was also found to produce few adverse effects in human clinical trials, significantly reducing estrogen levels with a single administration. However, development of the drug for clinical use was halted due to "technical issues" and it was never marketed.
Megestrol is a progestin of the 17α-hydroxyprogesterone group which was, until recently, never marketed or used clinically. It is now used for treatments of disease-related weight loss, endometrial cancer, and breast cancer. Its acylated derivative megestrol acetate is also a progestogen, which, in contrast to megestrol itself, has been extensively used as a pharmaceutical drug.
Butidrine, sold under the brand names Betabloc, Butidrate, and Recetan among others, is a beta blocker related to pronethalol and propranolol that was developed in the 1960s. It is not cardioselective. It has membrane stabilizing activity but no intrinsic sympathomimetic activity. Similarly to certain other beta blockers, butidrine additionally possesses local anesthetic properties.
Alifedrine is a drug described as a sympathomimetic and cardiotonic or positive inotropic agent which was never marketed. It is a β-adrenergic receptor partial agonist and was studied in the treatment of heart failure. The drug is taken by mouth or intravenously. It is a β-hydroxylated substituted amphetamine derivative.
Methestrol dipropionate or methoestrol dipropionate, also known as promethestrol dipropionate or promethoestrol dipropionate or as dimethylhexestrol dipropionate, is a synthetic nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol that is or was used clinically. It is the dipropionate form of methestrol, which, in contrast to methestrol dipropionate, was never marketed.
Flugestone acetate (FGA), sold under the brand name Cronolone among others, is a progestin medication which is used in veterinary medicine.
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