Designer prodrugs

Flunitrazepam, sold under the brand name Rohypnol among others, is a benzodiazepine used to treat severe insomnia and assist with anesthesia. As with other hypnotics, flunitrazepam has been advised to be prescribed only for short-term use or by those with chronic insomnia on an occasional basis.

1,4-Butanediol, also called butane-1,4-diol (other names include 1,4-B, BD, BDO, and 1,4-BD), is a primary alcohol and an organic compound with the formula HOCH2CH2CH2CH2OH. It is a colorless viscous liquid first synthesized in 1890 via acidic hydrolysis of N,N'-dinitro-1,4-butanediamine by Dutch chemist Pieter Johannes Dekkers, who called it "tetramethylene glycol".

Fenethylline (BAN, USAN) or fenetylline (INN) is a codrug of amphetamine and theophylline and so a mutual prodrug of both. It is also spelled phenethylline; other names for it are amphetaminoethyltheophylline and amfetyline. The drug was marketed for use as a psychostimulant under the brand names Captagon, Biocapton, and Fitton. The brand name "Captagon" (or in lowercase as "captagon") is often used generically to describe illicitly produced fenethylline.

γ-Butyrolactone (GBL) or '''gamma-butyrolactone''' is an organic compound with the formula . It is a hygroscopic, colorless, water-miscible liquid with a pleasant odor. It is the simplest 4-carbon lactone. It is mainly used as an intermediate in the production of other chemicals, such as N-methyl-2-pyrrolidone.

Amfepramone, also known as diethylpropion, is a stimulant drug of the phenethylamine, amphetamine, and cathinone classes that is used as an appetite suppressant. It is used in the short-term management of obesity, along with dietary and lifestyle changes. Amfepramone has a similar chemical structure to the antidepressant and smoking cessation aid bupropion (previously called amfebutamone), which has also been developed as a weight-loss medicine when in a combination product with naltrexone.

Phenazepam (also known in Russia as bromdihydrochlorphenylbenzodiazepine) is a benzodiazepine drug, first developed in the Soviet Union in 1975, and now produced in Russia and several other countries.

γ-Valerolactone (GVL) or gamma-valerolactone is an organic compound with the formula C5H8O2. This colourless liquid is one of the more common lactones. GVL is chiral but is usually used as the racemate. It is readily obtained from cellulosic biomass and is a potential fuel and green solvent.

Benzphetamine, sold under the brand name Didrex among others, is an amphetamine-type stimulant and appetite suppressant used short-term for weight loss along with a doctor-approved, reduced-calorie diet, exercise, and behavioral program. It is prescribed for obesity to people who have been unable to lose weight through exercise and dieting alone. It is a prodrug of dextromethamphetamine and dextroamphetamine.

Mefenorex (marketed as Rondimen, Pondinil, Anexate) is an amphetamine derivative with a relatively mild psychostimulant profile. Developed in the 1960s, it was used throughout the 1970s as an appetite suppressant for treating obesity. Mefenorex is a prodrug of amphetamine; upon ingestion, the compound will begin to metabolize into, as well as promote the production of, the active metabolites levoamphetamine and dextroamphetamine. Multiple sources have noted the substance as exerting "mild stimulant effects....[and having] relatively little abuse potential."

Benfluorex, sold under the brand name Mediator, is an anorectic and hypolipidemic agent that is structurally related to fenfluramine (a substituted amphetamine). It acts mostly as a prodrug of norfenfluramine. It was fraudulently claimed to improve glycemic control and decrease insulin resistance in people with poorly controlled type-2 diabetes through norfenfluramine acting as a 5-HT2B receptor agonist

Gidazepam, also known as hydazepam or hidazepam, is a drug which is an atypical benzodiazepine derivative, developed in the Soviet Union. It is a selectively anxiolytic benzodiazepine. It also has therapeutic value in the management of certain cardiovascular disorders.

Rilmazafone (リスミー, Rhythmy, previously known as 450191-S) is a water-soluble prodrug developed by Shionogi. Inside the human body, rilmazafone is converted into several benzodiazepine metabolites that have sedative and hypnotic effects.

Fenproporex (Perphoxene) (N-2-Cyanoethylamphetamine) (3-(1-phenylpropan-2-ylamino)propanenitrile) (3-[(1-Methyl-2-Phenylethyl)amino]propiononitrile) is a stimulant drug of the phenethylamine and amphetamine chemical classes that was developed in the 1960s. It is used as an appetite suppressant for the treatment of obesity.

Amfetaminil (also known as amphetaminil, '''N-cyanobenzylamphetamine, and AN-1; brand name Aponeuron''') is a stimulant drug derived from amphetamine, which was developed in the 1970s and used for the treatment of obesity, ADHD, and narcolepsy. It has largely been withdrawn from clinical use following problems with abuse. The drug is a prodrug to amphetamine.

1P-LSD, also known as 1-propionyl-LSD, is a psychedelic drug of the lysergamide family related to LSD. It is an ester derivative of LSD and a homologue of ALD-52 (1A-LSD). The drug originated in 2015 when it appeared as a designer drug sold online. It was first synthesized as a legal LSD alternative by Lizard Labs, a Netherlands based research chemical laboratory. It modifies the LSD molecule by adding a propionyl group to the nitrogen atom of LSD's indole group and is a prodrug of LSD.

'4-Acetoxy-N,N-dimethyltryptamine (4-AcO-DMT or 4-acetoxy-DMT), also known as O-acetylpsilocin or psilacetin', is a psychedelic drug of the tryptamine family related to psilocybin and psilocin. It is a synthetic derivative of psilocin (4-HO-DMT) in which the hydroxyl group has been acetylated, and is the analogue of psilocybin (4-PO-DMT) in which the phosphate ester has been replaced with an acetate ester. The drug is a prodrug of psilocin and is used orally similarly to psilocybin.

4-AcO-DET, also known as '4-acetoxy-N,N-diethyltryptamine as well as ethacetin or ethylacybin', is a psychedelic tryptamine. It was first synthesized in 1958 by Albert Hofmann in the Sandoz lab.

4-AcO-DiPT, also known as '4-acetoxy-N,N-diisopropyltryptamine or as ipracetin', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to 4-AcO-DMT (psilacetin). It is taken orally.

Propylamphetamine (code name PAL-424; also known as '''N-propylamphetamine or NPA''') is a psychostimulant of the amphetamine family which was never marketed. It was first developed in the 1970s, mainly for research into the metabolism of, and as a comparison tool to, other amphetamines.

ALD-52, also known as 1-acetyl-LSD (1A-LSD) and falsely as "Orange Sunshine", is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD). It is taken orally.

Avizafone (Pro-Diazepam) is a water-soluble prodrug of the benzodiazepine derivative diazepam. It can be administered intramuscularly.

Nalobrazepam (), also known as cinazepam or BD-798 and sold under the brand name Levana, is an atypical benzodiazepine derivative.

'3,4-Methylenedioxy-N-hydroxyamphetamine (MDOH, MDH), also known as N-hydroxy-MDA', is an entactogen, psychedelic, and stimulant of the phenethylamine, amphetamine, and MDxx families. It is the N-hydroxy homologue of MDA, and the N-desmethyl homologue of FLEA (MDMOH).

Morazone (Novartrina, Orsimon, Rosimon-Neu, Tarcuzate) is a nonsteroidal anti-inflammatory drug (NSAID), originally developed by the German pharmaceutical company Ravensberg in the 1950s, which is used as an analgesic. It produces phenmetrazine as a major metabolite and has been reported to have been abused as a recreational drug in the past.

Bolandiol (INN, also known as 19-nor-4-androstenediol, estr-4-ene-3β,17β-diol, or 3β-dihydronandrolone) is an anabolic-androgenic steroid (AAS) that was never marketed. However, a dipropionate ester derivative, bolandiol dipropionate, has been marketed. Bolandiol and its dipropionate ester are unique among AASs in that they reportedly also possesses estrogenic and progestogenic activity.

Furfenorex (Frugalan), also known as furfurylmethylamphetamine, is a stimulant drug which was developed in the 1960s and used as an appetite suppressant. It produces methamphetamine as a metabolite, and has been withdrawn from the market due to abuse potential.

Famprofazone (Gewodin, Gewolen) is a nonsteroidal anti-inflammatory agent (NSAID) of the pyrazolone series which is available over-the-counter in some countries such as Taiwan. It has analgesic, anti-inflammatory, and antipyretic effects. Famprofazone has been known to produce methamphetamine as an active metabolite, with 15–20% of an oral dose being converted to it. As a result, famprofazone has occasionally been implicated in causing positives on drug tests for amphetamines.

Etilamfetamine, also known as '''N-ethylamphetamine and formerly sold under the brand names Apetinil and Adiparthrol''', is a stimulant drug of the amphetamine family. It was invented in the early 20th century and was subsequently used as an anorectic or appetite suppressant in the 1950s, but was not as commonly used as other amphetamines such as amphetamine, methamphetamine, and benzphetamine, and was largely discontinued once newer drugs such as phenmetrazine were introduced.

1cP-LSD, or 1-CPA-LSD, also known as 1-cyclopropanoyl-LSD or as Curie, is a psychedelic drug of the lysergamide family and an acylated derivative of lysergic acid diethylamide (LSD) which has been sold as a designer drug. It is a prodrug of LSD.

Dimethylamphetamine (Metrotonin), also known as dimetamfetamine (INN), dimephenopan and '''N,N-dimethylamphetamine''', is a stimulant drug of the phenethylamine and amphetamine chemical classes. Dimethylamphetamine has weaker stimulant effects than amphetamine or methamphetamine and is considerably less addictive and less neurotoxic compared to methamphetamine. However, it still retains some mild stimulant effects and abuse potential, and is illegal in both the United States and Australia.

Fenbutrazate (INN), also known as phenbutrazate (BAN), is a psychostimulant used as an appetite suppressant under the trade names Cafilon, Filon, and Sabacid in Europe, Japan, and Hong Kong. It is a derivative of phenmetrazine and may function as a prodrug due to its similarity to phendimetrazine.

4-AcO-MiPT, also known as '4-acetoxy-N-methyl-N-isopropyltryptamine or as mipracetin', is a psychedelic tryptamine. It is closely related to 4-AcO-DMT and methylisopropyltryptamine (MiPT).

HOT-7, also known as '4-propylthio-2,5-dimethoxy-N-hydroxyphenethylamine or as N-hydroxy-2C-T-7', is a psychedelic drug of the phenethylamine, 2C, and HOT-x families. It is the N-hydroxy derivative of 2C-T-7. The drug is taken orally.

Prenylamine (Segontin) is a calcium channel blocker of the amphetamine chemical class that was used as a vasodilator in the treatment of angina pectoris. It produces amphetamine as a metabolite.

Clobenzorex is a central nervous system stimulant and anorectic drug, chemically classified as an N-substituted amphetamine and a phenethylamine. Marketed by Aventis under the trade name Asenlix in India, Mexico, Honduras, and other parts of Latin America.

Ethocybin also known as '4-phosphoryloxy-N,N-diethyltryptamine (4-PO-DET) or as CEY-19', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to the psilocybin-containing mushroom alkaloid psilocybin. It is assumed to act as a prodrug of 4-HO-DET (CZ-74) analogously to how psilocybin (4-PO-DMT) acts as a prodrug of psilocin (4-HO-DMT). The drug was first described in the literature by Albert Hofmann and colleagues at Sandoz by 1963.

4-AcO-DALT, also known as '4-acetoxy-N,N-diallyltryptamine or as dalcetin', is a tryptamine derivative. It has been sold as a designer drug, but little other information is available. It was first officially identified in seized drug samples in 2012.

HOT-2, also known as '4-ethylthio-2,5-dimethoxy-N-hydroxyphenethylamine or as N-hydroxy-2C-T-2', is a psychedelic drug of the phenethylamine, 2C, and HOT-x families. It is the N-hydroxy derivative of 2C-T-2. The drug is taken orally.

Bolandione, also known as 19-norandrostenedione, as well as 19-norandrost-4-en-3,17-dione or estr-4-ene-3,17-dione, is a precursor of the anabolic-androgenic steroid (AAS) nandrolone (19-nortestosterone). Until 2005, bolandione was available without prescription in United States, where it was marketed as a prohormone, but it is now classified as a Schedule III drug. It is also banned from use in many sports, including the Olympic Games, under the World Anti-Doping Code. Bolandione is readily metabolized to nandrolone after oral administration, but its potency to transactivate the androgen rece

thumb|Metabolic pathway of cloniprazepam

Fencamine (Altimina, Sicoclor), also known as methamphetaminoethylcaffeine, is a psychostimulant drug of the amphetamine class. It is closely related to fenethylline. It is a prodrug of amphetamine and/or methamphetamine. The drug also contains a caffeine moiety in its chemical structure.

'3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine, also known as MDMOH, MDHMA, or FLEA', is an entactogen, psychedelic, and stimulant of the phenethylamine, amphetamine, and MDxx families. It is the N-hydroxy homologue of MDMA ("Ecstasy"), and the N-methyl homologue of MDOH.