Dimethylamino compounds

Dimenoxadol (INN; also known as dimenoxadole (BAN) or dimenoxadole; brand name Estocin in Russia) is an opioid analgesic which is a benzilic acid derivative, closely related to benactyzine (an anticholinergic). Further, the structure is similar to methadone and related compounds like dextropropoxyphene.

Clofedanol (INN) or chlophedianol (BAN), sold under the brand name Ninjacof among others, is a centrally acting cough suppressant used in the treatment of dry cough. Clofedanol has local anesthetic, antispasmodic, and antihistamine properties, and may have anticholinergic effects at high doses.

Intriptyline is a tricyclic antidepressant (TCA) that was never marketed.

Depramine (INN; GP-31,406), also known as balipramine (BAN) and as 10,11-dehydroimipramine, is a tricyclic antidepressant (TCA) which was never marketed.

Niperotidine is a histamine antagonist selective for the H2 subtype. It was studied as a treatment for excessive gastric acidity, but withdrawn after human trials showed liver damage.

Alphamethadol (INN), or α-methadol, also known as alfametadol, is a synthetic opioid analgesic. It is an isomer of dimepheptanol (methadol), the other being betamethadol (β-methadol). Alphamethadol is composed of two isomers itself, L-α-methadol, and D-α-methadol. Both of alphamethadol's isomers bind to and activate the μ-opioid receptor and are active as opioid analgesics, similarly to those of alphacetylmethadol (α-acetylmethadol).

Moxastine (also known as mephenhydramine) is an antihistamine and anticholinergic.

chemical compound

chemical compound

Amitriptylinoxide (brand names Amioxid, Ambivalon, Equilibrin), or 'amitriptyline N-oxide', is a tricyclic antidepressant (TCA) which was introduced in Europe in the 1970s for the treatment of depression.

Betamethadol (INN), or β-methadol, also known as betametadol, is a synthetic opioid analgesic. It is an isomer of dimepheptanol (methadol), the other being alphamethadol (α-methadol). Betamethadol is composed of two isomers itself, L-β-methadol, and D-β-methadol. Based on structure-activity relationships it can be inferred that both isomers are likely to be active as opioid analgesics, similarly to those of betacetylmethadol (β-acetylmethadol).

Dimethylthiambutene (N,N-Dimethyl-1-methyl-3,3-di-2-thienylallylamine, DMTB, trade names Ohton, Aminobutene, Dimethibutin, Kobaton, Takaton, Dimethibutin) is an opioid analgesic drug, most often used in veterinary medicine in Japan and to a lesser extent in other countries in the region and around the world. It is the most prominent and widely used of the thiambutenes, a series of open-chain opioids structurally related to methadone which are also called the thienyl derivative opioids which also includes diethylthiambutene and ethylmethylthiambutene, as well as the non-opioid cough suppressant

Sarpogrelate (, ), sold under the brand names Anplag and Sapodifil, is a serotonin 5-HT2 receptor antagonist which is used in the treatment of arterial occlusive disorders such as peripheral artery disease in Japan, South Korea, and China. Development in the United States and the European Union was discontinued and it is not available in these regions.

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.

Lupitidine (INN; lupitidine hydrochloride (USAN); development code SKF-93479) is a long-acting H2 receptor antagonist developed by Smith, Kline & French and described as an antiulcerogenic that was never marketed. It was shown to inhibit nocturnal gastric acid secretion and, in experiments on rodents, produced diffuse neuroendocrine cell hyperplasia and an increase in multifocal glandular hyperplasia due to hypergastrinemia resulting from the pharmacological suppression of gastric acid secretion.

'3,4-Methylenedioxy-N,N-dimethylamphetamine (MDDM, MDDMA), also known as N,N-dimethyl-MDA or N-methyl-MDMA', is a lesser-known serotonin releasing agent and psychoactive drug of the phenethylamine, amphetamine, and MDxx families. It is the N,N-dimethyl analogue of 3,4-methylenedioxyamphetamine (MDA) and the N-methyl derivative of MDMA. The drug is a known synthetic impurity of MDMA and has also been described as a possible novel designer drug in 2025.

Tiazesim (), or thiazesim (, ), previously sold under the brand name Altinil, is a heterocyclic antidepressant related to the tricyclic antidepressants (TCAs) which, introduced in 1966 by Squibb Corporation (now Bristol-Myers Squibb), has since been discontinued and is no longer marketed.

Thozalinone (USAN) (brand name Stimsen; former developmental code name CL-39808) is a psychostimulant that has been used as an antidepressant in Europe. It has also been trialed as an anorectic. Thozalinone is described as a "dopaminergic stimulant", and likely acts via inducing the release of dopamine and to a minimal extent norepinephrine; similar to analogue pemoline, it is reportedly devoid of abuse potential unlike most other dopaminergic psychostimulants.

chemical compound

AH-7921 (Doxylam) is an opioid analgesic drug selective for the μ-opioid receptor, having around 90% the potency of morphine when administered orally. It was discovered in the 1970s by a team at Allen and Hanburys located in the United Kingdom. The drug is considered a new psychoactive substance (NPS), a designation of compounds designed to mimic the effects controlled substances. It has also been sold on the internet since 2012 as a "research chemical". When sold online it may be called the alternative name doxylam, not to be confused with doxylamine. AH-7921 has never progressed to clinical

Betacetylmethadol is a synthetic opioid. It is a diastereoisomer of alphacetylmethadol (as well as levacetylmethadol). In the United States, betacetylmethadol is a Schedule I drug Narcotic under the Controlled Substances Act, with an ACSCN of 9607 and a 2 gramme manufacturing quota as of 2014.

Cerlapirdine (USAN; SAM-531, WAY-262,531, PF-05212365) is a drug which was under development by Wyeth/Pfizer for the treatment of cognitive disorders associated with Alzheimer's disease and schizophrenia. In a phase II clinical trial it demonstrated a trend toward efficacy along with a good side effect profile and no incidence of serious adverse events, but no further development has occurred since 2011.

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 bas

Formetanate is an insecticide and acaricide. It is used on alfalfa grown for seed and on some fruits, including citrus, pome, and stone fruits.

Bromadoline (U-47931E) is an opioid analgesic selective for the μ-opioid receptor developed by the Upjohn company in the 1970s. The drug has a potency lying between that of codeine and morphine, being slightly stronger than pentazocine. Bromadoline is related to AH-7921 and U-47700.

'''p-Dimethylaminocinnamaldehyde (DMACA''') is an aromatic hydrocarbon. It is used in an acidic solution to detect indoles.

EA-4352 is an organophosphate nerve agent of the G-series. It is the isopropyl analog of tabun.

chemical compound

chemical compound

Cotriptyline (SD-2203-01) is a tricyclic antidepressant (TCA) which was never marketed.

Dimazole (or diamthazole) is an antifungal compound.

Mexacarbate is a carbamate pesticide developed by Alexander Shulgin and marketed in 1961 by Dow Chemical Company under the trade name Zectran. As of 2009, Mexacarbate is considered obsolete or discontinued, according to the World Health Organization. It is notable for being the first biodegradable pesticide. thumb|left|Canister of mexacarbate (Zectran) thumb|Mexacarbate being sprayed by helicopter.

Dimepheptanol (INN; Amidol, Pangerin), also known as methadol or racemethadol, is a synthetic opioid analgesic related to methadone. It has similar effects to other opioids, including analgesia, sedation and euphoria, as well as side effects like itching, nausea and respiratory depression.

Fluotracen (SKF-28,175) is a tricyclic drug which has both antidepressant and antipsychotic activity. This profile of effects is similar to that of related agents like amoxapine, loxapine, and trimipramine which may also be used in the treatment of both depression and psychosis. It was believed that such duality would be advantageous in the treatment of schizophrenia, as depression is often comorbid with the disorder and usual antipsychotics often worsen such symptoms. In any case, however, fluotracen was never marketed.

Dimaprit is a histamine analog working as a selective H2 histamine receptor agonist.

Eclanamine (U-48,753) is a drug which was patented as an antidepressant, but was never marketed. It acts by inhibiting the reuptake of serotonin and norepinephrine.

Difemerine is a little known antimuscarinic drug sold under the name Luostyl.

Dimdazenil, sold under the brand name Junoenil, is a medication used in the treatment of insomnia in China. It is a benzodiazepine derivative and a partial positive allosteric modulator of the GABAA receptor with two- to four-fold higher functional affinity for the α1 subunit relative to the α2, α3, and α5 subunits.

4-MeO-DMT, or 4-methoxy-DMT, also known as '4-methoxy-N,N-dimethyltryptamine or as O-methylpsilocin (PSOM'), is a serotonin receptor modulator and possible psychedelic drug of the tryptamine and 4-hydroxytryptamine families. It is the O-methylated analogue of psilocin (4-HO-DMT) and a positional isomer of 5-MeO-DMT.

BIM-1 (GF 109203X) and the related compounds BIM-2, BIM-3, and BIM-8 are bisindolylmaleimide-based protein kinase C (PKC) inhibitors. These inhibitors also inhibit PDK1 explaining the higher inhibitory potential of LY33331 compared to the other BIM compounds a bisindolylmaleimide inhibitor toward PDK1.

Mobocertinib, sold under the brand name Exkivity, is used for the treatment of non-small cell lung cancer.

Binedaline (also called binodaline or binedaline hydrochloride) is a drug that was investigated as an antidepressant in the 1980s but was never marketed. It acts as a selective norepinephrine reuptake inhibitor (Ki = 25 nM), with relatively insignificant influence on the serotonin (Ki = 847 nM) and dopamine (Ki >= 2 μM) transporters. It has negligible affinity for the α-adrenergic, mACh, H1, or 5-HT2 receptors.

Laurdan is an organic compound which is used as a fluorescent dye when applied to fluorescence microscopy. It is used to investigate membrane qualities of the phospholipid bilayers of cell membranes. One of its most important characteristics is its sensitivity to membrane phase transitions as well as other alterations to membrane fluidity such as the penetration of water.

5-Fluoro-DMT, or 5-F-DMT, also known as '5-fluoro-N,N-dimethyltryptamine', is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT) and to other psychedelic tryptamines like 5-chloro-DMT and 5-bromo-DMT.

'7,N,N-trimethyltryptamine (7,N,N-TMT or 7-TMT), also known as 7-methyl-DMT', is a serotonin receptor modulator and psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT). It was first described by 1978 and was encountered online as a novel designer drug in 2024.

LR-5182 is a stimulant drug which acts as a norepinephrine–dopamine reuptake inhibitor, structurally related to the better known drug fencamfamine. It was developed by the pharmaceutical company Eli Lilly in the 1970s, and researched for potential use as an antidepressant, although never marketed. LR-5182 has two stereoisomers, both of which are active, although one isomer blocks reuptake of only dopamine and noradrenaline, while the other blocks reuptake of serotonin as well.

Telapristone (), as telapristone acetate (proposed brand names Proellex, Progenta; former code name CDB-4124), is a synthetic, steroidal selective progesterone receptor modulator (SPRM) related to mifepristone which is under development by Repros Therapeutics for the treatment of breast cancer, endometriosis, and uterine fibroids. It was originally developed by the National Institutes of Health (NIH), and, as of 2017, is in phase II clinical trials for the aforementioned indications. In addition to its activity as an SPRM, the drug also has some antiglucocorticoid activity.

'5-Ethyl-N,N-dimethyltryptamine' is a tryptamine derivative which acts as an agonist at the 5-HT1A and 5-HT1D serotonin receptors, with around 3x selectivity for 5-HT1D.

Eplivanserin, also known by its former developmental code names SR-46349 and SR-46615 and by its former tentative brand names Ciltyri and Sliwens, is a serotonin 5-HT2A receptor antagonist which was under development by Sanofi Aventis for the treatment of a variety of medical conditions but was never marketed. It is taken orally.

Meprotixol is a cough suppressant. It has also been used for the treatment of rheumatic diseases.

IDNNA, also known as '4-iodo-2,5-dimethoxy-N,N-dimethylamphetamine or as N,N-dimethyl-DOI', is a chemical compound of the phenethylamine, amphetamine, and DOx families. It is the N,N-dimethyl derivative of the psychedelic drug DOI.

Enprazepine is a tricyclic antidepressant (TCA) which was never marketed.

Tampramine (AHR-9,377) is a tricyclic antidepressant (TCA) which was developed in the 1980s but was never marketed. Despite being a TCA, it acts as a selective norepinephrine reuptake inhibitor and has negligible affinity for adrenergic, histaminergic, and muscarinic receptors. It was found to be effective in the forced swim test (FST) model of depression in animal studies but is not known to have ever been trialed in humans.

'''N,N-Dimethyl-1-naphthylamine' is an aromatic amine. It is formally derived from 1-naphthylamine by replacing the hydrogen atoms on the amino group with methyl groups. N,N''-Dimethyl-1-naphthylamine is used in the nitrate reductase test to form a precipitate of a red azo dye by reacting with a nitrite-sulfanilic acid complex.

Flucindole (, ; developmental code name WIN-35150) is an antipsychotic of the tetrahydrocarbazolamine family with a tricyclic cyclized tryptamine structure that was never marketed. It is the 6,8-difluoro derivative of ciclindole. The drug is about 5 to 10times more potent than ciclindole both in vitro and in vivo.

Fluorotabun is a highly toxic organophosphate nerve agent of the G-series. It is the fluorinated analog of tabun, i.e. the cyanide group is replaced by a fluorine atom.

Isoaminile is an antitussive (cough suppressant) used under the trade-name Peracon.

Cyprodenate (Actebral) is a stimulant drug. It was used for counteracting the effects of benzodiazepine tranquillizer drugs before the development of newer antidotes such as flumazenil. It produces dimethylethanolamine as a metabolite.

Lometraline (INN; developmental code name CP-14,368) is a drug and an aminotetralin derivative. A structural modification of tricyclic neuroleptics, lometraline was originally patented by Pfizer as an antipsychotic, tranquilizer, and antiparkinsonian agent. However, it was instead later studied as a potential antidepressant and/or anxiolytic agent, though clinical studies revealed no psychoactivity at the doses used and further investigation was suspended. Further experimental modifications of the chemical structure of lometraline resulted in the discovery of tametraline, a potent inhibitor of

Phenyltoloxamine is an antihistamine with sedative and analgesic effects. It is available in combination with other drugs such as paracetamol (acetominophen).