Nitrogen heterocycles

Indole is an organic compound with the formula . Indole is classified as an aromatic heterocycle. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indoles are derivatives of indole where one or more of the hydrogen atoms have been replaced by substituent groups. Indoles are widely distributed in nature, most notably as amino acid tryptophan and neurotransmitter serotonin.. In plants, IAA is a common plant hormone which is a derivative of Indole.

Hexamethylenetetramine (HMTA), also known as 1,3,5,7-tetraazaadamantane, is a heterocyclic organic compound with diverse applications. It has the chemical formula (CH2)6N4 and is a white crystalline compound that is highly soluble in water and polar organic solvents. It is useful in the synthesis of other organic compounds, including plastics, pharmaceuticals, explosives, and rubber additives. The compound is also used medically for certain conditions. It sublimes in vacuum at 280°C. It has a tetrahedral cage-like structure similar to adamantane. The four vertices are occupied by nitrogen atom

Solanine is a glycoalkaloid poison found in species of the nightshade family within the genus Solanum, such as the potato (Solanum tuberosum). It can occur naturally in any part of the plant, including the leaves, fruit, and tubers. Solanine has pesticidal properties, and it is one of the plant's natural defenses. Solanine was first isolated in 1820 from the berries of the European black nightshade (Solanum nigrum), after which it was named. It belongs to the chemical family of saponins.

Levofloxacin, sold under the brand name Levaquin among others, is a broad-spectrum antibiotic of the fluoroquinolone drug class. It is the left-handed isomer of the medication ofloxacin. It is used to treat a number of bacterial infections including acute bacterial sinusitis, pneumonia, H. pylori (in combination with other medications), urinary tract infections, Legionnaires' disease, chronic bacterial prostatitis, and some types of gastroenteritis. Along with other antibiotics it may be used to treat tuberculosis, meningitis, or pelvic inflammatory disease. It is available by mouth, intraveno

Mirtazapine, sold under the brand name Remeron among others, is an atypical tetracyclic antidepressant, and as such is used primarily to treat depression. Its effects may take up to four weeks but can also manifest as early as one to two weeks. It is often used in cases of depression complicated by anxiety or insomnia. The effectiveness of mirtazapine is comparable to other commonly prescribed antidepressants. It is taken by mouth.

HMX, also called octogen, is a powerful and relatively insensitive nitroamine high explosive chemically related to RDX. The compound's name is the subject of much speculation, having been variously listed as High Melting Explosive, High-velocity Military Explosive, or High-Molecular-weight RDX, as well as '''Her Majesty's Explosive'''.

Praziquantel, sold under the brandname Biltricide among others, is a medication used to treat a number of types of parasitic worm infections in mammals, birds, amphibians, reptiles, and fish. In humans specifically, it is used to treat schistosomiasis, clonorchiasis, opisthorchiasis, tapeworm infections, cysticercosis, echinococcosis, paragonimiasis, fasciolopsiasis, and fasciolosis. It should not be used for worm infections of the eye. It is taken by mouth.

Berberine is an organic compound classified as benzylisoquinoline alkaloid. Chemically, it is a quaternary ammonia compound.

Morpholine is an organic chemical compound having the chemical formula O(CH2CH2)2NH. This heterocycle features both amine and ether functional groups. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. For example, treating morpholine with hydrochloric acid generates the salt morpholinium chloride. It is a colorless liquid with a weak, ammonia- or fish-like odor. The naming of morpholine is attributed to Ludwig Knorr, who incorrectly believed it to be part of the structure of morphine.

Borazine, also known as borazole, inorganic benzene, is an inorganic compound with the chemical formula B3H6N3. In this cyclic compound, the three BH units and three NH units alternate. The compound is isoelectronic and isostructural with benzene. For this reason borazine is sometimes referred to as “inorganic benzene”. Like benzene, borazine is a colourless liquid with an aromatic odor.

Adamsite or DM is an organic compound; technically, an arsenical diphenylaminechlorarsine, that can be used as a riot control agent. DM belongs to the group of chemical warfare agents known as vomiting agents or sneeze gases. First synthesized in Germany by Heinrich Otto Wieland in 1915, it was independently developed by the US chemist Roger Adams (for whom it is named) at the University of Illinois in 1918.

Irbesartan, sold under the brand name Aprovel among others, is a medication used to treat hypertension (high blood pressure), heart failure, and diabetic kidney disease. It is a reasonable initial treatment for high blood pressure. It is taken by mouth. Versions are available as the combination irbesartan/hydrochlorothiazide.

Saxitoxin (STX) is a potent neurotoxin and the best-known paralytic shellfish toxin. Ingestion of saxitoxin by humans, usually by consumption of shellfish contaminated by toxic algal blooms, is responsible for the illness known as paralytic shellfish poisoning (PSP).

Tianeptine, sold under the brand names Stablon, Tatinol, and Coaxil among others, is an atypical tricyclic antidepressant which is used mainly in the treatment of major depressive disorder, although it may also be used to treat anxiety, asthma, and irritable bowel syndrome.

Cytisine, also known as baptitoxine, cytisinicline, or sophorine, is an alkaloid that occurs naturally in several plant genera, such as Laburnum and Cytisus of the family Fabaceae. It has been used medically to help with smoking cessation. It has been found effective in several randomized clinical trials, including in the United States and New Zealand, and is being investigated in additional trials in the United States and a non-inferiority trial in Australia in which it is being compared head-to-head with the smoking cessation aid varenicline (sold in the United States as Chantix). It has als

Cilazapril is an angiotensin-converting enzyme inhibitor (ACE inhibitor) used for the treatment of hypertension and congestive heart failure.

pharmaceutical drug

Nedocromil sodium is a medication considered a mast cell stabilizer which acts to prevent wheezing, shortness of breath, and other breathing problems caused by asthma. It is administered by an inhaler under the brand name Tilade, and as an eye drop under the brand name Alocril. The effects of nedocromil versus asthma are gradual rather than fast-acting and it is not indicated for acute respiratory distress compared to fast acting bronchodilators like albuterol or other well-known inhaler medications. Liquid preparations of nedocromil are available in the UK under the name Rapitil for use for a

Tecovirimat, sold under the brand name Tpoxx among others, is an antiviral medication with activity against orthopoxviruses such as smallpox and mpox. In 2018 it was the first antipoxviral drug approved in the United States.

Asenapine, sold under the brand name Saphris among others, is an atypical antipsychotic medication used to treat schizophrenia and acute mania associated with bipolar disorder as well as the medium to long-term management of bipolar disorder.

chemical compound

Dibenzazepine (iminostilbene) is a chemical compound with two benzene rings fused to an azepine ring. Many pharmaceuticals, such as carbamazepine, oxcarbazepine, and depramine, are based on a dibenzazepine structure.

Azete, also known as azacyclobutadiene, is a heterocyclic compound consisting of an unsaturated four-membered ring with three carbon atoms and one nitrogen atom. It is inherently unstable due to its 4π-electron antiaromatic character and the strain of the four-membered ring.

Retapamulin is a topical antibiotic developed by GlaxoSmithKline. It is the first drug in the new class of pleuromutilin antibiotics to be approved for human use. It is marketed as an ointment under the brand names Altabax and Altargo.

Dolasetron (trade name Anzemet) is a serotonin 5-HT3 receptor antagonist used to treat nausea and vomiting following chemotherapy. Its main effect is to reduce the activity of the vagus nerve, which is a nerve that activates the vomiting center in the medulla oblongata. It does not have much antiemetic effect when symptoms are due to motion sickness. This drug does not have any effect on dopamine receptors or muscarinic receptors.

Saxagliptin, sold under the brand name Onglyza, is an oral hypoglycemic (anti-diabetic drug) of the dipeptidyl peptidase-4 (DPP-4) inhibitor class. Early development was solely by Bristol-Myers Squibb; in 2007 AstraZeneca joined with Bristol-Myers Squibb to co-develop the final compound and collaborate on the marketing of the drug.

chemical compound

Diquat is the ISO common name for an organic dication that, as a salt with counterions such as bromide or chloride is used as a contact herbicide that produces desiccation and defoliation. Diquat is no longer approved for use in the European Union, although its registration in many other countries including the USA is still valid.

A diaziridine is a heterocyclic compound containing two nitrogen atoms in a three-membered ring. Diaziridines can be considered as strained hydrazines. Unlike most amine types of structures, the nitrogen atoms of diaziridines are configurationally stable because the ring strain prevents Walden inversion. As a result, there can be various stereoisomeric forms of this structure.

Nefopam, sold under the brand name Acupan among others, is a centrally acting, non-opioid analgesic medication, with stimulant and sympathomimetic properties that is primarily used to treat moderate to severe pain.

thumb|right|class=skin-invert-image|A generic oxaziridine derivative.

chemical compound

'''N,N′-Dimethylpropyleneurea (DMPU''') is a cyclic urea sometimes used as a polar, aprotic organic solvent. Along with the dimethylethyleneurea, it was introduced as an analog of tetramethylurea.

Cyclopamine (11-deoxojervine) is a naturally occurring steroidal alkaloid. It is a teratogenic component of corn lily (Veratrum californicum), which when consumed during gestation has been demonstrated to induce birth defects, including the development of a single eye (cyclopia) in offspring. The molecule was named after this effect, which was originally observed by Idaho lamb farmers in 1957 after their herds gave birth to cycloptic lambs. It then took more than a decade to identify corn lily as the culprit. Later work suggested that differing rain patterns had changed grazing behaviours, whi

Quinacridone is an organic compound used as a pigment. Numerous derivatives constitute the quinacridone pigment family, which finds extensive use in industrial colorant applications such as robust outdoor paints, inkjet printer ink, tattoo inks, artists' watercolor paints, and color laser printer toner. As pigments, the quinacridones are insoluble. The development of this family of pigments supplanted the alizarin dyes.

Avibactam is a non-β-lactam β-lactamase inhibitor developed by Actavis (now Teva) jointly with AstraZeneca. A new drug application for avibactam in combination with ceftazidime was approved by the FDA in 2015 for treating complicated urinary tract (cUTI) and complicated intra-abdominal infections (cIAI) caused by antibiotic-resistant pathogens, including those caused by multidrug resistant Gram-negative bacterial pathogens.

Spirapril, sold under the brand name Renormax among others, is an ACE inhibitor antihypertensive drug used to treat hypertension. It belongs to dicarboxy group of ACE inhibitors.

thumb|right|Chemical structure of mitomycin C The mitomycins are a family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae. They include mitomycin A, mitomycin B, and mitomycin C. When the name mitomycin occurs alone, it usually refers to mitomycin C, its international nonproprietary name. Mitomycin C is used as a medicine for treating various disorders associated with the growth and spread of cells.

Trovafloxacin (sold as Trovan by Pfizer and Turvel by Laboratorios Almirall) is a broad spectrum antibiotic that inhibits the uncoiling of supercoiled DNA in various bacteria by blocking the activity of DNA gyrase and topoisomerase IV. It was withdrawn from the market due to the risk of hepatotoxicity. It had better Gram-positive bacterial coverage but less Gram-negative coverage than the previous fluoroquinolones.

Hexachlorophosphazene is an inorganic compound with the chemical formula . The molecule has a cyclic, unsaturated backbone consisting of alternating phosphorus and nitrogen atoms, and can be viewed as a trimer of the hypothetical compound (phosphazyl dichloride). Its classification as a phosphazene highlights its relationship to benzene. There is large academic interest in the compound relating to the phosphorus-nitrogen bonding and phosphorus reactivity.

chemical compound

Pacritinib, sold under the brand name Vonjo, is an anti-cancer medication used to treat myelofibrosis.

thumb|100px|A generic diazirine

1,8-Diazafluoren-9-one (DFO) is an aromatic ketone first synthesized in 1950. It is used to find fingerprints and blood on porous surfaces. It makes fingerprints glow when they are lit by blue-green light.

Bulbocapnine is an alkaloid found in Corydalis (notably the European species C. cava) and Dicentra, genera of the plant family Fumariaceae which have caused (notably the American species Corydalis caseana) the fatal poisoning of sheep and cattle. It has been shown to act as an acetylcholinesterase inhibitor, and inhibits biosynthesis of dopamine via inhibition of the enzyme tyrosine hydroxylase. Like apomorphine, it is reported to be an inhibitor of amyloid beta protein (Aβ) fiber formation, whose presence is a hallmark of Alzheimer's disease (AD). Bulbocapnine is thus a potential therapeutic

Cyclen (1,4,7,10-tetraazacyclododecane) is an aza-crown ether with the formula (CH2CH2NH)4. It is a white solid. It forms coordination complexes with metal cations and is used to synthesize the chelating agent DOTA which has several medical applications. Being structurally simple, symmetrical, and polyfunctional, cyclen has been widely investigated.

Rimegepant, sold under the brand name Nurtec ODT among others, is a medication used for the acute treatment of migraine with or without aura in adults and the prophylactic treatment of episodic migraine in adults. It is taken by mouth to dissolve on or under the tongue. It works by blocking CGRP receptors.

Plerixafor, sold under the brand name Mozobil, is an immunostimulant used to mobilize hematopoietic stem cells in cancer patients into the bloodstream. The stem cells are then extracted from the blood and transplanted back to the patient. The drug was developed by AnorMED, which was subsequently bought by Genzyme.

Iprindole, sold under the brand names Prondol, Galatur, and Tertran, is an atypical tricyclic antidepressant (TCA) that has been used in the United Kingdom and Ireland for the treatment of depression but appears to no longer be marketed. It was developed by Wyeth and was marketed in 1967. The drug has been described by some as the first "second-generation" antidepressant to be introduced. However, it was very little-used compared to other TCAs, with the number of prescriptions dispensed only in the thousands.

Tetramethylenedisulfotetramine (TETS) is an organic compound used as a rodenticide (rat poison). It is an odorless, tasteless white powder that is slightly soluble in water, DMSO and acetone, and insoluble in methanol and ethanol. It is a sulfamide derivative. It can be synthesized by reacting sulfamide with formaldehyde solution in acidified water. When crystallized from acetone, it forms cubic crystals with a melting point of 255–260 °C.

Anatoxin-a, also known as Very Fast Death Factor (VFDF), is a secondary, bicyclic amine alkaloid and cyanotoxin with acute neurotoxicity. It was first discovered in the early 1960s in Canada, and was isolated in 1972. The toxin is produced by multiple genera of cyanobacteria and has been reported in North America, South America, Central America, Europe, Africa, Asia, and Oceania. Symptoms of anatoxin-a toxicity include loss of coordination, muscular fasciculations, convulsions and death by respiratory paralysis. Its mode of action is through the nicotinic acetylcholine receptor (nAchR) where i

NBQX (2,3-dioxo-6-nitro-7-sulfamoyl-benzo[f]quinoxaline) is an antagonist of the AMPA receptor.

chemical compound

Selectfluor, a trademark of Air Products and Chemicals, is a reagent in chemistry that is used as a fluorine donor. This compound is a derivative of the nucleophillic base DABCO. It is a colourless salt that tolerates air and even water. It has been commercialized for use for electrophilic fluorination.

Isoalloxazine is the structural foundation of flavins such as riboflavin (vitamin B2) and is a heterocyclic compound. It has a tricyclic structure which means it has three interconnected rings of atoms and is a tautomer of alloxazine. The structure is formed by primary-secondary aromatic o-diamines and they are a high-melting crystalline substance. The R-group is used to attach various flavin groups It has a similar structure to pteridines which has two interconnected rings. Isoalloxazine was first obtained in 1934 by Richard Kuhn an Austrian-German biochemist and lab mates. thumb|Isoalloxazin

Ebselen (also called PZ 51, DR3305, and SPI-1005), is a synthetic organoselenium molecule under preliminary investigation as a drug candidate. It belongs to the class of compounds related to benzene and its derivatives. It is being developed by the Seattle biotechnology company, Sound Pharmaceuticals, Inc. It has also been reported to target tubulin, blocking its polymerization.

Pseudopelletierine is the main alkaloid derived from the root-bark of the pomegranate tree (Punica granatum), along with at least three other alkaloids: pelletierine, isopelletierine, and methylpelletierine (C9H17ON), which yield 1.8, 0.52, 0.01, and 0.20 grams per kilogram of raw bark.