1-Pyrrolidinyl compounds

Triprolidine is an over-the-counter antihistamine with anticholinergic properties. It is used to combat the symptoms associated with allergies and is sometimes combined with other cold medications designed to provide general relief for flu-like symptoms. As with many antihistamines, the most common side effect is drowsiness.

Acrivastine is a medication used for the treatment of allergies and hay fever. It is a second-generation H1-receptor antagonist antihistamine (like its base molecule triprolidine) and works by blocking histamine H1 receptors.

Almotriptan, sold under the brand names Axert and Almogran among others, is a triptan medication used in the treatment of heavy migraine headache.

Trifarotene, sold under the brand name Aklief, is a medication for the topical treatment of acne vulgaris. It is a retinoid; specifically, a fourth-generation selective retinoic acid receptor (RAR)-γ agonist.

Buflomedil, sold under the brand name Loftyl, is a vasoactive drug used to treat claudication or the symptoms of peripheral arterial disease. It is currently not approved by the Food and Drug Administration (FDA) for use in the United States.

Procyclidine is an anticholinergic drug principally used for the treatment of drug-induced parkinsonism, akathisia and acute dystonia, Parkinson's disease, and idiopathic or secondary dystonia.

Dextromoramide (Palfium, Palphium, Jetrium, Dimorlin) 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.

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

PyBOP (benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate) is a reagent used to prepare amides from carboxylic acids and amines in the context of peptide synthesis. It can be prepared from 1-hydroxybenzotriazole and a chlorophosphonium reagent under basic conditions. It is a substitute for the BOP reagent that avoids the formation of the carcinogenic waste product HMPA. Thermal hazard analysis by differential scanning calorimetry (DSC) shows PyBOP is potentially explosive.

Prolintane is a central nervous system (CNS) stimulant and norepinephrine–dopamine reuptake inhibitor (NDRI) of the phenylalkylpyrrolidine family developed in the 1950s. Being an amphetamine derivative, it is closely related in chemical structure to other drugs such as pyrovalerone, MDPV, and propylhexedrine, and has a similar mechanism of action. Many cases of prolintane abuse have been reported.

Ormeloxifene, also known as centchroman, is one of the selective estrogen receptor modulators, or SERMs, a class of medication which acts on the estrogen receptor. It is best known as a nonsteroidal oral contraceptive which is taken once per week. In India, ormeloxifene has been available as birth control since the early 1990s, and it was marketed there under the trade name Saheli, currently available free-of-cost for the women in India as Chhaya (Centchroman).

Bepridil (trade name Vascor) is an diamine calcium channel blocker once used to treat angina pectoris. It is no longer sold in the United States.

Lasofoxifene, sold under the brand name Fablyn, is a nonsteroidal selective estrogen receptor modulator (SERM) which is marketed by Pfizer in Lithuania and Portugal for the prevention and treatment of osteoporosis and for the treatment of vaginal atrophy, and the result of an exclusive research collaboration with Ligand Pharmaceuticals (LGND). It also appears to have had a statistically significant effect of reducing breast cancer in women according to a study published in The Journal of the National Cancer Institute.

Piretanide is a loop diuretic compound by using a then-new method for introducing cyclic amine residues in an aromatic nucleus in the presence of other aromatically bonded functional groups. Studies of piretanide in rats and dogs in comparison with other high-ceiling diuretics such as furosemide and bumetanide found a more suitable dose/response rate (regression line) and a more favourable sodium/potassium excretion ratio. These findings led eventually to studies in man and finally to the introduction as a saluretic and antihypertensive medication in Germany, France, Italy and other countries.

Rolitetracycline is a tetracycline antibiotic. Tetracycline is N-Mannich base prodrug that is prepared from tetracycline by condensation with pyrrolidine and formaldehyde to produce rolitetracycline. Rolitetracycline is used as an antibacterial drug, a protein synthesis inhibitor, an antiprotozoal drug and a prodrug.

Fedratinib, sold under the brand name Inrebic, is an anti-cancer medication used to treat myeloproliferative diseases including myelofibrosis. It is used in the form of fedratinib hydrochloride capsules that are taken by mouth. It is a semi-selective inhibitor of Janus kinase 2 (JAK-2). It was approved by the FDA on 16 August 2019.

Tremorine is a drug which is used in scientific research to produce tremor in animals. This is used for the development of drugs for the treatment of Parkinson's disease, as tremor is a major symptom which is treated by anti-Parkinson's drugs. Beta blockers are also effective in counteracting the effects of tremorine.

chemical compound

Histapyrrodine is an antihistamine with anticholinergic properties.

Glyclopyramide (INN, marketed under the tradename Deamelin-S) is a sulfonylurea drug used in the treatment of diabetes. It has been marketed in Japan since 1965.

Pyr-T, also known as '''N,N-tetramethylenetryptamine or as 3-(2-pyrrolidinoethyl)indole', is a lesser-known serotonin receptor modulator of the tryptamine and pyrrolidinylethylindole families. It is the cyclized derivative of diethyltryptamine (DET) in which the N,N''-diethyl groups have been fused into a pyrrolidine ring.

Rolicyclidine (PCPy) is a dissociative anesthetic that is similar in effects to phencyclidine, but is slightly less potent and has fewer stimulant effects. It instead produces a sedative effect described as being somewhat similar to a barbiturate, but with additional PCP-like dissociative, anaesthetic and hallucinogenic effects. Due to its similarity in effects to PCP, PCPy was placed into the Schedule I list of illegal drugs in the 1970s, although it has never been widely abused and is now little known.

Pyrrobutamine is an antihistamine and anticholinergic.

Eravacycline (TP-434, Xerava) is a synthetic halogenated tetracycline class antibiotic by Tetraphase Pharmaceuticals. It is closely related to tigecycline. It has a broad spectrum of activity including many multi-drug resistant strains of bacteria. Phase III studies in complicated intra-abdominal infections (cIAI) and complicated urinary tract infections (cUTI) were recently completed with mixed results. Eravacycline was granted fast track designation by the FDA and is currently available in USA.

Tirilazad is a drug that has been proposed to treat acute ischaemic stroke. When tested on animal models, tirilazad protects brain tissue, and reduces brain damage. However, the drug fails to treat, and even worsens a stroke when studied on a human being.

U-89843A (PNU-89843) is a sedative drug which acts as an agonist at GABAA receptors, specifically acting as a positive allosteric modulator selective for the α1, α3 and α6 subtypes. It has sedative effects in animals but without causing ataxia, and also acts as an antioxidant and may have neuroprotective effects. It was developed by a team at Upjohn in the 1990s.

Butinoline (Azulone) is an anticholinergic drug used as an antispasmodic.

Nafoxidine (; developmental code names U-11,000A) or nafoxidine hydrochloride () is a nonsteroidal selective estrogen receptor modulator (SERM) or partial antiestrogen of the triphenylethylene group that was developed for the treatment of advanced breast cancer by Upjohn in the 1970s but was never marketed. It was developed at around the same time as tamoxifen and clomifene, which are also triphenylethylene derivatives. The drug was originally synthesized by the fertility control program at Upjohn as a postcoital contraceptive, but was subsequently repurposed for the treatment of breast cancer

Racemoramide (INN, BAN), or simply moramide, is an opioid analgesic and a racemic mixture of the substances dextromoramide (the active component) and levomoramide (which is inactive), two enantiomers of a chiral molecule.

Cinepazide or cinepazide maleate (Kelinao or Anjieli in China) is a vasodilator used in China for the treatment of cardiovascular and cerebrovascular diseases, and peripheral vascular diseases. It appears to work by potentiating A2 adenosine receptors.

4-HO-pyr-T, also known as '4-hydroxy-N,N-tetramethylenetryptamine', is a serotonin receptor modulator of the tryptamine, 4-hydroxytryptamine, and pyrrolidinylethylindole families. It is the 4-hydroxyl analogue of pyr-T and the analogue of psilocin (4-HO-DMT) and 4-HO-DET in which the N,N-dialkyl moiety has been cyclized into a pyrrolidine ring.

Toceranib (INN), sold under the brand name Palladia, is a receptor tyrosine kinase inhibitor that is used in the treatment of canine mast cell tumor also called mastocytoma. It is the first medication developed specifically for the treatment of cancer in dogs. It is used as its phosphate salt, toceranib phosphate. It was developed by SUGEN as SU11654, a sister compound to sunitinib, which was later approved for human therapies. Toceranib is a tyrosine kinase inhibitor and works in two ways: by killing tumor cells and by cutting off the blood supply to the tumor.

5-MeO-pyr-T, also known as '5-methoxy-N,N-tetramethylenetryptamine or as 5-methoxy-3-(2-pyrrolidinoethyl)indole', is a serotonin receptor modulator and psychedelic drug of the tryptamine, 5-methoxytryptamine, and pyrrolidinylethylindole families. It is the 5-methoxy analogue of pyr-T and the derivative of 5-MeO-DMT and 5-MeO-DET in which their N,N-dialkyl groups have been cyclized into a pyrrolidine ring.

Clemizole, sold under the brand names Allercur and Histacur, is a histamine H1 receptor antagonist of the benzimidazole group described as an antihistamine, antipruritic, and sedative which is no longer marketed. It is a first-generation antihistamine.

1-(2-Phenylethyl)pyrrolidine (PEP) is a chemical compound of the phenethylamine family. It is an analogue of 2-phenylethylamine where the amine has been replaced by a pyrrolidine ring.

chemical compound

U-50488 is a drug which acts as a highly selective κ-opioid agonist, but without any μ-opioid antagonist effects. It has analgesic, diuretic and antitussive effects, and reverses the memory impairment produced by anticholinergic drugs. U-50488 was one of the first selective kappa agonists invented and research on its derivatives has led to the development of a large family of related compounds. This compound has never received FDA approval and there are no reported human cases in the literature involving an U-50488 overdose.

Amixetrine (INN; brand name Somagest; developmental code CERM-898) is a drug that was formerly marketed in France but is now no longer sold. According to various sources it has been said to be an anti-inflammatory, antidepressant, antispasmodic, anticholinergic, antihistamine, and antiserotonergic, but its definitive indications and pharmacology are unclear. The drug was first synthesized in 1969 and was introduced in France in 1972.

Fluorolintane (also known as 2-FPPP and 2-F-DPPy) is a dissociative anesthetic drug that has been sold online as a designer drug.

HBI-3000 (sulcardine sulfate) is an experimental drug candidate that is currently in phase II of human clinical trials as an antiarrhythmic agent. Clinical investigation will test the safety and efficacy of HBI-3000 as a treatment for both atrial and ventricular arrhythmias.

GR-89696 is a drug which acts as a highly selective κ-opioid agonist. It has been studied in various animal species, and has been described as selective for the κ2 subtype. Recent studies have suggested that GR-89696 and related κ2-selective agonists may be useful for preventing the itching which is a common side effect of conventional opioid analgesic drugs, without the additional side effects of non-selective kappa agonists. The structure bound to the κ-opioid receptor has been reported.

α-Pyrrolidinopentiothiophenone (also known as α-PVT) is a synthetic stimulant of the cathinone and thiopropamine (thiophenylpropylamine) families that has been sold online as a designer drug. It is an analogue of α-PVP where the phenyl ring has been replaced by thiophene.

'''N-Pyrrolidyllysergamide (LPD-824), also known as lysergic acid pyrrolidide (LA-Pyr'), is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD). It is the analogue of LSD in which the N,N-diethylamide moiety has been cyclized into an N,N''-pyrrolidide ring.