Classification Term: 2643
Tropane alkaloids (ontology term: CHEMONTID:0000492)
Organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane." []
found 32 associated metabolites at class metabolite taxonomy ontology rank level.
Ancestor: Alkaloids and derivatives
Child Taxonomies: Phenyltropanes
Hyoscyamine
(S)-atropine is an atropine with a 2S-configuration. It is functionally related to a (S)-tropic acid. It is a conjugate base of a (S)-atropinium. Hyoscyamine is a tropane alkaloid and the levo-isomer of [atropine]. It is commonly extracted from plants in the Solanaceae or nightshade family. Research into the action of hyoscyamine in published literature dates back to 1826. Hyoscyamine is used for a wide variety of treatments and therapeutics due to its antimuscarinic properties. Although hyoscyamine is marketed in the United States, it is not FDA approved. Hyoscyamine as a natural plant alkaloid derivative and anticholinergic that is used to treat mild to moderate nausea, motion sickness, hyperactive bladder and allergic rhinitis. Hyoscyamine has not been implicated in causing liver enzyme elevations or clinically apparent acute liver injury. L-Hyoscyamine is a natural product found in Datura ferox, Crenidium spinescens, and other organisms with data available. Hyoscyamine is a belladonna alkaloid derivative and the levorotatory form of racemic atropine isolated from the plants Hyoscyamus niger or Atropa belladonna, which exhibits anticholinergic activity. Hyoscyamine functions as a non-selective, competitive antagonist of muscarinic receptors, thereby inhibiting the parasympathetic activities of acetylcholine on the salivary, bronchial, and sweat glands, as well as the eye, heart, bladder, and gastrointestinal tract. These inhibitory effects cause a decrease in saliva, bronchial mucus, gastric juices, and sweat. Furthermore, its inhibitory action on smooth muscle prevents bladder contraction and decreases gastrointestinal motility. The 3(S)-endo isomer of atropine. Hyoscyamine is a chemical compound, a tropane alkaloid it is the levo-isomer to atropine. It is a secondary metabolite of some plants, particularly henbane (Hyoscamus niger.). Hyoscyamine is used to provide symptomatic relief to various gastrointestinal disorders including spasms, peptic ulcers, irritable bowel syndrome, pancreatitis, colic and cystitis. It has also been used to relieve some heart problems, control some of the symptoms of Parkinsons disease, as well as for control of respiratory secretions in end of life care. A - Alimentary tract and metabolism > A03 - Drugs for functional gastrointestinal disorders > A03B - Belladonna and derivatives, plain > A03BA - Belladonna alkaloids, tertiary amines C78272 - Agent Affecting Nervous System > C66880 - Anticholinergic Agent > C29704 - Antimuscarinic Agent D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents > D001993 - Bronchodilator Agents D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D010276 - Parasympatholytics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D009184 - Mydriatics D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2269 D002491 - Central Nervous System Agents KEIO_ID H045; [MS2] KO008998 KEIO_ID H045 L-Hyoscyamine (Daturine), a natural plant tropane alkaloid, is a potent and competitive muscarinic receptor (MR) antagonist. L-Hyoscyamine is a levo-isomer to Atropine (HY-B1205)[1][2]. L-Hyoscyamine (Daturine), a natural plant tropane alkaloid, is a potent and competitive muscarinic receptor (MR) antagonist. L-Hyoscyamine is a levo-isomer to Atropine (HY-B1205)[1][2]. L-Hyoscyamine (Daturine), a natural plant tropane alkaloid, is a potent and competitive muscarinic receptor (MR) antagonist. L-Hyoscyamine is a levo-isomer to Atropine (HY-B1205)[1][2].
Ecgonine methyl ester
Ecgonine methyl ester is a major metabolite of cocaine. It is generally not measured by HPLC because it is poorly detectable by UV, and its water solubility makes recovery from urine difficult. Using modified solid-phase extraction procedures, recoveries of 85\\% for ecgonine methyl ester could be obtained from urine. (PMID:1298401) [HMDB] Ecgonine methyl ester is a major metabolite of cocaine. It is generally not measured by HPLC because it is poorly detectable by UV, and its water solubility makes recovery from urine difficult. Using modified solid-phase extraction procedures, recoveries of 85\\% for ecgonine methyl ester could be obtained from urine. (PMID:1298401). CONFIDENCE standard compound; INTERNAL_ID 1618
tropinone
Tropinone, also known as 3-tropanone, is a member of the class of compounds known as tropane alkaloids. Tropane alkaloids are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane. Tropinone is soluble (in water) and an extremely weak acidic compound (based on its pKa). Tropinone can be found in a number of food items such as walnut, japanese persimmon, komatsuna, and chicory roots, which makes tropinone a potential biomarker for the consumption of these food products. Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. Its corresponding conjugate acid at pH 7.3 major species is known as tropiniumone . KEIO_ID T061 Tropinone, an alkaloid, acts as a synthetic intermediate to?Atropine[1].
Ecgonine
Ecgonine is an organic chemical and tropane alkaloid found naturally in coca leaves. It is has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance, as are all known substances which can be used as precursors to ecgonine itself. Structurally, ecgonine is a cycloheptane derivative with a nitrogen bridge. It is obtained by hydrolysis of cocaine with acids or alkalis, and crystallizes with one molecule of water, the crystals melting at 198-199oC. It is levorotary, and on warming with alkalis gives iso-ecgonine, which is dextrorotary. It is a tertiary base, and has the properties of an acid and an alcohol. It is the carboxylic acid corresponding to tropine, for it yields the same products on oxidation, and by treatment with phosphorus pentachloride is converted into anhydroecgonine, C9H13NO2, which, when heated to 280oC with hydrochloric acid, eliminates carbon dioxide and yields tropidine, C8H13N.(Wikipedia). Ecgonine is an organic chemical and tropane alkaloid found naturally in coca leaves. It is has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance, as are all known substances which can be used as precursors to ecgonine itself. Structurally, ecgonine is a cycloheptane derivative with a nitrogen bridge. It is obtained by hydrolysis of cocaine with acids or alkalis, and crystallizes with one molecule of water, the crystals melting at 198-199oC. It is levorotary, and on warming with alkalis gives iso-ecgonine, which is dextrorotary. It is a tertiary base, and has the properties of an acid and an alcohol. It is the carboxylic acid corresponding to tropine, for it yields the same products on oxidation, and by treatment with phosphorus pentachloride is converted into anhydroecgonine, C9H13NO2, which, when heated to 280oC with hydrochloric acid, eliminates carbon dioxide and yields tropidine, C8H13N. [HMDB] D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D009294 - Narcotics D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics
Ipratropium bromide
C20H30NO3+ (332.22255700000005)
Ipratropium bromide is only found in individuals that have used or taken this drug. It is a muscarinic antagonist structurally related to atropine but often considered safer and more effective for inhalation use. It is used for various bronchial disorders, in rhinitis, and as an antiarrhythmic. [PubChem]Ipratropium bromide is an anticholinergic agent. It blocks muscarinic cholinergic receptors, without specificity for subtypes, resulting in a decrease in the formation of cyclic guanosine monophosphate (cGMP). Most likely due to actions of cGMP on intracellular calcium, this results in decreased contractility of smooth muscle. D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents > D001993 - Bronchodilator Agents D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents
Calystegin A3
Alkaloid from Solanum tuberosum (potato). Calystegin A3 is found in many foods, some of which are eggplant, alcoholic beverages, potato, and sweet potato. Calystegin A3 is found in alcoholic beverages. Calystegin A3 is an alkaloid from Solanum tuberosum (potato).
Calystegine B2
Alkaloid from Solanum tuberosum (potato), Solanum melongena (aubergine). Calystegine B2 is found in many foods, some of which are alcoholic beverages, fruits, swamp cabbage, and eggplant. Calystegine B2 is found in alcoholic beverages. Calystegine B2 is an alkaloid from Solanum tuberosum (potato), Solanum melongena (aubergine).
Physoperuvine
Physoperuvine is found in fruits. Physoperuvine is an alkaloid from Physalis peruviana (Cape gooseberry
Tigloidine
C13H21NO2 (223.15722060000002)
Tigloyltropeine is found in fruits. Tigloyltropeine is an alkaloid from Physalis alkekengi (winter cherry) roots. Alkaloid from Physalis alkekengi (winter cherry). Tigloidine is found in fruits. Tigloidin is an analogue of atropine, with anticholinergic activity. Tigloidin is an analogue of atropine, with anticholinergic activity.
Pseudoecgonine
Pseudoecgonine is a metabolic byproduct of cocaine. Cocaine is extensively metabolized in the liver, with only about 1\\% excreted unchanged in the urine. The metabolism is dominated by hydrolytic ester cleavage, so the eliminated metabolites consist mostly of benzoylecgonine, the major metabolite, and in lesser amounts ecgonine methyl ester and ecgonine. Pseudoecgonine is a steroisomer of ecgonine and may be conjugated to CoA to form Pseudoecgonyl-CoA through the action of gut microlfora (PMID: 8572717). [HMDB] Pseudoecgonine is a metabolic byproduct of cocaine. Cocaine is extensively metabolized in the liver, with only about 1\\% excreted unchanged in the urine. The metabolism is dominated by hydrolytic ester cleavage, so the eliminated metabolites consist mostly of benzoylecgonine, the major metabolite, and in lesser amounts ecgonine methyl ester and ecgonine. Pseudoecgonine is a steroisomer of ecgonine and may be conjugated to CoA to form Pseudoecgonyl-CoA through the action of gut microlfora (PMID: 8572717).
Maraviroc
C29H41F2N5O (513.3279000000001)
Maraviroc (brand-named Selzentry, or Celsentri outside the U.S.) is a chemokine receptor antagonist drug developed by the drug company Pfizer that is designed to act against HIV by interfering with the interaction between HIV and CCR5. It was originally labelled as UK-427857 during development but was assigned the Maraviroc name as it entered trials. It was approved for use by the FDA in August, 2007. J - Antiinfectives for systemic use > J05 - Antivirals for systemic use > J05A - Direct acting antivirals D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D065147 - Viral Fusion Protein Inhibitors D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D044966 - Anti-Retroviral Agents COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials C254 - Anti-Infective Agent > C281 - Antiviral Agent > C1660 - Anti-HIV Agent D065147 - Viral Fusion Protein Inhibitors > D023581 - HIV Fusion Inhibitors C308 - Immunotherapeutic Agent > C63817 - Chemokine Receptor Antagonist D065100 - CCR5 Receptor Antagonists Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS
Calystegine A7
Calystegine A7 is an alkaloid from the roots of Lycium chinense (Chinese boxthorn). Alkaloid from the roots of Lycium chinense (Chinese boxthorn)
Calystegine C1
Alkaloid from Morus alba (white mulberry) and Lycium chinense (Chinese boxthorn). Calystegine C1 is found in many foods, some of which are tea, coffee and coffee products, fruits, and herbs and spices. Calystegine C2 is found in coffee and coffee products. Calystegine C2 is an alkaloid from Lycium chinense (Chinese boxthorn).
Nor-psi-tropine
Nor-psi-tropine is found in fruits. Nor-psi-tropine is an alkaloid from the fruit of Morus alba (white mulberry
Calystegine A6
Calystegine A6 is found in coffee and coffee products. Calystegine A6 is an alkaloid from and Lycium chinense (Chinese boxthorn
3beta,6beta-Dihydroxynortropane
(3S,6R)-8-Azabicyclo[3.2.1]octane-3,6-diol is found in fruits. (3S,6R)-8-Azabicyclo[3.2.1]octane-3,6-diol is an alkaloid from the fruit of Morus alba (white mulberry). Alkaloid from the fruit of Morus alba (white mulberry). 3beta,6beta-Dihydroxynortropane is found in fruits.
N-Methylcalystegine C1
N-Methylcalystegine C1 is an alkaloid from the roots of Lycium chinense (Chinese boxthorn). Alkaloid from the roots of Lycium chinense (Chinese boxthorn)
3,6-Ditigloyloxytropan-7-ol
3,6-Ditigloyloxytropan-7-ol is found in fruits. 3,6-Ditigloyloxytropan-7-ol is an alkaloid present in Cyphomandra betacea (tree tomato
(3beta,5alpha,6alpha)-Cholest-8-ene-3,6-diol
(3beta,5alpha,6alpha)-Cholest-8-ene-3,6-diol is found in fruits. (3beta,5alpha,6alpha)-Cholest-8-ene-3,6-diol is obtained from roots of Stenocereus thurberi (organ pipe cactus
N-Methylcalystegine B2
N-Methylcalystegine B2 is an alkaloid from the roots of Lycium chinense (Chinese boxthorn). Alkaloid from the roots of Lycium chinense (Chinese boxthorn)
Alkaloid AQC2
C19H22N2O3 (326.16303419999997)
Alkaloid AQC2 is an alkaloid AQC2 is an alkaloid from cell cultures of Aspidosperma quebracho-blanco (quebracho)
Calystegine B5
Calystegine B5 is an alkaloid from the roots of Lycium chinense (Chinese boxthorn). Alkaloid from the roots of Lycium chinense (Chinese boxthorn)
3alpha-Tigloyloxytropane N-oxide
3alpha-Tigloyloxytropane N-oxide is found in fruits. 3alpha-Tigloyloxytropane N-oxide is an alkaloid from Physalis alkekengi (winter cherry). Alkaloid from Physalis alkekengi (winter cherry). 3alpha-Tigloyloxytropane N-oxide is found in fruits.
(+)-Hyoscyamine
Atropine, a naturally occurring belladonna alkaloid, is a racemic mixture of equal parts of d- and l-hyoscyamine, whose activity is due almost entirely to the levo isomer of the drug. Atropine is commonly classified as an anticholinergic or antiparasympathetic (parasympatholytic) drug. More precisely, however, it is termed an antimuscarinic agent since it antagonizes the muscarine-like actions of acetylcholine and other choline esters. Adequate doses of atropine abolish various types of reflex vagal cardiac slowing or asystole. The drug also prevents or abolishes bradycardia or asystole produced by injection of choline esters, anticholinesterase agents or other parasympathomimetic drugs, and cardiac arrest produced by stimulation of the vagus. Atropine may also lessen the degree of partial heart block when vagal activity is an etiologic factor. Atropine in clinical doses counteracts the peripheral dilatation and abrupt decrease in blood pressure produced by choline esters. However, when given by itself, atropine does not exert a striking or uniform effect on blood vessels or blood pressure. Atropine is found in burdock. Atropine (Tropine tropate) is a competitive muscarinic acetylcholine receptor (mAChR) antagonist with IC50 values of 0.39 and 0.71 nM for Human mAChR M4 and Chicken mAChR M4, respectively. Atropine inhibits ACh-induced relaxations in human pulmonary veins. Atropine can be used for research of anti-myopia and bradycardia[1][2][3][4]. Atropine (Tropine tropate) is a competitive muscarinic acetylcholine receptor (mAChR) antagonist with IC50 values of 0.39 and 0.71 nM for Human mAChR M4 and Chicken mAChR M4, respectively. Atropine inhibits ACh-induced relaxations in human pulmonary veins. Atropine can be used for research of anti-myopia and bradycardia[1][2][3][4]. Atropine (Tropine tropate) is a competitive muscarinic acetylcholine receptor (mAChR) antagonist with IC50 values of 0.39 and 0.71 nM for Human mAChR M4 and Chicken mAChR M4, respectively. Atropine inhibits ACh-induced relaxations in human pulmonary veins. Atropine can be used for research of anti-myopia and bradycardia[1][2][3][4].
6-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
(8-Methyl-8-azabicyclo[3.2.1]octan-3-yl) 3-methoxy-2-phenylpropanoate
C18H25NO3 (303.18343400000003)
Tropine
Pseudotropine, also known as tropine hydrochloride, (endo)-isomer or tropine, (exo)-isomer, is a member of the class of compounds known as tropane alkaloids. Tropane alkaloids are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane. Pseudotropine is soluble (in water) and an extremely weak acidic compound (based on its pKa). Pseudotropine can be found in a number of food items such as winter savory, japanese chestnut, blackcurrant, and black walnut, which makes pseudotropine a potential biomarker for the consumption of these food products. Pseudotropine (3β-tropanol, ψ-tropine, 3-pseudotropanol or PTO) is a derivative of tropane and an isomer of tropine . Tropine is a secondary metabolite of Solanaceae plants, is an anticholinergic agent[1]. Tropine is a common intermediate in the synthesis of a variety of bioactive alkaloids, including hyoscyamine and scopolamine[2]. Tropine is a secondary metabolite of Solanaceae plants, is an anticholinergic agent[1]. Tropine is a common intermediate in the synthesis of a variety of bioactive alkaloids, including hyoscyamine and scopolamine[2].