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101-31-5 | Benzeneacetic acid, α-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (αS)-
CAS No: 101-31-5 Catalog No: AG0003FJ MDL No:MFCD00067306
Product Description
Catalog Number:
AG0003FJ
Chemical Name:
Benzeneacetic acid, α-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (αS)-
CAS Number:
101-31-5
Molecular Formula:
C17H23NO3
Molecular Weight:
289.3694
MDL Number:
MFCD00067306
IUPAC Name:
[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2S)-3-hydroxy-2-phenylpropanoate
InChI:
InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15?,16-/m1/s1
InChI Key:
RKUNBYITZUJHSG-VFSICIBPSA-N
SMILES:
OC[C@H](c1ccccc1)C(=O)OC1C[C@@H]2CC[C@H](C1)N2C
UNII:
PX44XO846X
Properties
Complexity:
353
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
3
Defined Bond Stereocenter Count:
0
Exact Mass:
289.168g/mol
Formal Charge:
0
Heavy Atom Count:
21
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
289.375g/mol
Monoisotopic Mass:
289.168g/mol
Rotatable Bond Count:
5
Topological Polar Surface Area:
49.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.8
Literature
| Title | Journal |
|---|---|
| Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine. | Bioorganic & medicinal chemistry 20121115 |
| Enhancing the production of tropane alkaloids in transgenic Anisodus acutangulus hairy root cultures by over-expressing tropinone reductase I and hyoscyamine-6β-hydroxylase. | Molecular bioSystems 20121101 |
| Induced production of mycotoxins in an endophytic fungus from the medicinal plant Datura stramonium L. | Bioorganic & medicinal chemistry letters 20121015 |
| Functional characterization of recombinant hyoscyamine 6β-hydroxylase from Atropa belladonna. | Bioorganic & medicinal chemistry 20120715 |
| Accidental poisoning after ingestion of 'aphrodisiac' berries: diagnosis by analytical toxicology. | The Journal of emergency medicine 20120601 |
| Antioxidant and cytotoxic effects of hexane extract of Morinda pubescens leaves in human liver cancer cell line. | Asian Pacific journal of tropical medicine 20120501 |
| Determination of tropane alkaloids atropine and scopolamine by liquid chromatography-mass spectrometry in plant organs of Datura species. | Journal of chromatography. A 20120406 |
| A non-aqueous solid phase extraction method for alkaloid enrichment and its application in the determination of hyoscyamine and scopolamine. | The Analyst 20120321 |
| Chromium-induced tropane alkaloid production and H6H gene expression in Atropa belladonna L. (Solanaceae) in vitro-propagated plantlets. | Plant physiology and biochemistry : PPB 20120301 |
| Norlittorine and norhyoscyamine identified as products of littorine and hyoscyamine metabolism by (13)C-labeling in Datura innoxia hairy roots. | Phytochemistry 20120201 |
| Massive atropine eye drop ingestion treated with high-dose physostigmine to avoid intubation. | The western journal of emergency medicine 20120201 |
| Application of an enantioselective LC-ESI MS/MS procedure to determine R- and S-hyoscyamine following intravenous atropine administration in swine. | Drug testing and analysis 20120101 |
| Natural products from ethnodirected studies: revisiting the ethnobiology of the zombie poison. | Evidence-based complementary and alternative medicine : eCAM 20120101 |
| Inorganic ions in the medium modify tropane alkaloids and riboflavin output in Hyoscyamus niger root cultures. | Pharmacognosy magazine 20120101 |
| Tropane alkaloids of Datura innoxia from Morocco. | Zeitschrift fur Naturforschung. C, Journal of biosciences 20120101 |
| Atropa belladonna intoxication: a case report. | The Pan African medical journal 20120101 |
| Enhancing the scopolamine production in transgenic plants of Atropa belladonna by overexpressing pmt and h6h genes. | Physiologia plantarum 20111201 |
| Atropine maintenance dosage in patients with severe organophosphate pesticide poisoning. | Toxicology letters 20110925 |
| Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | Journal of medicinal chemistry 20110714 |
| Functional identification of hyoscyamine 6β-hydroxylase from Anisodus acutangulus and overproduction of scopolamine in genetically-engineered Escherichia coli. | Biotechnology letters 20110701 |
| Treatment of irritable bowel syndrome. | Journal of clinical pharmacy and therapeutics 20110601 |
| Bone reaction to a biomimetic third-generation hydroxyapatite coating and new surface treatment for the Symax hip stem. | The Journal of bone and joint surgery. British volume 20110601 |
| Analgesic and antineuropathic drugs acting through central cholinergic mechanisms. | Recent patents on CNS drug discovery 20110501 |
| Treatment choice, duration, and cost in patients with interstitial cystitis and painful bladder syndrome. | International urogynecology journal 20110401 |
| Nine new tropane alkaloids from Datura stramonium L. identified by GC/MS. | Fitoterapia 20110301 |
| Identification of genes differentially expressed in a resistant reaction to Mycosphaerella pinodes in pea using microarray technology. | BMC genomics 20110101 |
| Multiple protein kinases determine the phosphorylated state of the small heat shock protein, HSP27, in SH-SY5Y neuroblastoma cells. | Neuropharmacology 20110101 |
| Nocturnal enuresis. | BMJ clinical evidence 20110101 |
| Co-expression of AaPMT and AaTRI effectively enhances the yields of tropane alkaloids in Anisodus acutangulus hairy roots. | BMC biotechnology 20110101 |
| Gallbladder agenesis. | Case reports in gastroenterology 20110101 |
| Biochemical and structural characterization of recombinant hyoscyamine 6β-hydroxylase from Datura metel L. | Plant physiology and biochemistry : PPB 20101201 |
| Hospice use and outcomes in nursing home residents with advanced dementia. | Journal of the American Geriatrics Society 20101201 |
| High-performance liquid-chromatographic tandem-mass spectrometric methods for atropinesterase-mediated enantioselective and chiral determination of R- and S-hyoscyamine in plasma. | Analytica chimica acta 20101108 |
| An anesthetic experience with cesarean section in a patient with vasovagal syncope -A case report-. | Korean journal of anesthesiology 20100801 |
| DFT-GIAO(1)H NMR chemical shifts prediction for the spectral assignment and conformational analysis of the anticholinergic drugs (-)-scopolamine and (-)-hyoscyamine. | Magnetic resonance in chemistry : MRC 20100601 |
| 'Divine stramonium': the rise and fall of smoking for asthma. | Medical history 20100401 |
| Anisodamine production from natural sources: seedlings and hairy root cultures of Argentinean and Colombian Brugmansia candida plants. | Planta medica 20100301 |
| Production of tropane alkaloids during de-differentiation of Scopolia parviflora calli. | Journal of natural products 20100226 |
| Cementless total hip replacement: a prospective clinical study of the early functional and radiological outcomes of three different hip stems. | Archives of orthopaedic and trauma surgery 20100101 |
| Tropane alkaloid profiling of hydroponic Datura innoxia Mill. Plants inoculated with Agrobacterium rhizogenes. | Phytochemical analysis : PCA 20100101 |
| Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions. | Clinical interventions in aging 20100101 |
| An unusual case of anisocoria by vegetal intoxication: a case report. | Italian journal of pediatrics 20100101 |
| Differential production of tropane alkaloids in hairy roots and in vitro cultured two accessions of Atropa belladonna L. under nitrate treatments. | Zeitschrift fur Naturforschung. C, Journal of biosciences 20100101 |
| Enantiomeric differentiation of atropine/hyoscyamine by (13) C NMR spectroscopy and its application to Datura stramonium extract. | Phytochemical analysis : PCA 20100101 |
| The pituri story: a review of the historical literature surrounding traditional Australian Aboriginal use of nicotine in Central Australia. | Journal of ethnobiology and ethnomedicine 20100101 |
| Optimization of the culture medium composition to improve the production of hyoscyamine in elicited Datura stramonium L. hairy roots using the Response Surface Methodology (RSM). | International journal of molecular sciences 20100101 |
| New approaches in the management of multiple sclerosis. | Drug design, development and therapy 20100101 |
| Biochemistry and occurrence of o-demethylation in plant metabolism. | Frontiers in physiology 20100101 |
| Screening pharmaceuticals for possible carcinogenic effects: initial positive results for drugs not previously screened. | Cancer causes & control : CCC 20091201 |
| Molecular cloning and characterization of two tropinone reductases in Anisodus acutangulus and enhancement of tropane alkaloid production in AaTRI-transformed hairy roots. | Biotechnology and applied biochemistry 20091023 |
| Mechanistic insights into the cytochrome P450-mediated oxidation and rearrangement of littorine in tropane alkaloid biosynthesis. | Chembiochem : a European journal of chemical biology 20090921 |
| Allosteric interaction of the anticholinergic drug [N-(4-phenyl)-phenacyl-l-hyoscyamine] (Phenthonium) with nicotinic receptors of post-ganglionic sympathetic neurons of the rat vas deferens. | European journal of pharmacology 20090815 |
| Hyoscyamine biosynthesis in Datura stramonium hairy root in vitro systems with different ploidy levels. | Applied biochemistry and biotechnology 20090501 |
| Molecular cloning and mRNA expression profiling of the first specific jasmonate biosynthetic pathway gene allene oxide synthase from Hyoscyamus niger. | Genetika 20090401 |
| Cloning, characterization and analysis of expression profiles of a cDNA encoding a hyoscyamine 6beta-hydroxylase (H6H) from Atropa baetica Willk. | Plant physiology and biochemistry : PPB 20090101 |
| Assessment of the initial stability of the Symax femoral stem with EBRA-FCA: a multicentric study of 85 cases. | Hip international : the journal of clinical and experimental research on hip pathology and therapy 20090101 |
| Responses of fungi to tropane alkaloids produced by a medicinal plant Hyoscyamus muticus (Egyptian henbane). | Folia microbiologica 20090101 |
| Yeast cell factory: fishing for the best one or engineering it? | Microbial cell factories 20090101 |
| The symptomatic management of multiple sclerosis. | Annals of Indian Academy of Neurology 20090101 |
| Choice of antimuscarinic agents for overactive bladder in the older patient: focus on darifenacin. | Clinical interventions in aging 20080901 |
| The carbon-skeleton rearrangement in tropane alkaloid biosynthesis. | Journal of the American Chemical Society 20080813 |
| [Determination of hyoscyamine and scopolamine in serum and urine of humans by liquid chromatography with tandem mass spectrometry]. | Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan 20080801 |
| Sublingual hyoscyamine spray as premedication for colonoscopy: a randomized double-blinded placebo-controlled trial. | American journal of surgery 20080701 |
| Effect of chromium species on phytochemical and physiological parameters in Datura innoxia. | Chemosphere 20080601 |
| Characterization of Atropa belladonna L. compounds by capillary electrophoresis-electrospray ionization-time of flight-mass spectrometry and capillary electrophoresis-electrospray ionization-ion trap-mass spectrometry. | Electrophoresis 20080501 |
| Neurogenic bladder: etiology and assessment. | Pediatric nephrology (Berlin, Germany) 20080401 |
| Evaluation of myorelaxant activity of 7-substituted hexahydroquinoline derivatives in isolated rabbit gastric fundus. | European journal of medicinal chemistry 20080301 |
| Treatment of pyridostigmine-induced AV block with hyoscyamine in a patient with myasthenia gravis. | Journal of cardiovascular electrophysiology 20080201 |
| Synthesis and SAR of selective muscarinic acetylcholine receptor subtype 1 (M1 mAChR) antagonists. | Bioorganic & medicinal chemistry letters 20080201 |
| Expression of Brugmansia candida Hyoscyamine 6beta-Hydroxylase gene in Saccharomyces cerevisiae and its potential use as biocatalyst. | Microbial cell factories 20080101 |
| A study of the teratogenic and fetotoxic effects of large doses of barbital, hexobarbital and butobarbital used for suicide attempts by pregnant women. | Toxicology and industrial health 20080101 |
| The scientific impact of microbial cell factories. | Microbial cell factories 20080101 |
| Endoscopic findings in loin pain hematuria syndrome: concentric clot in calyceal fornices. | Diagnostic and therapeutic endoscopy 20080101 |
| Synthesis and characterization of molecularly imprinted polymers for phenoxyacetic acids. | International journal of molecular sciences 20080101 |
| Reasons for noncompliance with five-yearly screening flexible sigmoidoscopy. | Patient preference and adherence 20080101 |
| HPLC-atmospheric pressure chemical ionization mass spectrometric method for enantioselective determination of R,S-propranolol and R,S-hyoscyamine in human plasma. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20071115 |
| Evaluation of the cholinergic and adrenergic effects of two tropane alkaloids from Erythroxylum pervillei. | Phytotherapy research : PTR 20071001 |
| Molecular cloning and characterization of a new cDNA encoding hyoscyamine 6beta-hydroxylase from roots of Anisodus acutangulus. | Journal of biochemistry and molecular biology 20070930 |
| Tropane and nicotine alkaloid biosynthesis-novel approaches towards biotechnological production of plant-derived pharmaceuticals. | Current pharmaceutical biotechnology 20070801 |
| Production of tropane alkaloids by small-scale bubble column bioreactor cultures of Scopolia parviflora adventitious roots. | Bioresource technology 20070701 |
| Biotransformation of hyoscyamine into scopolamine in transgenic tobacco cell cultures. | Journal of plant physiology 20070401 |
| Tropane alkaloids production in transgenic Hyoscyamus niger hairy root cultures over-expressing putrescine N-methyltransferase is methyl jasmonate-dependent. | Planta 20070301 |
| The development of anticholinergics in the management of COPD. | International journal of chronic obstructive pulmonary disease 20070301 |
| How polyamine synthesis inhibitors and cinnamic acid affect tropane alkaloid production. | Applied biochemistry and biotechnology 20070101 |
| Nocturnal enuresis. | BMJ clinical evidence 20070101 |
| Immunolocalisation of two tropinone reductases in potato (Solanum tuberosum L.) root, stolon, and tuber sprouts. | Planta 20061201 |
| Self-amputation of penis and tongue after use of Angel's Trumpet. | European archives of psychiatry and clinical neuroscience 20061001 |
| Comparison of glucagon and scopolamine butylbromide as premedication for colonoscopy in unsedated patients. | Diseases of the colon and rectum 20060901 |
| Tailoring tropane alkaloid accumulation in transgenic hairy roots of Atropa baetica by over-expressing the gene encoding hyoscyamine 6beta-hydroxylase. | Biotechnology letters 20060801 |
| Crystal structures of the complexes of a group IIA phospholipase A2 with two natural anti-inflammatory agents, anisic acid, and atropine reveal a similar mode of binding. | Proteins 20060701 |
| Current gut-directed therapies for irritable bowel syndrome. | Current treatment options in gastroenterology 20060701 |
| Microsphere-based protease assays and screening application for lethal factor and factor Xa. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501 |
| Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement. | Chemistry & biology 20060501 |
| Tropinone reductases, enzymes at the branch point of tropane alkaloid metabolism. | Phytochemistry 20060201 |
| Putrescine N-methyltransferase in Solanum tuberosum L., a calystegine-forming plant. | Planta 20060101 |
| Constitutive and jasmonate-inducible traits of Datura wrightii. | Journal of chemical ecology 20060101 |
| Heterologous expression of Vitreoscilla hemoglobin (VHb) and cultivation conditions affect the alkaloid profile of Hyoscyamus muticus hairy roots. | Biotechnology progress 20060101 |
| Studies on tropane alkaloid extraction by volatile organic solvents: dichloromethane vs. chloroform. | Phytochemical analysis : PCA 20060101 |
| The history of barbiturates a century after their clinical introduction. | Neuropsychiatric disease and treatment 20051201 |
| Simultaneous analysis of hyoscyamine, scopolamine, 6beta-hydroxyhyoscyamine and apoatropine in Solanaceous hairy roots by reversed-phase high-performance liquid chromatography. | Journal of chromatography. A 20051014 |
| Enhanced secretion of tropane alkaloids in Nicotiana tabacum hairy roots expressing heterologous hyoscyamine-6beta-hydroxylase. | Journal of experimental botany 20051001 |
| Pharmacokinetics and pharmacodynamics in clinical use of scopolamine. | Therapeutic drug monitoring 20051001 |
| Structural and functional comparison of HemN to other radical SAM enzymes. | Biological chemistry 20051001 |
| PVC membrane ion-selective electrodes for the determination of Hyoscyamine in pure solution and in pharmaceutical preparations under batch and flow modes. | Journal of pharmaceutical and biomedical analysis 20050901 |
| Post-marketing surveillance using pharmacy-based cohorts: results of a pilot study. | Pharmacoepidemiology and drug safety 20050501 |
| Molecular cloning, expression and characterization of hyoscyamine 6beta-hydroxylase from hairy roots of Anisodus tanguticus. | Planta medica 20050301 |
| Overexpression of tropinone reductases alters alkaloid composition in Atropa belladonna root cultures. | Journal of experimental botany 20050201 |
| Potentially inappropriate medication use by elderly persons in U.S. Health Maintenance Organizations, 2000-2001. | Journal of the American Geriatrics Society 20050201 |
| Expression of Vitreoscilla hemoglobin enhances growth of Hyoscyamus muticus hairy root cultures. | Planta medica 20050101 |
| Identification and estimation of the levo isomer in raw materials and finished products containing atropine and/or hyoscyamine. | Journal of AOAC International 20050101 |
| Conductimetric determination of phenylpropanolamine HCl, ranitidine HCl, hyoscyamine HBr and betaine HCl in their pure state and pharmaceutical preparations. | Farmaco (Societa chimica italiana : 1989) 20050101 |
| Rapid in vitro adventitious shoot propagation of Scopolia parviflora through rhizome cultures for enhanced production of tropane alkaloids. | Plant cell reports 20040901 |
| Fatal poisoning from ingestion of Datura stramonium seeds. | Veterinary and human toxicology 20040401 |
| A rapid densitometric method for the analysis of hyoscyamine and scopolamine in solanaceous plants and their transformed root cultures. | Phytochemical analysis : PCA 20040101 |
| Induction of tropane alkaloid formation in transformed root cultures of Brugmansia suaveolens (Solanaceae). | Zeitschrift fur Naturforschung. C, Journal of biosciences 20040101 |
| Alkaloids in plants and root cultures of Atropa belladonna overexpressing putrescine N-methyltransferase. | Journal of experimental botany 20030901 |
| Preparation of a molecularly imprinted polymer for the solid-phase extraction of scopolamine with hyoscyamine as a dummy template molecule. | Journal of chromatography. A 20030214 |
| Effect of pmt gene overexpression on tropane alkaloid production in transformed root cultures of Datura metel and Hyoscyamus muticus. | Journal of experimental botany 20030101 |
| Alkaloid spectrum in diploid and tetraploid hairy root cultures of Datura stramonium. | Zeitschrift fur Naturforschung. C, Journal of biosciences 20030101 |
| Alkaloids of Datura ceratocaula. | Zeitschrift fur Naturforschung. C, Journal of biosciences 20030101 |
| Tropane alkaloids from Latua pubiflora. | Zeitschrift fur Naturforschung. C, Journal of biosciences 20030101 |
| The effects of Unguentum Lymphaticum on skin in patients with obstructive lymphedema of the lower extremities. | Lymphology 20021201 |
| Warm water irrigation for dealing with spasm during colonoscopy: simple, inexpensive, and effective. | Gastrointestinal endoscopy 20021101 |
| Biosynthetic studies on the tropane alkaloid hyoscyamine in Datura stramonium; hyoscyamine is stable to in vivo oxidation and is not derived from littorine via a vicinal interchange process. | Phytochemistry 20021001 |
| Anticholinergic poisoning from a large dose of Scopolia extract. | Veterinary and human toxicology 20020801 |
| Kinetic study of littorine rearrangement in Datura innoxia hairy roots by (13)C NMR spectroscopy. | Journal of natural products 20020801 |
| Molecular cloning, expression and characterization of tropinone reductase II, an enzyme of the SDR family in Solanum tuberosum (L.). | Plant molecular biology 20020201 |
| Urinary antispasmodic use and the risks of ventricular arrhythmia and sudden death in older patients. | Journal of the American Geriatrics Society 20020101 |
| Constitutive inhibitory action of muscarinic receptors on adenylyl cyclase in cardiac membranes and its stereospecific suppression by hyoscyamine. | Physiological research 20020101 |
| Tropane alkaloids in auxin-independent root cultures of Physochlaina physaloides. | Kokuritsu Iyakuhin Shokuhin Eisei Kenkyujo hokoku = Bulletin of National Institute of Health Sciences 20020101 |
| Distribution of hyoscyamine and scopolamine in Datura stramonium. | Fitoterapia 20010801 |
| Occurrence of cadaverine in hairy roots of Brugmansia candida. | Phytochemistry 20010701 |
| HPLC evaluation of diclofenac in transdermal therapeutic preparations. | International journal of pharmaceutics 20010417 |
| Decreased scopolamine yield in field-grown Duboisia plants regenerated from hairy roots. | Planta medica 20010401 |
| Sublingual hyoscyamine sulfate in combination with ketorolac tromethamine for ureteral colic: a randomized, double-blind, controlled trial. | Annals of emergency medicine 20010201 |
| Tropane alkaloid production by shoot culture of Duboisia myoporoides R. Br. | Phytochemistry 20010101 |
| Hairy roots of Brugmansia candida that grow without agitation: biotechnological implications. | Biotechnology progress 20010101 |
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