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Catalog No.:AA0003CR

101-31-5 | Benzeneacetic acid, α-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (αS)-

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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
Chemical Name:
Benzeneacetic acid, α-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (αS)-
CAS Number:
Molecular Formula:
Molecular Weight:
MDL Number:
429.804 °C at 760 mmHg  
108.5 °C  

Computed Properties
Covalently-Bonded Unit Count:
Defined Atom Stereocenter Count:
Heavy Atom Count:
Hydrogen Bond Acceptor Count:
Hydrogen Bond Donor Count:
Rotatable Bond Count:


Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Enhancing the production of tropane alkaloids in transgenic Anisodus acutangulus hairy root cultures by over-expressing tropinone reductase I and hyoscyamine-6β-hydroxylase.

Journal: Molecular bioSystems 20121101

Title: Induced production of mycotoxins in an endophytic fungus from the medicinal plant Datura stramonium L.

Journal: Bioorganic & medicinal chemistry letters 20121015

Title: Functional characterization of recombinant hyoscyamine 6β-hydroxylase from Atropa belladonna.

Journal: Bioorganic & medicinal chemistry 20120715

Title: Accidental poisoning after ingestion of 'aphrodisiac' berries: diagnosis by analytical toxicology.

Journal: The Journal of emergency medicine 20120601

Title: Antioxidant and cytotoxic effects of hexane extract of Morinda pubescens leaves in human liver cancer cell line.

Journal: Asian Pacific journal of tropical medicine 20120501

Title: Determination of tropane alkaloids atropine and scopolamine by liquid chromatography-mass spectrometry in plant organs of Datura species.

Journal: Journal of chromatography. A 20120406

Title: A non-aqueous solid phase extraction method for alkaloid enrichment and its application in the determination of hyoscyamine and scopolamine.

Journal: The Analyst 20120321

Title: Chromium-induced tropane alkaloid production and H6H gene expression in Atropa belladonna L. (Solanaceae) in vitro-propagated plantlets.

Journal: Plant physiology and biochemistry : PPB 20120301

Title: Norlittorine and norhyoscyamine identified as products of littorine and hyoscyamine metabolism by (13)C-labeling in Datura innoxia hairy roots.

Journal: Phytochemistry 20120201

Title: Massive atropine eye drop ingestion treated with high-dose physostigmine to avoid intubation.

Journal: The western journal of emergency medicine 20120201

Title: Application of an enantioselective LC-ESI MS/MS procedure to determine R- and S-hyoscyamine following intravenous atropine administration in swine.

Journal: Drug testing and analysis 20120101

Title: Natural products from ethnodirected studies: revisiting the ethnobiology of the zombie poison.

Journal: Evidence-based complementary and alternative medicine : eCAM 20120101

Title: Inorganic ions in the medium modify tropane alkaloids and riboflavin output in Hyoscyamus niger root cultures.

Journal: Pharmacognosy magazine 20120101

Title: Tropane alkaloids of Datura innoxia from Morocco.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20120101

Title: Atropa belladonna intoxication: a case report.

Journal: The Pan African medical journal 20120101

Title: Enhancing the scopolamine production in transgenic plants of Atropa belladonna by overexpressing pmt and h6h genes.

Journal: Physiologia plantarum 20111201

Title: Atropine maintenance dosage in patients with severe organophosphate pesticide poisoning.

Journal: Toxicology letters 20110925

Title: Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.

Journal: Journal of medicinal chemistry 20110714

Title: Functional identification of hyoscyamine 6β-hydroxylase from Anisodus acutangulus and overproduction of scopolamine in genetically-engineered Escherichia coli.

Journal: Biotechnology letters 20110701

Title: Treatment of irritable bowel syndrome.

Journal: Journal of clinical pharmacy and therapeutics 20110601

Title: Bone reaction to a biomimetic third-generation hydroxyapatite coating and new surface treatment for the Symax hip stem.

Journal: The Journal of bone and joint surgery. British volume 20110601

Title: Analgesic and antineuropathic drugs acting through central cholinergic mechanisms.

Journal: Recent patents on CNS drug discovery 20110501

Title: Treatment choice, duration, and cost in patients with interstitial cystitis and painful bladder syndrome.

Journal: International urogynecology journal 20110401

Title: Nine new tropane alkaloids from Datura stramonium L. identified by GC/MS.

Journal: Fitoterapia 20110301

Title: Identification of genes differentially expressed in a resistant reaction to Mycosphaerella pinodes in pea using microarray technology.

Journal: BMC genomics 20110101

Title: Multiple protein kinases determine the phosphorylated state of the small heat shock protein, HSP27, in SH-SY5Y neuroblastoma cells.

Journal: Neuropharmacology 20110101

Title: Nocturnal enuresis.

Journal: BMJ clinical evidence 20110101

Title: Co-expression of AaPMT and AaTRI effectively enhances the yields of tropane alkaloids in Anisodus acutangulus hairy roots.

Journal: BMC biotechnology 20110101

Title: Gallbladder agenesis.

Journal: Case reports in gastroenterology 20110101

Title: Biochemical and structural characterization of recombinant hyoscyamine 6β-hydroxylase from Datura metel L.

Journal: Plant physiology and biochemistry : PPB 20101201

Title: Hospice use and outcomes in nursing home residents with advanced dementia.

Journal: Journal of the American Geriatrics Society 20101201

Title: High-performance liquid-chromatographic tandem-mass spectrometric methods for atropinesterase-mediated enantioselective and chiral determination of R- and S-hyoscyamine in plasma.

Journal: Analytica chimica acta 20101108

Title: An anesthetic experience with cesarean section in a patient with vasovagal syncope -A case report-.

Journal: Korean journal of anesthesiology 20100801

Title: DFT-GIAO(1)H NMR chemical shifts prediction for the spectral assignment and conformational analysis of the anticholinergic drugs (-)-scopolamine and (-)-hyoscyamine.

Journal: Magnetic resonance in chemistry : MRC 20100601

Title: 'Divine stramonium': the rise and fall of smoking for asthma.

Journal: Medical history 20100401

Title: Anisodamine production from natural sources: seedlings and hairy root cultures of Argentinean and Colombian Brugmansia candida plants.

Journal: Planta medica 20100301

Title: Production of tropane alkaloids during de-differentiation of Scopolia parviflora calli.

Journal: Journal of natural products 20100226

Title: Cementless total hip replacement: a prospective clinical study of the early functional and radiological outcomes of three different hip stems.

Journal: Archives of orthopaedic and trauma surgery 20100101

Title: Tropane alkaloid profiling of hydroponic Datura innoxia Mill. Plants inoculated with Agrobacterium rhizogenes.

Journal: Phytochemical analysis : PCA 20100101

Title: Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions.

Journal: Clinical interventions in aging 20100101

Title: An unusual case of anisocoria by vegetal intoxication: a case report.

Journal: Italian journal of pediatrics 20100101

Title: Differential production of tropane alkaloids in hairy roots and in vitro cultured two accessions of Atropa belladonna L. under nitrate treatments.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20100101

Title: Enantiomeric differentiation of atropine/hyoscyamine by (13) C NMR spectroscopy and its application to Datura stramonium extract.

Journal: Phytochemical analysis : PCA 20100101

Title: The pituri story: a review of the historical literature surrounding traditional Australian Aboriginal use of nicotine in Central Australia.

Journal: Journal of ethnobiology and ethnomedicine 20100101

Title: 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).

Journal: International journal of molecular sciences 20100101

Title: New approaches in the management of multiple sclerosis.

Journal: Drug design, development and therapy 20100101

Title: Biochemistry and occurrence of o-demethylation in plant metabolism.

Journal: Frontiers in physiology 20100101

Title: Screening pharmaceuticals for possible carcinogenic effects: initial positive results for drugs not previously screened.

Journal: Cancer causes & control : CCC 20091201

Title: Molecular cloning and characterization of two tropinone reductases in Anisodus acutangulus and enhancement of tropane alkaloid production in AaTRI-transformed hairy roots.

Journal: Biotechnology and applied biochemistry 20091023

Title: Mechanistic insights into the cytochrome P450-mediated oxidation and rearrangement of littorine in tropane alkaloid biosynthesis.

Journal: Chembiochem : a European journal of chemical biology 20090921

Title: 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.

Journal: European journal of pharmacology 20090815

Title: Hyoscyamine biosynthesis in Datura stramonium hairy root in vitro systems with different ploidy levels.

Journal: Applied biochemistry and biotechnology 20090501

Title: Molecular cloning and mRNA expression profiling of the first specific jasmonate biosynthetic pathway gene allene oxide synthase from Hyoscyamus niger.

Journal: Genetika 20090401

Title: Cloning, characterization and analysis of expression profiles of a cDNA encoding a hyoscyamine 6beta-hydroxylase (H6H) from Atropa baetica Willk.

Journal: Plant physiology and biochemistry : PPB 20090101

Title: Assessment of the initial stability of the Symax femoral stem with EBRA-FCA: a multicentric study of 85 cases.

Journal: Hip international : the journal of clinical and experimental research on hip pathology and therapy 20090101

Title: Responses of fungi to tropane alkaloids produced by a medicinal plant Hyoscyamus muticus (Egyptian henbane).

Journal: Folia microbiologica 20090101

Title: Yeast cell factory: fishing for the best one or engineering it?

Journal: Microbial cell factories 20090101

Title: The symptomatic management of multiple sclerosis.

Journal: Annals of Indian Academy of Neurology 20090101

Title: Choice of antimuscarinic agents for overactive bladder in the older patient: focus on darifenacin.

Journal: Clinical interventions in aging 20080901

Title: The carbon-skeleton rearrangement in tropane alkaloid biosynthesis.

Journal: Journal of the American Chemical Society 20080813

Title: [Determination of hyoscyamine and scopolamine in serum and urine of humans by liquid chromatography with tandem mass spectrometry].

Journal: Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan 20080801

Title: Sublingual hyoscyamine spray as premedication for colonoscopy: a randomized double-blinded placebo-controlled trial.

Journal: American journal of surgery 20080701

Title: Effect of chromium species on phytochemical and physiological parameters in Datura innoxia.

Journal: Chemosphere 20080601

Title: 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.

Journal: Electrophoresis 20080501

Title: Neurogenic bladder: etiology and assessment.

Journal: Pediatric nephrology (Berlin, Germany) 20080401

Title: Evaluation of myorelaxant activity of 7-substituted hexahydroquinoline derivatives in isolated rabbit gastric fundus.

Journal: European journal of medicinal chemistry 20080301

Title: Treatment of pyridostigmine-induced AV block with hyoscyamine in a patient with myasthenia gravis.

Journal: Journal of cardiovascular electrophysiology 20080201

Title: Synthesis and SAR of selective muscarinic acetylcholine receptor subtype 1 (M1 mAChR) antagonists.

Journal: Bioorganic & medicinal chemistry letters 20080201

Title: Expression of Brugmansia candida Hyoscyamine 6beta-Hydroxylase gene in Saccharomyces cerevisiae and its potential use as biocatalyst.

Journal: Microbial cell factories 20080101

Title: A study of the teratogenic and fetotoxic effects of large doses of barbital, hexobarbital and butobarbital used for suicide attempts by pregnant women.

Journal: Toxicology and industrial health 20080101

Title: The scientific impact of microbial cell factories.

Journal: Microbial cell factories 20080101

Title: Endoscopic findings in loin pain hematuria syndrome: concentric clot in calyceal fornices.

Journal: Diagnostic and therapeutic endoscopy 20080101

Title: Synthesis and characterization of molecularly imprinted polymers for phenoxyacetic acids.

Journal: International journal of molecular sciences 20080101

Title: Reasons for noncompliance with five-yearly screening flexible sigmoidoscopy.

Journal: Patient preference and adherence 20080101

Title: HPLC-atmospheric pressure chemical ionization mass spectrometric method for enantioselective determination of R,S-propranolol and R,S-hyoscyamine in human plasma.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20071115

Title: Evaluation of the cholinergic and adrenergic effects of two tropane alkaloids from Erythroxylum pervillei.

Journal: Phytotherapy research : PTR 20071001

Title: Molecular cloning and characterization of a new cDNA encoding hyoscyamine 6beta-hydroxylase from roots of Anisodus acutangulus.

Journal: Journal of biochemistry and molecular biology 20070930

Title: Tropane and nicotine alkaloid biosynthesis-novel approaches towards biotechnological production of plant-derived pharmaceuticals.

Journal: Current pharmaceutical biotechnology 20070801

Title: Production of tropane alkaloids by small-scale bubble column bioreactor cultures of Scopolia parviflora adventitious roots.

Journal: Bioresource technology 20070701

Title: Biotransformation of hyoscyamine into scopolamine in transgenic tobacco cell cultures.

Journal: Journal of plant physiology 20070401

Title: Tropane alkaloids production in transgenic Hyoscyamus niger hairy root cultures over-expressing putrescine N-methyltransferase is methyl jasmonate-dependent.

Journal: Planta 20070301

Title: The development of anticholinergics in the management of COPD.

Journal: International journal of chronic obstructive pulmonary disease 20070301

Title: How polyamine synthesis inhibitors and cinnamic acid affect tropane alkaloid production.

Journal: Applied biochemistry and biotechnology 20070101

Title: Nocturnal enuresis.

Journal: BMJ clinical evidence 20070101

Title: Immunolocalisation of two tropinone reductases in potato (Solanum tuberosum L.) root, stolon, and tuber sprouts.

Journal: Planta 20061201

Title: Self-amputation of penis and tongue after use of Angel's Trumpet.

Journal: European archives of psychiatry and clinical neuroscience 20061001

Title: Comparison of glucagon and scopolamine butylbromide as premedication for colonoscopy in unsedated patients.

Journal: Diseases of the colon and rectum 20060901

Title: Tailoring tropane alkaloid accumulation in transgenic hairy roots of Atropa baetica by over-expressing the gene encoding hyoscyamine 6beta-hydroxylase.

Journal: Biotechnology letters 20060801

Title: 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.

Journal: Proteins 20060701

Title: Current gut-directed therapies for irritable bowel syndrome.

Journal: Current treatment options in gastroenterology 20060701

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement.

Journal: Chemistry & biology 20060501

Title: Tropinone reductases, enzymes at the branch point of tropane alkaloid metabolism.

Journal: Phytochemistry 20060201

Title: Putrescine N-methyltransferase in Solanum tuberosum L., a calystegine-forming plant.

Journal: Planta 20060101

Title: Constitutive and jasmonate-inducible traits of Datura wrightii.

Journal: Journal of chemical ecology 20060101

Title: Heterologous expression of Vitreoscilla hemoglobin (VHb) and cultivation conditions affect the alkaloid profile of Hyoscyamus muticus hairy roots.

Journal: Biotechnology progress 20060101

Title: Studies on tropane alkaloid extraction by volatile organic solvents: dichloromethane vs. chloroform.

Journal: Phytochemical analysis : PCA 20060101

Title: The history of barbiturates a century after their clinical introduction.

Journal: Neuropsychiatric disease and treatment 20051201

Title: Simultaneous analysis of hyoscyamine, scopolamine, 6beta-hydroxyhyoscyamine and apoatropine in Solanaceous hairy roots by reversed-phase high-performance liquid chromatography.

Journal: Journal of chromatography. A 20051014

Title: Enhanced secretion of tropane alkaloids in Nicotiana tabacum hairy roots expressing heterologous hyoscyamine-6beta-hydroxylase.

Journal: Journal of experimental botany 20051001

Title: Pharmacokinetics and pharmacodynamics in clinical use of scopolamine.

Journal: Therapeutic drug monitoring 20051001

Title: Structural and functional comparison of HemN to other radical SAM enzymes.

Journal: Biological chemistry 20051001

Title: PVC membrane ion-selective electrodes for the determination of Hyoscyamine in pure solution and in pharmaceutical preparations under batch and flow modes.

Journal: Journal of pharmaceutical and biomedical analysis 20050901

Title: Post-marketing surveillance using pharmacy-based cohorts: results of a pilot study.

Journal: Pharmacoepidemiology and drug safety 20050501

Title: Molecular cloning, expression and characterization of hyoscyamine 6beta-hydroxylase from hairy roots of Anisodus tanguticus.

Journal: Planta medica 20050301

Title: Overexpression of tropinone reductases alters alkaloid composition in Atropa belladonna root cultures.

Journal: Journal of experimental botany 20050201

Title: Potentially inappropriate medication use by elderly persons in U.S. Health Maintenance Organizations, 2000-2001.

Journal: Journal of the American Geriatrics Society 20050201

Title: Expression of Vitreoscilla hemoglobin enhances growth of Hyoscyamus muticus hairy root cultures.

Journal: Planta medica 20050101

Title: Identification and estimation of the levo isomer in raw materials and finished products containing atropine and/or hyoscyamine.

Journal: Journal of AOAC International 20050101

Title: Conductimetric determination of phenylpropanolamine HCl, ranitidine HCl, hyoscyamine HBr and betaine HCl in their pure state and pharmaceutical preparations.

Journal: Farmaco (Societa chimica italiana : 1989) 20050101

Title: Rapid in vitro adventitious shoot propagation of Scopolia parviflora through rhizome cultures for enhanced production of tropane alkaloids.

Journal: Plant cell reports 20040901

Title: Fatal poisoning from ingestion of Datura stramonium seeds.

Journal: Veterinary and human toxicology 20040401

Title: A rapid densitometric method for the analysis of hyoscyamine and scopolamine in solanaceous plants and their transformed root cultures.

Journal: Phytochemical analysis : PCA 20040101

Title: Induction of tropane alkaloid formation in transformed root cultures of Brugmansia suaveolens (Solanaceae).

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20040101

Title: Alkaloids in plants and root cultures of Atropa belladonna overexpressing putrescine N-methyltransferase.

Journal: Journal of experimental botany 20030901

Title: Preparation of a molecularly imprinted polymer for the solid-phase extraction of scopolamine with hyoscyamine as a dummy template molecule.

Journal: Journal of chromatography. A 20030214

Title: Effect of pmt gene overexpression on tropane alkaloid production in transformed root cultures of Datura metel and Hyoscyamus muticus.

Journal: Journal of experimental botany 20030101

Title: Alkaloid spectrum in diploid and tetraploid hairy root cultures of Datura stramonium.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20030101

Title: Alkaloids of Datura ceratocaula.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20030101

Title: Tropane alkaloids from Latua pubiflora.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20030101

Title: The effects of Unguentum Lymphaticum on skin in patients with obstructive lymphedema of the lower extremities.

Journal: Lymphology 20021201

Title: Warm water irrigation for dealing with spasm during colonoscopy: simple, inexpensive, and effective.

Journal: Gastrointestinal endoscopy 20021101

Title: 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.

Journal: Phytochemistry 20021001

Title: Anticholinergic poisoning from a large dose of Scopolia extract.

Journal: Veterinary and human toxicology 20020801

Title: Kinetic study of littorine rearrangement in Datura innoxia hairy roots by (13)C NMR spectroscopy.

Journal: Journal of natural products 20020801

Title: Molecular cloning, expression and characterization of tropinone reductase II, an enzyme of the SDR family in Solanum tuberosum (L.).

Journal: Plant molecular biology 20020201

Title: Urinary antispasmodic use and the risks of ventricular arrhythmia and sudden death in older patients.

Journal: Journal of the American Geriatrics Society 20020101

Title: Constitutive inhibitory action of muscarinic receptors on adenylyl cyclase in cardiac membranes and its stereospecific suppression by hyoscyamine.

Journal: Physiological research 20020101

Title: Tropane alkaloids in auxin-independent root cultures of Physochlaina physaloides.

Journal: Kokuritsu Iyakuhin Shokuhin Eisei Kenkyujo hokoku = Bulletin of National Institute of Health Sciences 20020101

Title: Distribution of hyoscyamine and scopolamine in Datura stramonium.

Journal: Fitoterapia 20010801

Title: Occurrence of cadaverine in hairy roots of Brugmansia candida.

Journal: Phytochemistry 20010701

Title: HPLC evaluation of diclofenac in transdermal therapeutic preparations.

Journal: International journal of pharmaceutics 20010417

Title: Decreased scopolamine yield in field-grown Duboisia plants regenerated from hairy roots.

Journal: Planta medica 20010401

Title: Sublingual hyoscyamine sulfate in combination with ketorolac tromethamine for ureteral colic: a randomized, double-blind, controlled trial.

Journal: Annals of emergency medicine 20010201

Title: Tropane alkaloid production by shoot culture of Duboisia myoporoides R. Br.

Journal: Phytochemistry 20010101

Title: Hairy roots of Brugmansia candida that grow without agitation: biotechnological implications.

Journal: Biotechnology progress 20010101

Title: Lars Göran Axelsson, et al. Regulatory role of 5-HT and muscarinic receptor antagonists on the migrating myoelectric complex in rats. Eur J Pharmacol. 2003 Apr 25;467(1-3):211-8.

Title: Harald John, et al. Application of an enantioselective LC-ESI MS/MS procedure to determine R- and S-hyoscyamine following intravenous atropine administration in swine. Drug Test Anal. Mar-Apr 2012;4(3-4):194-8.

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Tags:101-31-5 Molecular Formula|101-31-5 MDL|101-31-5 SMILES|101-31-5 Benzeneacetic acid, α-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (αS)-