Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H23NO3 |
Molecular Weight | 289.3694 |
Optical Activity | ( - ) |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)[C@H](CO)C3=CC=CC=C3
InChI
InChIKey=RKUNBYITZUJHSG-FXUDXRNXSA-N
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
Molecular Formula | C17H23NO3 |
Molecular Weight | 289.3694 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Hyoscyamine as a natural plant alkaloid derivative and anticholinergic. Hyoscyamine is used to treat a variety of stomach/intestinal problems such as cramps and irritable bowel syndrome. It is also used to treat other conditions such as bladder and bowel control problems, cramping pain caused by kidney stones and gallstones, and Parkinson's disease. In addition, it is used to decrease side effects of certain medications (drugs used to treat myasthenia gravis) and insecticides. Hyoscyamine inhibits specifically the actions of acetylcholine on structures innervated by postganglionic cholinergic nerves and on smooth muscles that respond to acetylcholine but lack cholinergic innervation. These peripheral cholinergic receptors are present in the autonomic effector cells of the smooth muscle, cardiac muscle, the sinoatrial node, the atrioventricular node, and the exocrine glands. At therapeutic doses, it is completely devoid of any action on autonomic ganglia. Side effects include dry mouth and throat, increased appetite leading to weight gain, eye pain, blurred vision, restlessness, dizziness, arrhythmia, flushing, and faintness. Additive adverse effects resulting from cholinergic blockade may occur when hyoscyamine is administered concomitantly with other antimuscarinics, amantadine, haloperidol, phenothiazines, monoamine oxidase (MAO) inhibitors, tricyclic antidepressants or some antihistamines.
Approval Year
PubMed
Title | Date | PubMed |
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Distribution of hyoscyamine and scopolamine in Datura stramonium. | 2001 Aug |
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Constitutive inhibitory action of muscarinic receptors on adenylyl cyclase in cardiac membranes and its stereospecific suppression by hyoscyamine. | 2002 |
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Kinetic study of littorine rearrangement in Datura innoxia hairy roots by (13)C NMR spectroscopy. | 2002 Aug |
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Anticholinergic poisoning from a large dose of Scopolia extract. | 2002 Aug |
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The effects of Unguentum Lymphaticum on skin in patients with obstructive lymphedema of the lower extremities. | 2002 Dec |
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Molecular cloning, expression and characterization of tropinone reductase II, an enzyme of the SDR family in Solanum tuberosum (L.). | 2002 Feb 1 |
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Urinary antispasmodic use and the risks of ventricular arrhythmia and sudden death in older patients. | 2002 Jan |
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Warm water irrigation for dealing with spasm during colonoscopy: simple, inexpensive, and effective. | 2002 Nov |
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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. | 2002 Oct |
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Effect of pmt gene overexpression on tropane alkaloid production in transformed root cultures of Datura metel and Hyoscyamus muticus. | 2003 Jan |
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A rapid densitometric method for the analysis of hyoscyamine and scopolamine in solanaceous plants and their transformed root cultures. | 2004 May-Jun |
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Induction of tropane alkaloid formation in transformed root cultures of Brugmansia suaveolens (Solanaceae). | 2004 Nov-Dec |
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Rapid in vitro adventitious shoot propagation of Scopolia parviflora through rhizome cultures for enhanced production of tropane alkaloids. | 2004 Sep |
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The history of barbiturates a century after their clinical introduction. | 2005 Dec |
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Potentially inappropriate medication use by elderly persons in U.S. Health Maintenance Organizations, 2000-2001. | 2005 Feb |
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Expression of Vitreoscilla hemoglobin enhances growth of Hyoscyamus muticus hairy root cultures. | 2005 Jan |
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Identification and estimation of the levo isomer in raw materials and finished products containing atropine and/or hyoscyamine. | 2005 Jan-Feb |
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Structural and functional comparison of HemN to other radical SAM enzymes. | 2005 Oct |
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Pharmacokinetics and pharmacodynamics in clinical use of scopolamine. | 2005 Oct |
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Enhanced secretion of tropane alkaloids in Nicotiana tabacum hairy roots expressing heterologous hyoscyamine-6beta-hydroxylase. | 2005 Oct |
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Tailoring tropane alkaloid accumulation in transgenic hairy roots of Atropa baetica by over-expressing the gene encoding hyoscyamine 6beta-hydroxylase. | 2006 Aug |
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Putrescine N-methyltransferase in Solanum tuberosum L., a calystegine-forming plant. | 2006 Jan |
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Current gut-directed therapies for irritable bowel syndrome. | 2006 Jul |
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Self-amputation of penis and tongue after use of Angel's Trumpet. | 2006 Oct |
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Molecular cloning and characterization of a new cDNA encoding hyoscyamine 6beta-hydroxylase from roots of Anisodus acutangulus. | 2007 Sep 30 |
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Choice of antimuscarinic agents for overactive bladder in the older patient: focus on darifenacin. | 2008 |
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[Determination of hyoscyamine and scopolamine in serum and urine of humans by liquid chromatography with tandem mass spectrometry]. | 2008 Aug |
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The carbon-skeleton rearrangement in tropane alkaloid biosynthesis. | 2008 Aug 13 |
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Treatment of pyridostigmine-induced AV block with hyoscyamine in a patient with myasthenia gravis. | 2008 Feb |
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A study of the teratogenic and fetotoxic effects of large doses of barbital, hexobarbital and butobarbital used for suicide attempts by pregnant women. | 2008 Feb-Mar |
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Synthesis and characterization of molecularly imprinted polymers for phenoxyacetic acids. | 2008 Jan |
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Sublingual hyoscyamine spray as premedication for colonoscopy: a randomized double-blinded placebo-controlled trial. | 2008 Jul |
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Effect of chromium species on phytochemical and physiological parameters in Datura innoxia. | 2008 Jun |
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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. | 2008 May |
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Expression of Brugmansia candida Hyoscyamine 6beta-Hydroxylase gene in Saccharomyces cerevisiae and its potential use as biocatalyst. | 2008 May 27 |
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Responses of fungi to tropane alkaloids produced by a medicinal plant Hyoscyamus muticus (Egyptian henbane). | 2009 |
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Molecular cloning and mRNA expression profiling of the first specific jasmonate biosynthetic pathway gene allene oxide synthase from Hyoscyamus niger. | 2009 Apr |
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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. | 2009 Aug 15 |
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Screening pharmaceuticals for possible carcinogenic effects: initial positive results for drugs not previously screened. | 2009 Dec |
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Cloning, characterization and analysis of expression profiles of a cDNA encoding a hyoscyamine 6beta-hydroxylase (H6H) from Atropa baetica Willk. | 2009 Jan |
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Hyoscyamine biosynthesis in Datura stramonium hairy root in vitro systems with different ploidy levels. | 2009 May |
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Yeast cell factory: fishing for the best one or engineering it? | 2009 Oct 12 |
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Molecular cloning and characterization of two tropinone reductases in Anisodus acutangulus and enhancement of tropane alkaloid production in AaTRI-transformed hairy roots. | 2009 Oct 23 |
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"Divine stramonium": the rise and fall of smoking for asthma. | 2010 Apr |
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Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions. | 2010 Apr 7 |
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An anesthetic experience with cesarean section in a patient with vasovagal syncope -A case report-. | 2010 Aug |
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Hospice use and outcomes in nursing home residents with advanced dementia. | 2010 Dec |
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Cementless total hip replacement: a prospective clinical study of the early functional and radiological outcomes of three different hip stems. | 2010 Jan |
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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). | 2010 Nov 18 |
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Enantiomeric differentiation of atropine/hyoscyamine by (13) C NMR spectroscopy and its application to Datura stramonium extract. | 2010 Nov-Dec |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.rxlist.com/levsin-drug.htm#dosage
1 to 2 tablets (0.125 mg) every four hours or as needed. Do not exceed 12 tablets in 24 hours.
Route of Administration:
Oral
Substance Class |
Chemical
Created
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Fri Dec 15 15:18:24 GMT 2023
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Record UNII |
PX44XO846X
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QA03CB31
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WHO-ATC |
A03CB31
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LIVERTOX |
NBK548870
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WHO-ATC |
A03BA03
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WHO-VATC |
QA03BA03
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NCI_THESAURUS |
C29704
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PX44XO846X
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757064
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58164
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PX44XO846X
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SUB14160MIG
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153970
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HYOSCYAMINE
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100000077628
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DTXSID80889335
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3552
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C29104
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CHEMBL1331216
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DB00424
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101-31-5
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202-933-0
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17486
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m6167
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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RACEMATE -> ENANTIOMER | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SOLVATE->ANHYDROUS | |||
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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