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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Decreased scopolamine yield in field-grown Duboisia plants regenerated from hairy roots. | 2001 Apr |
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Distribution of hyoscyamine and scopolamine in Datura stramonium. | 2001 Aug |
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Occurrence of cadaverine in hairy roots of Brugmansia candida. | 2001 Jul |
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Hairy roots of Brugmansia candida that grow without agitation: biotechnological implications. | 2001 Jul-Aug |
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Tropane alkaloids in auxin-independent root cultures of Physochlaina physaloides. | 2002 |
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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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Warm water irrigation for dealing with spasm during colonoscopy: simple, inexpensive, and effective. | 2002 Nov |
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Preparation of a molecularly imprinted polymer for the solid-phase extraction of scopolamine with hyoscyamine as a dummy template molecule. | 2003 Feb 14 |
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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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Alkaloid spectrum in diploid and tetraploid hairy root cultures of Datura stramonium. | 2003 Jan-Feb |
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Alkaloids in plants and root cultures of Atropa belladonna overexpressing putrescine N-methyltransferase. | 2003 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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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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Enhanced secretion of tropane alkaloids in Nicotiana tabacum hairy roots expressing heterologous hyoscyamine-6beta-hydroxylase. | 2005 Oct |
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Studies on tropane alkaloid extraction by volatile organic solvents: dichloromethane vs. chloroform. | 2006 Mar-Apr |
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Heterologous expression of Vitreoscilla hemoglobin (VHb) and cultivation conditions affect the alkaloid profile of Hyoscyamus muticus hairy roots. | 2006 Mar-Apr |
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Comparison of glucagon and scopolamine butylbromide as premedication for colonoscopy in unsedated patients. | 2006 Sep |
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Tropane and nicotine alkaloid biosynthesis-novel approaches towards biotechnological production of plant-derived pharmaceuticals. | 2007 Aug |
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Tropane alkaloids production in transgenic Hyoscyamus niger hairy root cultures over-expressing putrescine N-methyltransferase is methyl jasmonate-dependent. | 2007 Mar |
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Nocturnal enuresis. | 2007 Oct 1 |
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Neurogenic bladder: etiology and assessment. | 2008 Apr |
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The carbon-skeleton rearrangement in tropane alkaloid biosynthesis. | 2008 Aug 13 |
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Sublingual hyoscyamine spray as premedication for colonoscopy: a randomized double-blinded placebo-controlled trial. | 2008 Jul |
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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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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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The symptomatic management of multiple sclerosis. | 2009 Oct |
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Yeast cell factory: fishing for the best one or engineering it? | 2009 Oct 12 |
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Hospice use and outcomes in nursing home residents with advanced dementia. | 2010 Dec |
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Tropane alkaloid profiling of hydroponic Datura innoxia Mill. Plants inoculated with Agrobacterium rhizogenes. | 2010 Jan-Feb |
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Anisodamine production from natural sources: seedlings and hairy root cultures of Argentinean and Colombian Brugmansia candida plants. | 2010 Mar |
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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 |
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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Wed Jul 05 22:49:20 UTC 2023
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Wed Jul 05 22:49:20 UTC 2023
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Record UNII |
PX44XO846X
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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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1402
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SUB14160MIG
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153970
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HYOSCYAMINE
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100000077628
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C29104
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CHEMBL1331216
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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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Related Record | Type | Details | ||
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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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