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
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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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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Constitutive inhibitory action of muscarinic receptors on adenylyl cyclase in cardiac membranes and its stereospecific suppression by hyoscyamine. | 2002 |
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Anticholinergic poisoning from a large dose of Scopolia extract. | 2002 Aug |
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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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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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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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Alkaloids in plants and root cultures of Atropa belladonna overexpressing putrescine N-methyltransferase. | 2003 Sep |
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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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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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Overexpression of tropinone reductases alters alkaloid composition in Atropa belladonna root cultures. | 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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Post-marketing surveillance using pharmacy-based cohorts: results of a pilot study. | 2005 May |
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Immunolocalisation of two tropinone reductases in potato (Solanum tuberosum L.) root, stolon, and tuber sprouts. | 2006 Dec |
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Tropinone reductases, enzymes at the branch point of tropane alkaloid metabolism. | 2006 Feb |
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Putrescine N-methyltransferase in Solanum tuberosum L., a calystegine-forming plant. | 2006 Jan |
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Studies on tropane alkaloid extraction by volatile organic solvents: dichloromethane vs. chloroform. | 2006 Mar-Apr |
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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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Endoscopic findings in loin pain hematuria syndrome: concentric clot in calyceal fornices. | 2008 |
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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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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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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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Assessment of the initial stability of the Symax femoral stem with EBRA-FCA: a multicentric study of 85 cases. | 2009 Jan-Mar |
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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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Tropane alkaloid profiling of hydroponic Datura innoxia Mill. Plants inoculated with Agrobacterium rhizogenes. | 2010 Jan-Feb |
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An unusual case of anisocoria by vegetal intoxication: a case report. | 2010 Jul 20 |
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Differential production of tropane alkaloids in hairy roots and in vitro cultured two accessions of Atropa belladonna L. under nitrate treatments. | 2010 May-Jun |
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Enantiomeric differentiation of atropine/hyoscyamine by (13) C NMR spectroscopy and its application to Datura stramonium extract. | 2010 Nov-Dec |
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The pituri story: a review of the historical literature surrounding traditional Australian Aboriginal use of nicotine in Central Australia. | 2010 Sep 12 |
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
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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
Created by
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Code System | Code | Type | Description | ||
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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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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 |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)