Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H23NO3.ClH |
Molecular Weight | 325.83 |
Optical Activity | ( - ) |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)[C@H](CO)C3=CC=CC=C3
InChI
InChIKey=OJIPQOWZZMSBGY-PGQIENJJSA-N
InChI=1S/C17H23NO3.ClH/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;1H/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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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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Fatal poisoning from ingestion of Datura stramonium seeds. | 2004 Apr |
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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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Conductimetric determination of phenylpropanolamine HCl, ranitidine HCl, hyoscyamine HBr and betaine HCl in their pure state and pharmaceutical preparations. | 2005 Jun-Jul |
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Molecular cloning, expression and characterization of hyoscyamine 6beta-hydroxylase from hairy roots of Anisodus tanguticus. | 2005 Mar |
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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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PVC membrane ion-selective electrodes for the determination of Hyoscyamine in pure solution and in pharmaceutical preparations under batch and flow modes. | 2005 Sep 1 |
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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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Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement. | 2006 May |
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Biotransformation of hyoscyamine into scopolamine in transgenic tobacco cell cultures. | 2007 Apr |
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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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Endoscopic findings in loin pain hematuria syndrome: concentric clot in calyceal fornices. | 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 scientific impact of microbial cell factories. | 2008 Dec 1 |
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Reasons for noncompliance with five-yearly screening flexible sigmoidoscopy. | 2008 Feb 2 |
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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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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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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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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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An unusual case of anisocoria by vegetal intoxication: a case report. | 2010 Jul 20 |
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DFT-GIAO(1)H NMR chemical shifts prediction for the spectral assignment and conformational analysis of the anticholinergic drugs (-)-scopolamine and (-)-hyoscyamine. | 2010 Jun |
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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227-686-6
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1D5WC802NO
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61808
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5934-50-9
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ACTIVE MOIETY
SUBSTANCE RECORD