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
| Molecular Formula | C17H23NO3 |
| Molecular Weight | 289.3694 |
| Charge | 0 |
| Count |
|
| Stereochemistry | EPIMERIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Tropane alkaloids in auxin-independent root cultures of Physochlaina physaloides. | 2002 |
|
| Constitutive inhibitory action of muscarinic receptors on adenylyl cyclase in cardiac membranes and its stereospecific suppression by hyoscyamine. | 2002 |
|
| Molecular cloning, expression and characterization of tropinone reductase II, an enzyme of the SDR family in Solanum tuberosum (L.). | 2002 Feb 1 |
|
| Preparation of a molecularly imprinted polymer for the solid-phase extraction of scopolamine with hyoscyamine as a dummy template molecule. | 2003 Feb 14 |
|
| Alkaloid spectrum in diploid and tetraploid hairy root cultures of Datura stramonium. | 2003 Jan-Feb |
|
| Alkaloids of Datura ceratocaula. | 2003 Jul-Aug |
|
| A rapid densitometric method for the analysis of hyoscyamine and scopolamine in solanaceous plants and their transformed root cultures. | 2004 May-Jun |
|
| Induction of tropane alkaloid formation in transformed root cultures of Brugmansia suaveolens (Solanaceae). | 2004 Nov-Dec |
|
| Rapid in vitro adventitious shoot propagation of Scopolia parviflora through rhizome cultures for enhanced production of tropane alkaloids. | 2004 Sep |
|
| The history of barbiturates a century after their clinical introduction. | 2005 Dec |
|
| Potentially inappropriate medication use by elderly persons in U.S. Health Maintenance Organizations, 2000-2001. | 2005 Feb |
|
| Overexpression of tropinone reductases alters alkaloid composition in Atropa belladonna root cultures. | 2005 Feb |
|
| Expression of Vitreoscilla hemoglobin enhances growth of Hyoscyamus muticus hairy root cultures. | 2005 Jan |
|
| Structural and functional comparison of HemN to other radical SAM enzymes. | 2005 Oct |
|
| Pharmacokinetics and pharmacodynamics in clinical use of scopolamine. | 2005 Oct |
|
| Immunolocalisation of two tropinone reductases in potato (Solanum tuberosum L.) root, stolon, and tuber sprouts. | 2006 Dec |
|
| Tropinone reductases, enzymes at the branch point of tropane alkaloid metabolism. | 2006 Feb |
|
| Constitutive and jasmonate-inducible traits of Datura wrightii. | 2006 Jan |
|
| Current gut-directed therapies for irritable bowel syndrome. | 2006 Jul |
|
| Studies on tropane alkaloid extraction by volatile organic solvents: dichloromethane vs. chloroform. | 2006 Mar-Apr |
|
| Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement. | 2006 May |
|
| Comparison of glucagon and scopolamine butylbromide as premedication for colonoscopy in unsedated patients. | 2006 Sep |
|
| Tropane alkaloids production in transgenic Hyoscyamus niger hairy root cultures over-expressing putrescine N-methyltransferase is methyl jasmonate-dependent. | 2007 Mar |
|
| Nocturnal enuresis. | 2007 Oct 1 |
|
| Molecular cloning and characterization of a new cDNA encoding hyoscyamine 6beta-hydroxylase from roots of Anisodus acutangulus. | 2007 Sep 30 |
|
| Endoscopic findings in loin pain hematuria syndrome: concentric clot in calyceal fornices. | 2008 |
|
| The carbon-skeleton rearrangement in tropane alkaloid biosynthesis. | 2008 Aug 13 |
|
| The scientific impact of microbial cell factories. | 2008 Dec 1 |
|
| Sublingual hyoscyamine spray as premedication for colonoscopy: a randomized double-blinded placebo-controlled trial. | 2008 Jul |
|
| Effect of chromium species on phytochemical and physiological parameters in Datura innoxia. | 2008 Jun |
|
| 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 |
|
| Expression of Brugmansia candida Hyoscyamine 6beta-Hydroxylase gene in Saccharomyces cerevisiae and its potential use as biocatalyst. | 2008 May 27 |
|
| Responses of fungi to tropane alkaloids produced by a medicinal plant Hyoscyamus muticus (Egyptian henbane). | 2009 |
|
| Screening pharmaceuticals for possible carcinogenic effects: initial positive results for drugs not previously screened. | 2009 Dec |
|
| 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 |
|
| Mechanistic insights into the cytochrome P450-mediated oxidation and rearrangement of littorine in tropane alkaloid biosynthesis. | 2009 Sep 21 |
|
| "Divine stramonium": the rise and fall of smoking for asthma. | 2010 Apr |
|
| Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions. | 2010 Apr 7 |
|
| Hospice use and outcomes in nursing home residents with advanced dementia. | 2010 Dec |
|
| Biochemical and structural characterization of recombinant hyoscyamine 6β-hydroxylase from Datura metel L. | 2010 Dec |
|
| Production of tropane alkaloids during de-differentiation of Scopolia parviflora calli. | 2010 Feb 26 |
|
| Cementless total hip replacement: a prospective clinical study of the early functional and radiological outcomes of three different hip stems. | 2010 Jan |
|
| Tropane alkaloid profiling of hydroponic Datura innoxia Mill. Plants inoculated with Agrobacterium rhizogenes. | 2010 Jan-Feb |
|
| An unusual case of anisocoria by vegetal intoxication: a case report. | 2010 Jul 20 |
|
| Anisodamine production from natural sources: seedlings and hairy root cultures of Argentinean and Colombian Brugmansia candida plants. | 2010 Mar |
|
| Differential production of tropane alkaloids in hairy roots and in vitro cultured two accessions of Atropa belladonna L. under nitrate treatments. | 2010 May-Jun |
|
| 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 |
|
| High-performance liquid-chromatographic tandem-mass spectrometric methods for atropinesterase-mediated enantioselective and chiral determination of R- and S-hyoscyamine in plasma. | 2010 Nov 8 |
|
| Enantiomeric differentiation of atropine/hyoscyamine by (13) C NMR spectroscopy and its application to Datura stramonium extract. | 2010 Nov-Dec |
|
| The pituri story: a review of the historical literature surrounding traditional Australian Aboriginal use of nicotine in Central Australia. | 2010 Sep 12 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 11:32:54 UTC 2023
by
admin
on
Thu Jul 06 11:32:54 UTC 2023
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| Record UNII |
1D5WC802NO
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| Record Status |
Validated (UNII)
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| Record Version |
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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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admin on Thu Jul 06 11:32:54 UTC 2023 , Edited by admin on Thu Jul 06 11:32:54 UTC 2023
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PARENT -> SALT/SOLVATE |
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