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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
Structure of HYOSCYAMINE HYDROCHLORIDE

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

HIDE SMILES / InChI

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

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

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.5 nM [IC50]
PubMed

PubMed

TitleDatePubMed
Alkaloids in plants and root cultures of Atropa belladonna overexpressing putrescine N-methyltransferase.
2003 Sep
Tropane alkaloids from Latua pubiflora.
2003 Sep-Oct
Fatal poisoning from ingestion of Datura stramonium seeds.
2004 Apr
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
Expression of Vitreoscilla hemoglobin enhances growth of Hyoscyamus muticus hairy root cultures.
2005 Jan
Conductimetric determination of phenylpropanolamine HCl, ranitidine HCl, hyoscyamine HBr and betaine HCl in their pure state and pharmaceutical preparations.
2005 Jun-Jul
Structural and functional comparison of HemN to other radical SAM enzymes.
2005 Oct
Pharmacokinetics and pharmacodynamics in clinical use of scopolamine.
2005 Oct
Simultaneous analysis of hyoscyamine, scopolamine, 6beta-hydroxyhyoscyamine and apoatropine in Solanaceous hairy roots by reversed-phase high-performance liquid chromatography.
2005 Oct 14
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
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
Putrescine N-methyltransferase in Solanum tuberosum L., a calystegine-forming plant.
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
Heterologous expression of Vitreoscilla hemoglobin (VHb) and cultivation conditions affect the alkaloid profile of Hyoscyamus muticus hairy roots.
2006 Mar-Apr
Comparison of glucagon and scopolamine butylbromide as premedication for colonoscopy in unsedated patients.
2006 Sep
The development of anticholinergics in the management of COPD.
2007
How polyamine synthesis inhibitors and cinnamic acid affect tropane alkaloid production.
2007 Jan
Production of tropane alkaloids by small-scale bubble column bioreactor cultures of Scopolia parviflora adventitious roots.
2007 Jul
Evaluation of the cholinergic and adrenergic effects of two tropane alkaloids from Erythroxylum pervillei.
2007 Oct
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
Choice of antimuscarinic agents for overactive bladder in the older patient: focus on darifenacin.
2008
Neurogenic bladder: etiology and assessment.
2008 Apr
[Determination of hyoscyamine and scopolamine in serum and urine of humans by liquid chromatography with tandem mass spectrometry].
2008 Aug
Treatment of pyridostigmine-induced AV block with hyoscyamine in a patient with myasthenia gravis.
2008 Feb
Reasons for noncompliance with five-yearly screening flexible sigmoidoscopy.
2008 Feb 2
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
Synthesis and characterization of molecularly imprinted polymers for phenoxyacetic acids.
2008 Jan
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
Molecular cloning and mRNA expression profiling of the first specific jasmonate biosynthetic pathway gene allene oxide synthase from Hyoscyamus niger.
2009 Apr
Cloning, characterization and analysis of expression profiles of a cDNA encoding a hyoscyamine 6beta-hydroxylase (H6H) from Atropa baetica Willk.
2009 Jan
Assessment of the initial stability of the Symax femoral stem with EBRA-FCA: a multicentric study of 85 cases.
2009 Jan-Mar
The symptomatic management of multiple sclerosis.
2009 Oct
Yeast cell factory: fishing for the best one or engineering it?
2009 Oct 12
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
"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
Cementless total hip replacement: a prospective clinical study of the early functional and radiological outcomes of three different hip stems.
2010 Jan
An unusual case of anisocoria by vegetal intoxication: a case report.
2010 Jul 20
DFT-GIAO(1)H NMR chemical shifts prediction for the spectral assignment and conformational analysis of the anticholinergic drugs (-)-scopolamine and (-)-hyoscyamine.
2010 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
Patents

Sample Use Guides

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
by admin
on Sat Dec 16 05:50:54 UTC 2023
Edited
by admin
on Sat Dec 16 05:50:54 UTC 2023
Record UNII
1D5WC802NO
Record Status Validated (UNII)
Record Version
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Name Type Language
HYOSCYAMINE HYDROCHLORIDE
Common Name English
HYOSCYAMINE HYDROCHLORIDE, [MI]
Common Name English
NSC-61808
Code English
HYOSCYAMINE HYDROCHLORIDE, (-)-
Common Name English
BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-, (3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, HYDROCHLORIDE, (.ALPHA.S)-
Common Name English
(-)-HYOSCYAMINE HYDROCHLORIDE
Common Name English
BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-, 8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, HYDROCHLORIDE, (3(S)-ENDO)-
Common Name English
Hyoscyamine hydrochloride [WHO-DD]
Common Name English
1.ALPHA.H,5.ALPHA.H-TROPAN-3.ALPHA.-OL, (-)-TROPATE (ESTER), HYDROCHLORIDE
Common Name English
BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-, (3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, HYDROCHLORIDE (1:1), (.ALPHA.S)-
Common Name English
HYOSCYAMINE HCL
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
227-686-6
Created by admin on Sat Dec 16 05:50:54 UTC 2023 , Edited by admin on Sat Dec 16 05:50:54 UTC 2023
PRIMARY
FDA UNII
1D5WC802NO
Created by admin on Sat Dec 16 05:50:54 UTC 2023 , Edited by admin on Sat Dec 16 05:50:54 UTC 2023
PRIMARY
NSC
61808
Created by admin on Sat Dec 16 05:50:54 UTC 2023 , Edited by admin on Sat Dec 16 05:50:54 UTC 2023
PRIMARY
CAS
5934-50-9
Created by admin on Sat Dec 16 05:50:54 UTC 2023 , Edited by admin on Sat Dec 16 05:50:54 UTC 2023
PRIMARY
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