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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C17H23NO3.H2O4S
Molecular Weight 676.8197
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYOSCYAMINE SULFATE ANHYDROUS

SMILES

CN1[C@]2([H])CC[C@@]1([H])C[C@]([H])(C2)OC(=O)[C@]([H])(CO)c3ccccc3.CN1[C@]2([H])CC[C@@]1([H])C[C@]([H])(C2)OC(=O)[C@]([H])(CO)c3ccccc3.OS(=O)(=O)O

InChI

InChIKey=HOBWAPHTEJGALG-XHJLRQJWSA-N
InChI=1S/2C17H23NO3.H2O4S/c2*1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12;1-5(2,3)4/h2*2-6,13-16,19H,7-11H2,1H3;(H2,1,2,3,4)/t2*13-,14+,15+,16-;/m11./s1

HIDE SMILES / InChI

Molecular Formula C17H23NO3
Molecular Weight 289.3701
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O4S
Molecular Weight 98.0796
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

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.5 nM [IC50]
PubMed

PubMed

TitleDatePubMed
A rapid densitometric method for the analysis of hyoscyamine and scopolamine in solanaceous plants and their transformed root cultures.
2004 May-Jun
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
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
Enhanced secretion of tropane alkaloids in Nicotiana tabacum hairy roots expressing heterologous hyoscyamine-6beta-hydroxylase.
2005 Oct
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
Tailoring tropane alkaloid accumulation in transgenic hairy roots of Atropa baetica by over-expressing the gene encoding hyoscyamine 6beta-hydroxylase.
2006 Aug
Immunolocalisation of two tropinone reductases in potato (Solanum tuberosum L.) root, stolon, and tuber sprouts.
2006 Dec
Putrescine N-methyltransferase in Solanum tuberosum L., a calystegine-forming plant.
2006 Jan
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
The development of anticholinergics in the management of COPD.
2007
Biotransformation of hyoscyamine into scopolamine in transgenic tobacco cell cultures.
2007 Apr
Tropane and nicotine alkaloid biosynthesis-novel approaches towards biotechnological production of plant-derived pharmaceuticals.
2007 Aug
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
HPLC-atmospheric pressure chemical ionization mass spectrometric method for enantioselective determination of R,S-propranolol and R,S-hyoscyamine in human plasma.
2007 Nov 15
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
Neurogenic bladder: etiology and assessment.
2008 Apr
The carbon-skeleton rearrangement in tropane alkaloid biosynthesis.
2008 Aug 13
The scientific impact of microbial cell factories.
2008 Dec 1
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
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
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
Hyoscyamine biosynthesis in Datura stramonium hairy root in vitro systems with different ploidy levels.
2009 May
The symptomatic management of multiple sclerosis.
2009 Oct
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
An anesthetic experience with cesarean section in a patient with vasovagal syncope -A case report-.
2010 Aug
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
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
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
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 Jun 26 11:46:52 UTC 2021
Edited
by admin
on Sat Jun 26 11:46:52 UTC 2021
Record UNII
OB570Z127K
Record Status Validated (UNII)
Record Version
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Name Type Language
HYOSCYAMINE SULFATE ANHYDROUS
Common Name English
ANHYDROUS HYOSCYAMINE SULFATE [MART.]
Common Name English
1.ALPHA.H,5.ALPHA.H-TROPAN-3.ALPHA.-OL (-)-TROPATE (ESTER) SULFATE (2:1) (SALT)
Common Name English
BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-, 8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, (3(S)-ENDO)-, SULFATE (2:1)
Common Name English
ANHYDROUS HYOSCYAMINE SULFATE
MART.  
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
210-644-6
Created by admin on Sat Jun 26 11:46:53 UTC 2021 , Edited by admin on Sat Jun 26 11:46:53 UTC 2021
PRIMARY
RXCUI
1742407
Created by admin on Sat Jun 26 11:46:53 UTC 2021 , Edited by admin on Sat Jun 26 11:46:53 UTC 2021
PRIMARY
FDA UNII
OB570Z127K
Created by admin on Sat Jun 26 11:46:53 UTC 2021 , Edited by admin on Sat Jun 26 11:46:53 UTC 2021
PRIMARY
CAS
620-61-1
Created by admin on Sat Jun 26 11:46:53 UTC 2021 , Edited by admin on Sat Jun 26 11:46:53 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY