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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C17H23NO3.H2O4S
Molecular Weight 676.817
Optical Activity ( - )
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYOSCYAMINE SULFATE ANHYDROUS

SMILES

OS(O)(=O)=O.CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)[C@H](CO)C3=CC=CC=C3.CN4[C@H]5CC[C@@H]4C[C@@H](C5)OC(=O)[C@H](CO)C6=CC=CC=C6

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 289.3694
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O4S
Molecular Weight 98.078
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
Decreased scopolamine yield in field-grown Duboisia plants regenerated from hairy roots.
2001 Apr
Distribution of hyoscyamine and scopolamine in Datura stramonium.
2001 Aug
Tropane alkaloid production by shoot culture of Duboisia myoporoides R. Br.
2001 Jan
Occurrence of cadaverine in hairy roots of Brugmansia candida.
2001 Jul
Hairy roots of Brugmansia candida that grow without agitation: biotechnological implications.
2001 Jul-Aug
Tropane alkaloids in auxin-independent root cultures of Physochlaina physaloides.
2002
Kinetic study of littorine rearrangement in Datura innoxia hairy roots by (13)C NMR spectroscopy.
2002 Aug
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
Alkaloids of Datura ceratocaula.
2003 Jul-Aug
Tropane alkaloids from Latua pubiflora.
2003 Sep-Oct
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
Overexpression of tropinone reductases alters alkaloid composition in Atropa belladonna root cultures.
2005 Feb
Conductimetric determination of phenylpropanolamine HCl, ranitidine HCl, hyoscyamine HBr and betaine HCl in their pure state and pharmaceutical preparations.
2005 Jun-Jul
Post-marketing surveillance using pharmacy-based cohorts: results of a pilot study.
2005 May
Structural and functional comparison of HemN to other radical SAM enzymes.
2005 Oct
Pharmacokinetics and pharmacodynamics in clinical use of scopolamine.
2005 Oct
Enhanced secretion of tropane alkaloids in Nicotiana tabacum hairy roots expressing heterologous hyoscyamine-6beta-hydroxylase.
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
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
Tropinone reductases, enzymes at the branch point of tropane alkaloid metabolism.
2006 Feb
Constitutive and jasmonate-inducible traits of Datura wrightii.
2006 Jan
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
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
Biotransformation of hyoscyamine into scopolamine in transgenic tobacco cell cultures.
2007 Apr
Production of tropane alkaloids by small-scale bubble column bioreactor cultures of Scopolia parviflora adventitious roots.
2007 Jul
[Determination of hyoscyamine and scopolamine in serum and urine of humans by liquid chromatography with tandem mass spectrometry].
2008 Aug
The scientific impact of microbial cell factories.
2008 Dec 1
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
Yeast cell factory: fishing for the best one or engineering it?
2009 Oct 12
Mechanistic insights into the cytochrome P450-mediated oxidation and rearrangement of littorine in tropane alkaloid biosynthesis.
2009 Sep 21
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions.
2010 Apr 7
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
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
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 Thu Jul 06 07:56:29 UTC 2023
Edited
by admin
on Thu Jul 06 07:56:29 UTC 2023
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 Thu Jul 06 07:56:29 UTC 2023 , Edited by admin on Thu Jul 06 07:56:29 UTC 2023
PRIMARY
RXCUI
1742407
Created by admin on Thu Jul 06 07:56:29 UTC 2023 , Edited by admin on Thu Jul 06 07:56:29 UTC 2023
PRIMARY
FDA UNII
OB570Z127K
Created by admin on Thu Jul 06 07:56:29 UTC 2023 , Edited by admin on Thu Jul 06 07:56:29 UTC 2023
PRIMARY
DAILYMED
OB570Z127K
Created by admin on Thu Jul 06 07:56:29 UTC 2023 , Edited by admin on Thu Jul 06 07:56:29 UTC 2023
PRIMARY
EPA CompTox
DTXSID001341118
Created by admin on Thu Jul 06 07:56:29 UTC 2023 , Edited by admin on Thu Jul 06 07:56:29 UTC 2023
PRIMARY
CAS
620-61-1
Created by admin on Thu Jul 06 07:56:29 UTC 2023 , Edited by admin on Thu Jul 06 07:56:29 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY