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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
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
Molecular cloning, expression and characterization of tropinone reductase II, an enzyme of the SDR family in Solanum tuberosum (L.).
2002 Feb 1
Urinary antispasmodic use and the risks of ventricular arrhythmia and sudden death in older patients.
2002 Jan
Warm water irrigation for dealing with spasm during colonoscopy: simple, inexpensive, and effective.
2002 Nov
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
Fatal poisoning from ingestion of Datura stramonium seeds.
2004 Apr
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
Conductimetric determination of phenylpropanolamine HCl, ranitidine HCl, hyoscyamine HBr and betaine HCl in their pure state and pharmaceutical preparations.
2005 Jun-Jul
Molecular cloning, expression and characterization of hyoscyamine 6beta-hydroxylase from hairy roots of Anisodus tanguticus.
2005 Mar
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
Heterologous expression of Vitreoscilla hemoglobin (VHb) and cultivation conditions affect the alkaloid profile of Hyoscyamus muticus hairy roots.
2006 Mar-Apr
Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement.
2006 May
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
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
Endoscopic findings in loin pain hematuria syndrome: concentric clot in calyceal fornices.
2008
[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
Synthesis and characterization of molecularly imprinted polymers for phenoxyacetic acids.
2008 Jan
Molecular cloning and mRNA expression profiling of the first specific jasmonate biosynthetic pathway gene allene oxide synthase from Hyoscyamus niger.
2009 Apr
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
Screening pharmaceuticals for possible carcinogenic effects: initial positive results for drugs not previously screened.
2009 Dec
Assessment of the initial stability of the Symax femoral stem with EBRA-FCA: a multicentric study of 85 cases.
2009 Jan-Mar
Hospice use and outcomes in nursing home residents with advanced dementia.
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
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
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 GMT 2023 , Edited by admin on Sat Dec 16 05:50:54 GMT 2023
PRIMARY
FDA UNII
1D5WC802NO
Created by admin on Sat Dec 16 05:50:54 GMT 2023 , Edited by admin on Sat Dec 16 05:50:54 GMT 2023
PRIMARY
NSC
61808
Created by admin on Sat Dec 16 05:50:54 GMT 2023 , Edited by admin on Sat Dec 16 05:50:54 GMT 2023
PRIMARY
CAS
5934-50-9
Created by admin on Sat Dec 16 05:50:54 GMT 2023 , Edited by admin on Sat Dec 16 05:50:54 GMT 2023
PRIMARY