U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H23NO3
Molecular Weight 289.3694
Optical Activity ( - )
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYOSCYAMINE

SMILES

CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)[C@H](CO)C3=CC=CC=C3

InChI

InChIKey=RKUNBYITZUJHSG-FXUDXRNXSA-N
InChI=1S/C17H23NO3/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/t13-,14+,15+,16-/m1/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

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
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
Identification and estimation of the levo isomer in raw materials and finished products containing atropine and/or hyoscyamine.
2005 Jan-Feb
Molecular cloning, expression and characterization of hyoscyamine 6beta-hydroxylase from hairy roots of Anisodus tanguticus.
2005 Mar
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
Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement.
2006 May
Self-amputation of penis and tongue after use of Angel's Trumpet.
2006 Oct
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
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
Choice of antimuscarinic agents for overactive bladder in the older patient: focus on darifenacin.
2008
The carbon-skeleton rearrangement in tropane alkaloid biosynthesis.
2008 Aug 13
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
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
Molecular cloning and mRNA expression profiling of the first specific jasmonate biosynthetic pathway gene allene oxide synthase from Hyoscyamus niger.
2009 Apr
Assessment of the initial stability of the Symax femoral stem with EBRA-FCA: a multicentric study of 85 cases.
2009 Jan-Mar
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
Mechanistic insights into the cytochrome P450-mediated oxidation and rearrangement of littorine in tropane alkaloid biosynthesis.
2009 Sep 21
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
Tropane alkaloid profiling of hydroponic Datura innoxia Mill. Plants inoculated with Agrobacterium rhizogenes.
2010 Jan-Feb
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 Fri Dec 15 15:18:24 GMT 2023
Edited
by admin
on Fri Dec 15 15:18:24 GMT 2023
Record UNII
PX44XO846X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HYOSCYAMINE
HSDB   MART.   MI   USP   VANDF   WHO-DD  
Common Name English
L-TROPIC ACID ESTER WITH TROPINE
Brand Name English
(S)-(-)-HYOSCYAMINE
Common Name English
HYOSCYAMINE [VANDF]
Common Name English
BELLAFOLINE
Brand Name English
Hyoscyamine [WHO-DD]
Common Name English
ATROPINE, (S)-
Common Name English
HYOSCYAMINUM
HPUS  
Common Name English
HYOSCYAMINE [MI]
Common Name English
BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-, (3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, (.ALPHA.S)-
Systematic Name English
(-)-ATROPINE
Common Name English
(-)-HYOSCYAMINE
Common Name English
HYOSCYAMINUM [HPUS]
Common Name English
L-HYOSCYAMINE
Common Name English
NSC-757064
Code English
DATURINE
Common Name English
HYOSCYAMINE [MART.]
Common Name English
HYOSCYAMINE [USP MONOGRAPH]
Common Name English
CYSTOSPAZ
Brand Name English
HYOSCYAMINE [HSDB]
Common Name English
DUBOISINE
Common Name English
Classification Tree Code System Code
WHO-VATC QA03CB31
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
WHO-ATC A03CB31
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
LIVERTOX NBK548870
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
WHO-ATC A03BA03
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
WHO-VATC QA03BA03
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
NCI_THESAURUS C29704
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
Code System Code Type Description
FDA UNII
PX44XO846X
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
NSC
757064
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
CHEBI
58164
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
DAILYMED
PX44XO846X
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
DRUG CENTRAL
1402
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
EVMPD
SUB14160MIG
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
RXCUI
153970
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
HYOSCYAMINE
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
SMS_ID
100000077628
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
EPA CompTox
DTXSID80889335
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
HSDB
3552
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
NCI_THESAURUS
C29104
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
ChEMBL
CHEMBL1331216
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
DRUG BANK
DB00424
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
CAS
101-31-5
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
ECHA (EC/EINECS)
202-933-0
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
CHEBI
17486
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
MERCK INDEX
m6167
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY Merck Index
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