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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
Decreased scopolamine yield in field-grown Duboisia plants regenerated from hairy roots.
2001 Apr
Distribution of hyoscyamine and scopolamine in Datura stramonium.
2001 Aug
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
The effects of Unguentum Lymphaticum on skin in patients with obstructive lymphedema of the lower extremities.
2002 Dec
Warm water irrigation for dealing with spasm during colonoscopy: simple, inexpensive, and effective.
2002 Nov
Preparation of a molecularly imprinted polymer for the solid-phase extraction of scopolamine with hyoscyamine as a dummy template molecule.
2003 Feb 14
Effect of pmt gene overexpression on tropane alkaloid production in transformed root cultures of Datura metel and Hyoscyamus muticus.
2003 Jan
Alkaloid spectrum in diploid and tetraploid hairy root cultures of Datura stramonium.
2003 Jan-Feb
Alkaloids in plants and root cultures of Atropa belladonna overexpressing putrescine N-methyltransferase.
2003 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
Identification and estimation of the levo isomer in raw materials and finished products containing atropine and/or hyoscyamine.
2005 Jan-Feb
Enhanced secretion of tropane alkaloids in Nicotiana tabacum hairy roots expressing heterologous hyoscyamine-6beta-hydroxylase.
2005 Oct
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
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
Neurogenic bladder: etiology and assessment.
2008 Apr
The carbon-skeleton rearrangement in tropane alkaloid biosynthesis.
2008 Aug 13
Sublingual hyoscyamine spray as premedication for colonoscopy: a randomized double-blinded placebo-controlled trial.
2008 Jul
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
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
The symptomatic management of multiple sclerosis.
2009 Oct
Yeast cell factory: fishing for the best one or engineering it?
2009 Oct 12
Hospice use and outcomes in nursing home residents with advanced dementia.
2010 Dec
Tropane alkaloid profiling of hydroponic Datura innoxia Mill. Plants inoculated with Agrobacterium rhizogenes.
2010 Jan-Feb
Anisodamine production from natural sources: seedlings and hairy root cultures of Argentinean and Colombian Brugmansia candida plants.
2010 Mar
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
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 Wed Jul 05 22:49:20 UTC 2023
Edited
by admin
on Wed Jul 05 22:49:20 UTC 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 Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
WHO-ATC A03CB31
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
LIVERTOX NBK548870
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
WHO-ATC A03BA03
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
WHO-VATC QA03BA03
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
NCI_THESAURUS C29704
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
Code System Code Type Description
FDA UNII
PX44XO846X
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
PRIMARY
NSC
757064
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
PRIMARY
CHEBI
58164
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
PRIMARY
DAILYMED
PX44XO846X
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
PRIMARY
DRUG CENTRAL
1402
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
PRIMARY
EVMPD
SUB14160MIG
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
PRIMARY
RXCUI
153970
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
PRIMARY RxNorm
WIKIPEDIA
HYOSCYAMINE
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
PRIMARY
SMS_ID
100000077628
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID80889335
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
PRIMARY
HSDB
3552
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
PRIMARY
NCI_THESAURUS
C29104
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
PRIMARY
ChEMBL
CHEMBL1331216
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
PRIMARY
DRUG BANK
DB00424
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
PRIMARY
CAS
101-31-5
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
PRIMARY
ECHA (EC/EINECS)
202-933-0
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
PRIMARY
CHEBI
17486
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
PRIMARY
MERCK INDEX
M6167
Created by admin on Wed Jul 05 22:49:20 UTC 2023 , Edited by admin on Wed Jul 05 22:49:20 UTC 2023
PRIMARY Merck Index
Related Record Type Details
RACEMATE -> ENANTIOMER
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SOLVATE->ANHYDROUS
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC