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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H23NO3
Molecular Weight 289.3701
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYOSCYAMINE

SMILES

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

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 289.3701
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
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
Expression of Vitreoscilla hemoglobin enhances growth of Hyoscyamus muticus hairy root cultures.
2005 Jan
Identification and estimation of the levo isomer in raw materials and finished products containing atropine and/or hyoscyamine.
2005 Jan-Feb
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
Simultaneous analysis of hyoscyamine, scopolamine, 6beta-hydroxyhyoscyamine and apoatropine in Solanaceous hairy roots by reversed-phase high-performance liquid chromatography.
2005 Oct 14
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
Current gut-directed therapies for irritable bowel syndrome.
2006 Jul
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
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
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
Tropane alkaloids production in transgenic Hyoscyamus niger hairy root cultures over-expressing putrescine N-methyltransferase is methyl jasmonate-dependent.
2007 Mar
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
Evaluation of the cholinergic and adrenergic effects of two tropane alkaloids from Erythroxylum pervillei.
2007 Oct
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
Treatment of pyridostigmine-induced AV block with hyoscyamine in a patient with myasthenia gravis.
2008 Feb
Reasons for noncompliance with five-yearly screening flexible sigmoidoscopy.
2008 Feb 2
Synthesis and characterization of molecularly imprinted polymers for phenoxyacetic acids.
2008 Jan
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
Responses of fungi to tropane alkaloids produced by a medicinal plant Hyoscyamus muticus (Egyptian henbane).
2009
Screening pharmaceuticals for possible carcinogenic effects: initial positive results for drugs not previously screened.
2009 Dec
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
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
An unusual case of anisocoria by vegetal intoxication: a case report.
2010 Jul 20
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 Jun 25 22:12:12 UTC 2021
Edited
by admin
on Fri Jun 25 22:12:12 UTC 2021
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
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
CYSTOSPAZ
Brand Name English
HYOSCYAMINE [WHO-DD]
Common Name English
HYOSCYAMINE [HSDB]
Common Name English
DUBOISINE
Common Name English
HYOSCYAMINE [USP]
Common Name English
Classification Tree Code System Code
WHO-VATC QA03CB31
Created by admin on Fri Jun 25 22:12:12 UTC 2021 , Edited by admin on Fri Jun 25 22:12:12 UTC 2021
WHO-ATC A03CB31
Created by admin on Fri Jun 25 22:12:12 UTC 2021 , Edited by admin on Fri Jun 25 22:12:12 UTC 2021
LIVERTOX 493
Created by admin on Fri Jun 25 22:12:12 UTC 2021 , Edited by admin on Fri Jun 25 22:12:12 UTC 2021
WHO-ATC A03BA03
Created by admin on Fri Jun 25 22:12:12 UTC 2021 , Edited by admin on Fri Jun 25 22:12:12 UTC 2021
WHO-VATC QA03BA03
Created by admin on Fri Jun 25 22:12:12 UTC 2021 , Edited by admin on Fri Jun 25 22:12:12 UTC 2021
NCI_THESAURUS C29704
Created by admin on Fri Jun 25 22:12:12 UTC 2021 , Edited by admin on Fri Jun 25 22:12:12 UTC 2021
Code System Code Type Description
FDA UNII
PX44XO846X
Created by admin on Fri Jun 25 22:12:12 UTC 2021 , Edited by admin on Fri Jun 25 22:12:12 UTC 2021
PRIMARY
DRUG CENTRAL
1402
Created by admin on Fri Jun 25 22:12:12 UTC 2021 , Edited by admin on Fri Jun 25 22:12:12 UTC 2021
PRIMARY
EVMPD
SUB14160MIG
Created by admin on Fri Jun 25 22:12:12 UTC 2021 , Edited by admin on Fri Jun 25 22:12:12 UTC 2021
PRIMARY
RXCUI
153970
Created by admin on Fri Jun 25 22:12:12 UTC 2021 , Edited by admin on Fri Jun 25 22:12:12 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
HYOSCYAMINE
Created by admin on Fri Jun 25 22:12:12 UTC 2021 , Edited by admin on Fri Jun 25 22:12:12 UTC 2021
PRIMARY
HSDB
3552
Created by admin on Fri Jun 25 22:12:12 UTC 2021 , Edited by admin on Fri Jun 25 22:12:12 UTC 2021
PRIMARY
NCI_THESAURUS
C29104
Created by admin on Fri Jun 25 22:12:12 UTC 2021 , Edited by admin on Fri Jun 25 22:12:12 UTC 2021
PRIMARY
ChEMBL
CHEMBL1331216
Created by admin on Fri Jun 25 22:12:12 UTC 2021 , Edited by admin on Fri Jun 25 22:12:12 UTC 2021
PRIMARY
DRUG BANK
DB00424
Created by admin on Fri Jun 25 22:12:12 UTC 2021 , Edited by admin on Fri Jun 25 22:12:12 UTC 2021
PRIMARY
CAS
101-31-5
Created by admin on Fri Jun 25 22:12:12 UTC 2021 , Edited by admin on Fri Jun 25 22:12:12 UTC 2021
PRIMARY
ECHA (EC/EINECS)
202-933-0
Created by admin on Fri Jun 25 22:12:12 UTC 2021 , Edited by admin on Fri Jun 25 22:12:12 UTC 2021
PRIMARY
MERCK INDEX
M6167
Created by admin on Fri Jun 25 22:12:12 UTC 2021 , Edited by admin on Fri Jun 25 22:12:12 UTC 2021
PRIMARY Merck Index
Related Record Type Details
RACEMATE -> ENANTIOMER
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
Related Record Type Details
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