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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
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
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
Constitutive inhibitory action of muscarinic receptors on adenylyl cyclase in cardiac membranes and its stereospecific suppression by hyoscyamine.
2002
Anticholinergic poisoning from a large dose of Scopolia extract.
2002 Aug
Molecular cloning, expression and characterization of tropinone reductase II, an enzyme of the SDR family in Solanum tuberosum (L.).
2002 Feb 1
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
Preparation of a molecularly imprinted polymer for the solid-phase extraction of scopolamine with hyoscyamine as a dummy template molecule.
2003 Feb 14
Alkaloids in plants and root cultures of Atropa belladonna overexpressing putrescine N-methyltransferase.
2003 Sep
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
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
Post-marketing surveillance using pharmacy-based cohorts: results of a pilot study.
2005 May
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
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
Tropane alkaloids production in transgenic Hyoscyamus niger hairy root cultures over-expressing putrescine N-methyltransferase is methyl jasmonate-dependent.
2007 Mar
Endoscopic findings in loin pain hematuria syndrome: concentric clot in calyceal fornices.
2008
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
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
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
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
Tropane alkaloid profiling of hydroponic Datura innoxia Mill. Plants inoculated with Agrobacterium rhizogenes.
2010 Jan-Feb
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
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
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 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
WHO-ATC A03CB31
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
LIVERTOX NBK548870
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
WHO-ATC A03BA03
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
WHO-VATC QA03BA03
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
NCI_THESAURUS C29704
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
Code System Code Type Description
FDA UNII
PX44XO846X
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
PRIMARY
NSC
757064
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
PRIMARY
CHEBI
58164
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
PRIMARY
DAILYMED
PX44XO846X
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
PRIMARY
DRUG CENTRAL
1402
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
PRIMARY
EVMPD
SUB14160MIG
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
PRIMARY
RXCUI
153970
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
PRIMARY RxNorm
WIKIPEDIA
HYOSCYAMINE
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
PRIMARY
EPA CompTox
DTXSID80889335
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
PRIMARY
HSDB
3552
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
PRIMARY
NCI_THESAURUS
C29104
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
PRIMARY
ChEMBL
CHEMBL1331216
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
PRIMARY
DRUG BANK
DB00424
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
PRIMARY
CAS
101-31-5
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
PRIMARY
ECHA (EC/EINECS)
202-933-0
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
PRIMARY
CHEBI
17486
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
PRIMARY
MERCK INDEX
M6167
Created by admin on Fri Dec 16 16:45:29 UTC 2022 , Edited by admin on Fri Dec 16 16:45:29 UTC 2022
PRIMARY Merck Index