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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H23NO3.ClH
Molecular Weight 325.8309
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYOSCYAMINE HYDROCHLORIDE

SMILES

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

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

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C17H23NO3
Molecular Weight 289.3701
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 3 / 3
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
HPLC evaluation of diclofenac in transdermal therapeutic preparations.
2001 Apr 17
Distribution of hyoscyamine and scopolamine in Datura stramonium.
2001 Aug
Sublingual hyoscyamine sulfate in combination with ketorolac tromethamine for ureteral colic: a randomized, double-blind, controlled trial.
2001 Feb
Tropane alkaloid production by shoot culture of Duboisia myoporoides R. Br.
2001 Jan
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
Molecular cloning, expression and characterization of tropinone reductase II, an enzyme of the SDR family in Solanum tuberosum (L.).
2002 Feb 1
Effect of pmt gene overexpression on tropane alkaloid production in transformed root cultures of Datura metel and Hyoscyamus muticus.
2003 Jan
Alkaloids of Datura ceratocaula.
2003 Jul-Aug
Tropane alkaloids from Latua pubiflora.
2003 Sep-Oct
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
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
Structural and functional comparison of HemN to other radical SAM enzymes.
2005 Oct
Putrescine N-methyltransferase in Solanum tuberosum L., a calystegine-forming plant.
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
Comparison of glucagon and scopolamine butylbromide as premedication for colonoscopy in unsedated patients.
2006 Sep
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
Evaluation of the cholinergic and adrenergic effects of two tropane alkaloids from Erythroxylum pervillei.
2007 Oct
Nocturnal enuresis.
2007 Oct 1
Treatment of pyridostigmine-induced AV block with hyoscyamine in a patient with myasthenia gravis.
2008 Feb
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
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
Hyoscyamine biosynthesis in Datura stramonium hairy root in vitro systems with different ploidy levels.
2009 May
The symptomatic management of multiple sclerosis.
2009 Oct
Yeast cell factory: fishing for the best one or engineering it?
2009 Oct 12
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions.
2010 Apr 7
Hospice use and outcomes in nursing home residents with advanced dementia.
2010 Dec
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 Sat Jun 26 06:39:01 UTC 2021
Edited
by admin
on Sat Jun 26 06:39:01 UTC 2021
Record UNII
1D5WC802NO
Record Status Validated (UNII)
Record Version
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Name Type Language
HYOSCYAMINE HYDROCHLORIDE
Common Name English
HYOSCYAMINE HYDROCHLORIDE, [MI]
Common Name English
NSC-61808
Code English
HYOSCYAMINE HYDROCHLORIDE [WHO-DD]
Common Name 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
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 Jun 26 06:39:01 UTC 2021 , Edited by admin on Sat Jun 26 06:39:01 UTC 2021
PRIMARY
FDA UNII
1D5WC802NO
Created by admin on Sat Jun 26 06:39:01 UTC 2021 , Edited by admin on Sat Jun 26 06:39:01 UTC 2021
PRIMARY
CAS
5934-50-9
Created by admin on Sat Jun 26 06:39:01 UTC 2021 , Edited by admin on Sat Jun 26 06:39:01 UTC 2021
PRIMARY
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ACTIVE MOIETY