ContaminantDB: Hyoscyamine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (5)XML

Record Information

Version

1.0

Creation Date

2009-07-23 18:26:14 UTC

Update Date

2016-11-09 01:08:46 UTC

Accession Number

CHEM002430

Identification

Common Name

Hyoscyamine

Class

Small Molecule

Description

Hyoscyamine is a chemical compound, a tropane alkaloid it is the levo-isomer to atropine. It is a secondary metabolite of some plants, particularly henbane (Hyoscamus niger.) Hyoscyamine is used to provide symptomatic relief to various gastrointestinal disorders including spasms, peptic ulcers, irritable bowel syndrome, pancreatitis, colic and cystitis. It has also been used to relieve some heart problems, control some of the symptoms of Parkinson's disease, as well as for control of respiratory secretions in end of life care.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amine
Anti-Arrhythmia Agent
Antispasmodic
Drug
Ester
Ether
Metabolite
Muscarinic Antagonist
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Atropine	ChEBI
(-)-Hyoscyamine	ChEBI
(S)-(-)-Hyoscyamine	ChEBI
[3(S)-endo]-alpha-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester	ChEBI
Daturine	ChEBI
Duboisine	ChEBI
L-Hyoscyamine	ChEBI
L-Tropine tropate	ChEBI
Tropine, (-)-tropate	ChEBI
[3(S)-endo]-a-(Hydroxymethyl)benzeneacetate 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester	Generator
[3(S)-endo]-a-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester	Generator
[3(S)-endo]-alpha-(Hydroxymethyl)benzeneacetate 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester	Generator
[3(S)-endo]-Α-(hydroxymethyl)benzeneacetate 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester	Generator
[3(S)-endo]-Α-(hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester	Generator
L-Tropine tropic acid	Generator
Tropine, (-)-tropic acid	Generator
(Leo)-atropine	HMDB
(Leo)-hyoscyamine	HMDB
(S)-(Leo)-hyoscyamine	HMDB
(S)Atropine	HMDB
Hyocyamine	HMDB
L-Atropine	HMDB
L-Hyopscyamine	HMDB
L-Hyoscamine	HMDB
Hyoscyamine	ChEBI

Chemical Formula

C₁₇H₂₃NO₃

Average Molecular Mass

289.369 g/mol

Monoisotopic Mass

289.168 g/mol

CAS Registry Number

101-31-5

IUPAC Name

(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2S)-3-hydroxy-2-phenylpropanoate

Traditional Name

L-hyoscyamine

SMILES

CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)[C@H](CO)C1=CC=CC=C1

InChI Identifier

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

InChI Key

RKUNBYITZUJHSG-FXUDXRNXSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Tropane alkaloids

Sub Class

Not Available

Direct Parent

Tropane alkaloids

Alternative Parents

Substituents

Tropane alkaloid
Beta-hydroxy acid
Monocyclic benzene moiety
Hydroxy acid
Piperidine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate (CHEBI:17486 )
Tropane alkaloids (C02046 )
Tropan alkaloids (C02046 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Salivary secretion	Not Available	map04970
Gastric acid secretion	Not Available	map04971
Insulin secretion	Not Available	map04911
Cholinergic synapse	Not Available	map04725

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	108.5°C
Boiling Point	Not Available
Solubility	3560 mg/L (at 20°C)

Predicted Properties

Property	Value	Source
Water Solubility	2.52 g/L	ALOGPS
logP	2.19	ALOGPS
logP	1.57	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	15.15	ChemAxon
pKa (Strongest Basic)	9.39	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.82 m³·mol⁻¹	ChemAxon
Polarizability	31.74 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-5900000000-f705f96b0219dcd47d66	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0006-4900000000-d0c3228da9df55297f7b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-006x-6951100000-43127e046c478d2643e1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-006x-6951100000-43127e046c478d2643e1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-006x-6960000000-96b74c70ce0011e5968d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-0790000000-b3809a4d9f3d53472626	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1920000000-5cf6a284aa0360bfa6f5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0g02-2900000000-03a359b67b71a8d41b5a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0490000000-42268e6db552a2d85a66	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05g3-1960000000-db1243e11ae5ea609f09	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00bc-5900000000-3453e9ae42b1ccba243c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-38746560650547c38a28	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-1590000000-abf830c79515feb657d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006y-9500000000-28e9eb9a8330fa4c60d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0490000000-4b2dacd04cd09b1229da	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0g4r-1910000000-6bc43ea9e9a781364124	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-1910000000-9a0fd9e7ddf07814092b	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-9810000000-bdd60b3a23f97899d426	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (ingestion) (3) ; dermal (3). Absorbed totally and completely by sublingual administration as well as oral administration.

Mechanism of Toxicity

Hyoscyamine is an anticholinergic, specifically an antimuscarinic, and works by blocking the action of acetylcholine at parasympathetic sites in smooth muscle, secretory glands, and the central nervous system. (1) Hyoscyamine competes favorably with acetylcholine for binding at muscarinic receptors in the salivary, bronchial, and sweat glands as well as in the eye, heart, and gastrointestinal tract. The actions of hyoscyamine result in a reduction in salivary, bronchial, gastric and sweat gland secretions, mydriasis, cycloplegia, change in heart rate, contraction of the bladder detrusor muscle and of the gastrointestinal smooth muscle, and decreased gastrointestinal motility.

Metabolism

Hepatic Half Life: 2-3.5 hours

Toxicity Values

LD₅₀=mg/kg (orally in rat)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Hyoscyamine is a plant toxin found in certain plants of the Solanaceae family, including henbane (Hyoscyamus niger), mandrake (Mandragora officinarum), jimsonweed (Datura stramonium), and deadly nightshade (Atropa belladonna). It is used as a drug to provide symptomatic relief to various gastrointestinal disorders including spasms, peptic ulcers, irritable bowel syndrome, pancreatitis, colic and cystitis. It has also been used to relieve some heart problems, control some of the symptoms of Parkinson's disease, as well as for control of respiratory secretions in palliative care.(1)

Minimum Risk Level

Not Available

Health Effects

Hyoscyamine affects the central nervous system. (1)

Symptoms

Side effects of hyoscyamine include dry mouth and throat, eye pain, blurred vision, restlessness, dizziness, arrythmia, flushing, and faintness. An overdose will cause headache, nausea, vomiting, and central nervous system symptoms including disorientation, hallucinations, euphoria, sexual arousal, short-term memory loss, and possible coma in extreme cases. (1)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00424

HMDB ID

HMDB0014568

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

C00002293

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Hyoscyamine

Chemspider ID

10246417

ChEBI ID

17486

PubChem Compound ID

Not Available

Kegg Compound ID

C02046

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Jeffrey Kiel, H. Thomas, Emily Ware, Brady Ware, “Phenolic acid complexes of hyoscyamine and process for preparing the same.” U.S. Patent US20060128637, issued June 15, 2006.

MSDS

Link

General References

Not Available

Hyoscyamine (CHEM002430)

Structure for CHEM002430: Hyoscyamine