T3DB: Hyoscyamine

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

Targets (5)

Record Information

Version

2.0

Creation Date

2009-07-23 18:26:14 UTC

Update Date

2014-12-24 20:25:58 UTC

Accession Number

T3D3095

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.

Compound 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

Synonym
(-)-Atropine
(-)-Hyoscyamine
(leo)-atropine
(leo)-hyoscyamine
(S)-(-)-Hyoscyamine
(S)-(leo)-hyoscyamine
(S)-(−)-hyoscyamine
(S)-atropine
(S)atropine
(−)-atropine
(−)-hyoscyamine
Acupaz
Anapaz
Anaspaz
Atropen
Boots Travel Calm
Buwecon
Cystospaz
Cytospaz
Daturin
Daturine
Donnamar
Duboisine
Egazil
Hyocyamine
Hyoscyamin
Hyoscyaminum
L-Atropine
L-Hyopscyamine
L-Hyoscamine
L-Hyoscyamine
L-Tropine Tropate
Levbid
Levsin
Levsinex
NuLev
Symax
Tropine, (-)-tropate
Tropine-L-tropate
[3(S)-Endo]-alpha-(hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester

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

[H][C@](CO)(C(=O)O[C@]1([H])C[C@]2([H])CC[C@]([H])(C1)N2C)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

InChIKey=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)
LogP	1.8

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	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-5900000000-f705f96b0219dcd47d66	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0006-4900000000-d0c3228da9df55297f7b	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-006x-6951100000-43127e046c478d2643e1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-006x-6951100000-43127e046c478d2643e1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-006x-6960000000-96b74c70ce0011e5968d	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-0790000000-b3809a4d9f3d53472626	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1920000000-5cf6a284aa0360bfa6f5	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0g02-2900000000-03a359b67b71a8d41b5a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0490000000-42268e6db552a2d85a66	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05g3-1960000000-db1243e11ae5ea609f09	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00bc-5900000000-3453e9ae42b1ccba243c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-38746560650547c38a28	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-1590000000-abf830c79515feb657d2	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006y-9500000000-28e9eb9a8330fa4c60d9	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0490000000-4b2dacd04cd09b1229da	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0g4r-1910000000-6bc43ea9e9a781364124	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-1910000000-9a0fd9e7ddf07814092b	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-9810000000-bdd60b3a23f97899d426	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View 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

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

17486

BioCyc ID

CPD-2202

CTD ID

Not Available

Stitch ID

L-Hyoscyamine

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Hyoscyamine

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

Wikipedia. Hyoscyamine. Last Updated 10 June 2009. [Link]
Drugs.com [Link]
Wikipedia. Phytotoxin. Last Updated 7 August 2009. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Muscarinic acetylcholine receptor M1

General Function:: Phosphatidylinositol phospholipase c activity
Specific Function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:: CHRM1
Uniprot ID:: P11229
Molecular Weight:: 51420.375 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
Wikipedia. Hyoscyamine. Last Updated 10 June 2009. [Link]

Target Details

2. Muscarinic acetylcholine receptor M2

General Function:: G-protein coupled acetylcholine receptor activity
Specific Function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then triggers calcium ion release into the cytosol.
Gene Name:: CHRM2
Uniprot ID:: P08172
Molecular Weight:: 51714.605 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
Wikipedia. Hyoscyamine. Last Updated 10 June 2009. [Link]

Target Details

3. Muscarinic acetylcholine receptor M3

General Function:: Receptor activity
Specific Function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:: CHRM3
Uniprot ID:: P20309
Molecular Weight:: 66127.445 Da

References

Wikipedia. Hyoscyamine. Last Updated 10 June 2009. [Link]

Target Details

4. Muscarinic acetylcholine receptor M4

General Function:: Guanyl-nucleotide exchange factor activity
Specific Function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase.
Gene Name:: CHRM4
Uniprot ID:: P08173
Molecular Weight:: 53048.65 Da

References

Wikipedia. Hyoscyamine. Last Updated 10 June 2009. [Link]

Target Details

5. Muscarinic acetylcholine receptor M5

General Function:: Phosphatidylinositol phospholipase c activity
Specific Function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:: CHRM5
Uniprot ID:: P08912
Molecular Weight:: 60073.205 Da

References

Wikipedia. Hyoscyamine. Last Updated 10 June 2009. [Link]

Hyoscyamine (T3D3095)

Structure for T3D3095: Hyoscyamine

Targets

References

References

References

References

References