(2S,4R,5S)-Muscarine (CED0048937)

Record Information

Version

1.0

Creation Date

2009-07-03 20:53:35 UTC

Update Date

2026-04-03 21:35:00 UTC

Accession Number

CHEM002041

Identification

Common Name

(2S,4R,5S)-Muscarine

Class

Small Molecule

Description

(2S,4R,5S)-Muscarine is an exogenous organic compound with the formula C9H20NO2 and an average molecular weight of 174.26 g/mol. It exists as a solid at room temperature. (2S,4R,5S)-Muscarine belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds. The compound acts as a competitive inhibitor that mimics the action of the neurotransmitter acetylcholine at acetylcholine receptors. It has eight recorded protein targets, including the acetylcholine receptor subunits alpha (CHRNA1), beta (CHRNB1), delta (CHRND), and epsilon (CHRNE). Additionally, it targets the muscarinic acetylcholine receptors M1 (CHRM1), M2 (CHRM2), and M4 (CHRM4).

Contaminant Type

Ether
Food Toxin
Fungal Toxin
Metabolite
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF 3D SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Muscarin	ChEMBL
L-(+)-Muscarine	ChEMBL

Chemical Formula

C₉H₂₀NO₂

Average Molecular Mass

174.260 g/mol

Monoisotopic Mass

174.149 g/mol

CAS Registry Number

300-54-9

IUPAC Name

{[(2S,4R,5S)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium

Traditional Name

(+)-muscarine

SMILES

[H][C@@]1(C)O[C@]([H])(C[N+](C)(C)C)C[C@@]1([H])O

InChI Identifier

InChI=1S/C9H20NO2/c1-7-9(11)5-8(12-7)6-10(2,3)4/h7-9,11H,5-6H2,1-4H3/q+1/t7-,8-,9+/m0/s1

InChI Key

UQOFGTXDASPNLL-XHNCKOQMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentoses

Alternative Parents

Substituents

Pentose monosaccharide
Quaternary ammonium salt
Tetraalkylammonium salt
Tetrahydrofuran
Secondary alcohol
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Amine
Organic salt
Alcohol
Organic cation
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

monosaccharide (CHEBI:7034 )
Alkaloids (C07473 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.64 g/L	ALOGPS
logP	-3	ALOGPS
logP	-4.3	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	14.11	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	59.89 m³·mol⁻¹	ChemAxon
Polarizability	20.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0f9y-6900000000-79763ab7b63262ffe2c2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0900000000-c226ed17dd770fa6c411	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-2900000000-67eb26beea6d618ebb7d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-5900000000-4e0964583deb72b35ef6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-05fr-9500000000-a0a0c909b980bb4769c2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-9200000000-be98c82a4035b83f8750	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-9100000000-e8830a6e2498d5ca0b6f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-9000000000-19f49df6db6e4b92cf3d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4l-9000000000-0755c01a97b2a22de481	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4l-9000000000-b0b62b0c3630f7342703	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-052f-9000000000-0a2f7b3f7e5bf0ef5ed3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-052f-9000000000-24069c492c822c8073ed	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0900000000-e02b9884b570bdfc5d5c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-2900000000-1be2813c25bfaa5cb10c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-05fr-9600000000-cb4c5b9dc39c97a63239	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0c00-9100000000-2e0e0d8c33dd5405906b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0bt9-9000000000-1c66632fe3ec85e7e9b7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0bt9-9000000000-b821cc1b0c3b1409a2a4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-9000000000-4556237f549b235f4c6e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-4900000000-2e898bb2167bdd163be9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-9000000000-e58e4ee62799955c0939	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05fr-0900000000-a0080208160655ea0b73	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ab9-2900000000-9edf94eafe412073184c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05fr-9100000000-c8c1131f5df11bfdcd19	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Muscarine is a competitive inhibitor. It mimics the action of the neurotransmitter acetylcholine at acetylcholine receptors. (2)

Carcinogenicity (IARC Classification)

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

Minimum Risk Level

Not Available

Symptoms

Muscarine poisoning is characterized by increased salivation, sweating (perspiration), and tearflow (lacrimation) within 15 to 30 minutes after ingestion of the mushroom. With large doses, these symptoms may be followed by abdominal pain, severe nausea, diarrhea, blurred vision, and labored breathing. (2)

Treatment

The specific antidote is atropine. (2)

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
1050.0	Log mg/kg	[590:1900]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	11.0546
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Predicted (SEA)	9.6533
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	115.606
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P08483	Rattus norvegicus	Predicted (SEA)	8.17417
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P08482	Rattus norvegicus	Predicted (SEA)	30.8283
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P10980	Rattus norvegicus	Predicted (SEA)	25.301
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08485	Rattus norvegicus	Predicted (SEA)	8.25202
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	3204.51
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	3592.51
Click to view 3D structure	Alpha-galactosidase	Q5DUH8	Coffea arabica	Predicted (SEA)	3.81461
Click to view 3D structure	High affinity choline transporter 1	Q9GZV3	Humans	Predicted (SEA)	1764.92
Click to view 3D structure	Short transient receptor potential channel 4	Q9QUQ5	Mus musculus	Predicted (SEA)	4111.14
Click to view 3D structure	PA-I galactophilic lectin	Q05097	Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)	Predicted (SEA)	15.1806
Click to view 3D structure	Plasma alpha-L-fucosidase	Q9BTY2	Humans	Predicted (SEA)	4.12601
Click to view 3D structure	Thymidine kinase, cytosolic	P04183	Humans	Predicted (SEA)	97.2337
Click to view 3D structure	Maltase-glucoamylase	O43451	Humans	Predicted (SEA)	164.962
Click to view 3D structure	Fucose-binding lectin PA-IIL	Q9HYN5	Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)	Predicted (SEA)	20.3965
Click to view 3D structure	Lectin	B4EH87	Burkholderia cenocepacia (strain ATCC BAA-245 / DSM 16553 / LMG 16656/ NCTC 13227 / J2315 / CF5610) (Burkholderia cepacia (strain J2315))	Predicted (SEA)	38.0683
Click to view 3D structure	Sucrase-isomaltase, intestinal	P23739	Rattus norvegicus	Predicted (SEA)	44.3741
Click to view 3D structure	Tissue alpha-L-fucosidase	P04066	Humans	Predicted (SEA)	10.9767
Click to view 3D structure	Lysosomal alpha-glucosidase	P10253	Humans	Predicted (SEA)	68.663
Click to view 3D structure	Muscarinic acetylcholine receptor M3	Q8VH26	Cavia porcellus	Predicted (SEA)	3016.03
Click to view 3D structure	Thymidine kinase, cytosolic	P27158	Rattus norvegicus	Predicted (SEA)	61.423
Click to view 3D structure	Sucrase-isomaltase, intestinal	P14410	Humans	Predicted (SEA)	54.5723
Click to view 3D structure	Thymidine kinase	P06479	Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1)	Predicted (SEA)	248.728
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Known	Not Available
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Known	Not Available
Click to view 3D structure	Acetylcholine receptor subunit alpha	P02708	Humans	Known	Muscarine is a competitive inhibitor. It mimics the action of the neurotransmitter acetylcholine at acetylcholine receptors. (L1011)
Click to view 3D structure	Acetylcholine receptor subunit beta	P11230	Humans	Known	Muscarine is a competitive inhibitor. It mimics the action of the neurotransmitter acetylcholine at acetylcholine receptors. (L1011)
Click to view 3D structure	Acetylcholine receptor subunit delta	Q07001	Humans	Known	Muscarine is a competitive inhibitor. It mimics the action of the neurotransmitter acetylcholine at acetylcholine receptors. (L1011)
Click to view 3D structure	Acetylcholine receptor subunit epsilon	Q04844	Humans	Known	Muscarine is a competitive inhibitor. It mimics the action of the neurotransmitter acetylcholine at acetylcholine receptors. (L1011)
Click to view 3D structure	Acetylcholine receptor subunit gamma	P07510	Humans	Known	Muscarine is a competitive inhibitor. It mimics the action of the neurotransmitter acetylcholine at acetylcholine receptors. (L1011)
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Known	Not Available