Muscarine Chloride

HCID 16817CAS 2303-35-7

Basic information

Standard SMILES
C[C@@H]1O[C@H](C[N+](C)(C)C)C[C@H]1O.[Cl-]
InChIKey
WUFRNEJYZWHXLC-CTERPIQNSA-M
Molecular formula
C9H20ClNO2
Average molar mass
209.71 g/mol
Monoisotopic mass
209.11825656

Overview

Main toxic constituent of the fly fungus Amanita muscaria and various Inocybe species (2S,4R,5S)-Muscarine belongs to the family of Oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms.

Names & identifiers

Preferred name
Muscarine Chloride
IUPAC
[(2S,4R,5S)-4-hydroxy-5-methyloxolan-2-yl]methyl-trimethylazanium chloride
English name
(+)-MUSCARINE CHLORIDE
Molecular formula
C9H20NO2.Cl
Molecular weight
209.71

Names & synonyms

(+)-Muscarine chloride2303-35-7MUSCARINE CHLORIDEL-(+)-Muscarine chlorideHSDB 3515EINECS 218-963-2U700RQ3UBQ(+-)-Muscarine chlorideD-ribo-Hexitol, 2,5-anhydro-1,4,6-trideoxy-6-(trimethylammonio)-, chloride (1:1)MUSCARINE CHLORIDE [MI]MUSCARINE CHLORIDE [HSDB]DTXSID30945718
Show more names
HSDB-35154beta,5alpha))-(2alphl-(+)-muscarinechloride(+)-Muscarine chloride in methanoltetrahydro-4-hydroxy-n,n,n,5-tetramethyl-,chloride,(2s-2-furanmethanaminiu[(2S,4R,5S)-4-hydroxy-5-methyloxolan-2-yl]methyl-trimethylazanium chloride[(2S,4R,5S)-4-hydroxy-5-methyl-oxolan-2-yl]methyl-trimethyl-azanium chloride(+)-Tetrahydro-4β-hydroxy-N,N,N,5α-tetramethyl-2α-furanmethanaminium chloride
DL-Muscarine chloride2-Furanmethanaminium, tetrahydro-4-hydroxy-N,N,N,5-tetramethyl-, chloride, (2S-(2alpha,4beta,5alpha))-2936-25-62-Furanmethanaminium, tetrahydro-4-hydroxy-N,N,N,5-tetramethyl-, chloride, (2alpha,4beta,5alpha)-(+-)-Muscarine, chlorideDTXSID40861854(+)Muscarine chlorideL(+)Muscarine chloride

Database identifiers

CAS
2303-35-7、2936-25-6
PubChem CID
16817
DTXSID
DTXSID30945718
ChEMBL
CHEMBL1255785
UNII
U700RQ3UBQ
EC Number
218-963-2、636-708-7

Properties

Computed structural properties

Topological polar surface area
29.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
2
Heavy atoms
13

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Mushroom Toxins
Color/FormSTOUT PRISMS FROM ETHANOL + ACETONE
SolubilityVERY SOL IN WATER, ETHANOL; SLIGHTLY SOL IN CHLOROFORM, ETHER, ACETONE
Melting Point180-181 °C
Optical RotationSPECIFIC OPTICAL ROTATION: +8.1 DEG @ 25 °C/D (CONCN= 3.5 IN ETHANOL)
Physical DescriptionExtremely hygroscopic solid; [Merck Index]

Physicochemical properties

Melting point
180 · 180-181 °C
solubility
2 O: · H2O: 50 mg/mL
form
powder
color
white
Water Solubility
2 O: · H2O: 50mg/mL
Stability
Hygroscopic

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

Hazard information

Hazards Summary · 1 item

Intravenous LD50 (mouse) = 230 ug/kg; [RTECS] Emergency treatment: Mushrooms- muscarine/histamine; Used in research because it causes excitatory effects on cells innervated by postganglionic cholinergic nerves, but none on nicotinic receptors of autonomic ganglia or skeletal muscles; [HSDB] Symptoms after ingestion are sweating, salivation, impaired vision, nausea, vomiting, abdominal pain, diarrhea, headache, and bronchospasm; High doses may cause lacrimation, incontinence, bradycardia, hypotension, and shock; [Merck Index] May cause irritation; Highly toxic by inhalation, skin absorption, and ingestion; Targets nerves; [MSDSonline]

Special Reports · 1 item

A REVIEW & DISCUSSION WITH 33 REFERENCES ON SCREENING METHODS FOR & PHARMACOLOGY OF MUSCARINE & OTHER CENTRALLY ACTIVE COMPONENTS OF AMANITA MUSCARIA.[WASER PG; THE PHARMACOLOGY OF AMANITA MUSCARIA; ETHNOPHARMACOL SEARCH PSYCHOACT DRUGS (PROC SYMP) 419-39 (1979)]

Hazard Classes and Categories · 2 items

Acute Tox. 2 (100%)

Acute Tox. 4 (100%)

Toxicology

TreatmentThe specific antidote is atropine. (L1011)
Health EffectsIntoxication generally subsides within 2 hours. Death is rare, but may result from cardiac or respiratory failure in severe cases. (L1011)
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity SummaryMuscarine is a competitive inhibitor. It mimics the action of the neurotransmitter acetylcholine at acetylcholine receptors. (L1011)
Signs and Symptoms · 1 item

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. (L1011)

Safety data

PPE
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
rtecs
QG3500000
ridadr
UN 2811 6.1/PG 2
risk_code
26/27/28
Signal word
Danger

Chemistry & industry

Pharmacology

Mechanism of Action · 2 items

MUSCARINE ACTS ALMOST EXCLUSIVELY AT MUSCARINIC RECEPTOR SITES... MUSCARINIC ALKALOIDS STIMULATE SMOOTH MUSCLES OF INTESTINAL TRACT... THE TONE & MOTILITY OF URETERS, URINARY BLADDER, GALLBLADDER, & BILIARY DUCTS ARE...ENHANCED... MUSCARINE.../IS/ POTENT DIAPHORETIC.../AGENT/. /MUSCARINE/

...ON SYSTEMIC ADMIN IT SOMEWHAT MORE FAITHFULLY SIMULATES PARASYMPATHETIC STIMULATION THAN DOES THE REAL PARASYMPATHETIC NEUROHUMOR, ACETYLCHOLINE. BECAUSE OF THIS & BECAUSE OF ITS TEMPORAL PRIORITY, MUSCARINE HAS BEEN A TIME-HONORED PROTOTYPE OF PARASYMPATHOMIMETICS, & THE NEUROEFFECTOR ACTIONS OF THE PARASYMPATHOMIMETICS ARE DESIGNATED AS MUSCARINIC ACTIONS. /MUSCARINE/

Absorption, Distribution and Excretion...VERY POORLY ABSORBED FROM GI TRACT... /MUSCARINE/

Uses & manufacturing

Uses · 3 items

Muscarine: Alkaloid found in red variety of Amanita muscaria and other fungi; Used as a cholinergic drug; [Merck Index] Used strictly for research purposes; [HSDB]

IN RESEARCH AS CHOLINERGIC AGENT /MUSCARINE/

Muscarine is only a trace compound in the fly agaric Amanita muscaria; the pharmacologically more relevant compound from this mushroom is muscimol. Mushrooms in the genera Entoloma and Mycena have also been found to contain levels of muscarine which can be dangerous if ingested. Muscarine has been found in harmless trace amounts in Boletus, Hygrocybe, Lactarius and Russula. (L1011)

Methods of Manufacturing · 1 item

STRUCTURE & SYNTHESIS OF RACEMATE: KOGL ET AL REC TRAV CHIM 76, 109 (1957); KOGL ET AL, EXPERIENTIA 13, 137 (1957); COX ET AL, HELV CHIM ACTA 41, 229 (1958). ALTERNATE SYNTHESES: BRITISH PATENT 828,395 (1960 TO HOFFMAN-LA ROCHE); MATSUMOTO ET AL, TETRAHEDRON 25, 5889 (1969); WC STILL, JA SCHNEIDER, J ORG CHEM 45, 3375 (1980). SYNTHESIS OF MUSCARINE: WHITING ET AL, CAN J CHEM 50, 3322 (1972); AM MUBARAK, DM BROWN, TETRAHEDRON LETTERS 21, 2453 (1980) /&/...J CHEM SOC PERKIN TRANS I 1982, 809; S POCHET, T HUYNHDINH, J ORG CHEM 47, 193 (1982). /MUSCARINE/

General Manufacturing Information · 3 items

MUSCARINE HAS NO CLINICAL USES... /MUSCARINE/

ONLY THE NATURALLY OCCURRING L-(+)-FORM EXHIBITS CHOLINOMIMETIC ACTIVITY. /MUSCARINE/

...USED IN RESEARCH... MUSCARINE HAS BEEN EMPLOYED EXPERIMENTALLY FOR MANY YEARS BECAUSE IT HAS VERY SELECTIVE EXCITATORY EFFECT ON THE EFFECTOR CELLS OF TISSUES INNERVATED BY POSTGANGLIONIC CHOLINERGIC NERVES. IT DOES NOT STIMULATE THE NICOTINIC RECEPTORS OF AUTONOMIC GANGLIA OR SKELETAL MUSCLE AS DOES ACETYLCHOLINE. /MUSCARINE/

Applications

Uses(+)-Muscarine Chloride modulates calcium channel currents in rats.

Suppliers16 total

艾吉析科技(上海)有限公司17717235263 · [email protected]
Aladdin Scientific[email protected]
怀化市冰峰化工有限公司0745-2866851 17711757908 · [email protected]
成都思天德生物科技有限公司028-83243028 19136088901 · [email protected]
常州翔龙医药科技有限公司18915873328 18915873328 · [email protected]

Related reactions

0 records

No reaction records under the current filter.

Linked notes

Loading…