(+)-ムスカリン クロリド

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]

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]

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)]

Acute Tox. 2 (100%)

Acute Tox. 4 (100%)

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)

ALKALOID FROM RED VARIETY OF AMANITA MUSCARIA (L) PERS, AGARICACEAE, THE FLY FUNGUS, A POISONOUS MUSHROOM. ALSO FOUND IN SOME OTHER FUNGI: INOCYBE PATOUILLARDI; I FASTIGIATA, I UMBRINA; I RIMOSA. ISOLATION PROCEDURE FOR THE NATURALLY OCCURRING L-(+)-FORM: KUEHL ET AL, J AM CHEM SOC 77, 6663 (1955); EUGSTER, HELV CHIM ACTA 39, 1002 (1956). /MUSCARINE/

ALTHOUGH AMANITA MUSCARIA IS THE SOURCE FROM WHICH MUSCARINE HAS GENERALLY BEEN ISOLATED, ITS CONTENT OF THE ALKALOID IS SO LOW (APPROX 0.003%) THAT MUSCARINE CANNOT BE RESPONSIBLE FOR THE MAJOR TOXIC EFFECTS. MUCH HIGHER CONCENTRATIONS OF MUSCARINE ARE PRESENT IN VARIOUS SPECIES OF INOCYBE & CLITOCYBE. /MUSCARINE/

AT LEAST 3 TYPES OF CLINICAL POISONINGS CAN BE INDUCED BY TOXIC SPECIES OF AMANITA. A RAPID TYPE (MYCETISMUS NERVOSA) FOLLOWS INGESTION OF A MUSCARIA OR A PANTHERINA. SYMPTOMS OCCUR WITHIN FEW MIN OR A FEW HR & MAY OR MAY NOT BE DUE TO ALKALOID MUSCARINE. EFFECTS MIMIC...STIMULATION OF PARASYMPATHETIC NERVOUS SYSTEM. RESULT IS COLICKY ABDOMINAL PAIN...BLURRED VISION...& HYPOTENSION. /AMANITA TOXINS/

INGESTION MAY CAUSE...DIAPHORESIS...MIOSIS, BRADYCARDIA, CIRCULATORY COLLAPSE. MAY PROGRESS TO CONVULSIONS, COMA & DEATH IN A FEW HOURS. /MUSCARINE/

RESULTS OF NEUROLOGICAL AND EEG EXAMINATIONS IN 26 CHILDREN INTOXICATED WITH MUSHROOMS OF VARIOUS SPECIES ARE DISCUSSED. ENCEPHALOPATHY, DEVELOPED FOLLOWING INGESTION OF AMANITA PHALLOIDES, IS SUGGESTED AS AN INDIRECT COMPLICATION. IT WAS SEEN IN CASES OF COMPLETE FAILURE OF LIVER FUNCTION. A NEW FINDING IS THAT OF THE EEG PICTURE IN CHILDREN INTOXICATED WITH INOCYBE PATOUILLARDI. IN EACH OF 3 CHILDREN INVESTIGATED, EEG DEMONSTRATED PRONOUNCED DIFFUSE ABNORMALITIES. CLINICALLY, ONLY 1 CHILD DEMONSTRATED SYMPTOMS & SIGNS TYPICAL OF MUSCARINE INTOXICATION, WHILE THE REMAINING 2 WERE DROWSY & CONFUSED & EXHIBITED TWITCHING OF EXTREMITY MUSCLES. INOCYBE PATOUILLARDI CONTAINS, IN ADDITION TO MUSCARINE, TOXINS WITH A DIRECT EFFECT ON CEREBRAL FUNCTION. CHILDREN INTOXICATED WITH AMANITA MUSCARIA HAD NORMAL EEG & CLINICAL SYMPTOMS & SIGNS OF CHOLINERGIC STIMULATION. TOXICITY OF INDIVIDUAL MUSHROOM SPECIES & SENSITIVITY & REACTIVITY OF INDIVIDUAL CHILDREN TO SPECIES VARIED & DEPENDED ON A NUMBER OF FACTORS.

...FOLLOWING IV INJECTION OF EXTREMELY SMALL DOSES (0.01-0.03 UG/KG) OF MUSCARINE IN VARIOUS SPECIES...MARKED FALL IN BLOOD PRESSURE & SLOWING OR TEMPORARY CESSATION OF THE HEART /OCCURRED/. /MUSCARINE/

(2-METHYL-3-HYDROXY-5-TRIMETHYL-AMMONIUM-METHYLTETRAHYDROFURAN)...INDUCES MIOSIS & ACCOMMODATION FOR NEAR WHEN ADMIN PARENTERALLY OR TOPICALLY TO...MONKEYS, DOGS, CATS, RABBITS, & MICE... /MUSCARINE/

TOXIC DOSES OF CHOLINOMIMETIC ALKALOIDS EVOKE SEVERE COLIC & DIARRHEA & EXOCRINE GLAND SECRETIONS. PUPIL IS MARKEDLY CONSTRICTED. DYSPNEA OCCURS BECAUSE OF CONSTRICTION OF BRONCHIOLES & ACCUMULATION OF MUCUS IN AIRWAYS. HYPOTENSION & EXTREME CARDIAC SLOWING, COMPLICATED BY EXCESSIVE BRONCHIOCONSTRICTION & BRONCHIAL SECRETIONS, LEAD TO DEATH. /CHOLINOMIMETIC ALKALOIDS/

IN UNANESTHETIZED & UNRESTRAINED CATS, MUSCARINE CHLORIDE & CARBACHOL CHLORIDE WERE INJECTED INTO THE CEREBRAL VENTRICLES. THE KIND OF AGGRESSIVE BEHAVIOR ELICITED DEPENDED ON THE CHOLINOMIMETIC DRUG AND WAS CLASSIFIED AS FEAR & IRRITABLE KIND OF AGGRESSION. MUSCARINE INDUCED THE FEAR KIND OF AGGRESSION. THE AGGRESSION WAS ACCOMPANIED BY INTENSE MOTOR BUT LESS AUTONOMIC ACTIVATION.

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/

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)

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/

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/