Amygdalin

457.43

457.43

66856

249-925-3

251222

29389090

202 Ų

-3.10802

White to Off-white Powder

1.6±0.1 g/cm3

223-226 °C

743.3ºC at 760 mmHg

403.3±32.9 °C

1.650

H2O: 0.1 g/mL hot, clear to very faintly turbid, colorless

-20°C

3.35E-23mmHg at 25°C

Oral-rat LD50: 522 mg/kg; Oral-Mouse LD50: 443 mg/kg

Flammable; heat produces toxic nitrogen oxide fumes

-38.5 º (c=4, H2O)

III

6.1(b)

2811

3

22

26-36/37/39-45-24/25

OO8450000

Xn

Warehouse ventilated, low temperature and dry

H302

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 58 companies from 2 notifications to the ECHA C&L Inventory.

highly toxic

THE ROSE FAMILY INCL MANY OF THE MOST COMMONLY GROWN FRUIT TREES: PLUM, CHERRY, PEACH, APRICOT, APPLE & ALMOND. THE KERNELS & LEAVES OF THESE (& THE PIPS OF THE APPLE) CONTAIN CYANOGENIC GLYCOSIDES. AMYGDALIN IS THE MOST COMMON, BUT PRUNASIN & PRULAURASIN ALSO OCCUR.

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)

THE MAX CYANIDE LEVEL AFTER ORAL ADMIN OF AMYGDALIN TO MICE WAS REACHED AT ABOUT 1 1/2-2 HR & WAS WITHIN THE RANGE OF VALUES SEEN AFTER KCN ADMIN. THE ABILITY OF THE CONTENTS OF VARIOUS REGIONS OF THE GI TRACT & OF TUMOR TISSUE TO RELEASE CYANIDE FROM AMYGDALIN WAS ASSESSED. THE STOMACH & UPPER INTESTINE HAD LITTLE ACTIVITY WHILE THE LOWER INTESTINE & FECES RELEASED LARGE AMOUNTS. THERE WAS A LARGE VARIATION BETWEEN MICE.

AMYGDALIN IS A CHEMICAL COMBINATION OF GLUCOSE, BENZALDEHYDE, & CYANIDE FROM WHICH THE LATTER CAN BE RELEASED BY THE ACTION OF BETA-GLUCOSIDASE OR EMULSIN. ALTHOUGH THESE ENZYMES ARE NOT FOUND IN MAMMALIAN TISSUES, THE HUMAN INTESTINAL MICROFLORA APPEARS TO POSSESS THESE OR SIMILAR ENZYMES CAPABLE OF EFFECTING CYANIDE RELEASE RESULTING IN HUMAN POISONING. FOR THIS REASON AMYGDALIN MAY BE AS MUCH AS 40 TIMES MORE TOXIC BY THE ORAL ROUTE AS COMPARED WITH IV INJECTION.|...PLANT GLYCOSIDES ARE CHARACTERIZED BY PRODN OF CYANIDE, TOGETHER WITH A SUGAR & AROMATIC ALDEHYDE, ON ENZYMIC OR ACID HYDROLYSIS. COMMON EXAMPLES ARE AMYGDALIN (GENTIOBIOSE + BENZALDEHYDE + HCN) WHICH IS PRESENT IN BITTER ALMONDS... AN ENZYME COMPLEX, EMULSIN, IS PRESENT TOGETHER WITH GLYCOSIDES IN PLANT TISSUES & CATALYZES THE HYDROLYSIS OF GLYCOSIDES, FIRST TO MANDELONITRILE OR P-HYDROXYMANDELONITRILE, & THEN TO BENZALDEHYDE OR P-HYDROXYBENZALDEHYDE, & HCN. ... THE ALDEHYDES ARE OXIDIZED TO CORRESPONDING AROMATIC ACIDS & EXCRETED AS PEPTIDE CONJUGATES.|...VARIOUS PRUNUS SPECIES CONTAIN...AMYGDALIN, WHICH IS HYDROLYZED BY ENZYME EMULSIN... IN INTACT PLANT NO SUCH ACTION TAKES PLACE; IT IS NOT UNTIL PLANT TISSUE IS DAMAGED OR STARTS TO DECAY THAT LIBERATION OF HCN BEGINS.|BREAKDOWN /OF GLYCOSIDES/ OFTEN OCCURS MORE READILY OR MORE RAPIDLY IN RUMEN THAN IN DIGESTIVE TRACT OF MONOGASTRIC ANIMALS. ALSO, SMALL MOLECULES CAN BE ABSORBED AT THE RUMEN & THUS ENTER CIRCULATION RAPIDLY. BREAKDOWN OF CYANOGENIC GLYCOSIDES, SUCH AS AMYGDALIN, FROM MEMBERS OF ROSE FAMILY...IS AN EXAMPLE.|For more Metabolism/Metabolites (Complete) data for AMYGDALIN (9 total), please visit the HSDB record page.

PLASMA & URINE CONCN OF AMYGDALIN, WHOLE-BLOOD CONCN OF CN- & SCN- CONCN IN SERUM & URINE WERE DETERMINED IN CANCER PT FOLLOWING IV (4.5 G/SQUARE M) & ORAL (500-MG TABLET) ADMIN OF AMYGDALIN. FOLLOWING IV ADMIN, CONCN OF PARENT DRUG AS HIGH AS 1401 MUG/ML WERE OBSERVED WITH NO INCR IN PLASMA CONCN OF CN- OR SERUM CONCN OF SCN-. PLASMA ELIM OF AMYGDALIN WAS BEST DESCRIBED BY 2-COMPARTMENT OPEN MODEL WITH MEAN DISTRIBUTIVE PHASE T/2 OF 6.2 MIN, MEAN ELIM PHASE T/2 OF 120.3 MIN, & MEAN CLEARANCE OF 99.3 ML/MIN. FOLLOWING ORAL ADMIN OF AMYGDALIN, PLASMA CONCN WERE MUCH LOWER, WITH PEAK VALUES OF LESS THAN 525 NG/ML. CN- CONCN INCR TO VALUES AS HIGH AS 2.1 MUG/ML WHOLE BLOOD. SCN- CONCN DID NOT INCR FOR SEVERAL DAYS, PLATEAUING AT VALUES AS HIGH AS 38 MUG/ML SERUM.

TWO CASES OF LAETRILE (AMYGDALIN) TOXICITY WERE REPORTED IN A 48-YR-OLD WOMAN WITH LYMPHOMA & A 46-YR-OLD MAN WITH A LARGE CELL ANAPLASTIC CARCINOMA OF THE LUNG. THE WOMAN EXHIBITED FEVER, MALAISE, HEADACHE, SEVERE ABDOMINAL CRAMPS, A DIFFUSE MACULAR ERYTHEMATOUS RASH, LYMPHADENOPATHY & HEPATOSPLENOMEGALY FOLLOWING A WEEKLY 6 MG IV INJECTION & 5OO MG 3 TIMES DAILY ORALLY. THE MAN PRESENTED WITH PROGRESSIVE NEUROMUSCULAR WEAKNESS OF BOTH LOWER & UPPER EXTREMITIES FOLLOWING ORAL ADMIN OF 500 MG OF AMYGDALIN DAILY. BOTH CASES OF TOXICITY RESULTING FROM ORAL ADMIN WAS RESOLVED FOLLOWING DISCONTINUATION OF THE DRUG.|A FATAL LAETRILE (AMYGDALIN) INGESTION BY A 57-YR-OLD FEMALE WITH BREAST CARCINOMA WAS PRESENTED. CYANIDE LEVEL ON ADMISSION TO HOSPITAL WAS 29.0 MCG/DL. THE PT IMPROVED WITH SYMPTOMATIC THERAPY & WAS TRANSFERRED TO ANOTHER HOSPITAL FROM WHICH SHE WAS DISCHARGED 3 DAYS LATER. TWELVE DAYS LATER, THE PT WAS RETURNED TO THE EMERGENCY DEPARTMENT WITH NO SIGN OF LIFE. AN AUTOPSY REVEALED A CYANIDE LEVEL OF 218 MCG/DL & DOCUMENTED THE CAUSE OF DEATH AS CYANIDE POISONING.|A NEAR FATAL CASE OF CYANIDE POISONING IS REPORTED IN A 48-YR-OLD WOMAN AFTER A 9 DAY COURSE OF LAETRILE (AMYGDALIN). LAETRILE WAS ADMIN IV, IM, ORALLY, & RECTALLY ALONG WITH A "DETOXIFICATION DIET". BLOOD LEVELS OF CYANIDE ON ADMISSION WERE 116 MUG/DL.|TWO EPISODES OF CYANIDE POISONING OCCURRED IN CHILDREN AFTER INGESTION OF APRICOT KERNELS. THE 1ST EPISODE INVOLVED 8 CHILDREN WHO EXHIBITED TYPICAL SIGNS & SYMPTOMS OF CYANIDE POISONING 2 HR AFTER INGESTION OF LARGE AMOUNTS; 7 CHILDREN RECOVERED & 1 DIED. THE 2ND EPISODE INVOLVED 16 CHILDREN WHO HAD EATEN SWEETS PREPARED FROM KERNELS. SYMPTOMS & SIGNS WERE THE SAME AS THOSE IN THE 1ST GROUP BUT APPEARED 1/2 HR AFTER INGESTION & WERE VERY SEVERE. THREE OF THE CHILDREN DIED.|AMYGDALIN IS A CHEMICAL COMBINATION OF GLUCOSE, BENZALDEHYDE, & CYANIDE FROM WHICH THE LATTER CAN BE RELEASED... AMYGDALIN IS THE MAJOR INGREDIENT OF LAETRILE, & THIS ALLEGED ANTICANCER DRUG HAS ALSO BEEN RESPONSIBLE FOR HUMAN CYANIDE POISONING.

Amygdalin

AMYGDALIN IS A CHEMICAL COMBINATION OF GLUCOSE, BENZALDEHYDE, & CYANIDE... AMYGDALIN IS THE MAJOR INGREDIENT OF LAETRILE...ALLEGED ANTICANCER DRUG...|ALTHOUGH AMYGDALIN HAS BEEN REPORTED TO HAVE BEEN USED IN CANCER CHEMOTHERAPY SINCE 1845, THERE IS AN ABSENCE OF PUBLISHED DATA SUBSTANTIATING ITS ANTICANCER ACTIVITY. THE TERM AMYGDALIN IS CURRENTLY USED INTERCHANGEABLY WITH LAETRILE.|THE RECENT US SUPREME COURT RULINGS DEALING WITH CASES OF LAETRILE (AMYGDALIN) USE ARE DISCUSSED. THE COURT DECIDED THAT LAETRILE WAS INEFFECTIVE AS AN ANTINEOPLASTIC AGENT FOR THE TERMINALLY ILL.

A RAPID SCREENING TEST FOR DETECTING AMYGDALIN IN TABLETS, SOLUTIONS, POWDERS, & SEEDS, BASED ON THE LIBERATION OF BOTH HYDROGEN CYANIDE & BENZALDEHYDE AS A RESULT OF ENZYMATIC DECOMPOSITION, IS DESCRIBED.|THE INVESTIGATION OF 3 INJECTABLE DOSAGE FORMS OF AMYGDALIN AND DETERMINATION OF THEIR CYANIDE CONTENT BY HIGH PERFORMANCE LIQUID CHROMATOGRAPHY, GAS CHROMATOGRAPHY, MICRODIFFUSION ANALYSIS & NMR SPECTROSCOPY ARE PRESENT.|NMR ANALYTICAL PROCEDURES WERE DESCRIBED FOR THE QUALITATIVE & QUANTITATIVE DETERMINATION OF AMYGDALIN. THE SPECTRUM WAS VERY SPECIFIC FOR AMYGDALIN, PARTICULARLY THE SUGAR REGION.|AMYGDALIN WAS HYDROLYZED BY BETA-GLUCOSIDASE. THE LIBERATED BENZALDEHYDE WAS CONVERTED BY PENTAFLUOROBENZYLOXYLAMINE TO ITS O-PENTAFLUOROBENZYL OXIME. THE LATTER WAS DETERMINED BY GC USING A FLAME IONIZATION OR ELECTRON CAPTURE DETECTOR.|AMYGDALIN WAS DETERMINED IN APRICOT KERNEL & APRICOT PRODUCTS BY HIGH-PRESSURE LIQUID CHROMATOGRAPHY.

AMYGDALIN & ITS MAJOR METABOLITE, PRUNASIN, IN BLOOD & URINE WERE SEPARATED FROM PROTEINS BY ULTRAFILTRATION & THEN SUBJECTED TO HIGH-PRESSURE LIQ CHROMATOGRAPHY, USING 10% METHYL CYANIDE AS ELUENT & DETERMINATION BY ABSORPTION AT 215 NM. THE METHOD GAVE LINEAR RESULTS IN THE RANGE 2-500 MG/L & WAS RELIABLE DOWN TO 1 MG/L.|AMYGDALIN WAS DETERMINED IN TISSUES OR SERUM INDIRECTLY OR DIRECTLY. IN THE INDIRECT METHOD, SERUM OR TISSUE HOMOGENATES WERE INCUBATED WITH BETA-GLUCOSIDASE & THE INCUBATE HYDROLYZED WITH AMMONIUM HYDROXIDE, ACIDIFIED, EXTRACTED WITH 95:5 METHYLENE CHLORIDE-HEPTANE, & THE FORMED BENZALDEHYDE DETERMINED SPECTROPHOTOMETRICALLY AT 243 NM OR BY MASS FRAGMENTOGRAPHY. IN THE DIRECT METHOD, AMYGDALIN WAS DETERMINED AFTER EXTRACTION WITH ACETONE BY TLC, HPLC & GC.