3-Aminopropionitrile

... It polymerizes to an explosive yellow solid.

In contact with ambient air, it polymerizes slowly, but rapidly in contact with acidic materials.

Liquid with an amine odor; [Merck Index]; [MSDSonline]

Solid

POLYMERIZATION TAKES PLACE SLOWLY DURING STORAGE IN AN OPEN CONTAINER, OR VERY RAPIDLY IN PRESENCE OF ACID OR ACIDIC COMPD

Easily oxidized and unstable.

Danger

H302 (91.7%): Harmful if swallowed [Warning Acute toxicity, oral]；H314 (20.8%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]；H361 (93.8%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

P203, P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P318, P321, P330, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

LATHYRISM ENCOMPASSES 2 ENTITIES: NEUROLATHYRISM IN A VARIETY OF ANIMALS, & OSTEOLATHYRISM OBSERVED MAINLY IN RATS & TURKEYS. BETA-AMINOPROPIONITRILE WAS IDENTIFIED AS INDUCER OF OSTEOLATHYRISM.[BARROW MV ET AL; LATHYRISM: A REVIEW; Q REV BIOL 49(2) 101 (1974)]

THE EFFECT OF CHRONIC BAPN INTOXICATION ON THE PERIODONTIUM OF THE RAT. A LIGHT MICROSCOPIC AND HISTOCHEMICAL STUDY WITH REVIEW OF THE LITERATURE.[BADEN E, BOUISSOU H; THE EFFECT OF CHRONIC BETA-AMINOPROPIONITRILE INTOXICATION ON THE PERIODONTIUM OF THE RAT. A LIGHT MICROSCOPIC AND HISTOCHEMICAL STUDY WITH REVIEW OF THE LITERATURE; ORAL SURG 55(1) 34 (1983)]

PURE, ANHYDROUS MATERIAL MAY BE STORED IN TIGHTLY STOPPERED BOTTLES FOR SEVERAL MONTHS. STORING UNDER REFRIGERATION IS RECOMMENDED TO AVOID DEVELOPMENT OF PRESSURE IN BOTTLES.

A bottle of uninhibited distilled material exploded after shelf storage for several months. It may be stored for several months out of contact with air under refrigeration.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)

USE OF BAPN (1 G/KG/DAY) FOR PERIOD OF 8 WK CAUSED SIMULTANEOUS CHANGES IN SKIN & AORTIC CONNECTIVE TISSUES OF RATS. IN SKIN, COLLAGEN TISSUE WAS DISLOCATED & BROKEN INTO FRAGMENTS, ELASTIC TISSUE DISAPPEARED & FIBROBLASTS WERE VACUOLIZED. ADDITION OF PYRIDINOL CARBAMATE (PDC) TO BAPN PREVENTS FORMATION OF LESIONS OF ELASTIC TISSUE & OF FIBROBLASTS. WHEN GIVEN AFTER CESSATION OF LATHYROGEN TREATMENT, PDC ARRESTED FORMATION OF LESIONS & ACCELERATED THEIR REGRESSION.

A DOSE OF 2,500 MG/KG BAPN GIVEN BY GAVAGE ON DAY 11 TO PREGNANT HAMSTERS PRODUCED 69.5% SKELETAL ANOMALIES IN THE OFFSPRING. ADMINISTRATION OF BETA-HYDROXYETHYLRUTOSIDES (WHICH PROTECT AGAINST COLLAGEN DAMAGE FROM LATHYROGENS) IMMEDIATELY AFTER BAPN TO THE PREGNANT ANIMALS RESULTED IN SIGNIFICANTLY DECREASED TERATOGENIC RESPONSE. THIS SUPPORTS THE VIEW THAT THE MECHANISM FOR BAPN-INDUCED SKELETAL DYSMORPHOGENESIS IS THE INHIBITION OF CROSS-LINKING DURING THE MATURATION OF COLLAGEN FIBERS.

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)

Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

CRYSTALLINE SUBSTANCE...ISOLATED FROM SEEDS OF L ODORATUS WHICH...PRODUCE SYNDROME OF LATHYRISM IN RATS...HAS BEEN IDENTIFIED AS BETA-AMINOPROPIONITRILE.

IN VITRO IN OX CORNEA IT HAS INHIBITED INCORPORATION OF RADIOACTIVE SULFATE INTO ACID MUCOPOLYSACCHARIDES, BUT HAS CAUSED NO ELUTION OF MUCOPOLYSACCHARIDES OR COLLAGEN. ... IN RATS IT HAS FAILED TO INDUCE RETINAL ANGIOPATHY.

In young rats, and various avian species, it produces severe skeletal deformities and aneurysms leading to rupture of aorta. Effective doses to turkey poults may be as low as 0.01% in diet

PATHOGENESIS OF FETAL RIB ABNORMALITY WAS STUDIED AT SHORT TIME INTERVALS IN GOLDEN SYRIAN HAMSTERS FOLLOWING MATERNAL TREATMENT WITH 2500 MG/KG ON DAY 11 OF GESTATION. RIBS FROM FETUSES INDICATED SLIGHT DECR IN LEVEL OF GLYCOSAMINOGLYCANS BUT AT TIME WHEN DEFECT WAS ALREADY MORPHOLOGICALLY ESTABLISHED. ULTRASTRUCTURAL OBSERVATIONS OF CHONDROCYTES REVEALED ALTERATIONS IN MITOCHONDRIAL STRUCTURE INDICATIVE OF SLIGHT CYTOTOXIC EFFECT. MITOCHONDRIAL CHANGES WERE TRANSIENT, OCCURRING INITIALLY AT 3 HR AFTER TREATMENT & LASTING FOR 9 HR. MEAN DIAMETER OF COLLAGEN FIBERS IN RIBS OF CONTROL FETUSES INCR THROUGHOUT COURSE OF STUDY, WHILE MEAN DIAMETER OF FIBERS IN FETUSES OF EXPOSED FEMALES FAILED TO SHOW ANY INCR & WAS SIGNIFICANTLY LESS THAN CONTROLS AS EARLY AS 3 HR FOLLOWING MATERNAL ADMIN.

For more Non-Human Toxicity Excerpts (Complete) data for BETA-AMINOPROPIONITRILE (14 total), please visit the HSDB record page.

QM - Musculo-skeletal system；QM01 - Antiinflammatory and antirheumatic products；QM01A - Antiinflammatory and antirheumatic products, non-steroids；QM01AX - Other antiinflammatory and antirheumatic agents, non-steroids；QM01AX91 - Aminopropionitrile

The mechanism of the effect is unknown, but it is thought to be by some action on growth of certain mesodermal tissues. It is not due to one of its major metabolites, cyanoacetic acid, and both the free amino group and the cyano group seem essential for activity. It is not produced if the amino group is in the alpha position, or if in the gamma position in butyronitrile.

IT HAS BEEN SUGGESTED THAT LATHYROGENIC AGENTS ACT BY BLOCKING CERTAIN CARBONYL GROUPS NORMALLY PRESENT IN COLLAGEN, & THUS INTERFERING WITH FORMATION OF CROSS LINKAGES. THEIR ACTION MAY BE RETARDED BY RESERPINE OR BY CALCIUM SALTS. /LATHYROGENIC AGENTS/

...BETA-AMINOPROPIONITRILE /IS METABOLIZED/ INTO CYANOACETIC ACID...

BETA-AMINOPROPIONITRILE (BAPN) WAS FOUND IN URINE WITHIN 1 HR OF ORAL ADMIN. ORAL 250 MG BAPN AT 6 HR INTERVALS EACH DAY FOR 21 DAYS RESULTED IN URINARY BAPN RECOVERIES APPROXIMATING 16% OF TOTAL DOSE. BAPN WAS NOT DETECTED IN SPECIMENS COLLECTED LATER THAN 7 HR AFTER CESSATION OF BAPN DOSAGE. URINARY CYANOACETIC ACID APPEARED MORE SLOWLY THAN BAPN & INCR GRADUALLY TO APPROX 3 TIMES THAT OF URINARY BAPN. AFTER BAPN WAS DISCONTINUED, THERE WAS PROLONGED URINARY EXCRETION OF BAPN-DERIVED CYANOACETIC ACID.

Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

BETA-AMINOPROPIONITRILE (BAPN) WAS FOUND IN URINE WITHIN 1 HR OF ORAL ADMIN. ORAL 250 MG BAPN AT 6 HR INTERVALS EACH DAY FOR 21 DAYS RESULTED IN URINARY BAPN RECOVERIES APPROXIMATING 16% OF TOTAL DOSE. BAPN WAS NOT DETECTED IN SPECIMENS COLLECTED LATER THAN 7 HR AFTER CESSATION OF BAPN DOSAGE. URINARY CYANOACETIC ACID APPEARED MORE SLOWLY THAN BAPN & INCR GRADUALLY TO APPROX 3 TIMES THAT OF URINARY BAPN. AFTER BAPN WAS DISCONTINUED, THERE WAS PROLONGED URINARY EXCRETION OF BAPN-DERIVED CYANOACETIC ACID.

AFTER APPLICATION TO THE SKIN OF RATS, (14)C-BAPN FREE BASE WAS ABSORBED MORE RAPIDLY AND TO A GREATER EXTENT THAN THE FUMARATE SALT. SIX HOURS AFTER TOPICAL ADMINISTRATION OF THE FREE BASE ONLY TRACES OF (14)C WERE FOUND ON THE SKIN AND LESS THAN 1% OF THE DOSE WITHIN THE SKIN SECTION SUGGESTING RAPID DRUG ABSORPTION.

Used as an intermediate in the production of beta-alanine and pantothenic acid; [Merck Index]

Intermediate in the manufacture of beta-alanine and pantothenic acid

beta-Aminopropionitrile is a reagent used as an intermediate in the manufacture of beta-alanine and pantothenic acid.

(1972) NOT PRODUCED COMMERCIALLY IN US

(1975) NOT PRODUCED COMMERCIALLY IN US