3-Aminopropionitrile

70.095

70.09

1698848

205-786-0

38D5LJ4KH2

40641

DTXSID6048418

Liquid

29269090

49.8

-1

Clear colorless to yellow Liquid

0.9584 g/cm³ @ Temp: 20 °C

<25 °C

185 °C @ Press: 760 Torr

79-81°C/16mm

1.4365-1.4395

soluble in water.

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.

2 mm Hg @ 38-40 deg C

Peritoneal-mouse LD50: 1152 mg/kg

Flammable; generates toxic nitrogen oxides and cyanide fumes when exposed to heat

A storage hazard; it polymerizes to an explosive yellow solid.

Amine odor

Crystalline solid /Hydrochloride/|May polymerize if stored in the presence of air.

III

8

3276

20/21/22-34-22-63

36/37-45-36/37/39-26

UG0350000

Xn,C

Warehouse ventilated, low temperature and dry

Easily oxidized and unstable; it can polymerize into an explosive yellow solid during storage

Easily oxidized and unstable.

P201, P202, P260, P264, P270, P280, P281, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P321, P330, P363, P405, P501

H302

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.

Easily oxidized and unstable.

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)]

A storage hazard; it polymerizes to an explosive yellow solid.

moderately toxic

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.

LD50 Mouse ip 1152 mg/kg

...HAS BEEN ISOLATED FROM SEEDS OF L ODORATUS... /IT/ EXISTS IN THE PLANT AS BETA-(GAMMA-L-GLUTAMYL)AMINOPROPIONITRILE, & IS ALSO FOUND IN L ROSEUS & L HIRSUTUS.

EXPTL USE: ADMIN OF LYSYL OXIDASE INHIBITOR, BAPN, PREVENTED DEVELOPMENT OF HYPERTENSION & DECR AMT OF VASCULAR COLLAGEN IN RATS IN WHICH HYPERTENSION HAD BEEN INDUCED. HISTOLOGICAL EXAM REVEALED THAT ARTERIOSCLEROTIC CHANGES WERE PREVENTED BY BAPN.|EXPTL USE: IN YOUNG HYPERTENSIVE RATS, BAPN (20 MG, IP DAILY, FOR 2 WK) PREVENTED DEVELOPMENT OF HYPERTENSION. IN ADULT SPONTANEOUS HYPERTENSIVE RATS (50 MG, IP, DAILY FOR 2 WK) DECR BLOOD PRESSURE.|EXPTL USE: RATS WITH SC IMPLANTED POLYVINYL ALCOHOL SPONGES AND WITH INFLICTED SKIN INCISION WOUNDS RECEIVED A SINGLE INJECTION OF BETA-AMINOPROPIONITRILE (BAPN) AT 4 DOSAGES RANGING FROM 1-40 MG/100 G. EVEN THE LOWEST DOSE OF BAPN INHIBITED LYSYL OXIDASE ACTIVITY FOR 6 HOURS; WITH LARGER DOSAGES THE INHIBITION LASTED LONGER, AT 40 MG BAPN, AT LEAST 48 HOURS. THE MAGNITUDE AND DURATION OF INHIBITION WERE REFLECTED IN THE EXTRACTABILITY OF COLLAGEN AND BURSTING STRENGTH OF THE WOUND. THE DATA SUGGEST THAT A MINIMAL DOSE OF BAPN WOULD BE CLINICALLY EFFECTIVE IF EITHER THE METABOLISM OF THE DRUG WERE REDUCED (BY MONOAMINE OXIDASE INHIBITORS) OR A SUSTAINED-RELEASE PREPARATION OF BAPN WERE USED.|EXPTL USE: BETA-AMINOPROPIONITRILE (BAPN) WAS TESTED FOR ABILITY TO PREVENT EXCESS COLLAGEN FORMATION IN BLEOMYCIN-INDUCED PULMONARY FIBROSIS IN THE HAMSTER. TWO GROUPS RECEIVED 1 ENDOTRACHEAL DOSE OF BLEOMYCIN; ONE OF THESE WAS INJECTED WITH BAPN TWICE DAILY FOR 30 DAYS. A 3RD GROUP RECEIVED SALINE AND BAPN. THE BLEOMYCIN INCREASED COLLAGEN CONTENT, DECREASED LUNG VOLUME, AND PRODUCED FIBROSIS AND A MORTALITY RATE OF 51%. ADMINISTRATION OF BAPN TO BLEOMYCIN-TREATED ANIMALS PREVENTED EXCESS COLLAGEN ACCUMULATION, PRODUCED LESS FIBROSIS, AND LESSENED MORTALITY RATE TO 24%; BAPN ALONE HAD NO EFFECT ON LUNG MECHANICS OR COLLAGEN CONTENT.

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.

...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.

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/

... Its glutamyl derivative ... /is/ probable causative factor in toxicity of sweet peas.

Aminopropionitrile

Propanenitrile, 3-amino-: ACTIVE|Propanenitrile, 3-amino-, N-C11-13-isoalkyl derivs.: INACTIVE|Propanenitrile, 3-amino-, N-[3-(C12-18-alkyloxy)propyl] derivs.: INACTIVE

THIN-LAYER CHROMATOGRAPHY OF BETA-AMINOPROPIONITRILE PERMITTED ITS SEPARATION FROM AMINO ACIDS IN RAT LIVER PERFUSION FLUID WITHOUT PRIOR SOLVENT EXTRACTION.