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3-Aminopropionitrile
Also known as: 3-aminopropionitrile, 151-18-8, 2-cyanoethylamine, Aminopropionitrile, Beta-aminopropionitrile, Bapn
Molecular Formula
C3H6N2
Molecular Weight
70.09  g/mol
InChI Key
AGSPXMVUFBBBMO-UHFFFAOYSA-N
FDA UNII
38D5LJ4KH2

Reagent used as an intermediate in the manufacture of beta-alanine and pantothenic acid.
1 2D Structure

3-Aminopropionitrile

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-aminopropanenitrile
2.1.2 InChI
InChI=1S/C3H6N2/c4-2-1-3-5/h1-2,4H2
2.1.3 InChI Key
AGSPXMVUFBBBMO-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(CN)C#N
2.2 Other Identifiers
2.2.1 UNII
38D5LJ4KH2
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Aminopropionitrile

2. Bapn

3. Beta Aminopropionitrile

4. Beta-aminopropionitrile

2.3.2 Depositor-Supplied Synonyms

1. 3-aminopropionitrile

2. 151-18-8

3. 2-cyanoethylamine

4. Aminopropionitrile

5. Beta-aminopropionitrile

6. Bapn

7. 3-aminopropiononitrile

8. Propanenitrile, 3-amino-

9. Beta-cyanoethylamine

10. Beta-alaninenitrile

11. Propionitrile, 3-amino-

12. Beta-aminoethyl Cyanide

13. Beta-alaminenitrile

14. .beta.-aminopropionitrile

15. Nsc 40641

16. 3-amino-propionitrile

17. .beta.-alaninenitrile

18. Chebi:27413

19. .beta.-cyanoethylamine

20. H2nch2ch2cn

21. 38d5lj4kh2

22. Chembl1618272

23. Nsc-40641

24. 3-aminopropionitrile; Aminopropionitrile; Bapn; N-(2-cyanoethyl)amine; Nsc 40641

25. Hsdb 2897

26. Einecs 205-786-0

27. Brn 1698848

28. Cyanoethylamine

29. Unii-38d5lj4kh2

30. Aminoethylcyanide

31. B-alaminenitrile

32. B-alaninenitrile

33. Ccris 8134

34. B-cyanoethylamine

35. 3-aminopropanitrile

36. B-aminoethyl Cyanide

37. Mfcd00014820

38. 3-aminopropanonitrile

39. Beta-aminoproprionitrile

40. N-(2-cyanoethyl)amine

41. Beta-amino Propionitrile

42. Beta-amino-propionitrile

43. Lopac-a-3134

44. .beta.-aminoethyl Cyanide

45. Wln: Z2cn

46. Lopac0_000055

47. Beta-aminopropionitrile Liquid

48. Propanenitrile, 3-amino-, N-c11-13-isoalkyl Derivs.

49. Dtxsid6048418

50. Agspxmvufbbbmo-uhfffaoysa-

51. Aminopropionitrile [hsdb]

52. 3-aminopropionitrile [mi]

53. 3-amino-propionitrile, Aldrichcpr

54. Sodiumbitartrate,monohydrate

55. Cs-d1507

56. Hy-y1750

57. Nsc40641

58. Str02529

59. Zinc1530259

60. Bbl101609

61. Bdbm50232678

62. Propanenitrile, 3-amino-, N-[3-(c12-18-alkyloxy)propyl] Derivs.

63. Stl555405

64. Akos000121388

65. Beta-aminopropionitrile [mart.]

66. Sb75359

67. Ncgc00015048-01

68. Ncgc00015048-02

69. Ncgc00015048-03

70. Ncgc00015048-05

71. Ncgc00162054-01

72. 68130-65-4

73. 68130-66-5

74. 3-aminopropionitrile Stabilized With K2co3

75. Beta-aminopropionitrile [green Book]

76. A0408

77. Ft-0615060

78. 3-aminopropionitrile (stabilized With K2co3)

79. C05670

80. D77355

81. Q3614347

82. W-109080

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 70.09 g/mol
Molecular Formula C3H6N2
XLogP3-1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass70.053098200 g/mol
Monoisotopic Mass70.053098200 g/mol
Topological Polar Surface Area49.8 Ų
Heavy Atom Count5
Formal Charge0
Complexity49.2
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

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.

PMID:909131 OOSHIMA A; JPN CIRC J 41(8): 912 (1977)


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.

PMID:723006 OGAWA M, OZAKI M; JPN J PHARMACOL 28(5): 785 (1978)


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.

PMID:39201 AREM AJ ET AL; J SURG RES 27(4): 228 (1979)


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.

PMID:6175260 RILEY DJ ET AL; AM REV RESPIR DIS 125(1): 67 (1982)


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

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.

PMID:639425 FLEISHER JH ET AL; CLIN PHARMACOL THER 23(5): 520 (1978)


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.

PMID:6119597 FLEISHER JH ET AL; LIFE SCI 29(24): 2553 (1981)


5.2 Metabolism/Metabolites

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

The Royal Society of Chemistry. Foreign Compound Metabolism in Mammals. Volume 6: A Review of the Literature Published during 1978 and 1979. London: The Royal Society of Chemistry, 1981., p. 336


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.

PMID:639425 FLEISHER JH ET AL; CLIN PHARMACOL THER 23(5): 520 (1978)


5.3 Mechanism of Action

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.

Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3156


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/

Clarke, M. L., D. G. Harvey and D. J. Humphreys. Veterinary Toxicology. 2nd ed. London: Bailliere Tindall, 1981., p. 233


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