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Chemistry

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Also known as: Phenylmethanamine, 100-46-9, Benzenemethanamine, Monobenzylamine, (phenylmethyl)amine, Alpha-aminotoluene
Molecular Formula
C7H9N
Molecular Weight
107.15  g/mol
InChI Key
WGQKYBSKWIADBV-UHFFFAOYSA-N
FDA UNII
A1O31ROR09

Benzylamine
benzylamine is a natural product found in Peucedanum palustre, Reseda media, and Thysselinum palustre with data available.
1 2D Structure

Benzylamine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
phenylmethanamine
2.1.2 InChI
InChI=1S/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2
2.1.3 InChI Key
WGQKYBSKWIADBV-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)CN
2.2 Other Identifiers
2.2.1 UNII
A1O31ROR09
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Benzylamine Hydrobromide

2. Benzylamine Hydrochloride

3. Benzylamine Monosulfate

2.3.2 Depositor-Supplied Synonyms

1. Phenylmethanamine

2. 100-46-9

3. Benzenemethanamine

4. Monobenzylamine

5. (phenylmethyl)amine

6. Alpha-aminotoluene

7. 1-phenylmethanamine

8. (aminomethyl)benzene

9. N-benzylamine

10. Moringine

11. Phenylmethylamine

12. Sumine 2005

13. 89551-24-6

14. Aminotoluene

15. Benzyl Amine

16. Sumine 2006

17. Omega-aminotoluene

18. .omega.-aminotoluene

19. Benzyl-amine

20. A-aminotoluene

21. 1utj

22. 1utn

23. 2bza

24. Nsc 8046

25. Mfcd00008106

26. .alpha.-aminotoluene

27. Chebi:40538

28. Toluene,alpha-amino

29. Chembl522

30. A1o31ror09

31. Nsc-8046

32. Abn

33. Mfcd00145849

34. Hsdb 2795

35. Einecs 202-854-1

36. Benzylarnine

37. Bezylamine

38. Brn 0741984

39. Unii-a1o31ror09

40. Ai3-15299

41. Aminomethylbenzene

42. N-(phenylmethyl)amine

43. Bnnh2

44. Nh2bn

45. Quadrapure(tm) Bza

46. Bzl-nh2

47. Benzenemethanamine, 9ci

48. Benzylamine [mi]

49. Benzylamine On Polystyrene

50. Benzylamine, Reagent Grade

51. Dsstox_cid_1839

52. Schembl373

53. Benzylamine [hsdb]

54. Epitope Id:141489

55. Ec 202-854-1

56. Quadrapure(tm) Benzylamine

57. Dsstox_rid_76359

58. Nciopen2_007746

59. Dsstox_gsid_21839

60. 4-12-00-02155 (beilstein Handbook Reference)

61. Laquo Omegaraquo -aminotoluene

62. Benzylamine, Analytical Standard

63. Dtxsid5021839

64. Bdbm10999

65. Nsc8046

66. Tetracyclohexylorthosilicate

67. Str00195

68. Zinc6096244

69. Benzylamine, Reagentplus(r), 99%

70. Tox21_300933

71. Mfcd00130502

72. Mfcd00135579

73. Mfcd08561140

74. Stl115534

75. Akos000119096

76. Quadrapure Bza, 400-1100 Micron

77. Db02464

78. Ncgc00166029-01

79. Ncgc00166029-02

80. Ncgc00254835-01

81. Cas-100-46-9

82. Lacosamide Impurity J [ep Impurity]

83. B0406

84. Ft-0622834

85. Ft-0622836

86. Benzylamine, For Gc Derivatization, >=99.0%

87. Benzylamine, Purified By Redistillation, >=99.5%

88. Q424000

89. Brd-k76133116-001-01-2

90. Z54748260

91. F2190-0388

92. 3f830b2a-abaa-4e26-971c-53b1c7485954

93. Aminomethyl Polystyrene (160-200 ?m, 0.8-1.3 Mmol/g)

94. Aminomethyl Polystyrene (rigid, Macroporous 200-400?m, 2-3.5 Mmol/g)

95. Aminomethyl Polystyrene Resin Cross-linked With 1% Dvb (200-400mesh) (2.0-3.0mmol/g)

96. Poly(styrene-divinylbenzene), Aminomethylated, 1% Cross-linked, 100-200 Mesh

97. Quadrapure(r) Bza, 400-1100 Mum, Extent Of Labeling: 20 Mg/g Loading, Macroporous

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 107.15 g/mol
Molecular Formula C7H9N
XLogP31.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Exact Mass107.073499291 g/mol
Monoisotopic Mass107.073499291 g/mol
Topological Polar Surface Area26 Ų
Heavy Atom Count8
Formal Charge0
Complexity55.4
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

Benzylamine is found in Moringa oleifera, a plant used to treat diabetes in traditional medicine.

PMID:20045461 Iffiu-Soltez Z et al; Pharmacol Res 61 (4): 355-63 (2010)


/Experimental Therapy/ Benzylamine/vanadate administration generates peroxovanadium locally in pancreatic islets, which stimulates insulin secretion, and also produces peroxovanadium in adipose tissue, thereby activating glucose metabolism in adipocytes and in neighboring muscle. This opens up the possibility of using the semicarbazide-sensitive amine oxidase (SSAO)/vascular adhesion protein-1 (VAP-1) activity as a local generator of protein tyrosine phosphatase inhibitors in anti-diabetic therapy...

PMID:19246098 Zorzano A et al; J Inorg Biochem 103 (4): 559-66 (2009)


/Experimental Therapy/ ... Benzylamine on its own can improve glucose tolerance in rabbit and mouse, likely by stimulating glucose uptake via amine oxidase activation in insulin-sensitive tissues.

PMID:14978192 Iglesias-Osma MC et al; J Pharmacol Exp Ther 309 (3): 1020-8 (2004)


/Experimental Therapy/ The combination of vanadate plus benzylamine has been reported to stimulate glucose transport in rodent adipocytes and to mimic other insulin actions in diverse studies. However, benzylamine alone activates glucose uptake in human fat cells and increases glucose tolerance in rabbits. The aim of this work was to unravel the benzylamine antihyperglycemic action and to test whether its chronic oral administration could restore the defective glucose handling of mice rendered slightly obese and diabetic by very high-fat diet (VHFD). When VHFD mice were i.p. injected with benzylamine at 0.7 to 700 umol/kg before glucose tolerance test, they exhibited reduced hyperglycemic response without alteration of insulin secretion. Whole body glucose turnover, as assessed by the glucose isotopic dilution technique, was unchanged in mice perfused with benzylamine (total dose of 75 umol/kg). However, their in vivo glycogen synthesis rate was increased. Benzylamine appeared therefore to directly facilitate glucose utilisation in peripheral tissues. When given chronically at 2000 or 4000 micromol/kg/d in drinking water, benzylamine elicited a slight reduction of water consumption but did not change body weight or adiposity and did not modify oxidative stress markers. Benzylamine treatment improved glucose tolerance but failed to normalize the elevated glucose fasting plasma levels of VHFD mice. There was no influence of benzylamine ingestion on lipolytic activity, basal and insulin-stimulated glucose uptake, and on inflammatory adipokine expression in adipocytes. The improvement of glucose tolerance and the lack of adverse effects on adipocyte metabolism, reported here in VHFD mice allow to consider orally given benzylamine as a potential antidiabetic strategy which deserves to be further studied in other diabetic models.

PMID:18457006 Iffiu-Soltesz Z et al; J Physiol biochem 63 (4): 305-15 (2007)


5 Pharmacology and Biochemistry
5.1 Metabolism/Metabolites

The in vivo and in vitro disposition of benzylamine was investigated in rats. Benzylamine was metabolized to only a small extent by rat liver subcellular fractions. In contrast, it was extensively metabolized in vivo in rats. In vivo studies performed with stable isotope-labeled benzylamine enabled rapid mass spectrometric identification of metabolites present in rat bile and urine. The major metabolite of benzylamine was the hippuric acid formed by glycine conjugation of benzoic acid. LC/MS analysis of bile and urine obtained from rats dosed with 1:1 equimolar mixture of either d(0):d(7)- or d(0):d(2)-benzylamine showed the presence of several glutathione adducts in addition to the hippuric acid metabolite. The presence of various glutathione adducts indicated that benzylamine was metabolized to a number of reactive intermediates. Various metabolic pathways, including those independent of P450, were found to produce these intermediates. A previously undocumented pathway included the formation of a new carbon-nitrogen bond that led to a potentially reactive intermediate, Ar-CH(2)-NH(CO)-X, capable of interacting with various nucleophiles. The origin of this reactive intermediate is postulated to occur via the formation of either a formamide or carbamic acid metabolites. Metabolites which were produced by the reaction of this intermediate, Ar-CH(2)-NH(CO)-X with nucleophiles included S-[benzylcarbamoyl] glutathione, N-acetyl-S-[benzylcarbamoyl]cysteine, S-[benzylcarbamoyl] cysteinylglycine, S-[benzylcarbamoyl] cysteinylglutamate, N-[benzylcarbamoyl] glutamate, and an oxidized glutathione adduct. Bioactivation of amines via this pathway has not been previously described. The oxidative deamination of benzylamine yielding the benzaldehyde was demonstrated to be a precursor to the hippuric acid metabolite and S-benzyl-L-glutathione. The formation of the S-benzyl-L-glutathione conjugate showed that a net displacement of amine from benzylamine had taken place with a subsequent addition of glutathione at the benzylic position. In addition to these novel pathways, a number of other glutathione-derived adducts formed as a result of epoxide formation was characterized. It was demonstrated that benzylamine was converted by rat P450 2A1 and 2E1 to benzamide that was rapidly metabolized to an epoxide. Mechanisms are proposed for the formation of various GSH adducts of benzylamine.

PMID:12230413 Mutlib AE et al; Chem Res Toxicol 15 (9): 1190-207 (2002)


In mammals, benzylamine is metabolized by semicarbazide-sensitive amine oxidase (SSAO) to benzaldehyde and hydrogen peroxide. This latter product has insulin-mimicking action, and is involved in the effects of benzylamine on human adipocytes: stimulation of glucose transport and inhibition of lipolysis.

PMID:20045461 Iffiu-Soltez Z et al; Pharmacol Res 61 (4): 355-63 (2010)


Hippuric acid was excreted after ingestion of benzylamine by humans.

PMID:698137 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1008410 WOOD SG ET AL; BR J IND MED 35 (3): 230-31 (1978)


The activity of monoamine oxidase was studied in the mitochondria fraction of the brain stem of active sleeping, or hibernating ground squirrels. During hibernation, deamination of serotonin and conversion of monoamine oxide serotonin complex decr more than benzylamine deamination and monoamine oxide benzylamine complex conversion.

VOITENKO NN, POPOVA NK; NEIROKHIMIYA 2 (2): 148-55 (1983)


For more Metabolism/Metabolites (Complete) data for Benzylamine (7 total), please visit the HSDB record page.


5.2 Mechanism of Action

Glucose, 3-deoxyglucosone (3-DG), and methylglyoxal (MG) oxidatively deaminated benzylamine to benzaldehyde in the presence of Cu(2+) at a physiological pH and temperature but not glyoxal. 3-DG and MG were more effective oxidants than glucose. We have determined the effects of metal ions, pH, oxygen, and radical scavengers on the oxidative deamination. The formation of benzaldehyde was greatest with Cu(2+), and was accelerated at a higher pH and in the presence of oxygen. EDTA, catalase, and dimethyl sulfoxide significantly inhibited the oxidation, suggesting the participation of reactive oxygen species. From these results, we propose a mechanism for the oxidative deamination by the Strecker-type reaction and the reactive oxygen species-mediated oxidation during glycoxidation.

PMID:12628667 Akagawa M et al; Bioorg Med Chem 11 (7)" 1411-7 (2003)


Human semicarbazide-sensitive amine oxidase (SSAO) is a target for novel anti-inflammatory drugs that inhibit enzymatic activity. However, progress in developing such drugs has been hampered by an incomplete understanding of mechanisms involved in substrate turnover. We report here results of a comparative study of human and bovine SSAO enzymes that reveal binding of substrates and other ligands to at least two (human) and up to four (bovine) distinct sites on enzyme monomers. Anaerobic spectroscopy reveals binding of substrates (spermidine and benzylamine) and of an imidazoline site ligand (clonidine) to the reduced active site of bovine SSAO, whereas interactions with oxidized enzyme are evident in kinetic assays and crystallization studies. Radioligand binding experiments with [(3)H]tetraphenylphosphonium, an inhibitor of bovine SSAO that binds to an anionic cavity outside the active site, reveal competition with spermidine, benzylamine, and clonidine, indicating that these ligands also bind to this second anionic region. Kinetic models of bovine SSAO are consistent with one spermidine molecule straddling the active and secondary sites on both oxidized and reduced enzyme, whereas these sites are occupied by two individual molecules of smaller substrates such as benzylamine. Clonidine and other imidazoline site ligands enhance or inhibit activity as a result of differing affinities for both sites on oxidized and reduced enzyme. In contrast, although analyses of kinetic data obtained with human SSAO are also consistent with ligands binding to oxidized and reduced enzyme, ... no apparent requirement for substrate or modulator binding to any secondary site to model enzyme behavior /was observed/.

PMID:17989349 Holt A et al; Mol Pharmacol 73 (2): 525-38 (2008)


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02-Jan-2021
13-Feb-2025
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ABOUT THIS PAGE

Looking for 100-46-9 / Benzylamine API manufacturers, exporters & distributors?

Benzylamine manufacturers, exporters & distributors 1

46

PharmaCompass offers a list of Benzylamine API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Benzylamine manufacturer or Benzylamine supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Benzylamine manufacturer or Benzylamine supplier.

PharmaCompass also assists you with knowing the Benzylamine API Price utilized in the formulation of products. Benzylamine API Price is not always fixed or binding as the Benzylamine Price is obtained through a variety of data sources. The Benzylamine Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Benzylamine

Synonyms

Phenylmethanamine, 100-46-9, Benzenemethanamine, Monobenzylamine, (phenylmethyl)amine, Alpha-aminotoluene

Cas Number

100-46-9

Unique Ingredient Identifier (UNII)

A1O31ROR09

About Benzylamine

benzylamine is a natural product found in Peucedanum palustre, Reseda media, and Thysselinum palustre with data available.

Benzylamine Manufacturers

A Benzylamine manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Benzylamine, including repackagers and relabelers. The FDA regulates Benzylamine manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Benzylamine API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Benzylamine Suppliers

A Benzylamine supplier is an individual or a company that provides Benzylamine active pharmaceutical ingredient (API) or Benzylamine finished formulations upon request. The Benzylamine suppliers may include Benzylamine API manufacturers, exporters, distributors and traders.

click here to find a list of Benzylamine suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Benzylamine USDMF

A Benzylamine DMF (Drug Master File) is a document detailing the whole manufacturing process of Benzylamine active pharmaceutical ingredient (API) in detail. Different forms of Benzylamine DMFs exist exist since differing nations have different regulations, such as Benzylamine USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Benzylamine DMF submitted to regulatory agencies in the US is known as a USDMF. Benzylamine USDMF includes data on Benzylamine's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Benzylamine USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Benzylamine suppliers with USDMF on PharmaCompass.

Benzylamine GMP

Benzylamine Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Benzylamine GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Benzylamine GMP manufacturer or Benzylamine GMP API supplier for your needs.

Benzylamine CoA

A Benzylamine CoA (Certificate of Analysis) is a formal document that attests to Benzylamine's compliance with Benzylamine specifications and serves as a tool for batch-level quality control.

Benzylamine CoA mostly includes findings from lab analyses of a specific batch. For each Benzylamine CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Benzylamine may be tested according to a variety of international standards, such as European Pharmacopoeia (Benzylamine EP), Benzylamine JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Benzylamine USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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