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Sigma-Aldrich

1-Phenylbiguanide

98%

Synonym(s):

1-(Diaminomethylidene)-2-phenylguanidine, 1-Carbamimidamido-N-phenylmethanimidamide, N-Phenyl-N′-guanylguanidine, N-Phenylbiguanide, N-Phenylimidodicarbonimidic diamide, N1-Phenylbiguanide, PBG

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About This Item

Linear Formula:
C6H5NHC(=NH)NHC(=NH)NH2
CAS Number:
102-02-3
Molecular Weight:
177.21
EC Number:
202-998-5
MDL number:
MFCD00179077
UNSPSC Code:
12352100
PubChem Substance ID:
24850064
NACRES:
NA.22

Quality Level

100

assay

98%

form

solid

mp

135-142 °C (lit.)

solubility

alcohol: freely soluble
water: freely soluble

functional group

amine

SMILES string

NC(=N)\N=C(/N)Nc1ccccc1

InChI

1S/C8H11N5/c9-7(10)13-8(11)12-6-4-2-1-3-5-6/h1-5H,(H6,9,10,11,12,13)

InChI key

CUQCMXFWIMOWRP-UHFFFAOYSA-N

Gene Information

mouse ... Htr3a(15561)

General description

1-Phenylbiguanide is a 5-hydroxytryptamine receptor agonist and increases extracellular dopamine release in rat nucleus accumbens in vivo. It serves as building block for synthesis of heterocyclic compounds.

Application

1-Phenylbiguanide was used in one pot synthesis of :
  • 4-chloro-2,5-dihydro-2,5-dioxonaphtho[1,2-d]imidazole-3-carboxylic acid phenyl amide
  • 6-chloro-8-phenylamino-9H-7,9,11-triaza-cyclohepta[a]naphthalene-5,10-dione
  • 4-dimethylamino-5,10-dioxo-2-phenylimino-5,10-dihydro-2H-benzo[g]quinazoline-1-carboxylic acid amide

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
STBD6566V
S42463V
S42750
15528JE
S37189

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Mateus R Amorim et al.
Journal of neuroinflammation, 16(1), 125-125 (2019-06-22)
Lipopolysaccharide (LPS)-induced systemic inflammation (SI) is associated with neuroinflammation in the brain, hypotension, tachycardia, and multiple organs dysfunctions. Considering that during SI these important cardiovascular and inflammatory changes take place, we measured the sensitivity of the cardiovascular reflexes baroreflex, chemoreflex
Reaction of 2, 3-Dichloro-1, 4-Naphthoquinone with 1-Phenylbiguanide and 2-Guanidinebenzimidazole.
El-Shaieb KM.
J. Chin. Chem. Soc., 54(5), 1353-1358 (2007)
J P Chen et al.
Brain research, 543(2), 354-357 (1991-03-15)
The serotonin-3 (5-HT3) agonist 1-phenylbiguanide (0.1-1.0 mM in perfusate) caused a robust, dose-dependent enhancement of extracellular dopamine content in nucleus accumbens as measured by in vivo microdialysis. This action was antagonized by co-perfusion of the 5-HT3 antagonists zacopride and GR38032F
A Dutta et al.
Acta physiologica (Oxford, England), 200(1), 87-95 (2010-03-25)
Stimulation of pulmonary C fibre receptors by phenylbiguanide (PBG, 5-HT(3) agonist) produces hypotension, bradycardia and tachypnoea or apnoea. However, tachypnoeic or apnoeic responses are not consistent. Therefore, this study was undertaken to delineate the actions of PBG on respiration and
Daniela M Sartor et al.
Naunyn-Schmiedeberg's archives of pharmacology, 376(4), 241-252 (2007-11-17)
Cholecystokinin (CCK) elicits a sympathetic vasomotor reflex that is implicated in gastrointestinal circulatory control. We sought to determine (1) the site in the solitary tract nucleus (NTS) responsible for mediating this reflex and (2) the possible involvement of excitatory amino
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