PHENYL BIGUANIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H11N5
Molecular Weight	177.2064
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=N)NC(=N)NC1=CC=CC=C1

InChI

InChIKey=CUQCMXFWIMOWRP-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C8H11N5
Molecular Weight	177.2064
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1711914 | https://www.ncbi.nlm.nih.gov/pubmed/8450478 | http://www.drugfuture.com/chemdata/Amanozine.html

Phenyl biguanide (phenylbuguanide, PBG) is a 5-hydroxytryptamine receptor 3 agonist used to study the role of serotonin receptors in the central nervous system. It has been found to trigger dopamine release in the nucleus accumbens of rats. Phenylbiguanide is used to make amanozine.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 3a (5-HT3a) receptor 48 Target ID: CHEMBL1899 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7790853	Agonist 2752		7.1 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Participation of cyclooxygenase pathway in the vasoconstriction induced by 5-HT in the in situ autoperfused kidney of long-term diabetic rats.	2011-05-20	21414306
Altered cardiovascular reflexes responses in conscious Angiotensin-(1-7) receptor Mas-knockout mice.	2010-10	20603170
Pharmacological profile of 5-hydroxytryptamine-induced inhibition on the pressor effect elicited by sympathetic stimulation in long-term diabetic pithed rats.	2010-09-15	20547148
Cardio-respiratory reflexes evoked by phenylbiguanide in rats involve vagal afferents which are not sensitive to capsaicin.	2010-09	20331538
Dorsal vagal preganglionic neurons: differential responses to CCK1 and 5-HT3 receptor stimulation.	2010-08-25	20346737
5-HT3 receptor-dependent modulation of respiratory burst frequency, regularity, and episodicity in isolated adult turtle brainstems.	2010-06-30	20399913
Attenuated baroreflex control of sympathetic nerve activity in obese Zucker rats by central mechanisms.	2010-05-01	20211978
Study of 5HT3 and HT4 receptor expression in HT29 cell line and human colon adenocarcinoma tissues.	2010-03	20187666
Y25130 hydrochloride, a selective 5HT3 receptor antagonist has potent antimitogenic and apoptotic effect on HT29 colorectal cancer cell line.	2010-03	20010428
Peripheral 5-HT1A and 5-HT7 serotonergic receptors modulate parasympathetic neurotransmission in long-term diabetic rats.	2010	21403818
ATZ (3-amino-1,2,4-triazole) injected into the fourth cerebral ventricle influences the Bezold-Jarisch reflex in conscious rats.	2010	21340224
Roles of arterial baroreceptor reflex during bezold-jarisch reflex.	2009-11	21037842
Evidence that 5-hydroxytryptamine(7) receptors play a role in the mediation of afferent transmission within the nucleus tractus solitarius in anaesthetized rats.	2009-11	19785653
Involvement of nitric oxide in 5-HT(3) receptor agonist-induced fluid accumulation in jejunum and colon of anesthetized rats.	2009-10	20177493
B(2) kinin receptors mediate the Indian red scorpion venom-induced augmentation of visceral reflexes via the nitric oxide cyclic guanosine monophosphate pathway.	2009-08	19133874
Inhibition of the bradycardic component of the von Bezold-Jarisch reflex and carotid chemoreceptor reflex by periaqueductal gray stimulation: involvement of medullary receptors.	2009-05	19453625
5-HT inhibition of rat insulin 2 promoter Cre recombinase transgene and proopiomelanocortin neuron excitability in the mouse arcuate nucleus.	2009-03-03	19135134
Wavelet-based system identification of short-term dynamic characteristics of arterial baroreflex.	2009-01	19003536
Consequences of post-weaning social isolation on anxiety behavior and related neural circuits in rodents.	2009	19738931
Respiratory pattern in midline-lesioned brainstems and hemibrainstems from adult turtles.	2008-12-31	18775518
Activation of cholecystokinin (CCK 1) and serotonin (5-HT 3) receptors increases the discharge of pancreatic vagal afferents.	2008-12-28	19026634
Cough reflex responses during pulmonary C-fibre receptor activation in anesthetized rabbits.	2008-12-26	18955115
Excitability of small-diameter trigeminal ganglion neurons by 5-HT is mediated by enhancement of the tetrodotoxin-resistant sodium current due to the activation of 5-HT(4) receptors and/or by the inhibition of the transient potassium current.	2008-12-02	18926885
Involvement of phospholipase A2 pathway for the Indian red scorpion venom-induced augmentation of cardiopulmonary reflexes elicited by phenyldiguanide.	2008-08-08	18571849
Ovalbumin sensitizes vagal pulmonary C-fiber afferents in Brown Norway rats.	2008-08	18535139
5-HT-induced depression of the spinal monosynaptic reflex potential utilizes different types of 5-HT receptors depending on Mg2+ availability.	2008-06-20	19443937
Angiotensin-(1-7) and baroreflex function in nucleus tractus solitarii of (mRen2)27 transgenic rats.	2008-06	18475201
Modulation of reflex function by endogenous angiotensins in older transgenic rats with low glial angiotensinogen.	2008-05	18347230
The role of NMDA and non-NMDA receptors in the NTS in mediating three distinct sympathoinhibitory reflexes.	2007-12	18008064
Activation of 5-hydroxytryptamine type 3 receptor-expressing C-fiber vagal afferents inhibits retrotrapezoid nucleus chemoreceptors in rats.	2007-12	17928558
Effect of systemic B-type natriuretic peptide on cardiac vagal motoneuron activity.	2007-12	17906112
Cardiac vagal preganglionic neurones in the intermediate zone of the brainstem in anaesthetized cats.	2007-11	17644702
Demonstration of 5-HT(3) receptor function and expression in the mouse bladder.	2007-08	17607564
Nonuniformity in the von Bezold-Jarisch reflex.	2007-08	17567718
5-HT2 and 5-HT3 receptors in the lateral parabrachial nucleus mediate opposite effects on sodium intake.	2007-06-08	17434681
Identification of an immune-responsive mesolimbocortical serotonergic system: potential role in regulation of emotional behavior.	2007-05-11	17367941
The 1:1 cocrystals of the proton-transfer compound dilituric acid--phenylbiguanide monohydrate.	2007-03	17339726
5-HT(3) receptors in the central amygdala mediate the modulation of thymus function in rats.	2007-02-25	17294041
Vagal afferent input alters the discharge of osmotic and ANG II-responsive median preoptic neurons projecting to the hypothalamic paraventricular nucleus.	2007-02-02	17161831
RVLM glycine receptors mediate GABAA and GABAB)independent sympathoinhibition from CVLM in rats.	2006-12-13	17112484
Ptychodiscus brevis toxin-induced depression of spinal reflexes involves 5-HT via 5-HT3 receptors modulated by NMDA receptor.	2006-11-27	17014958
Discovery of small molecule inhibitors of integrin alphavbeta3 through structure-based virtual screening.	2006-11-15	16982193
Ablation of NK1 receptor bearing neurons in the nucleus of the solitary tract blunts cardiovascular reflexes in awake rats.	2006-11-13	16982039
The sympathoinhibitory effects of systemic cholecystokinin are dependent on neurons in the caudal ventrolateral medulla in the rat.	2006-11	16793934
Tooth-pulp-evoked rostral spinal trigeminal neuronal excitation is attenuated by the activation of 5-HT3 receptors via GABAergic interneurons in the rat.	2006-09-13	16836984
Pulmonary sensory and reflex responses in the mouse.	2006-09	16675617
Pancreatic vasoconstrictor responses are regulated by neurons in the rostral ventrolateral medulla.	2006-08-02	16781679
Influence of short-term versus prolonged cardiopulmonary receptor stimulation on renal and preganglionic adrenal sympathetic nerve activity in rats.	2006-05	16382286
Characterisation of c-Fos expression in the central nervous system of mice following right atrial injections of the 5-HT3 receptor agonist phenylbiguanide.	2005-12-30	16298172
Endogenous nitrosyl factors may inhibit the desensitization of 5-HT3 receptors on vagal cardiopulmonary afferents.	2005-10-19	16185669

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Phenylbiguanide (PBG) and 2-methyl-5-hydroxytryptamine (2-methyl-5-HT) were found to mimic the effects of 5-hydroxytryptamine (5-HT) on the rat isolated cervical vagus nerve. Their EC50 values were respectively 2.0 fold and 3.9 fold greater than that of 5-HT. Metoclopramide behaved as a reversible competitive antagonist of depolarization induced by PBG and 2-methyl-5-HT, with pKb values of 6.48 +/- 0.04, respectively.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:53:06 GMT 2025` Edited by `admin` on `Mon Mar 31 19:53:06 GMT 2025`
Record UNII	W8PKA3T2I3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHENYL BIGUANIDE

Systematic Name

English

PHENYL BIGUANIDE [MI]

Preferred Name

English

PHENYL DIGUANIDE

Common Name

English

1-PHENYLBIGUANIDE

Systematic Name

English

N-PHENYL-N'-GUANYLGUANIDINE

Systematic Name

English

N-PHENYLIMIDODICARBONIMIDIC DIAMIDE

Systematic Name

English

Code System Code Type Description

CHEBI

75377