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 46 Target ID: CHEMBL1899 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7790853	Agonist 2678		7.1 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Characterisation of c-Fos expression in the central nervous system of mice following right atrial injections of the 5-HT3 receptor agonist phenylbiguanide.	2005 Dec 30	16298172
Endogenous nitrosyl factors may inhibit the desensitization of 5-HT3 receptors on vagal cardiopulmonary afferents.	2005 Oct 19	16185669
Pancreatic vasoconstrictor responses are regulated by neurons in the rostral ventrolateral medulla.	2006 Aug 2	16781679
RVLM glycine receptors mediate GABAA and GABAB)independent sympathoinhibition from CVLM in rats.	2006 Dec 13	17112484
Influence of short-term versus prolonged cardiopulmonary receptor stimulation on renal and preganglionic adrenal sympathetic nerve activity in rats.	2006 May	16382286
The sympathoinhibitory effects of systemic cholecystokinin are dependent on neurons in the caudal ventrolateral medulla in the rat.	2006 Nov	16793934
Ablation of NK1 receptor bearing neurons in the nucleus of the solitary tract blunts cardiovascular reflexes in awake rats.	2006 Nov 13	16982039
Discovery of small molecule inhibitors of integrin alphavbeta3 through structure-based virtual screening.	2006 Nov 15	16982193
Ptychodiscus brevis toxin-induced depression of spinal reflexes involves 5-HT via 5-HT3 receptors modulated by NMDA receptor.	2006 Nov 27	17014958
Pulmonary sensory and reflex responses in the mouse.	2006 Sep	16675617
Tooth-pulp-evoked rostral spinal trigeminal neuronal excitation is attenuated by the activation of 5-HT3 receptors via GABAergic interneurons in the rat.	2006 Sep 13	16836984
Demonstration of 5-HT(3) receptor function and expression in the mouse bladder.	2007 Aug	17607564
Nonuniformity in the von Bezold-Jarisch reflex.	2007 Aug	17567718
The role of NMDA and non-NMDA receptors in the NTS in mediating three distinct sympathoinhibitory reflexes.	2007 Dec	18008064
Activation of 5-hydroxytryptamine type 3 receptor-expressing C-fiber vagal afferents inhibits retrotrapezoid nucleus chemoreceptors in rats.	2007 Dec	17928558
Effect of systemic B-type natriuretic peptide on cardiac vagal motoneuron activity.	2007 Dec	17906112
Vagal afferent input alters the discharge of osmotic and ANG II-responsive median preoptic neurons projecting to the hypothalamic paraventricular nucleus.	2007 Feb 2	17161831
5-HT(3) receptors in the central amygdala mediate the modulation of thymus function in rats.	2007 Feb 25	17294041
5-HT2 and 5-HT3 receptors in the lateral parabrachial nucleus mediate opposite effects on sodium intake.	2007 Jun 8	17434681
The 1:1 cocrystals of the proton-transfer compound dilituric acid--phenylbiguanide monohydrate.	2007 Mar	17339726
Identification of an immune-responsive mesolimbocortical serotonergic system: potential role in regulation of emotional behavior.	2007 May 11	17367941
Cardiac vagal preganglionic neurones in the intermediate zone of the brainstem in anaesthetized cats.	2007 Nov	17644702
Ovalbumin sensitizes vagal pulmonary C-fiber afferents in Brown Norway rats.	2008 Aug	18535139
Involvement of phospholipase A2 pathway for the Indian red scorpion venom-induced augmentation of cardiopulmonary reflexes elicited by phenyldiguanide.	2008 Aug 8	18571849
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 Dec 2	18926885
Cough reflex responses during pulmonary C-fibre receptor activation in anesthetized rabbits.	2008 Dec 26	18955115
Activation of cholecystokinin (CCK 1) and serotonin (5-HT 3) receptors increases the discharge of pancreatic vagal afferents.	2008 Dec 28	19026634
Respiratory pattern in midline-lesioned brainstems and hemibrainstems from adult turtles.	2008 Dec 31	18775518
Angiotensin-(1-7) and baroreflex function in nucleus tractus solitarii of (mRen2)27 transgenic rats.	2008 Jun	18475201
Modulation of reflex function by endogenous angiotensins in older transgenic rats with low glial angiotensinogen.	2008 May	18347230
Consequences of post-weaning social isolation on anxiety behavior and related neural circuits in rodents.	2009	19738931
B(2) kinin receptors mediate the Indian red scorpion venom-induced augmentation of visceral reflexes via the nitric oxide cyclic guanosine monophosphate pathway.	2009 Aug	19133874
Wavelet-based system identification of short-term dynamic characteristics of arterial baroreflex.	2009 Jan	19003536
5-HT inhibition of rat insulin 2 promoter Cre recombinase transgene and proopiomelanocortin neuron excitability in the mouse arcuate nucleus.	2009 Mar 3	19135134
5-HT-induced depression of the spinal monosynaptic reflex potential utilizes different types of 5-HT receptors depending on Mg2+ availability.	2009 Mar-Apr	19443937
Inhibition of the bradycardic component of the von Bezold-Jarisch reflex and carotid chemoreceptor reflex by periaqueductal gray stimulation: involvement of medullary receptors.	2009 May	19453625
Roles of arterial baroreceptor reflex during bezold-jarisch reflex.	2009 Nov	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 Nov	19785653
Involvement of nitric oxide in 5-HT(3) receptor agonist-induced fluid accumulation in jejunum and colon of anesthetized rats.	2009 Oct	20177493
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
Dorsal vagal preganglionic neurons: differential responses to CCK1 and 5-HT3 receptor stimulation.	2010 Aug 25	20346737
5-HT3 receptor-dependent modulation of respiratory burst frequency, regularity, and episodicity in isolated adult turtle brainstems.	2010 Jun 30	20399913
Study of 5HT3 and HT4 receptor expression in HT29 cell line and human colon adenocarcinoma tissues.	2010 Mar	20187666
Y25130 hydrochloride, a selective 5HT3 receptor antagonist has potent antimitogenic and apoptotic effect on HT29 colorectal cancer cell line.	2010 Mar	20010428
Attenuated baroreflex control of sympathetic nerve activity in obese Zucker rats by central mechanisms.	2010 May 1	20211978
Altered cardiovascular reflexes responses in conscious Angiotensin-(1-7) receptor Mas-knockout mice.	2010 Oct	20603170
Cardio-respiratory reflexes evoked by phenylbiguanide in rats involve vagal afferents which are not sensitive to capsaicin.	2010 Sep	20331538
Pharmacological profile of 5-hydroxytryptamine-induced inhibition on the pressor effect elicited by sympathetic stimulation in long-term diabetic pithed rats.	2010 Sep 15	20547148
Participation of cyclooxygenase pathway in the vasoconstriction induced by 5-HT in the in situ autoperfused kidney of long-term diabetic rats.	2011 May 20	21414306

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 `Fri Dec 15 19:40:38 UTC 2023` Edited by `admin` on `Fri Dec 15 19:40:38 UTC 2023`
Record UNII	W8PKA3T2I3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHENYL BIGUANIDE

Systematic Name

English

PHENYL DIGUANIDE

Common Name

English

PHENYL BIGUANIDE [MI]

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