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Phenylbiguanide

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Phenylbiguanide
Systematic (IUPAC) name

1-Phenylbiguanide
Legal status
Legal status	UN: Unscheduled
Identifiers
CAS Number	102-02-3
Chemical data
Formula	C₈H₁₁N₅
Molar mass	177.206
Physical data
Melting point	135–142 °C (275–288 °F)

Phenylbiguanide (PBG) is a 5-HT3 agonist used to study the role of 5-HT3 receptors in the central nervous system.^[1] It has been found to trigger dopamine release in the nucleus accumbens of rats.^[2]

References[edit]

^ Behavioral effects of the 5-hydroxytryptamine3 receptor agonists 1-phenylbiguanide and m-chlorophenylbiguanide in rats., Journal of Pharmacology and Experimental Therapeutics, 1993, retrieved 27 November 2015
^ Activation of 5-HT3 receptor by 1-phenylbiguanide increases dopamine release in the rat nucleus accumbens., Brain Research., 1991, retrieved 28 November 2015

5-HT₁ receptor ligands

Antagonists: Atypical antipsychotics (e.g., iloperidone, risperidone, sertindole)
AV965
Beta blockers (e.g., alprenolol, cyanopindolol, iodocyanopindolol, oxprenolol, pindobind, pindolol, propranolol, tertatolol)
BMY-7378
CSP-2503
Dotarizine
Ergolines (e.g., metergoline)
Flopropione
GR-46611
Isamoltane
Lecozotan
Mefway
Metitepine (methiothepin)
MIN-117 (WF-516)
MPPF
NAN-190
Robalzotan
S-15535
SB-649915
SDZ 216-525
Spiperone
Spiramide
Spiroxatrine
UH-301
WAY-100135
WAY-100635
Xylamidine

Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine))

Agonists: CGS-12066A
CP-93129
CP-94253
CP-122,288
CP-135807
Eltoprazine
Ergolines (e.g., bromocriptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide)
mCPP
RU-24969
Serotonin (5-HT)
Triptans (e.g., avitriptan, donitriptan, eletriptan, sumatriptan, zolmitriptan)
TFMPP
Tryptamines (e.g., 5-BT, 5-CT, 5-MT, DMT)
Vortioxetine

Unknown/unsorted: Ergolines (e.g., cabergoline, ergometrine (ergonovine), lisuride)

Agonists: CP-122,288
CP-135807
CP-286601
Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, LSD, methysergide)
GR-46611
L-694247
L-772405
mCPP
PNU-109291
PNU-142633
Serotonin (5-HT)
TGBA01AD
Triptans (e.g., almotriptan, avitriptan, donitriptan, eletriptan, frovatriptan, naratriptan, rizatriptan, sumatriptan, zolmitriptan)
Tryptamines (e.g., 5-BT, 5-CT, 5-Et-DMT, 5-MT, 5-(nonyloxy)tryptamine, DMT)

Unknown/unsorted: Ergolines (e.g., lisuride, lysergol, pergolide)

Antagonists: Metitepine (methiothepin)

Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine), lysergol, methylergometrine (methylergonovine)

Agonists: BRL-54443
CP-122,288
Ergolines (e.g., bromocriptine, lysergol, methylergometrine (methylergonovine) methysergide)
Lasmiditan
LY-334370
Serotonin (5-HT)
Triptans (e.g., eletriptan, naratriptan, sumatriptan)
Tryptamines (e.g., 5-MT)

Antagonists: Mianserin
Metitepine (methiothepin)

5-HT₂ receptor ligands

Agonists: 25H/NB series (e.g., 25I-NBF, 25I-NBMD, 25I-NBOH, 25I-NBOMe, 25B-NBOMe, 25C-NBOMe, 25TFM-NBOMe, 2CBCB-NBOMe, 25CN-NBOH, 2CBFly-NBOMe)
2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21)
2C-B-FLY
2CB-Ind
5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT)
α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT)
AL-34662
AL-37350A
Bromo-DragonFLY
Dimemebfe
DMBMPP
DOx (e.g., DOB, DOC, DOI, DOM)
Efavirenz
Ergolines (e.g., 1P-LSD, ALD-52, bromocriptine, cabergoline, ergine (LSA), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, methylergometrine (methylergonovine), pergolide)
Flumexadol
Jimscaline
Lorcaserin
MDxx (e.g., MDA, MDMA, MDOH, MMDA)
O-4310
Oxaflozane
PHA-57378
PNU-22394
PNU-181731
RH-34
Phenethylamines (e.g., lophophine, mescaline)
Piperazines (e.g., BZP, mCPP, quipazine, TFMPP)
Serotonin (5-HT)
TCB-2
TFMFly
Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine)

Unknown/unsorted: Ergolines (e.g., dihydroergotamine, ergometrine (ergonovine), nicergoline)
MIN-117 (WF-516)

Agonists: 4-Methylaminorex
Aminorex
Amphetamines (eg., chlorphentermine, cloforex, dexfenfluramine, fenfluramine, levofenfluramine, norfenfluramine)
BW-723C86
DOx (e.g., DOB, DOC, DOI, DOM)
Ergolines (e.g., cabergoline, dihydroergocryptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide)
MDxx (e.g., MDA, MDMA, MDOH, MMDA)
Piperazines (e.g., mCPP)
PNU-22394
Ro60-0175
Serotonin (5-HT)
Tryptamines (e.g., 5-BT, 5-CT, 5-MT, α-Me-5-HT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine)

Antagonists: Agomelatine
Asenapine
Cyproheptadine
EGIS-7625
Ergolines (e.g., amesergide, bromocriptine, lisuride, LY-53857, LY-272015, mesulergine)
Ketanserin
LY-393558
Metadoxine
Metitepine (methiothepin)
Pirenperone
Propranolol
PRX-08066
Rauwolscine
Ritanserin
RS-127445
Sarpogrelate
SB-200646
SB-204741
SB-206553
SB-215505
SB-221284
SB-228357
SDZ SER-082
Tegaserod
Tetracyclic antidepressants (e.g., amoxapine, mianserin)
TIK-301
Yohimbine

Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine))

Agonists: 2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21)
5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT)
α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT)
A-372159
AL-38022A
Alstonine
CP-809101
Dimemebfe
DOx (e.g., DOB, DOC, DOI, DOM)
Ergolines (e.g., ALD-52, cabergoline, dihydroergotamine, ergine (LSA), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, pergolide)
Flumexadol
Lorcaserin
MDxx (e.g., MDA, MDMA, MDOH, MMDA)
MK-212
Org 12962
Org 37684
Oxaflozane
PHA-57378
Phenethylamines (e.g., lophophine, mescaline)
Piperazines (e.g., aripiprazole, BZP, mCPP, quipazine, TFMPP)
PNU-22394
PNU-181731
Ro60-0175
Ro60-0213
Serotonin (5-HT)
Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine)
Vabicaserin
WAY-629
WAY-161503
YM-348

Unknown/unsorted: Efavirenz
Ergolines (e.g., ergometrine (ergonovine), methylergometrine (methylergonovine))

Agonists: Alcohols (e.g., butanol, ethanol, trichloroethanol)
m-CPBG
Phenylbiguanide
Piperazines (e.g., BZP, mCPP, quipazine)
RS-56812
Serotonin (5-HT)
SR-57227
SR-57227A
Tryptamines (e.g., 2-Me-5-HT, 5-CT, bufotenidine (5-HTQ))
Volatiles/gases (e.g., halothane, isoflurane, toluene, trichloroethane)
YM-31636

Antagonists: Alosetron
AS-8112
Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine)
Azasetron
Batanopride
Bemesetron (MDL-72222)
Cilansetron
CSP-2503
Dazopride
Dolasetron
Galanolactone
Granisetron
ICS-205930
Lerisetron
Memantine
Ondansetron
Palonosetron
Ramosetron
Renzapride
Ricasetron
Tedatioxetine
Tetracyclic antidepressants (e.g., amoxapine, mianserin, mirtazapine)
Thujone
Tropanserin
Tropisetron
Typical antipsychotics (e.g., loxapine)
Volatiles/gases (e.g., nitrous oxide, sevoflurane, xenon)
Vortioxetine
Zacopride
Zatosetron

Unknown/unsorted: LY-53857
Piperazines (e.g., naphthylpiperazine)

Agonists: Ergolines (e.g., 2-Br-LSD (BOL-148), ergotamine, LSD)
Serotonin (5-HT)
Tryptamines (e.g., 5-CT)
Valerenic Acid

Antagonists: Asenapine
Latrepirdine (dimebolin)
Metitepine (methiothepin)
Ritanserin
SB-699551
Unknown/unsorted: Ergolines (e.g., metergoline, methysergide)
Piperazines (e.g., naphthylpiperazine)

Agonists: Ergolines (e.g., dihydroergocryptine, dihydroergotamine, ergotamine, lisuride, LSD, mesulergine, metergoline, methysergide)
Serotonin (5-HT)
Tryptamines (e.g., 2-Me-5-HT, 5-BT, 5-CT, 5-MT, Bufotenin, E-6801, E-6837, EMD-386088, EMDT, LY-586713, N-Me-5-HT, tryptamine)
WAY-181187
WAY-208466

Antagonists: ABT-354
Atypical antipsychotics (e.g., aripiprazole, asenapine, clorotepine, clozapine, fluperlapine, iloperidone, olanzapine, tiospirone)
AVN-101
AVN-211
AVN-322
AVN-397
BGC20-760
BVT-5182
BVT-74316
Cerlapirdine
EGIS-12233
GW-742457
Idalopirdine
Ketanserin
Latrepirdine (dimebolin)
Metitepine (methiothepin)
MS-245
PRX-07034
Ritanserin
Ro04-6790
Ro 63-0563
SB-258585
SB-271046
SB-357134
SB-399885
SB-742457
Tetracyclic antidepressants (e.g., amoxapine, mianserin)
Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, nortriptyline)
Typical antipsychotics (e.g., chlorpromazine, loxapine)

Unknown/unsorted: Ergolines (e.g., 2-Br-LSD (BOL-148), bromocriptine, lergotrile, pergolide)
Piperazines (e.g., naphthylpiperazine)

Agonists: 8-OH-DPAT
AS-19
Bifeprunox
E-55888
Ergolines (e.g., LSD)
LP-12
LP-44
RU-24969
Sarizotan
Serotonin (5-HT)
Triptans (e.g., frovatriptan)
Tryptamines (e.g., 5-CT, 5-MT, bufotenin, N-Me-5-HT)

Antagonists: Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, clorotepine, clozapine, fluperlapine, olanzapine, risperidone, sertindole, tiospirone, ziprasidone, zotepine)
Butaclamol
DR-4485
EGIS-12233
Ergolines (e.g., 2-Br-LSD (BOL-148), amesergide, bromocriptine, cabergoline, dihydroergotamine, ergotamine, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole)
Ketanserin
LY-215840
Metitepine (methiothepin)
Ritanserin
SB-258719
SB-258741
SB-269970
SB-656104
SB-656104A
SB-691673
SLV-313
SLV-314
Spiperone
SSR-181507
Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine)
Tricyclic antidepressants (e.g., amitriptyline, clomipramine, imipramine)
Typical antipsychotics (e.g., acetophenazine, chlorpromazine, chlorprothixene, fluphenazine, loxapine, pimozide)
Vortioxetine

Unknown/unsorted: Ergolines (e.g., lisuride, pergolide)
Piperazines (e.g., naphthylpiperazine)

Reuptake inhibitors

Selective serotonin reuptake inhibitors (SSRIs): Alaproclate
Cericlamine
Citalopram
Dapoxetine
Desmethylcitalopram
Escitalopram
Femoxetine
Fluoxetine
Fluvoxamine
Indalpine
Ifoxetine
Omiloxetine
Panuramine
Paroxetine
Pirandamine
RTI-353
Seproxetine
Sertraline
Vilazodone
Zimelidine

Serotonin-norepinephrine reuptake inhibitors (SNRIs): Bicifadine
BTS-54505
Desvenlafaxine
Duloxetine
Eclanamine
Levomilnacipran
McN-5652
Milnacipran
N-Methyl-PPPA
PPPA
Sibutramine
Venlafaxine
WY-45233

Tricyclic antidepressants (TCAs): Amitriptyline
Butriptyline
Cianopramine
Clomipramine
Desipramine
Dosulepin
Doxepin
Imipramine
Lofepramine
Nortriptyline
Pipofezine
Protriptyline
Trimipramine

Amiodarone
Amphetamines (e.g., amphetamine, methamphetamine, MDMA)
APP
AZIK
Bietaserpine
Deserpidine
Dihydrotetrabenazine
Efavirenz
GBR-12935
GZ-793A
Ibogaine
Ketanserin
Lobeline
Methoxytetrabenazine
NBI-98854
Reserpine
Rose bengal
SD-809
Tetrabenazine
Vanoxerine (GBR-12909)

Releasing agents

Aminoindanes: 5-IAI
AMMI
ETAI
MDAI
MDMAI
MMAI
TAI

Aminotetralins: 6-CAT
8-OH-DPAT
MDAT
MDMAT

Enzyme inhibitors

MAO-A-selective: Amiflamine
Bazinaprine
Befloxatone
Brofaromine
Cimoxatone
Clorgiline
Eprobemide
Esuprone
Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine)
Methylene blue
Metralindole
Minaprine
Moclobemide
Pirlindole
Sercloremine
Tetrindole
Toloxatone
Tyrima

Others

Precursors	L-Tryptophan → 5-HTP

Cofactors	Ferrous iron (Fe²⁺) Magnesium (Mg²⁺) Tetrahydrobiopterin Vitamin B₃ (Niacin Nicotinamide → NADPH) Vitamin B₆ (Pyridoxine Pyridoxamine Pyridoxal → Pyridoxal phosphate) Vitamin B₉ (Folic Acid → Tetrahydrofolic acid) Vitamin C (Ascorbic acid) Zinc (Zn²⁺)

Neurotoxins	3-CA 4-CAB 5,7-DHT α-Me-DA (3,4-DHA) αET αMT DCA MDA MDMA PBA PCA PIA

Others	Activity enhancers: BPAP PPAP

Receptor ligands

Agonists

Adamantanes: Amantadine; Memantine; Rimantadine

Aminotetralins: 7-OH-DPAT; 8-OH-PBZI; Rotigotine; UH-232

Benzazepines: 6-Br-APB; Fenoldopam; SKF-38,393; SKF-77,434; SKF-81,297; SKF-82,958; SKF-83,959

Ergolines: Bromocriptine; Cabergoline; Dihydroergocryptine; Epicriptine; Lisuride; LSD; Pergolide

Dihydrexidine derivatives: 2-OH-NPA; A-86929; Adrogolide (ABT-431, DAS-431); Ciladopa; Dihydrexidine; Dinapsoline; Dinoxyline; Doxanthrine

Others: A-68930; A-77636; A-412,997; ABT-670; ABT-724; Aplindore; Apomorphine; Aripiprazole; Arketamine; Bifeprunox; BP-897; Captodiame; CY-208,243; Dizocilpine; Esketamine; Etilevodopa; Flibanserin; Ketamine; Melevodopa; Modafinil; Pardoprunox; Phencyclidine; PD-128,907; PD-168,077; PF-219,061; Piribedil; Pramipexole; Propylnorapomorphine; Pukateine; Quinagolide; Quinelorane; Quinpirole; RDS-127; Ro10-5824; Ropinirole; Rotigotine; Roxindole; Salvinorin A; SKF-89,145; Sumanirole; Terguride; Umespirone; WAY-100,635

Antagonists

Typical antipsychotics: Acepromazine; Azaperone; Benperidol; Bromperidol; Clopenthixol; Chlorpromazine; Chlorprothixene; Droperidol; Flupentixol; Fluphenazine; Fluspirilene; Haloperidol; Levomepromazine; Levosulpiride; Loxapine; Mesoridazine; Nemonapride; Penfluridol; Perazine; Periciazine; Perphenazine; Pimozide; Prochlorperazine; Promazine; Sulforidazine; Sulpiride; Sultopride; Thioridazine; Thiothixene; Trifluoperazine; Triflupromazine; Trifluperidol; Zuclopenthixol

Atypical antipsychotics: Amisulpride; Asenapine; Blonanserin; Cariprazine; Carpipramine; Clocapramine; Clorotepine; Clozapine; Gevotroline; Iloperidone; Lurasidone; Melperone; Molindone; Mosapramine; Olanzapine; Paliperidone; Perospirone; Piquindone; Quetiapine; Remoxipride; Risperidone; Sertindole; Tiospirone; Zicronapine; Ziprasidone; Zotepine

Antiemetics: AS-8112; Alizapride; Bromopride; Clebopride; Domperidone; Metoclopramide; Thiethylperazine

Others: Amoxapine; Buspirone; Butaclamol; Ecopipam; EEDQ; Eticlopride; Fananserin; Hydroxyzine; L-745,870; Nafadotride; Nuciferine; PNU-99,194; Raclopride; Sarizotan; SB-277,011-A; SCH 23390; SKF-83,959; Sonepiprazole; Spiperone; Spiroxatrine; Stepholidine; Tetrahydropalmatine; Tiapride; UH-232; Yohimbine

Reuptake modulators

Inhibitors

Piperazines: DBL-583; GBR-12783; GBR-12935; GBR-13069; GBR-13098; Nefazodone; Vanoxerine

Piperidines: 4-Fluoropethidine; Benocyclidine (BTCP); Desoxypipradrol; Dexmethylphenidate; Difemetorex; Ethylphenidate; HDMP-28; Methylphenidate; Pethidine (meperidine); Phencyclidine; Pipradrol

Pyrrolidines: Diphenylprolinol; MDPV; Naphyrone; Prolintane; Pyrovalerone

Tropanes: Altropane; Benzatropine (benztropine); Brasofensine; CFT; Cocaine; Dichloropane; Difluoropine; Etybenzatropine (ethybenztropine); FE-β-CPPIT; FP-β-CPPIT; Ioflupane (¹²³I); RTI-55; RTI-112; RTI-113; RTI-121; RTI-126; RTI-150; RTI-177; RTI-229; RTI-336; Tenocyclidine; Tesofensine; Troparil; Tropoxane; WF-11; WF-23; WF-31; WF-33

Others: Adrafinil; Amifitadine; Armodafinil; Amfonelic acid; Amineptine; Ansofaxine; BTQ; BTS 74,398; Bupropion; Chaenomeles speciosa; Ciclazindol; Dasotraline; Desmethylsertraline; Diclofensine; Dimethocaine; Diphenylpyraline; Dizocilpine (MK-801); DOV-102,677; DOV-216,303; Efavirenz; Esketamine; EXP-561; Fencamfamine; Fezolamine; Fluorenol; GYKI-52895; Indatraline; Ketamine; Lefetamine; Levophacetoperane; Liafensine; LR-5182; Manifaxine; Mazindol; Medifoxamine; Mesocarb; Metaphit; MIN-117 (WF-516); Modafinil; Nefopam; Nomifensine; NS-2359; O-2172; Oroxylin A; Perafensine; Pridefine; Radafaxine; Rimcazole; Sertraline; Sibutramine; Tametraline; Tedatioxetine; Tripelennamine; Venlafaxine

Enhancers

Luteolin

Modulators

Agonist-like: SoRI-9804

Antagonist-like: SoRI-20041

Inhibitors: Amiodarone; Amphetamines (e.g., amphetamine, methamphetamine, MDMA); Bietaserpine; Deserpidine; Efavirenz; GBR-12935; Ibogaine; Ketanserin; Lobeline; Reserpine; Rose bengal; Tetrabenazine; Vanoxerine (GBR-12909)

Releasing agents

Morpholines: Fenbutrazate; Fenmetramide; Morazone; Morforex; Phendimetrazine; Phenmetrazine; Pseudophenmetrazine

Oxazolines: 4-MAR; Aminorex; Clominorex; Cyclazodone; Fenozolone; Fluminorex; Pemoline; Thozalinone

Phenethylamines (also amphetamines, cathinones, etc)

Amphetamine (Dextroamphetamine

Levoamphetamine)

Dimethylamphetamine

4-Hydroxyamphetamine

Iofetamine (123I)

Methamphetamine

Dextromethamphetamine

Levomethamphetamine

Phenpromethamine

Propylamphetamine

Pseudoephedrine

Piperazines: 2C-B-BZP; BZP; MBZP; MDBZP; MeOPP

Others

Methylhexanamine

Naphthylaminopropane

Phthalimidopropiophenone

Phenylbiguanide

Propylhexedrine

Levopropylhexedrine

Enzyme inhibitors

3,4-Dihydroxystyrene

Nonselective: Benmoxin; Caroxazone; Echinopsidine; Furazolidone; Hydralazine; Indantadol; Iproclozide; Iproniazid; Isocarboxazid; Isoniazid; Linezolid; Mebanazine; Metfendrazine; Nialamide; Octamoxin; Paraxazone; Phenelzine; Pheniprazine; Phenoxypropazine; Pivhydrazine; Procarbazine; Safrazine; Tranylcypromine

MAO-A selective: Amiflamine; Bazinaprine; Befloxatone; Brofaromine; Cimoxatone; Clorgiline; CX157 (Tyrima); Eprobemide; Esuprone; Harmala alkaloids; Methylene Blue; Metralindole; Minaprine; Moclobemide; Pirlindole; Sercloremine; Tetrindole; Toloxatone

MAO-B selective: Almoxatone; D-Deprenyl; Ethanol; Ladostigil; Lazabemide; Milacemide; Nicotine; Pargyline^‡; Rasagiline; Safinamide; Selegiline (L-Deprenyl)

Others

L-Phenylalanine → L-Tyrosine → L-DOPA (levodopa)

Ferrous iron (Fe²⁺)
Tetrahydrobiopterin
Vitamin B₃ (Niacin
Nicotinamide → NADPH)
Vitamin B₆ (Pyridoxine
Pyridoxamine
Pyridoxal → Pyridoxal phosphate)
Vitamin B₉ (Folic acid → Tetrahydrofolic acid)
Vitamin C (Ascorbic acid)
Zinc (Zn²⁺)

Others

Activity enhancers: BPAP; PPAP

Levodopa prodrugs: XP21279

Others: Bromantane (dopamine synthesis enhancer)

See also:: Adrenergics; Melatonergics; Serotonergics; List of dopaminergic drugs

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