2C-B-PP

Chemical compound

Pharmaceutical compound

2C-B-PP
Clinical data

ATC code	none
Legal status
Legal status	In general Unscheduled.
Identifiers
IUPAC name 1-(2,5-dimethoxy-4-bromophenyl)piperazine
CAS Number	100939-87-5 ^checkY
PubChem CID	4738744
ChemSpider	3925965
UNII	9AF4JQU2FM
ChEMBL	ChEMBL348140
Chemical and physical data
Formula	C₁₂H₁₇BrN₂O₂
Molar mass	301.184 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COC1=CC(=C(C=C1N2CCNCC2)OC)Br
InChI InChI=1S/C12H17BrN2O2/c1-16-11-8-10(12(17-2)7-9(11)13)15-5-3-14-4-6-15/h7-8,14H,3-6H2,1-2H3 Key:JLAQUWGWRNMYGA-UHFFFAOYSA-N

2,5-dimethoxy-4-bromophenylpiperazine (2C-B-PP) is a drug of the phenylpiperazine class. It acts as an agonist at serotonin receptors, and in studies on rats substituted for the psychedelic amphetamine derivative DOM with around 1/10 the potency but similar rates of stimulus-appropriate responding at the highest dose.^[1]^[2]^{: 867–868}

References

[edit ]

^ Lyon RA, Titeler M, McKenney JD, Magee PS, Glennon RA (May 1986). "Synthesis and evaluation of phenyl- and benzoylpiperazines as potential serotonergic agents". Journal of Medicinal Chemistry. 29 (5): 630–634. doi:10.1021/jm00155a008. PMID 3701781.
^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.

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Psychedelics

Tryptamines

No ring subs.	CYB004 (deuDMT) DALT DBT DcPT DET (T-9) DiPT DMT DPT EiPT EPT iPALT (ALiPT) MALT MET MiPT MPT NBoc-DMT NMT PALT PiPT Tryptamine (T)
4-Hydroxytryptamines	4-HO-DALT (daltocin) 4-HO-DBT 4-HO-DET (ethocin; CZ-74) 4-HO-DiPT (iprocin) 4-HO-DPT (deprocin) 4-HO-EPT (eprocin) 4-HO-MALT (maltocin) 4-HO-McPT 4-HO-MET (metocin) 4-HO-MiPT (miprocin) 4-HO-MPT (meprocin) 4-HO-NALT 4-HO-NBnT 4-HO-NET 4-HO-NiPT 4-HO-NPT 4-HO-T 4-HO-TMT 4-HO-5-MeO-DMT 4-MeO-DMT CYB003 (deupsilocin) Psilocin (4-HO-DMT; CX-59) 4-Phosphoryloxytryptamines: Aeruginascin (4-PO-TMT) Baeocystin (4-PO-NMT) Ethocybin (4-PO-DET; CEY-19) Norbaeocystin (4-PO-T) Psilocybin (4-PO-DMT; CY-39) 4-Acetoxytryptamines: 4-AcO-DALT (daltacetin) 4-AcO-DET (ethacetin) 4-AcO-DiPT (ipracetin) 4-AcO-DMT (psilacetin) 4-AcO-DPT (depracetin) 4-AcO-MALT 4-AcO-MET (metacetin) 4-AcO-MiPT (mipracetin) 4-GO-DMT (RE-109) 4-PrO-DiPT 4-PrO-DMT Luvesilocin (4-GO-DiPT; RE-104, FT-104)
5-Hydroxytryptamines	Bufotenin (5-HO-DMT) Serotonin (5-HT; 5-HO-T) 5-Acetoxytryptamines: O-Acetylbufotenine (5-AcO-DMT) O-Pivalylbufotenine (5-t-BuCO-DMT)
5-Methoxytryptamines	4-HO-5-MeO-DMT 5-MeO-2,N,N-TMT 5-MeO-4,N,N-TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (mebufotenin) 5-MeO-DPT 5-MeO-EiPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-NiPT 5-MeO-NMT ASR-3001 (5-MeO-iPALT)
Other ring subs.	2,N,N-TMT 4,N,N-TMT 5-Bromo-DMT 5-Chloro-DMT 5-Fluoro-DMT 5-N,N-TMT 7,N,N-TMT 5-MeO-2,N,N-TMT 5-MeO-4,N,N-TMT 6-Fluoro-DMT 6-Hydroxy-DET (6-HO-DET) Bretisilocin (GM-2505; 5-fluoro-MET)
α-Alkyltryptamines	4-HO-AMT 4-Methyl-AMT 5-Fluoro-AMT 6-Fluoro-AMT AMT (Indopan) α-Methylserotonin (5-HO-αMT) 5-Methoxy-α-alkyltryptamines: 5-MeO-AET α,N,N-TMT (α-Me-DMT; Alpha-N) 5-MeO-AMT (α,O-DMS; Alpha-O) α,N,O-TMS (5-MeO-α,N-DMT) α,N,N,O-TeMS (5-MeO-α,N,N-TMT)
Others	N-DEAOP-Ts (e.g., N-DEAOP-NET, N-DEAOP-NMT, 5-MeO-N-DEAOP-NMT, 5-MeO-N-DEAOP-NET) Structure undisclosed: CT-4201 EB-002 (EB-373) MSP-1014 MYCO-004
Cyclized	Ergolines/lysergamides (e.g., LSD) β-Carbolines and Harmala alkaloids (e.g., harmine, harmaline, 6-methoxyharmalan) Iboga alkaloids (e.g., 18-MAC, 18-MC, coronaridine, ibogaine, ibogamine, ME-18-MC, noribogaine, tabernanthine, voacangine) Ibogalogs (e.g., ibogainalog) O-Methylnordehydrobufotenine Partial ergolines (e.g., NDTDI, RU-28306, CT-5252) Piperidinylethylindoles (e.g., pip-T) Pyrrolidinylethylindoles (e.g., pyr-T, 5-MeO-pyr-T) Pyrrolidinylmethylindoles (e.g., MPMI, 4-HO-MPMI (lucigenol), 5-MeO-MPMI) Tetrahydropyridinylindoles (e.g., RU-28253 (5-MeO-THPI), NEtPhOH-THPI)
Bioisosteres	Benzofurans (e.g., 5-MeO-DiBF, dimemebfe (5-MeO-BFE), mebfap) Benzothiophenes (e.g., 3-APBT) Indazolethylamines (e.g., AL-38022A, O-methyl-AL-34662) Indenylethylamines (e.g., C-DMT) Isotryptamines (e.g., 6-MeO-isoDMT, Ro60-0175) MYCO-005 Quinolinylethylamines (e.g., mefloquine)

Phenethylamines

Scalines	2-Bromomescaline 3-TE 3-TM 4-Desoxymescaline (DESOXY) 4-TE 4-TM Allylescaline Beta-D Cyclopropylmescaline Difluoroescaline Difluoromescaline N,N-Diformylmescaline Escaline Fluoroescaline Fluoroproscaline N-Formylmescaline Isobuscaline Isoproscaline Jimscaline Mescaline (3,4,5-TMPEA) Metadifluoromescaline (MDFM) Metaescaline Methallylescaline N-Methylmescaline (M-M) NBOMe-escaline NBOMe-mescaline Proscaline Thioproscaline Tomscaline Trichocereine (N,N-dimethylmescaline; MM-M) Trifluoroescaline Trifluoromescaline
2C-x	2C-B 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-H 2C-I 2C-iBu 2C-iP 2C-N 2C-NH2 2C-P 2C-Se 2C-Se-TFM 2C-tBu 2C-TFE 2C-TFM 2C-YN 2C-V 2C-T-x: 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 CYB210010 (2C-T-TFM, 2C-T-36) 2C-O-x: 2C-O 2C-O-2 2C-O-4 Others: 2C-B-AN 2C-DB 2C-G-x (e.g., 2C-G-3, 2C-G-5) β-Keto-2C-B (βk-2C-B) β-Keto-2C-I (βk-2C-I) β-Methyl-2C-B (BMB) BOx (e.g., BOB, BOD, BOH-2C-B) HOT-x (e.g., HOT-2, HOT-7, HOT-17) N-Ethyl-2C-B TWEETIOs (e.g., 2CD-2-ETO, 2CD-5-ETO, 2CE-5-ETO, 2CE-5iPrO, 2CT2-5-ETO, ASR-2001 (2CB-5PrO))
3C-x	3C-AL 3C-BZ 3C-DFE 3C-E 3C-MAL 3C-P TMA (3C-M)
DOx	DOAM DOB DOBU DOC DOEF DOET DOH (2,5-DMA) DOI DOIB DOIP DOM DON DOPR DOTFM DOYN Aleph-x (DOT-x): Aleph (DOT) Aleph-2 Aleph-4 Aleph-6 Aleph-7 TMA-2 and derivatives (Mxx): MALM MEM MDFEM MFEM MIPM MMALM MPM MTFEM TMA-2 Others: DODB DODC DOM-NBOMe DOTMA Ganeshas (G-x) (e.g., Ganesha (G, G-0)
4C-x	4C-B 4C-C 4C-D (Ariadne) 4C-E 4C-I 4C-N 4C-P 4C-T-2
Ψ-PEA	Ψ-2C-DFMO (ψ-2C-O-35) Ψ-2C-T-4 Ψ-DODFMO Ψ-DOM TMA-6 (Ψ-TMA-2)
MDxx	5-Methyl-MDA 6-Methyl-MDA DMMDA DMMDA-2 EIDA EMDA-2 IDA Lophophine (MMDPEA) Lys-MDA MDA (tenamfetamine) MDHMA MDMA (midomafetamine; ecstasy) MDOH MMDA MMDA-2 MMDA-3a MMDA-3b MMDMA N-t-BOC-MDMA (R)-MDMA
FLY	2C-B-FLY 2C-B-BUTTERFLY 2C-B-DragonFLY 2C-B-DragonFLY-NBOH 2C-B-FLY-NB2EtO5Cl 2CB-5-hemifly 2CBFly-NBOMe Bromo-DragonFLY DOB-FLY DOH-FLY TFMFly
25x-NB (NBOMes)	25x-NBOMe: 25B-NBOMe 25C-NBOMe 25CN-NBOMe 25D-NBOMe 25E-NBOMe 25F-NBOMe 25G-NBOMe 25H-NBOMe 25I-NBOMe 25iP-NBOMe 25N-NBOMe 25O-NBOMe 25P-NBOMe 25T-NBOMe 25T2-NBOMe 25T4-NBOMe 25T7-NBOMe 25TFM-NBOMe 25x-NBOH: 25B-NBOH 25C-NBOH 25CN-NBOH 25D-NBOH 25E-NBOH 25I-NBOH 25P-NBOH Others: 25B-NB (N-benzyl-2C-B) 2C-B-AN 2C2-NBOMe 2CBCB-NBOMe 2CBFly-NBOMe DOM-NBOMe NBOMe-escaline NBOMe-mescaline TGF-8027
Others	2-TOET 2-TOM 25B-NAcPip 4-HA 5-TOET 5-TOM Benzofurans (e.g., 5-APB, 5-APDB, 6-APB, 6-APDB, F, F-2, F-22) Benzothiophenes (e.g., 5-APBT, 6-APBT) CT-5172 DMAs (e.g., 2,4-DMA, 3,4-DMA) Fenfluramine MMA (3-MeO-4-MA) Norfenfluramine PEA-NDEPAs (e.g., 25D-NM-NDEAOP, DOB-NDEPA, DOI-NDEPA, DOM-NDEPA, DOTFM-NDEPA, M-NDEPA, TMA-2-NDEPA) PMA (4-MA) TMAs (e.g., TMA-3, TMA-4, TMA-5) TOMSO ZDCM-04 Structure undisclosed: CYB005
Cyclized	1-Aminomethylindanes (e.g., 2CB-Ind, jimscaline) 2-Aminoindanes (e.g., DOM-AI) 3-Benzazepines (e.g., lorcaserin) 3-Phenylpiperidines (e.g., LPH-5, LPH-48) Benzocyclobutenes (e.g., 2CBCB-NBOMe, TCB-2, tomscaline) Benzoxepins (e.g., BBOX, IBOX, TFMBOX) DMBMPP (juncosamine) Ergolines/lysergamides (e.g., LSD) Glaucine Partial ergolines (e.g., NDTDI, DEIMDHPCA, DEMPDHPCA, DEMTMPDHPCA, DEMNDHPCA) Phenylcyclopropylamines (e.g., DMCPA, TMT) Phenyloxazolamines (aminorexes) (e.g., 2C-B-aminorex) Pyridopyrroloquinoxalines (e.g., IHCH-7113) Z3517967757 ZC-B

Lysergamides

1-Alkyllysergamides (prodrugs): Methysergide (1-methylmethylergonovine; UML-491)
MLA-74 (1-methyl-LAE)
MLD-41 (1-methyl-LSD)
MPD-75 (1-methyl-LPD)
OML-632 (1-hydroxymethyl-LSD)

Other ring system-substituted lysergamides: 12-Hydroxy-LSD
12-Methoxy-LSD

Bioisosteres: JRT

Others

Arylpiperazines (e.g., 2C-B-PP, 2-NP, mCPP, MK-212, ORG-12962, pCPP, pFPP, quipazine, TFMPP)
Dihydrobenzoxazines (e.g., efavirenz)
Phenoxyethylamines (e.g., CT-4719, ORG-37684)
Pyridopyrroloquinoxalines (e.g., IHCH-7113)
Quinazolinylethylamines (e.g., RH-34)

Natural sources

Cyclized tryptamines: Banisteriopsis caapi (yagé)
Peganum harmala (Syrian rue)
Silene undulata
Tabernanthe iboga (iboga)

Phenethylamines: Pachycereus pringlei (saguesa, elephant cactus, cardon)
Peyote (Lophophora williamsii; peyotl)
Trichocereus cacti (e.g., San Pedro, Peruvian torch)

v t e Arylpiperazines
Phenylpiperazines	1-Phenylpiperazine (1-PP; PP) 3,4-CFP 2C-B-PP Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-7625 EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Fluanisone Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635
Benzylpiperazines	2C-B-BZP 3-Methylbenzylpiperazine Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP EGIS-7625 Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide NSI-189 Piberaline Piribedil RN-1747 Sunifiram Trimetazidine Vesnarinone
Naphthylpiperazines	1-Naphthylpiperazine (1-NP) 2-Naphthylpiperazine (2-NP) CSP-2503 F-11,461 S-14,506 S-14671
Quinolinylpiperazines	FPPQ 6-Nitroquipazine Isoquipazine Quipazine
Diphenylalkylpiperazines	AD-1211 Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenpipenol Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,783 GBR-12,935 GBR-13,069 GBR-13,098 GBR-13,119 Hydroxyzine JJC8-088 Lidoflazine Manidipine Meclozine MT-45 Oxatomide SNC-80 Vanoxerine
Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone
Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine ORG-12962 Pyridinylpiperazine
Benzo(iso)thiazolyl piperazines	Lurasidone Perospirone Revospirone Tiospirone Ziprasidone
Tricyclic-linked piperazines	Amoxapine Clopenthixol Clorotepine Clozapine Cyanothepin Doclothepin Docloxythepin Flupentixol Fluphenazine Isofloxythepin Loxapine Meperathiepin Metitepine Octomethothepin Olanzapine Opipramol Oxyclothepin Oxyprothepin Peradithiepin Perathiepin Perazine Perphenazine Pirenzepine Prochlorperazine Thiethylperazine Thiothixene Trifluoperazine Trifluthepin Zuclopenthixol
Others/uncategorized	AP-238 Azimilide Bucinnazine Cinepazet Cinepazic acid Cinepazide CPD-1 Cyclohexylpiperazine Hexocyclium Indinavir JNJ-7777120 Lodenafil MK-212 Mirodenafil PB-28 Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 WY-46824 Zipeprol

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See also

References