Substituted piperazine

Short description: Class of chemical compounds

Substituted piperazines are a class of chemical compounds based on a piperazine core.[1] Some are used as recreational drugs and some are used in scientific research.[2]

## Contents

* 1 List of substituted piperazines
* 1.1 Benzylpiperazines
* 1.2 Phenylpiperazines
* 1.2.1 ortho-Substituted
* 1.2.2 meta-Substituted
* 1.2.3 para-Substituted
* 1.2.4 Multiple substitutions
* 1.2.5 Others
* 1.3 Other arylpiperazines
* 1.4 By drug class
* 2 Activities
* 3 See also
* 4 References
* 5 External links

## List of substituted piperazines

### Benzylpiperazines

Chemical structures of selected benzylpiperazines

* 1-Benzylpiperazine (BZP)

1-Benzylpiperazine (BZP)

* 1-Methyl-4-benzylpiperazine (MBZP)

1-Methyl-4-benzylpiperazine (MBZP)

* 1,4-Dibenzylpiperazine (DBZP)

* 3,4-Methylenedioxy-1-benzylpiperazine (MDBZP)

3,4-Methylenedioxy-1-benzylpiperazine (MDBZP)

* 4-Bromo-2,5-dimethoxy-1-benzylpiperazine (2C-B-BZP)

* Methoxypiperamide (MeOP, MEXP) ((4-methoxyphenyl)(4-methylpiperazin-1-yl)methanone)

Methoxypiperamide (MeOP, MEXP) ((4-methoxyphenyl)(4-methylpiperazin-1-yl)methanone)

* Sunifiram (1-benzoyl-4-propanoylpiperazine)

Sunifiram (1-benzoyl-4-propanoylpiperazine)

* 3-Methylbenzylpiperazine (3-MeBZP)

* Befuraline
(also produces benzylpiperazine as a metabolite)

* Fipexide
(also produces substituted benzylpiperazine as a metabolite)

* Piberaline
(also produces benzylpiperazine as a metabolite)

### Phenylpiperazines

See also: Chemistry:Phenylpiperazine

File:1-Phenylpiperazine.svg1-Phenylpiperazine (1-PP).

#### ortho-Substituted

* 2-Chlorophenylpiperazine (oCPP)
* 2-Methylphenylpiperazine (oMPP)
* 2-Methoxyphenylpiperazine (oMeOPP)
* Mefeclorazine
* Vortioxetine

Enpiprazole is known to produce oCPP as a metabolite. It was initially anticipated to produce oMeOPP as a metabolite, but this proved not to be the case.

#### meta-Substituted

* 3-Chlorophenylpiperazine (mCPP)
* 3-Methoxyphenylpiperazine (mMeOPP)
* 3-Trifluoromethylphenylpiperazine (TFMPP)
* 1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine (3C-PEP)

Trazodone, nefazodone, etoperidone, mepiprazole, and others produce mCPP as a metabolite.[3]

#### para-Substituted

* 4-Chlorophenylpiperazine (pCPP)
* 4-Fluorophenylpiperazine (pFPP)
* 4-Methylphenylpiperazine (pMPP)
* 4-Methoxyphenylpiperazine (pMeOPP, MeOPP)
* 4-Nitrophenylpiperazine (pNPP; PAL-175) – selective partial serotonin releasing agent[4]
* 4-Trifluoromethylphenylpiperazine (pTFMPP)

#### Multiple substitutions

* 2,3-Dichlorophenylpiperazine (2,3-DCPP)
* 3,4-Dichlorophenylpiperazine (3,4-DCPP)
* 2,3-Dimethylphenylpiperazine (DMPP)
* 3-Trifluoromethyl-4-chlorophenylpiperazine (TFMCPP; PAL-179) – selective partial serotonin releasing agent[4]

#### Others

* 1-Phenylpiperazine (PP)

### Other arylpiperazines

* 1-(1-Naphthyl)piperazine (1-NP)
* 1-(2-Pyrimidinyl)piperazine (1-PP)
* 6-Chloro-2-(1-piperazinyl)quinoxaline (CPQ)
* ORG-12962 (1-(5-trifluoromethyl-6-chloropyridin-2-yl)piperazine)
* Quipazine (2-piperazin-1-ylquinoline)

Many azapirones such as buspirone, gepirone, and tandospirone produce 1-PP as a metabolite.

### By drug class

Antianginals

* Ranolazine
* Trimetazidine

Antidepressants

* Amoxapine
* Befuraline
* Buspirone
* Flesinoxan
* Gepirone
* Ipsapirone
* Nefazodone
* Piberaline
* Tandospirone
* Trazodone
* Vilazodone
* Vortioxetine
* Zalospirone

Antihistamines

* Buclizine
* Cetirizine
* Cinnarizine
* Cyclizine
* Hydroxyzine
* Levocetirizine
* Meclizine
* Niaprazine

Antiserotonergics

* EGIS-7625

Antipsychotics

* Typical
* Flupentixol
* Fluphenazine
* Perphenazine
* Prochlorperazine
* Thiothixene
* Trifluoperazine
* Zuclopenthixol
* Acetophenazine
* Carfenazine
* Atypical
* Amperozide
* Aripiprazole
* Clozapine
* Lurasidone
* Olanzapine
* Perospirone
* Ziprasidone
* Quetiapine
* Cariprazine

Recreational Drugs

* 4-Bromo-2,5-dimethoxy-1-benzylpiperazine (2C-B-BZP)
* 1-Benzylpiperazine (BZP)
* 2,3-Dichlorophenylpiperazine (DCPP)
* 1,4-Dibenzylpiperazine (DBZP)
* 4-Methyl-1-benzylpiperazine (MBZP)
* 3-Chlorophenylpiperazine (mCPP)
* 3,4-Methylenedioxy-1-benzylpiperazine (MDBZP)
* 4-Methoxyphenylpiperazine (MeOPP)
* Methoxypiperamide (MeOP or MEXP)
* 4-Chlorophenylpiperazine (pCPP)
* 4-Fluorophenylpiperazine (pFPP)
* 3-Trifluoromethylphenylpiperazine (TFMPP)

Urologicals

* Sildenafil
* Vardenafil

Others

* 6-Nitroquipazine
* Antrafenine
* Diethylcarbamazine
* Diphenazine
* Fipexide
* Imatinib
* NSI-189
* Pipobroman (antineoplastic agent)
* Quipazine
* Sunifiram (nootropic)
* Tolpiprazole (tranquilizer)

## Activities

Template:Sticky

Monoamine release (EC50, nM) of arylpiperazines Compound | PAL # | Serotonin | Norepinephrine | Dopamine | Type | Ref

|
|
|
|
|
|

1-Benzylpiperazine (BZP) | ND | 6050–>100000 | 62.2–68 | 175–600 | NDRA | [5][6][7][8][9][10]
1-Phenylpiperazine (PP) | ND | 880 | 186 | 2530 | SNRA | [11]
2-Me-PP (oMPP) | PAL-169 | 175 | 39.1 | 296–542 | SNDRA | [11][12][10]
2-OMe-PP (oMeOPP) | ND | ND | ND | ND | ND | ND
2-TFM-PP (oTFMPP) | ND | 570 | 350 | 11200 | SNRA | [11]
2-SMe-PP (oMTPP) | ND | 270 | >10000 | >10000 | SRA | [11]
2-Et-PP (oEtPP) | ND | 290 | 830 | >10000 | SNRA | [11]
2-Chloro-PP (oCPP) | ND | 310 | 26 | >3000 | NRA | [11]
2-Bromo-PP (oBPP) | ND | 132 | 33 | 250 | SNDRA | [11]
2-Nitro-PP (oNPP) | ND | 1870 | 770 | >10000 | SNRA | [11]
3-Chloro-PP (mCPP) | ND | 28–39 | 1400–>10000 | >10000–63000 | SRA | [6][13][14][15]
3-Fluoro-PP (mFPP) | ND | 115 | 340 | 2400 | SNRA | [11]
3-Me-PP (mMPP) | ND | 110 | >20000 | >20000 | SRA | [11]
3-OMe-PP (mMeOPP) | ND | 650 | >10000 | >10000 | SRA | [11]
3-OH-PP (mOHPP) | ND | 230 | 174 | 2500 | SNRA | [11]
3-TFM-PP (TFMPP) | ND | 121 | >10000 | >10000 | SRA | [8][7][9]
4-Chloro-PP (pCPP) | ND | ND | ND | ND | ND | ND
4-Fluoro-PP (pFPP) | ND | 230 | 3200 | >10000 | SRA | [11]
4-Me-PP (pMPP) | PAL-233 | 220 | >10000 | >20000 | SRA | [11][10]
4-OMe-PP (pMeOPP) | ND | 3200 | 440–1500 | 6300–11000 | SNDRA | [11][6]
4-TFM-PP (pTFMPP) | ND | ND | ND | ND | ND | ND
4-Ac-PP (pAcPP) | ND | 50 | 150 | 3000 | SNRA | [11]
4-CN-PP (pCNPP) | ND | 36 | 6300 | >10000 | SRA | [11]
4-Phenyl-PP (pPhPP) | ND | >10000 | 1520 | 5200 | NDRA | [11]
4-OH-PP (pOHPP) | ND | >10000 | 230 | 850 | NDRA | [11]
4-Nitro-PP (pNPP) | PAL-175 | 19–43 | >10000 | >10000 | SRA | [11][4]
2,3-Dichloro-PP (2,3-DCPP) | ND | 10 | 36 | 108 | SNDRA | [11]
2,3-DiMe-PP (2,3-DMPP) | PAL-218 | 24–26 | 13.7–56 | 1207–1320 | SNRA | [11][4][10]
2,4-Difluoro-PP (2,4-DFPP) | ND | 470 | 2300 | >10000 | SNRA | [11]
3,4-Dichloro-PP (3,4-DCPP) | ND | ND | ND | ND | ND | ND
3,4-Difluoro-PP (3,4-DFPP) | ND | 76 | 9200 | >10000 | SRA | [11]
3-TFM-4-Cl-PP (TFMCPP) | PAL-179 | 33 | >10000 | >10000 | SRA | [4]
Notes: Assays were done using rat brain synaptosomes.

## See also

* Substituted α-alkyltryptamine
* Substituted amphetamine
* Substituted cathinone
* Substituted methylenedioxyphenethylamine
* Substituted phenethylamine
* Substituted phenylmorpholine
* Substituted tryptamine

## References

1. ↑ Laras, Y.; Garino, C.; Dessolin, J.; Weck, C.; Moret, V.; Rolland, A.; Kraus, J.-L. (2009-02-01). "New N4-substituted piperazine naphthamide derivatives as BACE-1 inhibitors". Journal of Enzyme Inhibition and Medicinal Chemistry 24 (1): 181–187. doi:10.1080/14756360802048939. ISSN 1475-6366. PMID 18770069. https://doi.org/10.1080/14756360802048939.
2. ↑ Alghamdi, Saad; Alshehri, Mohammed M.; Asif, Mohammad (2022). "The Neuropharmacological Potential of Piperazine Derivatives: A Mini- Review" (in en). Mini-Reviews in Organic Chemistry 19 (7): 798–810. doi:10.2174/1570193x19666220119120211. https://www.eurekaselect.com/article/120285.
3. ↑ "Metabolism of m-CPP, trazodone, nefazodone, and etoperidone: clinical and forensic aspects". Drug Metab Rev 57 (2): 115–146. February 2025. doi:10.1080/03602532.2025.2465482. PMID 39945551.
4. ↑ 4.0 4.1 4.2 4.3 4.4 "Studies of the biogenic amine transporters. 14. Identification of low-efficacy "partial" substrates for the biogenic amine transporters". J Pharmacol Exp Ther 341 (1): 251–262. April 2012. doi:10.1124/jpet.111.188946. PMID 22271821.
5. ↑ "Therapeutic potential of monoamine transporter substrates". Curr Top Med Chem 6 (17): 1845–1859. 2006. doi:10.2174/156802606778249766. PMID 17017961.
6. ↑ 6.0 6.1 6.2 "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". Eur J Pharmacol 559 (2–3): 132–137. March 2007. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=00665d67c36dcf1777989b70cc901c654420a0c7.
7. ↑ 7.0 7.1 "Effects of "Legal X" piperazine analogs on dopamine and serotonin release in rat brain". Ann N Y Acad Sci 1025: 189–197. October 2004. doi:10.1196/annals.1316.024. PMID 15542717. Bibcode: 2004NYASA1025..189B.
8. ↑ 8.0 8.1 "N-substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA, or 'Ecstasy')". Neuropsychopharmacology 30 (3): 550–560. March 2005. doi:10.1038/sj.npp.1300585. PMID 15496938.
9. ↑ 9.0 9.1 "Dopamine-releasing agents". Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. July 2008. pp. 305–320. ISBN 978-0-470-11790-3. OCLC 181862653. https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf.
10. ↑ 10.0 10.1 10.2 10.3 "Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter". Drug Alcohol Depend 147: 1–19. February 2015. doi:10.1016/j.drugalcdep.2014.12.005. PMID 25548026.
11. ↑ 11.00 11.01 11.02 11.03 11.04 11.05 11.06 11.07 11.08 11.09 11.10 11.11 11.12 11.13 11.14 11.15 11.16 11.17 11.18 11.19 11.20 11.21 11.22 11.23 "Binding of the amphetamine-like 1-phenyl-piperazine to monoamine transporters". ACS Chem Neurosci 3 (9): 693–705. September 2012. doi:10.1021/cn300040f. PMID 23019496.
12. ↑ "Cocaine-like discriminative stimulus effects of "norepinephrine-preferring" monoamine releasers: time course and interaction studies in rhesus monkeys". Psychopharmacology (Berl) 234 (23–24): 3455–3465. December 2017. doi:10.1007/s00213-017-4731-5. PMID 28889212.
13. ↑ "Therapeutic and adverse actions of serotonin transporter substrates". Pharmacol Ther 95 (1): 73–88. July 2002. doi:10.1016/s0163-7258(02)00234-6. PMID 12163129.
14. ↑ "Serotonin releasing agents. Neurochemical, therapeutic and adverse effects". Pharmacol Biochem Behav 71 (4): 825–836. April 2002. doi:10.1016/s0091-3057(01)00669-4. PMID 11888573.
15. ↑ "Evidence for noncompetitive modulation of substrate-induced serotonin release". Synapse 64 (11): 862–869. November 2010. doi:10.1002/syn.20804. PMID 20842720.

## External links

* "BZP/piperazines". European Union Drugs Agency (EUDA). https://www.euda.europa.eu/publications/drug-profiles/bzp_en.

* v
* t
* e

Piperazines

Simple piperazines
(no additional rings)|

* 1-Cyclohexylpiperazine
* Aminoethylpiperazine
* Diethylcarbamazine
* HEPPS
* Midafotel
* Piperazine
* PIPES

Phenylpiperazines|

* Acaprazine
* Antrafenine
* Aripiprazole
* Batoprazine
* Bifeprunox
* BRL-15,572
* Ciprofloxacin
* CSP-2503
* Dapiprazole
* DCPP
* DMPP
* Diphenylpiperazine
* Dropropizine
* EGIS-12,233
* Elopiprazole
* Eltoprazine
* Enpiprazole
* Ensaculin
* Etoperidone
* Flesinoxan
* Fluanisone
* Flibanserin
* Fluprazine
* Itraconazole
* Ketoconazole
* Levodropropizine
* Lorpiprazole
* mCPP
* Mefway
* MeOPP
* Mepiprazole
* Naftopidil
* Naluzotan
* Naphthylpiperazine
* 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
* Befuraline
* Bifeprunox
* Buclizine
* BZP
* Chlorbenzoxamine
* DBZP
* Fipexide
* Imatinib
* MBZP
* MDBZP
* Meclozine
* Methoxypiperamide
* Piberaline
* Piribedil
* Sunifiram
* Trimetazidine
* Vesnarinone

Diphenylalkylpiperazines
(benzhydrylalkylpiperazines)|

* 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
* Lidoflazine
* Manidipine
* Meclozine
* MT-45
* Oxatomide
* SNC-80
* Vanoxerine

Pyrimidinylpiperazines|

* Buspirone
* Dasatinib
* Eptapirone
* Gepirone
* Ipsapirone
* Piribedil
* Prazitone
* Pyrimidinylpiperazine
* Revospirone
* Tandospirone
* Tirilazad
* Trimazosin
* Umespirone
* Zalospirone

Pyridinylpiperazines|

* Atevirdine
* Azaperone
* Delavirdine
* Mirtazapine
* Pyridinylpiperazine

Benzo(iso)thiazolylpiperazines|

* Lurasidone
* Perospirone
* Revospirone
* Tiospirone
* Ziprasidone

Tricyclics
(piperazine attached via side chain)|

* 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|

* 6-Nitroquipazine
* Azimilide
* Cinepazet
* Cinepazic acid
* Cinepazide
* Cyclohexylpiperazine
* EGIS-7625
* Hexocyclium
* Indinavir
* JNJ-7777120
* Lodenafil
* Mirodenafil
* PB-28
* Quipazine
* Ranolazine
* SA-4503
* Sildenafil
* Tadalafil
* Vardenafil
* VUF-6002
* WY-46824
* Zipeprol

* v
* t
* e

Chemical classes of psychoactive drugs

Stimulants|

* Amphetamine-type/dopamine releasing agents: Alkylamines
* Cycloalkylaminopropanes
* Arylpiperazines
* Benzylpiperazines
* Phenylpiperazines
* Phenethylamines
* Aminorexes/phenyloxazolamines
* Amphetamines/α-methylphenethylamines
* Cathinones/β-ketoamphetamines
* β-Hydroxyamphetamines/cathinols
* Naphthylaminopropanes
* Phentermines
* Phenylisobutylamines/α-ethylphenethylamines
* α-Propylphenethylamines
* Phenylmorpholines/phenmetrazines
* Thiopropamines/thienylaminopropanes

* Cocaine-type/typical dopamine reuptake inhibitors: Phenethylamines
* Phenidates/benzylpiperidines
* Phenylethylpyrrolidines
* Pyrrolidinophenones
* Phenyltropanes/cocaine analogues

* Modafinil-type/atypical dopamine reuptake inhibitors: Modafinil analogues
* Phenylpiracetams

* Caffeine-type/adenosine receptor antagonists: Xanthines/methylxanthines

* Nicotine-type/nicotinic acetylcholine receptor agonists: Nicotine analogues

Depressants|

* GABAA receptor positive allosteric modulators: Alcohols/ethanol analogues
* Barbiturates
* Benzodiazepines
* Pyrrolobenzodiazepines
* Thienobenzodiazepines
* Thienodiazepines
* Thienotriazolodiazepines
* Triazolobenzodiazepines
* Carbamates
* Ethers
* Neuroactive steroids
* Nonbenzodiazepines
* β-Carbolines
* Cyclopyrrolones
* Imidazopyridines
* Pyrazolopyrimidines
* Phenols
* Piperidinediones
* Quinazolinones

* GABAA receptor agonists: Isoxazoles

* GHB receptor agonists: 1,4-Butanediols

* α2δ subunit-containing voltage-gated calcium channel blockers: Gabapentinoids

* Opioids/μ-opioid receptor agonists: Benzimidazoles
* Nitazenes
* Fentanyl analogues/phenylpiperidines
* Mitragyna alkaloids
* Morphinans/phenanthrenes
* Opiates/opium alkaloids
* Utopioids

* Antihistamines/H1 receptor antagonists: Benzimidazoles
* Diarylmethanes
* Ethylenediamines
* Tricyclics
* Dibenzocycloheptenes

Hallucinogens|

* Serotonergic psychedelics/serotonin 5-HT2A receptor agonists: Arylpiperazines
* Phenylpiperazines
* Quinolinylpiperazines
* Cyclized phenethylamines
* 3-Benzazepines
* Cyclized tryptamines
* Azepinoindoles
* Ibogalogs
* Iboga alkaloids
* β-Carbolines
* Harmala alkaloids
* Ergolines
* Lysergamides
* Simplified/partial lysergamides
* Phenethylamines (methoxyphenethylamines)
* 2Cs
* 25-NB/NBOMes
* 2C-Os
* 2C-Ts
* HOT-x
* TWEETIOs
* Amphetamines/α-methylphenethylamines
* 3Cs
* Dimethoxyamphetamines/DMAs
* DOx
* Alephs
* Ethylenedioxyamphetamines/EDxx
* Methylenedioxyamphetamines/MDxx
* Trimethoxyamphetamines/TMAs
* BOx
* FLYs/benzofurans
* Phenylisobutylamines/α-ethylphenethylamines
* 4Cs
* Scalines
* Ψ-PEAs
* Tryptamines
* α-Alkyltryptamines
* α-Alkyl-β-ketotryptamines
* 4-Hydroxytryptamines
* 5-Hydroxytryptamines
* 5-Methoxytryptamines
* Miscellaneous

* Dissociatives/NMDA receptor antagonists: Adamantanes
* Arylcyclohexylamines
* Diarylethylamines
* Morphinans

* κ-Opioid receptor agonists: Benzomorphans
* Salvinorins

* GABAA receptor agonists: Isoxazoles

* Deliriants/anticholinergics/muscarinic acetylcholine receptor antagonists: Diarylmethanes
* Tropanes

* Others: Cyclized tryptamines
* Azepinoindoles
* Iboga alkaloids
* (Phyto)cannabinoids

Entactogens|

* Serotonin releasing agents: Phenethylamines
* 2-Aminoindanes
* 2-Aminotetralins
* Amphetamines
* Benzofuranylaminopropanes
* Benzothiophenylaminopropanes
* Ethylenedioxyamphetamines/EDxx
* Indanylaminopropanes
* Indolylaminopropanes
* Methylenedioxyamphetamines/MDxx
* Tetralinylaminopropanes
* Tryptamines
* α-Alkyltryptamines
* Miscellaneous

Psychiatric drugs|

* Anxiolytics: Azapirones
* Benzodiazepines
* Pyrrolobenzodiazepines
* Thienobenzodiazepines
* Thienodiazepines
* Thienotriazolodiazepines
* Triazolobenzodiazepines

* Antidepressants: Tricyclic antidepressants
* Dibenzazepines
* Dibenzocycloheptenes
* Dibenzothiepins
* Dibenzoxazepines
* Dibenzoxepins
* Tetracyclic antidepressants

* Antipsychotics/dopamine D2 receptor antagonists or partial agonists: Benzamides
* Benzimidazoles
* Benzisothiazoles
* Benzisoxazoles
* Butyrophenones
* Diphenylbutylpiperidines
* Phenylpiperazines
* Tricyclics
* Dibenzazepines
* Dibenzodiazepines
* Dibenzothiazepines
* Dibenzothiepins
* Dibenzoxazepines
* Phenothiazines
* Thienobenzodiazepines

* Mood stabilizers/anticonvulsants: Gabapentinoids
* Tricyclics
* Dibenzazepines
* Valproates

Others|

* Nootropics: Racetams
* Phenylpiracetams

* Miscellaneous: 3-Benzazepines
* Adamantanes
* Catecholamines
* Tetrahydroisoquinolines
* Yohimbans

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*[EC50]: half-maximal effective concentration
*[PAL #]: Phenyl Amine Library Number
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