Substituted piperazine

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]

List of substituted piperazines

Benzylpiperazines

1-Benzylpiperazine (BZP)
1-Methyl-4-benzylpiperazine (MBZP)
1,4-Dibenzylpiperazine (DBZP)
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)
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

ortho-Substituted

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)
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

Antidepressants

Antihistamines

Antiserotonergics

EGIS-7625

Antipsychotics

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

Others

Activities

Monoamine release (EC₅₀Tooltip half-maximal effective concentration, 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.

References

^ 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. S2CID 85385527.
^ Alghamdi, Saad; Alshehri, Mohammed M.; Asif, Mohammad (2022). "The Neuropharmacological Potential of Piperazine Derivatives: A Mini- Review". Mini-Reviews in Organic Chemistry. 19 (7): 798–810. doi:10.2174/1570193x19666220119120211.
^ Costa Alegre MD, Barbosa DJ, Dinis-Oliveira RJ (February 2025). "Metabolism of m-CPP, trazodone, nefazodone, and etoperidone: clinical and forensic aspects". Drug Metab Rev: 1–32. doi:10.1080/03602532.2025.2465482. PMID 39945551.
^ ^a ^b ^c ^d ^e Rothman RB, Partilla JS, Baumann MH, Lightfoot-Siordia C, Blough BE (April 2012). "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. doi:10.1124/jpet.111.188946. PMC 3364510. PMID 22271821.
^ Rothman RB, Baumann MH (2006). "Therapeutic potential of monoamine transporter substrates". Curr Top Med Chem. 6 (17): 1845–1859. doi:10.2174/156802606778249766. PMID 17017961.
^ ^a ^b ^c Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". Eur J Pharmacol. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
^ ^a ^b Baumann MH, Clark RD, Budzynski AG, Partilla JS, Blough BE, Rothman RB (October 2004). "Effects of "Legal X" piperazine analogs on dopamine and serotonin release in rat brain". Ann N Y Acad Sci. 1025: 189–197. doi:10.1196/annals.1316.024. PMID 15542717.
^ ^a ^b Baumann MH, Clark RD, Budzynski AG, Partilla JS, Blough BE, Rothman RB (March 2005). "N-substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA, or 'Ecstasy')". Neuropsychopharmacology. 30 (3): 550–560. doi:10.1038/sj.npp.1300585. PMID 15496938.
^ ^a ^b Blough B (July 2008). "Dopamine-releasing agents" (PDF). In Trudell ML, Izenwasser S (eds.). Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. pp. 305–320. ISBN 978-0-470-11790-3. OCLC 181862653. OL 18589888W.
^ ^a ^b ^c ^d Reith ME, Blough BE, Hong WC, Jones KT, Schmitt KC, Baumann MH, Partilla JS, Rothman RB, Katz JL (February 2015). "Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter". Drug Alcohol Depend. 147: 1–19. doi:10.1016/j.drugalcdep.2014.12.005. PMC 4297708. PMID 25548026.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r ^s ^t ^u ^v ^w ^x Severinsen K, Kraft JF, Koldsø H, Vinberg KA, Rothman RB, Partilla JS, Wiborg O, Blough B, Schiøtt B, Sinning S (September 2012). "Binding of the amphetamine-like 1-phenyl-piperazine to monoamine transporters". ACS Chem Neurosci. 3 (9): 693–705. doi:10.1021/cn300040f. PMC 3447394. PMID 23019496.
^ Kohut SJ, Jacobs DS, Rothman RB, Partilla JS, Bergman J, Blough BE (December 2017). "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. doi:10.1007/s00213-017-4731-5. PMC 5747253. PMID 28889212.
^ Rothman RB, Baumann MH (July 2002). "Therapeutic and adverse actions of serotonin transporter substrates". Pharmacol Ther. 95 (1): 73–88. doi:10.1016/s0163-7258(02)00234-6. PMID 12163129.
^ Rothman RB, Baumann MH (April 2002). "Serotonin releasing agents. Neurochemical, therapeutic and adverse effects". Pharmacol Biochem Behav. 71 (4): 825–836. doi:10.1016/s0091-3057(01)00669-4. PMID 11888573.
^ Rothman RB, Baumann MH, Blough BE, Jacobson AE, Rice KC, Partilla JS (November 2010). "Evidence for noncompetitive modulation of substrate-induced serotonin release". Synapse. 64 (11): 862–869. doi:10.1002/syn.20804. PMC 2941209. PMID 20842720.

External links

"BZP/piperazines". European Union Drugs Agency (EUDA).

[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. S2CID 85385527.

[2] Alghamdi, Saad; Alshehri, Mohammed M.; Asif, Mohammad (2022). "The Neuropharmacological Potential of Piperazine Derivatives: A Mini- Review". Mini-Reviews in Organic Chemistry. 19 (7): 798–810. doi:10.2174/1570193x19666220119120211.

[CostaAlegreBarbosaDinis-Oliveira2025-3] Costa Alegre MD, Barbosa DJ, Dinis-Oliveira RJ (February 2025). "Metabolism of m-CPP, trazodone, nefazodone, and etoperidone: clinical and forensic aspects". Drug Metab Rev: 1–32. doi:10.1080/03602532.2025.2465482. PMID 39945551.

[RothmanPartillaBaumann2012-4] Rothman RB, Partilla JS, Baumann MH, Lightfoot-Siordia C, Blough BE (April 2012). "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. doi:10.1124/jpet.111.188946. PMC 3364510. PMID 22271821.

[RothmanBaumann2006-5] Rothman RB, Baumann MH (2006). "Therapeutic potential of monoamine transporter substrates". Curr Top Med Chem. 6 (17): 1845–1859. doi:10.2174/156802606778249766. PMID 17017961.

[NagaiNonakaSatohHisashiKamimura2007-6] Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". Eur J Pharmacol. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.

[BaumannClarkBudzynski2004-7] Baumann MH, Clark RD, Budzynski AG, Partilla JS, Blough BE, Rothman RB (October 2004). "Effects of "Legal X" piperazine analogs on dopamine and serotonin release in rat brain". Ann N Y Acad Sci. 1025: 189–197. doi:10.1196/annals.1316.024. PMID 15542717.

[BaumannClarkBduzynski2005-8] Baumann MH, Clark RD, Budzynski AG, Partilla JS, Blough BE, Rothman RB (March 2005). "N-substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA, or 'Ecstasy')". Neuropsychopharmacology. 30 (3): 550–560. doi:10.1038/sj.npp.1300585. PMID 15496938.

[Blough2008-9] Blough B (July 2008). "Dopamine-releasing agents" (PDF). In Trudell ML, Izenwasser S (eds.). Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. pp. 305–320. ISBN 978-0-470-11790-3. OCLC 181862653. OL 18589888W.

[ReithBloughHong2015-10] Reith ME, Blough BE, Hong WC, Jones KT, Schmitt KC, Baumann MH, Partilla JS, Rothman RB, Katz JL (February 2015). "Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter". Drug Alcohol Depend. 147: 1–19. doi:10.1016/j.drugalcdep.2014.12.005. PMC 4297708. PMID 25548026.

[SeverinsenKraftKoldsø2012-11] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r ^s ^t ^u ^v ^w ^x Severinsen K, Kraft JF, Koldsø H, Vinberg KA, Rothman RB, Partilla JS, Wiborg O, Blough B, Schiøtt B, Sinning S (September 2012). "Binding of the amphetamine-like 1-phenyl-piperazine to monoamine transporters". ACS Chem Neurosci. 3 (9): 693–705. doi:10.1021/cn300040f. PMC 3447394. PMID 23019496.

[KohutJacobsRothman2017-12] Kohut SJ, Jacobs DS, Rothman RB, Partilla JS, Bergman J, Blough BE (December 2017). "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. doi:10.1007/s00213-017-4731-5. PMC 5747253. PMID 28889212.

[RothmanBaumann2002a-13] Rothman RB, Baumann MH (July 2002). "Therapeutic and adverse actions of serotonin transporter substrates". Pharmacol Ther. 95 (1): 73–88. doi:10.1016/s0163-7258(02)00234-6. PMID 12163129.

[RothmanBaumann2002b-14] Rothman RB, Baumann MH (April 2002). "Serotonin releasing agents. Neurochemical, therapeutic and adverse effects". Pharmacol Biochem Behav. 71 (4): 825–836. doi:10.1016/s0091-3057(01)00669-4. PMID 11888573.

[RothmanBaumannBlough2010-15] Rothman RB, Baumann MH, Blough BE, Jacobson AE, Rice KC, Partilla JS (November 2010). "Evidence for noncompetitive modulation of substrate-induced serotonin release". Synapse. 64 (11): 862–869. doi:10.1002/syn.20804. PMC 2941209. PMID 20842720.

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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

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	GABA_A 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 GABA_A 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-HT_2A receptor agonists: Arylpiperazines Phenylpiperazines Quinolinylpiperazines 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 Methylenedioxyamphetamines/MDxx Trimethoxyamphetamines/TMAs BOx FLYs/benzofurans Phenylisobutylamines/α-ethylphenethylamines 4Cs Scalines 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 GABA_A receptor agonists: Isoxazoles Deliriants/anticholinergics/muscarinic acetylcholine receptor antagonists: Diarylmethanes Tropanes Others: Cyclized tryptamines Azepinoindoles Iboga alkaloids (Phyto)cannabinoids
Entactogens	Serotonin releasing agents: Phenethylamines Aminoindanes Aminotetralins Amphetamines Benzofuranylaminopropanes Benzothiophenylaminopropanes Ethylenedioxyamphetamines Indanylaminopropanes Indolylaminopropanes Methylenedioxyamphetamine/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: Adamantanes Catecholamines Tetrahydroisoquinolines Yohimbans

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Substituted piperazine

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Multiple substitutions

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