Benzydamine

Benzydamine
Clinical data
Trade names	Maxtra Gargle, Difflam, Tantum verde
AHFS/Drugs.com	International Drug Names
Pregnancy; category	AU: B2; ;
Routes of; administration	Oral, topical
ATC code	A01AD02 (WHO) ; G02CC03 (WHO); M01AX07 (WHO); M02AA05 (WHO); R02AX03 (WHO);
Legal status
Legal status	AU: S4 (Prescription only) / Schedule 2; BR: Class C1 (Other controlled substances); UK: P and POM; EU: OTC;
Pharmacokinetic data
Protein binding	<20%
Elimination half-life	13 hours
Excretion	Kidney
Identifiers
	IUPAC name 3-(1-benzyl-1H-indazol-3-yloxy)-N,N-dimethylpropan-1-amine;
CAS Number	642-72-8 ;
PubChem CID	12555;
ChemSpider	12036 ;
UNII	4O21U048EF;
KEGG	D07516 ;
ChEBI	CHEBI:94563 ;
ChEMBL	ChEMBL12610 ;
CompTox Dashboard (EPA)	DTXSID7047859 ;
ECHA InfoCard	100.010.354
Chemical and physical data
Formula	C19H23N3O
Molar mass	309.413 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES n2c(OCCCN(C)C)c1ccccc1n2Cc3ccccc3;
	InChI InChI=1S/C19H23N3O/c1-21(2)13-8-14-23-19-17-11-6-7-12-18(17)22(20-19)15-16-9-4-3-5-10-16/h3-7,9-12H,8,13-15H2,1-2H3 ; Key:CNBGNNVCVSKAQZ-UHFFFAOYSA-N ;
	(verify)

Benzydamine (also known as Tantum Verde and branded in some countries as Maxtra Gargle, Difflam and Septabene), available as the hydrochloride salt, is a locally acting nonsteroidal anti-inflammatory drug (NSAID) with local anaesthetic and analgesic properties for pain relief and anti-inflammatory treatment of inflammatory conditions of the mouth and throat.^[4] It falls under class of chemicals known as indazoles.

History

It was synthesized in Italy in 1964 and marketed in 1966.^[5]

Uses

Medical

Odonto stomatology: gingivitis, stomatitis, glossitis, aphthous ulcers, dental surgery and oral ulceration due to radiation therapy.
Otorhinolaryngology: glandular fever, pharyngitis, tonsillitis, post-tonsillectomy, radiation or intubation mucositis.

It may be used alone or as an adjunct to other therapy giving the possibility of increased therapeutic effect with little risk of interaction.

In some markets, the drug is supplied as an over-the-counter cream (Lonol in Mexico from Boehringer Ingelheim) used for topical treatment of musculoskeletal system disorders: sprains, strains, bursitis, tendinitis, synovitis, myalgia, periarthritis.

Recreational

Benzydamine has been used recreationally. If taken in excess amounts, it acts as a deliriant and CNS stimulant.^[6] Such use, particularly among teenagers, has been reported in Brazil,^[7]^[8] Poland,^[6] Romania, and Turkey.^{[citation needed]}

Contraindications

There are no contraindications to the use of benzydamine except for known hypersensitivity.

Side effects

Benzydamine is well tolerated. Occasionally oral tissue numbness or stinging sensations may occur, as well as itching, a skin rash, skin swelling or redness, difficulty breathing and wheezing.

Pharmacology

It selectively binds to inflamed tissues (Prostaglandin synthetase inhibitor) and is normally free of adverse systemic effects. Unlike other NSAIDs, it does not inhibit cyclooxygenase or lipooxygenase, and is not ulcerogenic.^[6]^[9]

It is described as having powerful reinforcing effects in animals and showing cross-sensitization with drugs of misuse such as heroin and cocaine. It is hypothesized that it has cannabinoid agonistic activity and this may account for its recreational and hallucinogenic effects.^[10] However, it has also been theorized that, based on structural similarity to lysergic acid diethylamide (LSD) and descriptions of its visual hallucinatory effects, benzydamine might be acting as a serotonin 5-HT_2A receptor agonist and hence as a serotonergic psychedelic.^[11]^[12] More research is needed to determine the mechanism of action of the effects of benzydamine as a drug of misuse.^[11]^[12]

Pharmacokinetic

Benzydamine is poorly absorbed through skin^[13] and vagina.^[14]

Synthesis

Synthesis starts with the reaction of the N-benzyl derivative from methyl anthranilate with nitrous acid to give the N-nitroso derivative. Reduction by means of sodium thiosulfate leads to the transient hydrazine (3), which undergoes spontaneous internal hydrazide formation. Treatment of the enolate of this amide with 3-chloro-1-dimethylamino propane gives benzydamine (5). Please note there is an error in this section: US3318905 states that the nitroso derivative is reduced with sodium hydrosulfite (sodium dithionite) and not with sodium hyposulfite (sodium thiosulfate), as shown in the above scheme and stated in text.

An interesting alternative synthesis of this substance starts by sequential reaction of N-benzylaniline with phosgene, and then with sodium azide to produce the corresponding carbonyl azide. On heating, nitrogen is evolved and a separatable mixture of nitrene insertion product and the desired ketoindazole # results. The latter reaction appears to be a Curtius rearrangement type product to produce an N-isocyanate #, which then cyclizes. Alkylation of the enol with sodium methoxide and 3-dimethylaminopropyl chloride gives benzydamine.

Alternatively, use of chloroacetamide in the alkylation step followed by acid hydrolysis produces bendazac instead.

Research

Studies indicate that benzydamine has notable in vitro antibacterial activity and also shows synergism in combination with other antibiotics, especially tetracyclines, against antibiotic-resistant strains of Staphylococcus aureus and Pseudomonas aeruginosa.^[18]^[19]

It also has some cannabinoid activity in rats but has not been tested in humans.^[10] It is also hypothesized to act on 5-HT2A receptors due to its structural similarity with serotonin.^[5]

References

^ "Therapeutic Goods (Poisons Standard— June 2025) Instrument 2025" (pdf). Therapeutic Goods Administration (TGA). May 2025. Retrieved 31 August 2025.
^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ "Benzydamine hydrochloride Medicinal forms". BNF. Retrieved 12 April 2025.
^ Turnbull RS (February 1995). "Benzydamine Hydrochloride (Tantum) in the management of oral inflammatory conditions". Journal. 61 (2): 127–34. PMID 7600413.
^ ^a ^b "DEXTROMETHORPHAN AND BENZYDAMINE'S USE AND MISUSE". Flipper.diff.org. Retrieved 25 June 2022.
^ ^a ^b ^c Anand JS, Glebocka ML, Korolkiewicz RP (2007). "Recreational abuse with benzydamine hydrochloride (tantum rosa)". Clinical Toxicology. 45 (2): 198–9. doi:10.1080/15563650600981210. PMID 17364645.
^ Opaleye ES, Noto AR, Sanchez Z, Moura YG, Galduróz JC, Carlini EA (September 2009). "Recreational use of benzydamine as a hallucinogen among street youth in Brazil". Revista Brasileira de Psiquiatria. 31 (3): 208–13. doi:10.1590/S1516-44462009000300005. PMID 19784487.
^ Mota DM, Costa AA, Teixeira C, Bastos AA, Dias MF (May 2010). "Use abusive of benzydamine in Brazil: an overview in pharmacovigilance". Ciencia & Saude Coletiva (in Portuguese). 15 (3): 717–24. doi:10.1590/S1413-81232010000300014. PMID 20464184.
^ Müller-Peddinghaus R (May 1987). "New pharmacologic and biochemical findings on the mechanism of action of the non-steroidal antiphlogistic, benzydamine. A synopsis". Arzneimittel-Forschung (in German). 37 (5A): 635–45. PMID 3304305.
^ ^a ^b Avvisati R, Meringolo M, Stendardo E, Malavasi E, Marinelli S, Badiani A (March 2018). "Intravenous self-administration of benzydamine, a non-steroidal anti-inflammatory drug with a central cannabinoidergic mechanism of action" (PDF). Addiction Biology. 23 (2): 610–619. doi:10.1111/adb.12516. PMID 28429885. S2CID 206970991.
^ ^a ^b Ősz BE, Jîtcă G, Sălcudean A, Rusz CM, Vari CE (April 2023). "Benzydamine-An Affordable Over-the-Counter Drug with Psychoactive Properties-From Chemical Structure to Possible Pharmacological Properties". Pharmaceuticals (Basel). 16 (4): 566. doi:10.3390/ph16040566. PMC 10144213. PMID 37111323.
^ ^a ^b Chiappini S, Miuli A, Mosca A, Pettorruso M, Guirguis A, John MC, Martinotti G, Di Giannantonio M, Schifano F (October 2021). "The Benzydamine Experience: A Systematic Review of Benzydamine Abuse". Curr Neuropharmacol. 19 (10): 1728–1737. doi:10.2174/1570159X19666210113151136. PMC 8977632. PMID 33441070.
^ Baldock GA, Brodie RR, Chasseaud LF, Taylor T, Walmsley LM, Catanese B (October 1991). "Pharmacokinetics of benzydamine after intravenous, oral, and topical doses to human subjects". Biopharmaceutics & Drug Disposition. 12 (7): 481–92. doi:10.1002/bdd.2510120702. PMID 1932611. S2CID 42167110.
^ Maamer M, Aurousseau M, Colau JC (1987). "Concentration of benzydamine in vaginal mucosa following local application: an experimental and clinical study". International Journal of Tissue Reactions. 9 (2): 135–45. PMID 3610512.
^ ^a ^b Palazzo G, Corsi G, Baiocchi L, Silvestrini B (January 1966). "Synthesis and pharmacological properties of 1-substituted 3-dimethylaminoalkoxy-1H-indazoles". Journal of Medicinal Chemistry. 9 (1): 38–41. doi:10.1021/jm00319a009. PMID 5958958.
^ FR 1382855 ; Palazzo, U.S. patent 3,318,905 (1964, 1967 both to Angelini Francesco).
^ Baiocchi L, Corsi G, Palazzo G (1965). "Ricerche nel campo degli indazoli.—Nota 1. Sulla ciclizzazione termica di azidi di acidi N-aril-N-benzil-carbamici". Annali di Chimica. 55: 116–25.
^ Fanaki NH, el-Nakeeb MA (December 1992). "Antimicrobial activity of benzydamine, a non-steroid anti-inflammatory agent". Journal of Chemotherapy. 4 (6): 347–52. doi:10.1080/1120009X.1992.11739190. PMID 1287137.
^ Fanaki NH, El-Nakeeb MA (March 1996). "Antibacterial activity of benzydamine and antibiotic-benzydamine combinations against multifold resistant clinical isolates". Arzneimittel-Forschung. 46 (3): 320–3. PMID 8901158.

External links

"Benzydamine oral rinse". Medicinenet.
"Difflam spray (benzydamine)". Net Doctor, UK. 8 March 2020. Archived from the original on 22 December 2006. Retrieved 30 December 2006.
"Tantum Verde (benzydamine)". Carysfort Healthcare Limited, Ireland. Archived from the original on 2015-11-25.

[1] "Therapeutic Goods (Poisons Standard— June 2025) Instrument 2025" (pdf). Therapeutic Goods Administration (TGA). May 2025. Retrieved 31 August 2025.

[2] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[3] "Benzydamine hydrochloride Medicinal forms". BNF. Retrieved 12 April 2025.

[4] Turnbull RS (February 1995). "Benzydamine Hydrochloride (Tantum) in the management of oral inflammatory conditions". Journal. 61 (2): 127–34. PMID 7600413.

[flipper6989-5] "DEXTROMETHORPHAN AND BENZYDAMINE'S USE AND MISUSE". Flipper.diff.org. Retrieved 25 June 2022.

[clintox-6] Anand JS, Glebocka ML, Korolkiewicz RP (2007). "Recreational abuse with benzydamine hydrochloride (tantum rosa)". Clinical Toxicology. 45 (2): 198–9. doi:10.1080/15563650600981210. PMID 17364645.

[7] Opaleye ES, Noto AR, Sanchez Z, Moura YG, Galduróz JC, Carlini EA (September 2009). "Recreational use of benzydamine as a hallucinogen among street youth in Brazil". Revista Brasileira de Psiquiatria. 31 (3): 208–13. doi:10.1590/S1516-44462009000300005. PMID 19784487.

[8] Mota DM, Costa AA, Teixeira C, Bastos AA, Dias MF (May 2010). "Use abusive of benzydamine in Brazil: an overview in pharmacovigilance". Ciencia & Saude Coletiva (in Portuguese). 15 (3): 717–24. doi:10.1590/S1413-81232010000300014. PMID 20464184.

[pmid3304305-9] Müller-Peddinghaus R (May 1987). "New pharmacologic and biochemical findings on the mechanism of action of the non-steroidal antiphlogistic, benzydamine. A synopsis". Arzneimittel-Forschung (in German). 37 (5A): 635–45. PMID 3304305.

[pmid28429885-10] Avvisati R, Meringolo M, Stendardo E, Malavasi E, Marinelli S, Badiani A (March 2018). "Intravenous self-administration of benzydamine, a non-steroidal anti-inflammatory drug with a central cannabinoidergic mechanism of action" (PDF). Addiction Biology. 23 (2): 610–619. doi:10.1111/adb.12516. PMID 28429885. S2CID 206970991.

[ŐszJîtcăSălcudean2023-11] Ősz BE, Jîtcă G, Sălcudean A, Rusz CM, Vari CE (April 2023). "Benzydamine-An Affordable Over-the-Counter Drug with Psychoactive Properties-From Chemical Structure to Possible Pharmacological Properties". Pharmaceuticals (Basel). 16 (4): 566. doi:10.3390/ph16040566. PMC 10144213. PMID 37111323.

[ChiappiniMiuliMosca2021-12] Chiappini S, Miuli A, Mosca A, Pettorruso M, Guirguis A, John MC, Martinotti G, Di Giannantonio M, Schifano F (October 2021). "The Benzydamine Experience: A Systematic Review of Benzydamine Abuse". Curr Neuropharmacol. 19 (10): 1728–1737. doi:10.2174/1570159X19666210113151136. PMC 8977632. PMID 33441070.

[pmid1932611-13] Baldock GA, Brodie RR, Chasseaud LF, Taylor T, Walmsley LM, Catanese B (October 1991). "Pharmacokinetics of benzydamine after intravenous, oral, and topical doses to human subjects". Biopharmaceutics & Drug Disposition. 12 (7): 481–92. doi:10.1002/bdd.2510120702. PMID 1932611. S2CID 42167110.

[pmid3610512-14] Maamer M, Aurousseau M, Colau JC (1987). "Concentration of benzydamine in vaginal mucosa following local application: an experimental and clinical study". International Journal of Tissue Reactions. 9 (2): 135–45. PMID 3610512.

[Palazzo-15] Palazzo G, Corsi G, Baiocchi L, Silvestrini B (January 1966). "Synthesis and pharmacological properties of 1-substituted 3-dimethylaminoalkoxy-1H-indazoles". Journal of Medicinal Chemistry. 9 (1): 38–41. doi:10.1021/jm00319a009. PMID 5958958.

[16] FR 1382855 ; Palazzo, U.S. patent 3,318,905 (1964, 1967 both to Angelini Francesco).

[17] Baiocchi L, Corsi G, Palazzo G (1965). "Ricerche nel campo degli indazoli.—Nota 1. Sulla ciclizzazione termica di azidi di acidi N-aril-N-benzil-carbamici". Annali di Chimica. 55: 116–25.

[18] Fanaki NH, el-Nakeeb MA (December 1992). "Antimicrobial activity of benzydamine, a non-steroid anti-inflammatory agent". Journal of Chemotherapy. 4 (6): 347–52. doi:10.1080/1120009X.1992.11739190. PMID 1287137.

[19] Fanaki NH, El-Nakeeb MA (March 1996). "Antibacterial activity of benzydamine and antibiotic-benzydamine combinations against multifold resistant clinical isolates". Arzneimittel-Forschung. 46 (3): 320–3. PMID 8901158.

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[3]

[4]

[5]

[6]

[7]

[8]

[9]

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[17]

[18]

[19]

v t e Stomatological preparations (A01)
Caries prophylaxis	Dectaflur Olaflur Sodium fluoride Sodium monofluorophosphate Stannous fluoride
Infection and antiseptics	Amphotericin B Benzoxonium chloride Chlorhexidine Chlortetracycline Clotrimazole Cetylpyridinium chloride Domiphen bromide Doxycycline Eugenol Hexetidine Hydrogen peroxide Mepartricin Metronidazole Miconazole Minocycline Natamycin Neomycin Oxyquinoline Polynoxylin Sodium perborate Tetracycline Tibezonium iodide
Corticosteroids (Glucocorticoids)	Dexamethasone Hydrocortisone Triamcinolone
Other	Amlexanox Acetylsalicylic acid Becaplermin Benzydamine Epinephrine/Adrenalone

v t e Nonsteroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Grapiprant^‡ Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Meloxicam/rizatriptan Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
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Adenosine antagonists	8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Istradefylline Paraxanthine SCH-58261 Theobromine Theophylline
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Ampakines	CX-516 CX-546 CX-614 CX-691 CX-717 IDRA-21 LY-404,187 LY-503,430 Nooglutyl Org 26576 PEPA S-18986 Sunifiram Unifiram
Arylcyclohexylamines	Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine
Benzazepines	6-Br-APB SKF-77434 SKF-81297 SKF-82958
Cathinones	3-FMC 3-MMC 3,4-DMMC 4-BMC 4-CMC 4-Methylbuphedrone 4-Methylcathinone 4-MEAP 4-Methylpentedrone Amfepramone Benzedrone Buphedrone Bupropion Butylone Cathinone Dimethylcathinone Ethcathinone Ethylone Flephedrone Hexedrone Isoethcathinone Mephedrone Methcathinone Methedrone Methylenedioxycathinone Methylone Mexedrone N-Ethylbuphedrone N-Ethylhexedrone Pentedrone Pentylone Phthalimidopropiophenone
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Phenethylamines	1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fluoroamphetamine 2-Fluoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fluoroamphetamine 3-Fluoroethamphetamine 3-Methoxyamphetamine 3-Methylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-MMA 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Camfetamine Cathine Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethylnorepinephrine Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Feprosidnine Fludorex 4-Fluorodeprenyl Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methoxyphenamine MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Prenylamine Propylamphetamine Pseudoephedrine Pyr-AI Ropinirole Salbutamol (Levosalbutamol) Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine
Phenylmorpholines	3-Fluorophenmetrazine Fenbutrazate Fenmetramide G-130 Manifaxine Morazone Morforex Oxaflozane PD-128,907 Phendimetrazine Phenmetrazine 2-Phenyl-3,6-dimethylmorpholine Pseudophenmetrazine Radafaxine
Piperazines	2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 JJC8-088 MeOPP MBZP oMPP Vanoxerine
Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate JZ-IV-10 Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate Serdexmethylphenidate SCH-5472
Phenethylpyrrolidines	2-Diphenylmethylpyrrolidine 4-Cl-PVP 5-DBFPV α-PPP α-PBP α-PCYP α-PHiP α-PHP α-PHPP α-PVP α-PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPEP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone
Racetams	Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide
Psychedelics	2,5-DMA (DOH) 2C-B 2C-D 2C-G-N 5-MeO-DiPT 5-MeO-MiPT Ariadne (4C-DOM; BL-3912; Dimoxamine) ASR-2001 (2CB-5PrO) DOET DOM DON DOPR LSD MTFEM
Tropanes	4-fluorotropacocaine 4'-Fluorococaine Altropane (IACFT) Brasofensine CFT (WIN 35,428) β-CIT (RTI-55) Cocaethylene Cocaine Dichloropane (RTI-111) Difluoropine FE-β-CPPIT FP-β-CPPIT Ioflupane (¹²³I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-120 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (β-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33
Tryptamines	4-HO-αMT 4-Methyl-αET 4-Methyl-αMT 5-Chloro-αMT 5-Fluoro-αMT 5-MeO-αET 5-MeO-αMT 5-MeO-DIPT 6-Fluoro-αMT 7-Methyl-αET αET αMT
Others	2-MDP 3,3-Diphenylcyclobutanamine Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Centanafadine Ciclazindol Clofenciclan Cropropamide Crotetamide D-161 Desipramine Diclofensine Dimethocaine Efaroxan Etamivan Fenisorex Fenpentadiol Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 Lazabemide Leptacline Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Methamnetamine Methastyridone Methiopropamine Naphthylaminopropane Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline PNU-99,194 PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Thiopropamine Thiothinone Trazium UH-232 Yohimbine
ATC code: N06B

v t e Prolactin inhibitors and anti-inflammatory products for vaginal administration (G02CB–G02CC)
Prolactin inhibitors	Bromocriptine Cabergoline Ergoloid Lisuride Metergoline Pergolide Quinagolide Terguride
Anti-inflammatory products for vaginal administration	Benzydamine Ibuprofen Flunoxaprofen Naproxen

v t e Hallucinogens
Psychedelics (5-HT_2A agonists)	Tryptamines (e.g., DMT, psilocin, psilocybin, bufotenin, 5-MeO-DMT, AMT) Phenethylamines (e.g., mescaline, 2C-B, DOM, MDA, TMA, 2C-B-FLY, 25I-NBOMe) Lysergamides (e.g., LSD, ergine, isoergine) Others (e.g., efavirenz, IHCH-7113, MK-212, quipazine, RH-34) For a full list of serotonergic psychedelics, see the navbox here and the list here instead.
Dissociatives (NMDA antagonists)	Arylcyclohexylamines (e.g., ketamine (K), phencyclidine (PCP), methoxetamine (MXE), tiletamine) Adamantanes (e.g., memantine, amantadine) Diarylethylamines (e.g., diphenidine, ephenidine, methoxphenidine) Morphinans (e.g., dextromethorphan (DXM), dextrorphan (DXO)) Inhalants (e.g., nitrous oxide (N₂O), xenon (Xe)) Others (e.g., alkyl nitrites/poppers, aptiganel, dexoxadrol, dizocilpine (MK-801), etoxadrol, selfotel) For a full list of dissociatives, see the navbox here instead.
Deliriants (mACh antagonists)	Tropanes: Atropine Hyoscyamine Scopolamine (hyoscine) Antihistamines: Brompheniramine Chloropyramine Chlorphenamine (chlorpheniramine) Clemastine Cyclizine Cyproheptadine Dimenhydrinate Diphenhydramine Doxylamine Meclizine Mepyramine Pheniramine Phenyltoloxamine Promethazine Tripelennamine Triprolidine Others: Benactyzine Benapryzine (benaprizine) Benzatropine (benztropine) Biperiden BZ (QNB) CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,668 CS-27349 Cycrimine Dicycloverine Ditran (JB-329) EA-3167 EA-3443 EA-3580 EA-3834 Flavoxate JB-318 JB-336 Orphenadrine Oxybutynin Procyclidine Tolterodine Trihexyphenidyl Tropicamide Tropine benzilate WIN-2299
KOR agonists	Salvinoids (terpenoids): 2-EMSB 2-MMSB RB-64 (22-thiocyanatosalvinorin A) Salvinorin A Benzomorphans: Alazocine Bremazocine Cyclazocine Ketazocine Metazocine MR-2034 Pentazocine Phenazocine Morphinans: Butorphanol Cyclorphan Cyprenorphine Diprenorphine Heroin Levallorphan Levomethorphan Levorphanol Morphine Nalbuphine Nalmefene Nalorphine Oxilorphan Proxorphan Racemethorphan Racemorphan Xorphanol Arylacetamides: Enadoline LPK-26 Niravoline Spiradoline U-50488 U-69593 Others: HZ-2 Tifluadom
GABA_A agonists	Isoxazoles: Gaboxadol (THIP) Ibotenic acid (Amanita muscaria) Muscimol (Amanita muscaria) Indirect GABA_A receptor agonists: GABA_A receptor positive allosteric modulators (nonbenzodiazepines/Z-drugs) (e.g., eszopiclone, zaleplon, zolpidem, zopiclone) GABA reuptake inhibitors (e.g., CI-966)
Oneirogens (unknown mech.)	Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis caapi) Iboga alkaloids/azepinoindoles (e.g., ibogaine, noribogaine) (found in Tabernanthe iboga)
Cannabinoids (CB₁ agonists)	Phytocannabinoids (e.g., Δ⁹-THC (dronabinol), CBN, Δ⁸-THC) Synthetic cannabinoids (e.g., nabilone, JWH-018, JWH-073, HU-210) For a full list of cannabinoids, see the navbox here and the list here instead.
Others	Aminochromes (e.g., adrenochrome, adrenolutin) Carbogen Glaucine Hallucinogenic bolete mushrooms (e.g., Lanmaoa asiatica) Jenkem Kykeon (Eleusinian Mysteries) Nutmeg (e.g., myristicin, elemicin) Soma (haoma)
See also: Psychedelics Dissociatives Entactogens Stimulants Depressants List of hallucinogens

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