Diphenhydramine
|
| Systematic (IUPAC) name |
| 2-(diphenylmethoxy)-N,N-dimethylethanamine |
| Clinical data |
| Trade names |
Benadryl, Unisom, Sominex |
| AHFS/Drugs.com |
monograph |
| MedlinePlus |
a682539 |
| Pregnancy cat. |
A (AU) B (US) |
| Legal status |
Over the counter |
| Dependence liability |
Very low |
| Routes |
Oral, Parenteral (IM), Parenteral (IV), Topical, Suppository |
| Pharmacokinetic data |
| Bioavailability |
40-60%[1] |
| Protein binding |
98-99% |
| Metabolism |
Various cytochrome P450 liver enzymes: CYP2D6 (80%), 3A4 (10%)[2] |
| Half-life |
8 hours (children)[3]
9 to 12 hours (adults)[3]
17 hours (elderly)[3] |
| Excretion |
94% through the urine, 6% through feces [4] |
| Identifiers |
| CAS number |
58-73-1 Y |
| ATC code |
D04AA32 D04AA33, R06AA02 |
| PubChem |
CID 3100 |
| IUPHAR ligand |
1224 |
| DrugBank |
DB01075 |
| ChemSpider |
2989 Y |
| UNII |
8GTS82S83M Y |
| KEGG |
D00669 N |
| ChEBI |
CHEBI:4636 Y |
| ChEMBL |
CHEMBL657 N |
| Chemical data |
| Formula |
C17H21NO |
| Mol. mass |
255.355 g/mol |
SMILES
- O(CCN(C)C)C(c1ccccc1)c2ccccc2
|
InChI
-
InChI=1S/C17H21NO/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,17H,13-14H2,1-2H3 Y
Key:ZZVUWRFHKOJYTH-UHFFFAOYSA-N Y
|
N (what is this?) (verify)
|
Diphenhydramine (pron.: /ˌdaɪfɛnˈhaɪdrəmiːn/; abbreviated DPH, sometimes DHM) is a first-generation antihistamine possessing anticholinergic, antitussive, antiemetic, sedative and properties which is mainly used to treat allergies. It is also used in the management of drug induced Parkinsonian extrapyramidal. The drug has a strong hypnotic effect and is FDA approved as as a non-prescription sleep aid; especially in the form of diphenhydramine citrate. It is produced and marketed under the trade name Benadryl by McNeil-PPC (a division of Johnson & Johnson) in the U.S., Canada and South Africa (other trade names in other countries: Dimedrol, Daedalon). It is also available as a generic or store brand medication. It is also found in the name-brand products Nytol, Unisom, Tylenol PM, Excedrin PM, Midol PM, Zzzquil and Advil PM, though some Unisom products contain doxylamine instead. It is available as an over-the-counter (OTC) or prescribed HCl injectable. In addition, injectable diphenhydramine can be used for life-threatening reactions (anaphylaxis) to allergens such as bee stings, peanuts, or latex, as an adjunct to epinephrine. It is a member of the ethanolamine class of antihistaminergic agents.
Diphenhydramine was invented in 1943 by Dr. George Rieveschl, a former professor at the University of Cincinnati.[5] In 1946, it became the first prescription antihistamine approved by the U.S. Food and Drug Administration (FDA).[6]
|
Contents
- 1 Uses
- 1.1 Medicinal
- 1.2 Recreational
- 2 Adverse effects
- 3 Chemistry
- 4 Pharmacology
- 5 Quantification
- 6 See also
- 7 References
- 7.1 Notes
- 7.2 Further reading
- 8 External links
|
Uses
Medicinal
Diphenhydramine is a first generation antihistamine used to treat a number of conditions including allergic symptoms and itchiness, the common cold, insomnia, motion sickness, and extrapyramidal symptoms.[7][8]
Diphenhydramine is significantly more potent in treatment of allergies than newer generation of antihistamines.[9] Consequently, it is frequently used when an allergic reaction requires fast, effective reversal of the often dangerous effects of a massive histamine release.
It is a potent antagonist to acetylcholine affecting muscarinic receptors and as a result is used to treat parkinson's disease like extrapyramidal symptoms caused by typical antipsychotics. The muscarinic receptor antagonism leads to correction of dopamine, the neurotransmitter responsible for control of motor function in the brain, similar to other antimuscarinic agents such as atropine.
Diphenhydramine has sedative properties and is widely used in nonprescription sleep aids for insomnia. The maximum recommended dose of 50 mg (as the hydrochloride salt) being mandated by the U.S. FDA. The drug is an ingredient in several products sold as sleep aids, either alone or in combination with other ingredients such as acetaminophen (paracetamol). An example of the latter is Tylenol PM. Examples of products having diphenhydramine as the only active ingredient include Unisom, Tylenol Simply Sleep, Nytol, ZzzQuil, and Sominex (the version sold in the US; that sold in the UK uses promethazine).
Diphenhydramine also has antiemetic properties which make it useful in treating the nausea that occurs in motion sickness. As it causes marked sedation in many individuals, newer generation antihistamines including Loratadine, Cetirizine, and Dimenhydrinate may be preferred for this purpose.
There are also topical formulations of diphenhydramine available, including creams, lotions, gels, and sprays. They are used to relieve itching, and have the advantage of causing much less systemic effect (i.e. drowsiness) than oral forms. [10] Diphenhydramine also has local anesthetic properties, and has been used for patients allergic to common local anesthetics like lidocaine.[11]
Diphenhydramine has potent anticholinergic properties, recent clinical evidence revealed this medication can be helpful in treating asthma and chronic obstructive pulmonary disease, allowing the bronchi to relax and causing airflow obstruction to subside[citation needed].
Recreational
Diphenhydramine acts as an analgesia potentiator with morphine in rats.[12] It is used recreationally as a deliriant, or as a potentiator of alcohol[citation needed], opiates[13] and other depressants. CNS effects occur within the limbic system and hippocampus, causing confusion and temporary amnesia.[citation needed]
Like its chemical relatives, diphenhydramine has mild to moderate euphoriant actions of its own.
Toxicology also manifests in the autonomic nervous system, causing urinary retention, pupil dilation, tachycardia, irregular urination, and dry skin and mucous membranes.[citation needed] Severe restlessness or akathesia can also be a side effect that is made worse by increased levels of diphenhydramine.[14] Considerable overdosage can lead to cardiac arrest, serious ventricular dysrhythmias, coma, and death.[citation needed]Such a side-effect profile is commonly thought to give ethanolamine-class antihistamines a relatively low abuse liability. The specific antidote for diphenhydramine poisoning (similar to that of Datura or Atropa belladonna poisoning) is physostigmine.[citation needed]
Diphenhydramine is among the prohibited and controlled substances in the Republic of Zambia.[15] Travelers are advised not to bring this drug into the country. Several Americans have been detained by the Zambian Drug Enforcement Commission for possession of Benadryl and other over-the-counter medications containing diphenhydramine.[16]
Adverse effects
Like many other first-generation antihistamines, diphenhydramine can cause strong sedation. As such, diphenhydramine has also been used as an anxiolytic because of this side-effect. It is also a potent anticholinergic agent, leading to the side-effects of dry mouth and throat, increased heart rate, pupil dilation, urinary retention, constipation, and, at high doses, hallucinations or delirium. Further side-effects include motor impairment (ataxia), flushed skin, blurred vision at nearpoint owing to lack of accommodation (cycloplegia), abnormal sensitivity to bright light (photophobia), difficulty concentrating, short-term memory loss, visual disturbances, irregular breathing, dizziness, irritability, itchy skin, confusion, decreased body temperature (in general, in the hands and/or feet), erectile dysfunction, excitability, and, although it can be used to treat nausea, higher doses may cause vomiting.[17] Some side-effects, such as twitching, may be delayed until the drowsiness begins to cease and the person is in more of an awakening mode. There are several levels of evidence strongly indicating diphenhydramine (similar to chlorpheniramine) can block the delayed rectifier potassium channel and consequently prolong the QT-interval, leading to cardiac arrhythmias, such as torsade de pointes.[18] Some patients have an allergic reaction to diphenhydramine in the form of hives.[19][20]
FDA Classification of Drug Safety During Pregnancy of Diphendranydramine is a Category B. [21] Diphenhydramine is also excreted in breast milk. [21] The medication is not recommended for children under the age of six years and should only be used in children under the age of six after consulting a physician. [22] Paradoxical reactions to diphenhydramine are documented, in particular, among children, and it may cause excitation instead of sedation[23]
Diphenhydramine is on the "Beers list" to avoid in the elderly.[24] As diphenhydramine is extensively metabolized by the liver, caution should be exercised when giving the drug to individuals with hepatic impairment.
Since 2002, the US FDA requires special labeling warning against using multiple products that contain diphenhydramine.[25] Diphenhydramine has been shown to build tolerance against its sedation effectiveness very quickly, with placebo-like results after a third day of common dosage.[26]
Chemistry
Diphenhydramine, N,N-dimethyl-(diphenylmethoxy)ethylamine, is synthesized by a simple reaction of benzhydrylbromide and 2-dimethylaminoethanol.[27][28][29]
Pharmacology
Diphenhydramine is an inverse agonist of the histamine H1 receptor.[30] By blocking histamine in the capillaries it can reduce the intensity of allergic symptoms. Diphenhydramine crosses the blood–brain barrier (BBB) and antagonizes the H1 receptors centrally. Its effects on central H1 receptors cause drowsiness.[31]
Like many other first-generation antihistamines, diphenhydramine is also a potent competitive antagonist of muscarinic cholinergic receptors, and, as such, at high doses can cause anticholinergic syndrome.[32] Diphenhydramine can also act as an antiparkinson agent as a result of the blocking properties to the muscarinic acetylcholine receptors in the brain.
In the 1960s, diphenhydramine was found to inhibit reuptake of the neurotransmitter serotonin.[33] This discovery led to a search for viable antidepressants with similar structures and fewer side-effects, culminating in the invention of fluoxetine (Prozac), a selective serotonin reuptake inhibitor (SSRI).[33][34] A similar search had previously led to the synthesis of the first SSRI, zimelidine, from brompheniramine, also an antihistamine.
Diphenhydramine also acts as an intracellular sodium channel blocker, which is responsible for its actions as a local anesthetic.[35]
Quantification
Diphenhydramine may be quantitated in blood, plasma, or serum to monitor therapy, confirm a diagnosis of poisoning in hospitalized patients, provide evidence in an impaired driving arrest, or assist in a medicolegal death investigation.[citation needed] Blood or plasma diphenhydramine concentrations are usually in a range of 10–150 μg/L in persons taking the drug orally for its antiemetic, antihistaminic or sedative effects, 0.7–2.7 mg/L (700–2700 μg/L) in those arrested for impaired driving, 1–5 mg/L in survivors of acute overdosage and 5–30 mg/L in victims of fatal overdosage.[citation needed] In some jurisdictions, diphenhydramine is often present in postmortem specimens collected during investigation of sudden infant deaths; the drug may play a role in these events.[36][37]
Rapid urine drug screens using immunoassays based on the principle of competitive binding may show false-positive methadone results for patients who have ingested Diphenhydramine.[38]
See also
- Acrivastine
- Anticholinergic
- Cetirizine
- H1 antagonist
References
Notes
- ^ Paton DM, Webster DR (1985). "Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines)". Clinical Pharmacokinetics 10 (6): 477–97. PMID 2866055. http://content.wkhealth.com/linkback/openurl?issn=0312-5963&volume=10&issue=6&spage=477.
- ^ "Showing Diphenhydramine (DB01075)". DrugBank. http://www.drugbank.ca/drugs/DB01075. Retrieved 5 September 2009.
- ^ a b c Simons KJ, Watson WT, Martin TJ, Chen XY, Simons FE (July 1990). "Diphenhydramine: pharmacokinetics and pharmacodynamics in elderly adults, young adults, and children". Journal of Clinical Pharmacology 30 (7): 665–71. PMID 2391399. http://jcp.sagepub.com/cgi/pmidlookup?view=long&pmid=2391399.
- ^ Garnett, WR (1986). "Diphenhydramine". Am Pharm (NS26(2)): 35–40.
- ^ Hevesi D (2007-09-29). "George Rieveschl, 91, Allergy Reliever, Dies". The New York Times. http://www.nytimes.com/2007/09/29/business/29rieveschl.html?ref=health. Retrieved 2008-10-14.
- ^ Ritchie J (2007-09-24). "UC prof, Benadryl inventor dies". Business Courier of Cincinnati. http://www.bizjournals.com/cincinnati/stories/2007/09/24/daily52.html. Retrieved 2008-10-14.
- ^ "Diphenhydramine Hydrochloride Monograph". Drugs.com. The American Society of Health-System Pharmacists. http://www.drugs.com/monograph/diphenhydramine-hydrochloride.html.
- ^ http://stg.currentpsychiatry.com/pdf/1112/1112CP_Freudenreich.pdf
- ^ Raphael GD, Angello JT, Wu MM, Druce HM (April 2006). "Efficacy of diphenhydramine vs desloratadine and placebo in patients with moderate-to-severe seasonal allergic rhinitis". Ann. Allergy Asthma Immunol. 96 (4): 606–14. doi:10.1016/S1081-1206(10)63557-0. PMID 16680933.
- ^ http://www.nlm.nih.gov/medlineplus/druginfo/meds/a601044.html
- ^ Smith DW, Peterson MR, DeBerard SC (August 1999). "Local anesthesia. Topical application, local infiltration, and field block". Postgrad Med 106 (2): 57–60, 64–6. doi:10.3810/pgm.1999.08.650. PMID 10456039.
- ^ Carr KD, Hiller JM, Simon EJ (February 1985). "Diphenhydramine potentiates narcotic but not endogenous opioid analgesia". Neuropeptides 5 (4-6): 411–4. doi:10.1016/0143-4179(85)90041-1. PMID 2860599.
- ^ Sandor I (2000-07-30). "Using Antihistamines, Anticholinergics, and Depressants To Potentiate Opiates, And Dealing With Opiate Side Effects". Antihistamine Aficionado Magazine. http://www.opioids.com/opiates/index.html.
- ^ http://www.medicalnewstoday.com/releases/129785.php
- ^ "The Drug Enforcement Commission ZAMBIA: LIST OF PROHIBITED AND CONTROLLED DRUGS ACCORDING TO CHAPTER 96 OF THE LAWS OF ZAMBIA". http://www.deczambia.gov.zm/listofdrugs.html.
- ^ "travel.state.gov: Zambia". http://travel.state.gov/travel/cis_pa_tw/cis/cis_1062.html.
- ^ "Diphenhydramine Side Effects". Drugs.com. http://www.drugs.com/sfx/diphenhydramine-side-effects.html. Retrieved 2009-04-06.
- ^ Nia AM, Fuhr U, Gassanov N, Erdmann E, Er F (2010). "Torsades de pointes tachycardia induced by common cold compound medication containing chlorpheniramine". European Journal of Clinical Pharmacology 66 (11): 1173–1175. doi:10.1007/s00228-010-0875-5. PMID 20676621. edit
- ^ Heine A (November 1996). "Diphenhydramine: a forgotten allergen?". Contact Derm. 35 (5): 311–2. doi:10.1111/j.1600-0536.1996.tb02402.x. PMID 9007386.
- ^ Coskey RJ (February 1983). "Contact dermatitis caused by diphenhydramine hydrochloride". J. Am. Acad. Dermatol. 8 (2): 204–6. doi:10.1016/S0190-9622(83)70024-1. PMID 6219138.
- ^ a b Template:Cite journal author= RONALD A. BLACK, M.D.,
- ^ (in English) Physicians’ Desk Reference for Nonprescription Drugs and Dietary Supplements (21st ed.). Montvale, NJ: Medical Economics Company. 2000.
- ^ de Leon J, Nikoloff DM (February 2008). "Paradoxical excitation on diphenhydramine may be associated with being a CYP2D6 ultrarapid metabolizer: three case reports". CNS Spectr 13 (2): 133–135. PMID 18227744.
- ^ "High risk medications as specified by NCQA’s HEDIS Measure: Use of High Risk Medications in the Elderly" (pdf). National Committee for Quality Assurance (NCQA). http://www.ncqa.org/Portals/0/Newsroom/SOHC/Drugs_Avoided_Elderly.pdf.
- ^ Food and Drug Administration, HHS (2002). "Labeling of Diphenhydramine-Containing Drug Products for Over-the-Counter Human Use". Federal Register 67 (235): 72555–9. PMID 12474879. http://www.fda.gov/OHRMS/DOCKETS/98fr/120602a.htm. Retrieved 2008-10-14.
- ^ Richardson GS, Roehrs TA, Rosenthal L, Koshorek G, Roth T (October 2002). "Tolerance to daytime sedative effects of H1 antihistamines". J Clin Psychopharmacol 22 (5): 511–5. doi:10.1097/00004714-200210000-00012. PMID 12352276.
- ^ US patent 2397799, Martin H, Hafliger F, Gatzi K, Grob A, "Amino-ethers and a process for their manufacture", published 1946-04-02, assigned to JR Geigy AG
- ^ US patent 2421714, Riveschl G, "Dialkylaminoalkyl benzhydryl ethers and salts thereof", published 1947-06-03, assigned to Parke Davis & Company
- ^ US patent 2427878, Riveschl G, "Dialkylaminopropyl ethers of benzhydrol", published 1947-09-23, assigned to Parke Davis & Company
- ^ Yamashiro K, Kiryu J, Tsujikawa A, Nonaka A, Honjo M, Tanihara H, Nishiwaki H, Honda Y, Ogura Y (July 2001). "Suppressive effects of histamine H1 receptor antagonist diphenhydramine on the leukocyte infiltration during endotoxin-induced uveitis". Exp. Eye Res. 73 (1): 69–80. doi:10.1006/exer.2001.1008. PMID 11428864.
- ^ Reiner PB, Kamondi A (April 1994). "Mechanisms of antihistamine-induced sedation in the human brain: H1 receptor activation reduces a background leakage potassium current". Neuroscience 59 (3): 579–88. doi:10.1016/0306-4522(94)90178-3. PMID 8008209.
- ^ "Antihistamine Toxicity". Medscape Reference. WebMD LLC. 2010-05-10. http://emedicine.medscape.com/article/812828-overview.
- ^ a b Domino EF (1999). "History of modern psychopharmacology: a personal view with an emphasis on antidepressants". Psychosom Med 61 (5): 591–8. PMID 10511010.
- ^ Awdishn RAL, Whitmill M, Coba V, Killu K (2008-10-27). "Serotonin reuptake inhibition by diphenhydramine and concomitant linezolid use can result in serotonin syndrome". Chest Meeting Abstracts. Chest. http://meeting.chestpubs.org/cgi/content/abstract/134/4/c4002.
- ^ Kim YS, Shin YK, Lee C, Song J (October 2000). "Block of sodium currents in rat dorsal root ganglion neurons by diphenhydramine". Brain Research 881 (2): 190–8. doi:10.1016/S0006-8993(00)02860-2. PMID 11036158.
- ^ Marinetti L, Lehman L, Casto B, Harshbarger K, Kubiczek P, Davis J (October 2005). "Over-the-counter cold medications-postmortem findings in infants and the relationship to cause of death". J Anal Toxicol 29 (7): 738–43. PMID 16419411.
- ^ Baselt RC (2008). Disposition of Toxic Drugs and Chemicals in Man. Biomedical Publications. pp. 489–492. ISBN 0-9626523-7-7.
- ^ Rogers SC, Pruitt CW, Crouch DJ, Caravati EM (September 2010). "Rapid urine drug screens: diphenhydramine and methadone cross-reactivity". Pediatr Emerg Care 26 (9): 665–6. doi:10.1097/PEC.0b013e3181f05443. PMID 20838187.
Further reading
- Charlton BG (2005). "Self-management of psychiatric symptoms using over-the-counter (OTC) psychopharmacology: the S-DTM therapeutic model--Self-diagnosis, self-treatment, self-monitoring". Med. Hypotheses 65 (5): 823–8. doi:10.1016/j.mehy.2005.07.013. PMID 16111835.
- Lieberman JA (2003). "History of the use of antidepressants in primary care". Primary Care Companion, J. Clinical Psychiatry 5 (supplement 7).
External links
- Prescription Information (PDF)
- Diphenhydramine University of Maryland Medical Center Medical References
- Diphenhydramine entry for recreational use at Drugs-Wiki
- Man 'took own life' in courtroom – suicide by Diphenhydramine – BBC News
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Psychedelics
5-HT2AR agonists |
- Lysergamides: AL-LAD
- ALD-52
- BU-LAD
- CYP-LAD
- DAM-57
- Diallyllysergamide
- Ergometrine
- ETH-LAD
- LAE-32
- LSA
- LSD
- LSH
- LPD-824
- LSM-775
- Lysergic acid 2-butyl amide
- Lysergic acid 2,4-dimethylazetidide
- Lysergic acid 3-pentyl amide
- Methylergometrine
- Methylisopropyllysergamide
- Methysergide
- MLD-41
- PARGY-LAD
- PRO-LAD
Phenethylamines: Aleph
- 2C-B
- 2C-B-Dragonfly
- 2C-B-FLY
- 2C-C-FLY
- 2C-D-FLY
- 2C-E-FLY
- 2C-I-FLY
- 2CBFly-NBOMe
- 2C-T-7-FLY
- 2C-C
- 2C-C-NBOMe
- 2C-CN-NBOMe
- 2C-D
- 2CD-5EtO
- 2C-D-NBOMe
- 2C-E
- 2C-EF
- 2C-E-NBOMe
- 2C-F
- 2C-F-NBOMe
- 2C-G
- 2C-G-NBOMe
- 2C-H-NBOMe
- 2C-I
- 2C-N
- 2C-N-NBOMe
- 2C-O
- 2C-O-4
- 2C-P
- 2C-T
- 2C-T-2
- 2C-T-4
- 2C-T-4-NBOMe
- 2C-T-7
- 2C-T-7-NBOH
- 2C-T-8
- 2C-T-9
- 2C-T-13
- 2C-T-15
- 2C-T-17
- 2C-T-21
- 2C-TFM
- 2C-TFM-NBOMe
- 2C-YN
- 2CBCB-NBOMe
- 25B-NBOMe
- 25I-NBMD
- 25I-NBOH
- 25I-NBOMe
- 3C-AL
- 3C-E
- 3C-P
- 5-APB
- 5-APDB
- 6-APB
- 6-APDB
- Br-DFLY
- DESOXY
- DMMDA
- DMMDA-2
- DOB
- DOB-FLY
- DOM-FLY
- DOC
- DOEF
- DOET
- DOF
- DOI
- DOM
- DON
- DOPR
- DOTFM
- Escaline
- Ganesha
- HOT-2
- HOT-7
- HOT-17
- IAP
- Isoproscaline
- Jimscaline
- Lophophine
- MDA
- MDEA
- MDMA
- MMA
- MMDA
- MMDA-2
- MMDA-3a
- MMDMA
- Macromerine
- Mescaline
- Methallylescaline
- NBOMe-mescaline
- Proscaline
- TCB-2
- TFMFly
- TMA
Piperazines: pFPP
- TMFPP
Tryptamines: 1-Methyl-5-methoxy-diisopropyltryptamine
- 2,N,N-TMT
- 4,N,N-TMT
- 4-HO-5-MeO-DMT
- 4-Acetoxy-DET
- 4-Acetoxy-DIPT
- 4-Acetoxy-DMT
- 4-Acetoxy-DPT
- 4-Acetoxy-MiPT
- 4-HO-DPT
- 4-HO-MET
- 4-Propionyloxy-DMT
- 4-HO-MPMI
- 5-Me-MIPT
- 5-N,N-TMT
- 5-AcO-DMT
- 5-MeO-2,N,N-TMT
- 5-MeO-4,N,N-TMT
- 5-MeO-α,N,N-TMT
- 5-MeO-α-ET
- 5-MeO-α-MT
- 5-MeO-DALT
- 5-MeO-DET
- 5-MeO-DIPT
- 5-MeO-DMT
- 5-MeO-DPT
- 5-MeO-EiPT
- 5-MeO-MET
- 5-MeO-MIPT
- 5-MeO-MPMI
- 7,N,N-TMT
- α,N,N-TMT
- α-ET
- α-MT
- AL-37350A
- Baeocystin
- Bufotenin
- DALT
- DBT
- DCPT
- DET
- DIPT
- DMT
- DPT
- EiPT
- Ethocin
- Ethocybin
- Iprocin
- MET
- Miprocin
- MIPT
- Norbaeocystin
- PiPT
- Psilocin
- Psilocybin
Others: AL-38022A
- Elemicin
- Ibogaine
- Myristicin
- Noribogaine
- Voacangine
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|
Dissociatives
NMDAR antagonists |
- Adamantanes: Amantadine
- Memantine
- Rimantadine
Arylcyclohexylamines: 3-MeO-PCP
- 4-MeO-PCP
- Dieticyclidine
- Esketamine
- Eticyclidine
- Gacyclidine
- Ketamine
- Methoxetamine
- Methoxyketamine
- Neramexane
- Phencyclidine
- PCPr
- Rolicyclidine
- Tenocyclidine
- Tiletamine
Morphinans: Dextrallorphan
- Dextromethorphan
- Dextrorphan
- Racemethorphan
- Racemorphan
Others: 2-MDP
- 8A-PDHQ
- Aptiganel
- Dexoxadrol
- Dizocilpine
- Etoxadrol
- Ibogaine
- Midafotel
- NEFA
- Nitrous oxide
- Noribogaine
- Perzinfotel
- Remacemide
- Selfotel
- Xenon
|
|
Deliriants
mAChR antagonists |
- 3-Quinuclidinyl benzilate
- Atropine
- BRN-1484501
- Benactyzine
- Benzatropine
- Benzydamine
- Biperiden
- Brompheniramine
- CAR-226,086
- CAR-301,060
- CAR-302,196
- CAR-302,282
- CAR-302,368
- CAR-302,537
- CAR-302,668
- Chlorpheniramine
- Chloropyramine
- Clemastine
- CS-27349
- Cyclizine
- Cyproheptadine
- Dicyclomine
- Dimenhydrinate
- Diphenhydramine
- Ditran
- Doxylamine
- EA-3167
- EA-3443
- EA-3580
- EA-3834
- Flavoxate
- Hydroxyzine
- Hyoscyamine
- Meclizine
- N-Ethyl-3-piperidyl benzilate
- N-Methyl-3-piperidyl benzilate
- Pyrilamine
- Orphenadrine
- Oxybutynin
- Pheniramine
- Phenyltoloxamine
- Procyclidine
- Promethazine
- Scopolamine
- Tolterodine
- Trihexyphenidyl
- Tripelennamine
- Triprolidine
- WIN-2299
|
|
| Miscellaneous |
|
Cannabinoids
CB1R agonists
|
- Cannabinol
- CP-47,497
- CP-55,244
- CP-55,940
- DMHP
- HU-210
- JWH-018
- JWH-030
- JWH-073
- JWH-081
- JWH-200
- JWH-250
- Nabilone
- Nabitan
- Nantradol
- Parahexyl
- THC (Dronabinol)
- WIN-55,212-2
|
|
|
D2R agonists
|
- Apomorphine
- Bromocriptine
- Cabergoline
- Lisuride
- Memantine
- Pergolide
- Piribedil
- Pramipexole
- Ropinirole
- Rotigotine
* Also indirect D2 agonists such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa).
|
|
|
GABAAR agonists
|
- Eszopiclone
- Gaboxadol
- Ibotenic acid
- Muscimol
- Zaleplon
- Zolpidem
- Zopiclone
|
|
|
Inhalants
Mixed MOA
|
- Aliphatic hydrocarbons
- Butane
- Propane
- Gasoline
- Kerosene
- Aromatic hydrocarbons
- Ethers
- Haloalkanes
- Chloroform
- Chlorofluorocarbons
|
|
|
κOR agonists
|
- 2-EMSB
- 2-MMSB
- Alazocine
- Bremazocine
- Butorphanol
- Cyclazocine
- Cyprenorphine
- Dextrallorphan
- Dezocine
- Enadoline
- Herkinorin
- HZ-2
- Ibogaine
- Ketazocine
- LPK-26
- Metazocine
- Nalbuphine
- Nalorphine
- Noribogaine
- Pentazocine
- Phenazocine
- Salvinorin A
- Spiradoline
- Tifluadom
- U-50,488
- U-69,593
|
|
|
σR agonists
|
- Dextrallorphan
- Dextromethorphan
- Dextrorphan
- Noscapine
|
|
|
Others
|
- Efavirenz
- Glaucine
- Isoaminile
|
|
|
|
Cholinergics
|
|
|
Receptor ligands
|
|
|
mAChR
|
- Agonists: 77-LH-28-1
- AC-42
- AC-260,584
- Aceclidine
- Acetylcholine
- AF30
- AF150(S)
- AF267B
- AFDX-384
- Alvameline
- AQRA-741
- Arecoline
- Bethanechol
- Butyrylcholine
- Carbachol
- CDD-0034
- CDD-0078
- CDD-0097
- CDD-0098
- CDD-0102
- Cevimeline
- Choline
- cis-Dioxolane
- Ethoxysebacylcholine
- LY-593,039
- L-689,660
- LY-2,033,298
- McNA343
- Methacholine
- Milameline
- Muscarine
- NGX-267
- Ocvimeline
- Oxotremorine
- PD-151,832
- Pilocarpine
- RS86
- Sabcomeline
- SDZ 210-086
- Sebacylcholine
- Suberylcholine
- Talsaclidine
- Tazomeline
- Thiopilocarpine
- Vedaclidine
- VU-0029767
- VU-0090157
- VU-0152099
- VU-0152100
- VU-0238429
- WAY-132,983
- Xanomeline
- YM-796
Antagonists: 3-Quinuclidinyl Benzilate
- 4-DAMP
- Aclidinium Bromide
- Anisodamine
- Anisodine
- Atropine
- Atropine Methonitrate
- Benactyzine
- Benzatropine/Benztropine
- Benzydamine
- BIBN 99
- Biperiden
- Bornaprine
- CAR-226,086
- CAR-301,060
- CAR-302,196
- CAR-302,282
- CAR-302,368
- CAR-302,537
- CAR-302,668
- CS-27349
- Cyclobenzaprine
- Cyclopentolate
- Darifenacin
- DAU-5884
- Dimethindene
- Dexetimide
- DIBD
- Dicyclomine/Dicycloverine
- Ditran
- EA-3167
- EA-3443
- EA-3580
- EA-3834
- Etanautine
- Etybenzatropine/Ethylbenztropine
- Flavoxate
- Himbacine
- HL-031,120
- Ipratropium bromide
- J-104,129
- Hyoscyamine
- Mamba Toxin 3
- Mamba Toxin 7
- Mazaticol
- Mebeverine
- Methoctramine
- Metixene
- N-Ethyl-3-Piperidyl Benzilate
- N-Methyl-3-Piperidyl Benzilate
- Orphenadrine
- Otenzepad
- Oxybutynin
- PBID
- PD-102,807
- PD-0298029
- Phenglutarimide
- Phenyltoloxamine
- Pirenzepine
- Piroheptine
- Procyclidine
- Profenamine
- RU-47,213
- SCH-57,790
- SCH-72,788
- SCH-217,443
- Scopolamine/Hyoscine
- Solifenacin
- Telenzepine
- Tiotropium bromide
- Tolterodine
- Trihexyphenidyl
- Tripitamine
- Tropatepine
- Tropicamide
- WIN-2299
- Xanomeline
- Zamifenacin; Others: 1st Generation Antihistamines (Brompheniramine
- chlorphenamine
- cyproheptadine
- dimenhydrinate
- diphenhydramine
- doxylamine
- mepyramine/pyrilamine
- phenindamine
- pheniramine
- tripelennamine
- triprolidine, etc)
- Tricyclic Antidepressants (Amitriptyline
- doxepin
- trimipramine, etc)
- Tetracyclic Antidepressants (Amoxapine
- maprotiline, etc)
- Typical Antipsychotics (Chlorpromazine
- thioridazine, etc)
- Atypical Antipsychotics (Clozapine
- olanzapine
- quetiapine, etc)
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nAChR
|
- Agonists: 5-HIAA
- A-84,543
- A-366,833
- A-582,941
- A-867,744
- ABT-202
- ABT-418
- ABT-560
- ABT-894
- Acetylcholine
- Altinicline
- Anabasine
- Anatoxin-a
- AR-R17779
- Butinoline
- Butyrylcholine
- Carbachol
- Choline
- Cotinine
- Cytisine
- Decamethonium
- Desformylflustrabromine
- Dianicline
- Dimethylphenylpiperazinium
- Epibatidine
- Epiboxidine
- Ethanol
- Ethoxysebacylcholine
- EVP-4473
- EVP-6124
- Galantamine
- GTS-21
- Ispronicline
- Lobeline
- MEM-63,908/RG-3487
- Nicotine
- NS-1738
- PHA-543,613
- PHA-709,829
- PNU-120,596
- PNU-282,987
- Pozanicline
- Rivanicline
- RJR-2429
- Sazetidine A
- Sebacylcholine
- SIB-1508Y
- SIB-1553A
- SSR-180,711
- Suberylcholine
- Suxamethonium/Succinylcholine
- TC-1698
- TC-1734
- TC-1827
- TC-2216
- TC-5214
- TC-5619
- TC-6683
- Tebanicline
- Tropisetron
- UB-165
- Varenicline
- WAY-317,538
- XY-4083
Antagonists: 18-Methoxycoronaridine
- α-Bungarotoxin
- α-Conotoxin
- Alcuronium
- Amantadine
- Anatruxonium
- Atracurium
- Bupropion
- Chandonium
- Chlorisondamine
- Cisatracurium
- Coclaurine
- Coronaridine
- Dacuronium
- Decamethonium
- Dextromethorphan
- Dextropropoxyphene
- Dextrorphan
- Diadonium
- DHβE
- Dimethyltubocurarine/Metocurine
- Dipyrandium
- Dizocilpine/MK-801
- Doxacurium
- Duador
- Esketamine
- Fazadinium
- Gallamine
- Hexafluronium
- Hexamethonium/Benzohexonium
- Ibogaine
- Isoflurane
- Ketamine
- Kynurenic acid
- Laudexium/Laudolissin
- Levacetylmethadol
- Malouetine
- Mecamylamine
- Memantine
- Methadone (Levomethadone)
- Methorphan/Racemethorphan
- Methyllycaconitine
- Metocurine
- Mivacurium
- Morphanol/Racemorphan
- Neramexane
- Nitrous Oxide
- Pancuronium
- Pempidine
- Pentamine
- Pentolinium
- Phencyclidine
- Pipecuronium
- Radafaxine
- Rapacuronium
- Rocuronium
- Surugatoxin
- Thiocolchicoside
- Toxiferine
- Trimethaphan
- Tropeinium
- Tubocurarine
- Vecuronium
- Xenon
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Reuptake inhibitors
|
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Plasmalemmal
|
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CHT Inhibitors
|
- Hemicholinium-3/Hemicholine
- Triethylcholine
|
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Vesicular
|
|
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|
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Enzyme inhibitors
|
|
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Anabolism
|
|
ChAT inhibitors
|
- 1-(-Benzoylethyl)pyridinium
- 2-(α-Naphthoyl)ethyltrimethylammonium
- 3-Chloro-4-stillbazole
- 4-(1-Naphthylvinyl)pyridine
- Acetylseco hemicholinium-3
- Acryloylcholine
- AF64A
- B115
- BETA
- CM-54,903
- N,N-Dimethylaminoethylacrylate
- N,N-Dimethylaminoethylchloroacetate
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Catabolism
|
|
AChE inhibitors
|
|
|
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BChE inhibitors
|
- Cymserine * Many of the acetylcholinesterase inhibitors listed above act as butyrylcholinesterase inhibitors.
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Others
|
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Precursors
|
- Choline (Lecithin)
- Citicoline
- Cyprodenate
- Dimethylethanolamine
- Glycerophosphocholine
- Meclofenoxate/Centrophenoxine
- Phosphatidylcholine
- Phosphatidylethanolamine
- Phosphorylcholine
- Pirisudanol
|
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Cofactors
|
- Acetic acid
- Acetylcarnitine
- Acetyl-coA
- Vitamin B5 (Pantethine
- Pantetheine
- Panthenol)
|
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Others
|
- Acetylcholine releasing agents: α-Latrotoxin
- β-Bungarotoxin; Acetylcholine release inhibitors: Botulinum toxin (Botox); Acetylcholinesterase reactivators: Asoxime
- Obidoxime
- Pralidoxime
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|
Euphoriants
|
|
| Canabinoids |
- THC (found in Cannabis)
- JWH-018
|
|
| Depressants |
|
General
|
- GHB
- Benzodiazepines
- Barbiturates
- z-drugs
|
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Alcohols
|
- 2M2B
- Ethanol
- Ethchlorvynol
- Methylpentynol
- UMB68
|
|
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Opioids
|
- Heroin
- Morphine
- Fentanyl
- Oxycodone
- Buprenorphine
- Methadone
- Pethidine
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| Stimulants |
|
General
|
Nicotine (found in Tobacco)
|
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Releasing agents (RA)
|
- Amphetamine
- Methamphetamine
|
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reuptake inhibitors
|
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| Entactogens |
|
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| Hallucinogens |
|
Deliriant
|
- Atropine
- Diphenhydramine
- Orphenadrine
- Scopolamine
|
|
|
Dissociativess
|
- Ketamine (K)
- Dextromethorphan (DXM)
- Phencyclidine (PCP)
- Nitrous oxide (N2O)
|
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Psychedelics
|
|
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Histaminergics
|
|
| Receptor |
|
H1
|
- Agonists: 2-Pyridylethylamine
- Betahistine
- Histamine
- HTMT
- UR-AK49
Antagonists: 1st generation: 4-Methyldiphenhydramine
- Alimemazine
- Antazoline
- Azatadine
- Bamipine
- Benzatropine/Benztropine
- Bepotastine
- Bromazine
- Brompheniramine
- Buclizine
- Captodiame
- Carbinoxamine
- Chlorcyclizine
- Chloropyramine
- Chlorothen
- Chlorphenamine
- Chlorphenoxamine
- Cinnarizine
- Clemastine
- Clobenzepam
- Clocinizine
- Cyclizine
- Cyproheptadine
- Dacemazine
- Deptropine
- Dexbrompheniramine
- Dexchlorpheniramine
- Dimenhydrinate
- Dimetindene
- Diphenhydramine
- Diphenylpyraline
- Doxylamine
- Embramine
- Etodroxizine
- Etybenzatropine/Ethylbenztropine
- Etymemazine
- Flunarizine
- Histapyrrodine
- Homochlorcyclizine
- Hydroxyethylpromethazine
- Hydroxyzine
- Isopromethazine
- Isothipendyl
- Meclozine
- Mepyramine/Pyrilamine
- Mequitazine
- Methafurylene
- Methapyrilene
- Methdilazine
- Moxastine
- Niaprazine
- Orphenadrine
- Oxatomide
- Oxomemazine
- Phenindamine
- Pheniramine
- Phenyltoloxamine
- Pimethixene
- Piperoxan
- Pipoxizine
- Promethazine
- Propiomazine
- Pyrrobutamine
- Talastine
- Thenalidine
- Thenyldiamine
- Thiazinamium
- Thonzylamine
- Tolpropamine
- Tripelennamine
- Triprolidine
- 2nd generation: Acrivastine
- Alinastine
- Astemizole
- Azelastine
- Bamirastine
- Barmastine
- Bepiastine
- Bepotastine
- Bilastine
- Cabastinen
- Carebastine
- Cetirizine
- Clemastine
- Clemizole
- Clobenztropine
- Dorastine
- Ebastine
- Emedastine
- Epinastine
- Flezelastine
- Ketotifen
- Latrepirdine
- Levocabastine
- Linetastine
- Loratadine
- Mapinastine
- Mebhydrolin
- Mizolastine
- Moxastine
- Noberastine
- Octastine
- Olopatadine
- Perastine
- Piclopastine
- Rocastine
- Rupatadine
- Setastine
- Talastine
- Temelastine
- Terfenadine
- Zepastine
- 3rd generation: Desloratadine
- Fexofenadine
- Levocetirizine
- Ungrouped: Belarizine
- Efletirizine
- Elbanizine
- Flotrenizine
- Medrylamine
- Napactadine
- Pibaxizine
- Tagorizine
- Trelnarizine
- Trenizine
- Vapitadine
- Miscellaneous: Tricyclic antidepressants (amitriptyline,
- doxepin,
- trimipramine, etc)
- Tetracyclic antidepressants (mianserin,
- mirtazapine, etc)
- Typical antipsychotics (chlorpromazine,
- thioridazine, etc)
- Atypical antipsychotics (clozapine,
- olanzapine,
- quetiapine, etc)
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H2
|
- Agonists: Amthamine
- Betazole
- Dimaprit
- Histamine
- HTMT
- Impromidine
- UR-AK49
Antagonists: Bisfentidine
- Burimamide
- Cimetidine
- Dalcotidine
- Donetidine
- Ebrotidine
- Etintidine
- Famotidine
- Lafutidine
- Lamtidine
- Lavoltidine/Loxtidine
- Lupitidine
- Metiamide
- Mifentidine
- Niperotidine
- Nizatidine
- Osutidine
- Oxmetidine
- Pibutidine
- Quisultazine/Quisultidine
- Ramixotidine
- Ranitidine
- Roxatidine
- Sufotidine
- Tiotidine
- Tuvatidine
- Venritidine
- Xaltidine
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H3
|
- Agonists: α-Methylhistamine
- Cipralisant
- Histamine
- Imetit
- Immepip
- Immethridine
- Methimepip
- Proxyfan
Antagonists: A-349,821
- A-423,579
- ABT-239
- Betahistine
- Burimamide
- Ciproxifan
- Clobenpropit
- Conessine
- GSK-189,254
- Impentamine
- Iodophenpropit
- JNJ-5,207,852
- MK-0249
- NNC-38-1,049
- PF-03654746
- Pitolisant
- SCH-79,687
- Thioperamide
- VUF-5,681
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H4
|
- Agonists: 4-Methylhistamine
- Histamine
- VUF-8,430
Antagonists: JNJ-7,777,120
- Thioperamide
- VUF-6,002
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|
|
| Transporter |
|
VMAT
|
- Inhibitors: Ibogaine
- Reserpine
- Tetrabenazine
|
|
|
| Enzyme |
|
HDC
|
- Inhibitors: Catechin
- Meciadanol
- Naringenin
- Tritoqualine
|
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|
DAO
|
- Inhibitors: Aminoguanidine
|
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| Others |
|
Endogenous
|
- Histamine; Precursors: L-Histidine; Cofactors: Vitamin B6
|
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|
Serotonergics
|
|
|
5-HT1 receptor ligands
|
|
|
5-HT1A
|
- Agonists: Azapirones: Alnespirone
- Binospirone
- Buspirone
- Enilospirone
- Eptapirone
- Gepirone
- Ipsapirone
- Perospirone
- Revospirone
- Tandospirone
- Tiospirone
- Umespirone
- Zalospirone; Antidepressants: Etoperidone
- Nefazodone
- Trazodone
- Vortioxetine; Antipsychotics: Aripiprazole
- Asenapine
- Clozapine
- Quetiapine
- Ziprasidone; Ergolines: Dihydroergotamine
- Bromocriptine
- Ergotamine
- Lisuride
- Methysergide
- LSD; Tryptamines: 5-CT
- 5-MeO-DMT
- 5-MT
- Bufotenin
- DMT
- Indorenate
- Psilocin
- Psilocybin; Others: 8-OH-DPAT
- Adatanserin
- Bay R 1531
- Befiradol
- BMY-14802
- Cannabidiol
- Dimemebfe
- Ebalzotan
- Eltoprazine
- F-11,461
- F-12,826
- F-13,714
- F-14,679
- F-15,063
- F-15,599
- Flesinoxan
- Flibanserin
- Lesopitron
- LY-293,284
- LY-301,317
- MKC-242
- Naluzotan
- NBUMP
- Osemozotan
- Oxaflozane
- Pardoprunox
- Piclozotan
- Rauwolscine
- Repinotan
- Roxindole
- RU-24,969
- S 14,506
- S-14,671
- S-15,535
- Sarizotan
- SSR-181,507
- Sunepitron
- U-92,016-A
- Urapidil
- Vilazodone
- Xaliproden
- Yohimbine
Antagonists: Antipsychotics: Iloperidone
- Risperidone
- Sertindole; Beta blockers: Alprenolol
- Cyanopindolol
- Iodocyanopindolol
- Oxprenolol
- Pindobind
- Pindolol
- Propranolol
- Tertatolol; Others: AV965
- BMY-7,378
- CSP-2503
- Dotarizine
- Flopropione
- GR-46611
- Isamoltane
- Lecozotan
- Mefway
- Metitepine/Methiothepin
- MPPF
- NAN-190
- Robalzotan
- S-15535
- SB-649,915
- SDZ 216-525
- Spiperone
- Spiramide
- Spiroxatrine
- UH-301
- WAY-100,135
- WAY-100,635
- Xylamidine
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|
|
5-HT1B
|
- Agonists: Lysergamides: Dihydroergotamine
- Ergotamine
- Methysergide; Piperazines: Eltoprazine
- TFMPP; Triptans: Avitriptan
- Eletriptan
- Sumatriptan
- Zolmitriptan; Tryptamines: 5-CT
- 5-MT; Others: CGS-12066A
- Bromocriptine
- CP-93,129
- CP-94,253
- CP-135,807
- RU-24,969
- Vortioxetine
Antagonists: Lysergamides: Metergoline; Others: AR-A000002
- Elzasonan
- GR-127,935
- Isamoltane
- Metitepine/Methiothepin
- SB-216,641
- SB-224,289
- SB-236,057
- Yohimbine
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|
|
5-HT1D
|
- Agonists: Lysergamides: Dihydroergotamine
- Methysergide; Triptans: Almotriptan
- Avitriptan
- Eletriptan
- Frovatriptan
- Naratriptan
- Rizatriptan
- Sumatriptan
- Zolmitriptan; Tryptamines: 5-CT
- 5-Ethyl-DMT
- 5-MT
- 5-(Nonyloxy)tryptamine; Others: CP-135,807
- Bromocriptine
- CP-286,601
- GR-46611
- L-694,247
- L-772,405
- PNU-109,291
- PNU-142633
Antagonists: Lysergamides: Metergoline; Others: Alniditan
- BRL-15,572
- Elzasonan
- GR-127,935
- Ketanserin
- LY-310,762
- LY-367,642
- LY-456,219
- LY-456,220
- Metitepine/Methiothepin
- Ritanserin
- Yohimbine
- Ziprasidone
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|
|
5-HT1E
|
- Agonists: Lysergamides: Methysergide; Triptans: Eletriptan; Tryptamines: BRL-54443
- Tryptamine
Antagonists: Metitepine/Methiothepin
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|
5-HT1F
|
- Agonists: Triptans: Eletriptan
- Naratriptan
- Sumatriptan; Tryptamines: 5-MT; Others: BRL-54443
- Bromocriptine
- Lasmiditan
- LY-334,370
Antagonists: Metitepine/Methiothepin
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|
|
|
5-HT2 receptor ligands
|
|
|
|
5-HT2A
|
|
|
|
5-HT2B
|
- Agonists: Oxazolines: 4-Methylaminorex
- Aminorex; Phenethylamines: Chlorphentermine
- Cloforex
- DOB
- DOC
- DOI
- DOM
- Fenfluramine (Dexfenfluramine, Levofenfluramine)
- MDA
- MDMA
- Norfenfluramine; Tryptamines: 5-CT
- 5-MT
- α-Methyl-5-HT; Others: BW-723C86
- Bromocriptine
- Cabergoline
- mCPP
- Pergolide
- PNU-22394
- Ro60-0175
Antagonists: Agomelatine
- Asenapine
- EGIS-7625
- Ketanserin
- Lisuride
- LY-272,015
- Metitepine/Methiothepin
- PRX-08066
- Rauwolscine
- Ritanserin
- RS-127,445
- Sarpogrelate
- SB-200,646
- SB-204,741
- SB-206,553
- SB-215,505
- SB-221,284
- SB-228,357
- SDZ SER-082
- Tegaserod
- Yohimbine
|
|
|
5-HT2C
|
- Agonists: Phenethylamines: 2C-B
- 2C-E
- 2C-I
- 2C-T-2
- 2C-T-7
- 2C-T-21
- DOB
- DOC
- DOI
- DOM
- MDA
- MDMA
- Mescaline; Piperazines: Aripiprazole
- mCPP
- TFMPP; Tryptamines: 5-CT
- 5-MeO-α-ET
- 5-MeO-α-MT
- 5-MeO-DET
- 5-MeO-DiPT
- 5-MeO-DMT
- 5-MeO-DPT
- 5-MT
- α-ET
- α-Methyl-5-HT
- α-MT
- Bufotenin
- DET
- DiPT
- DMT
- DPT
- Psilocin
- Psilocybin; Others: A-372,159
- Bromocriptine
- AL-38022A
- CP-809,101
- Dimemebfe
- Lorcaserin
- Medifoxamine
- MK-212
- Org 12,962
- ORG-37,684
- Oxaflozane
- PNU-22394
- Ro60-0175
- Ro60-0213
- Vabicaserin
- WAY-629
- WAY-161,503
- YM-348
Antagonists: Atypical antipsychotics: Clorotepine
- Clozapine
- Iloperidone
- Melperone
- Olanzapine
- Paliperidone
- Pimozide
- Quetiapine
- Risperidone
- Sertindole
- Ziprasidone
- Zotepine; Typical antipsychotics: Chlorpromazine
- Loxapine
- Pipamperone; Antidepressants: Agomelatine
- Amitriptyline
- Amoxapine
- Aptazapine
- Etoperidone
- Fluoxetine
- Mianserin
- Mirtazapine
- Nefazodone
- Nortriptyline
- Tedatioxetine
- Trazodone; Others: Adatanserin
- CEPC
- Cinanserin
- Cyproheptadine
- Deramciclane
- Dotarizine
- Eltoprazine
- Esmirtazapine
- FR-260,010
- Ketanserin
- Ketotifen
- Latrepirdine
- Metitepine/Methiothepin
- Methysergide
- Pizotifen
- Ritanserin
- RS-102,221
- S-14,671
- SB-200,646
- SB-206,553
- SB-221,284
- SB-228,357
- SB-242,084
- SB-243,213
- SDZ SER-082
- Xylamidine
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|
|
|
- 5-HT3
- 5-HT4
- 5-HT5
- 5-HT6
- 5-HT7 ligands
|
|
|
|
5-HT3
|
- Agonists: Piperazines: BZP
- Quipazine; Tryptamines: 2-Methyl-5-HT
- 5-CT; Others: Chlorophenylbiguanide
- Butanol
- Ethanol
- Halothane
- Isoflurane
- RS-56812
- SR-57,227
- SR-57,227-A
- Toluene
- Trichloroethane
- Trichloroethanol
- Trichloroethylene
- YM-31636
Antagonists: Antiemetics: AS-8112
- Alosetron
- Azasetron
- Batanopride
- Bemesetron
- Cilansetron
- Dazopride
- Dolasetron
- Granisetron
- Lerisetron
- Ondansetron
- Palonosetron
- Ramosetron
- Renzapride
- Tropisetron
- Zacopride
- Zatosetron; Atypical antipsychotics: Clozapine
- Olanzapine
- Quetiapine; Tetracyclic antidepressants: Amoxapine
- Mianserin
- Mirtazapine; Others: CSP-2503
- ICS-205,930
- MDL-72,222
- Memantine
- Nitrous Oxide
- Ricasetron
- Sevoflurane
- Tedatioxetine
- Thujone
- Tropanserin
- Vortioxetine
- Xenon
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|
|
5-HT4
|
- Agonists: Gastroprokinetic Agents: Cinitapride
- Cisapride
- Dazopride
- Metoclopramide
- Mosapride
- Prucalopride
- Renzapride
- Tegaserod
- Velusetrag
- Zacopride; Others: 5-MT
- BIMU8
- CJ-033,466
- PRX-03140
- RS-67333
- RS-67506
- SL65.0155
- Antagonists: GR-113,808
- GR-125,487
- L-Lysine
- Piboserod
- RS-39604
- RS-67532
- SB-203,186
- SB-204,070
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|
5-HT5A
|
- Agonists: Lysergamides: Ergotamine
- LSD; Tryptamines: 5-CT; Others: Valerenic Acid
Antagonists: Asenapine
- Latrepirdine
- Metitepine/Methiothepin
- Ritanserin
- SB-699,551
* Note that the 5-HT5B receptor is not functional in humans.
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5-HT6
|
- Agonists: Lysergamides: Dihydroergotamine
- Ergotamine
- Lisuride
- LSD
- Mesulergine
- Metergoline
- Methysergide; Tryptamines: 2-Methyl-5-HT
- 5-BT
- 5-CT
- 5-MT
- Bufotenin
- E-6801
- E-6837
- EMD-386,088
- EMDT
- LY-586,713
- N-Methyl-5-HT
- Tryptamine; Others: WAY-181,187
- WAY-208,466
Antagonists: Antidepressants: Amitriptyline
- Amoxapine
- Clomipramine
- Doxepin
- Mianserin
- Nortriptyline; Atypical antipsychotics: Aripiprazole
- Asenapine
- Clorotepine
- Clozapine
- Fluperlapine
- Iloperidone
- Olanzapine
- Tiospirone; Typical antipsychotics: Chlorpromazine
- Loxapine; Others: BGC20-760
- BVT-5182
- BVT-74316
- Cerlapirdine
- EGIS-12,233
- GW-742,457
- Ketanserin
- Latrepirdine
- Lu AE58054
- Metitepine/Methiothepin
- MS-245
- PRX-07034
- Ritanserin
- Ro04-6790
- Ro 63-0563
- SB-258,585
- SB-271,046
- SB-357,134
- SB-399,885
- SB-742,457
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5-HT7
|
- Agonists: Lysergamides: LSD; Tryptamines: 5-CT
- 5-MT
- Bufotenin; Others: 8-OH-DPAT
- AS-19
- Bifeprunox
- E-55888
- LP-12
- LP-44
- RU-24,969
- Sarizotan
Antagonists: Lysergamides: 2-Bromo-LSD
- Bromocriptine
- Dihydroergotamine
- Ergotamine
- Mesulergine
- Metergoline
- Methysergide; Antidepressants: Amitriptyline
- Amoxapine
- Clomipramine
- Imipramine
- Maprotiline
- Mianserin; Atypical antipsychotics: Amisulpride
- Aripiprazole
- Clorotepine
- Clozapine
- Olanzapine
- Risperidone
- Sertindole
- Tiospirone
- Ziprasidone
- Zotepine; Typical antipsychotics: Chlorpromazine
- Loxapine; Others: Butaclamol
- EGIS-12,233
- Ketanserin
- LY-215,840
- Metitepine/Methiothepin
- Pimozide
- Ritanserin
- SB-258,719
- SB-258,741
- SB-269,970
- SB-656,104
- SB-656,104-A
- SB-691,673
- SLV-313
- SLV-314
- Spiperone
- SSR-181,507
- Vortioxetine
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|
Reuptake inhibitors
|
|
|
SERT
|
- Selective serotonin reuptake inhibitors (SSRIs): Alaproclate
- Citalopram
- Dapoxetine
- Desmethylcitalopram
- Desmethylsertraline
- Escitalopram
- Femoxetine
- Fluoxetine
- Fluvoxamine
- Indalpine
- Ifoxetine
- Litoxetine
- Lubazodone
- Omiloxetine
- Panuramine
- Paroxetine
- Pirandamine
- RTI-353
- Seproxetine
- Sertraline
- Vilazodone
- Vortioxetine
- Zimelidine; Serotonin-norepinephrine reuptake inhibitors (SNRIs): Bicifadine
- Desvenlafaxine
- Duloxetine
- Eclanamine
- Levomilnacipran
- Milnacipran
- Sibutramine
- Venlafaxine; Serotonin-norepinephrine-dopamine reuptake inhibitors (SNDRIs): Brasofensine
- Diclofensine
- DOV-102,677
- DOV-21,947
- DOV-216,303
- NS-2359
- SEP-225289
- SEP-227,162
- Tedatioxetine
- Tesofensine; Tricyclic antidepressants (TCAs): Amitriptyline
- Butriptyline
- Cianopramine
- Clomipramine
- Desipramine
- Dosulepin
- Doxepin
- Imipramine
- Lofepramine
- Nortriptyline
- Pipofezine
- Protriptyline
- Trimipramine; Tetracyclic antidepressants (TeCAs): Amoxapine; Piperazines: Nefazodone
- Trazodone; Antihistamines: Brompheniramine
- Chlorphenamine
- Diphenhydramine
- Mepyramine/Pyrilamine
- Pheniramine
- Tripelennamine; Opioids: Pethidine
- Methadone
- Propoxyphene; Others: Cocaine
- CP-39,332
- Cyclobenzaprine
- Dextromethorphan
- Dextrorphan
- EXP-561
- Fezolamine
- Mesembrine
- Nefopam
- PIM-35
- Pridefine
- Roxindole
- SB-649,915
- Tofenacin
- Ziprasidone
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|
|
VMAT
|
- Ibogaine
- Reserpine
- Tetrabenazine
|
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|
Releasing agents
|
|
- Aminoindanes: 5-IAI
- AMMI
- ETAI
- MDAI
- MDMAI
- MMAI
- TAI; Aminotetralins: 6-CAT
- 8-OH-DPAT
- MDAT
- MDMAT; Oxazolines: 4-Methylaminorex
- Aminorex
- Clominorex
- Fluminorex; Phenethylamines (also Amphetamines, Cathinones, Phentermines, etc): 2-Methyl-MDA
- 4-CAB
- 4-FA
- 4-FMA
- 4-HA
- 4-MTA
- 5-APDB
- 5-Methyl-MDA
- 6-APDB
- 6-Methyl-MDA
- AEMMA
- Amiflamine
- BDB
- BOH
- Brephedrone
- Butylone
- Chlorphentermine
- Cloforex
- Amfepramone
- Metamfepramone
- DCA
- DFMDA
- DMA
- DMMA
- EBDB
- EDMA
- Ethylone
- Etolorex
- Fenfluramine (Dexfenfluramine, Levofenfluramine)
- Flephedrone
- IAP
- IMP
- Iofetamine
- Lophophine
- MBDB
- MDA
- MDEA
- MDHMA
- MDMA
- MDMPEA
- MDOH
- MDPEA
- Mephedrone
- Methedrone
- Methylone
- MMA
- MMDA
- MMDMA
- MMMA
- NAP
- Norfenfluramine
- 4-TFMA
- pBA
- pCA
- pIA
- PMA
- PMEA
- PMMA
- TAP; Piperazines: 2C-B-BZP
- 3-MeOPP
- BZP
- DCPP
- MBZP
- mCPP
- MDBZP
- MeOPP
- Mepiprazole
- pCPP
- pFPP
- pTFMPP
- TFMPP; Tryptamines: 4-Methyl-αET
- 4-Methyl-αMT
- 5-CT
- 5-MeO-αET
- 5-MeO-αMT
- 5-MT
- αET
- αMT
- DMT
- Tryptamine (itself); Others: Indeloxazine
- Tramadol
- Viqualine
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|
Enzyme inhibitors
|
|
|
Anabolism
|
|
TPH
|
|
|
|
AAAD
|
- Benserazide
- Carbidopa
- Genistein
- Methyldopa
|
|
|
|
Catabolism
|
|
MAO
|
- Nonselective: Benmoxin
- Caroxazone
- Echinopsidine
- Furazolidone
- Hydralazine
- Indantadol
- Iproclozide
- Iproniazid
- Isocarboxazid
- Isoniazid
- Linezolid
- Mebanazine
- Metfendrazine
- Nialamide
- Octamoxin
- Paraxazone
- Phenelzine
- Pheniprazine
- Phenoxypropazine
- Pivalylbenzhydrazine
- Procarbazine
- Safrazine
- Tranylcypromine; MAO-A Selective: Amiflamine
- Bazinaprine
- Befloxatone
- Befol
- Brofaromine
- Cimoxatone
- Clorgiline
- Esuprone
- Harmala alkaloids (Harmine
- Harmaline
- Tetrahydroharmine
- Harman
- Norharman, etc)
- Methylene Blue
- Metralindole
- Minaprine
- Moclobemide
- Pirlindole
- Sercloremine
- Tetrindole
- Toloxatone
- Tyrima
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Others
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Precursors
|
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|
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+)
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Others
|
- Activity enhancers: BPAP
- PPAP; Reuptake enhancers: Tianeptine
|
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|
|
Antiparkinson agents (N04)
|
|
| Dopaminergics |
|
DA precursors/prodrugs
|
- Etilevodopa
- Droxidopa
- Levodopa#
- Melevodopa
|
|
|
DA receptor agonists
|
- Aplindore
- Apomorphine
- Bromocriptine
- Cabergoline
- Ciladopa
- Dihydroergocryptine
- Lisuride
- Pardoprunox
- Pergolide
- Piribedil
- Pramipexole
- Ropinirole
- Rotigotine
|
|
|
MAO-B inhibitors
|
- Ladostigil
- Lazabemide
- Mofegiline
- Pargyline
- Rasagiline
- Selegiline
|
|
|
COMT inhibitors
|
- Entacapone
- Nitecapone
- Tolcapone
|
|
|
Aromatic L-amino acid decarboxylase inhibitors
|
- Benserazide
- Carbidopa#
- Methyldopa
|
|
|
| Anticholinergics |
- Benzatropine
- Biperiden#
- Bornaprine
- Chlorphenoxamine
- Cycrimine
- Dexetimide
- Dimenhydrinate
- Diphenhydramine
- Etanautine
- Etybenzatropine
- Mazaticol
- Metixene
- Orphenadrine
- Phenglutarimide
- Piroheptine
- Procyclidine
- Profenamine
- Trihexyphenidyl
- Tropatepine
|
|
| Others |
- Amantadine
- Budipine
- MDMA
- Memantine
- Methylxanthines
- Rimantadine
- UWA-101
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
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anat (n/s/m/p/4/e/b/d/c/a/f/l/g)/phys/devp
|
noco (m/d/e/h/v/s)/cong/tumr, sysi/epon, injr
|
proc, drug (N1A/2AB/C/3/4/7A/B/C/D)
|
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