Solvent, now banned for ozone depletion
1,1,1-Trichloroethane Skeletal formula of 1,1,1-trichloroethane Space-filling model of 1,1,1-trichloroethane
Names Preferred IUPAC name Other names1,1,1-TCA, Methyl chloroform, Chlorothene, Solvent 111, R-140a, Genklene, monochlorethylidene chloride (archaic)
Identifiers ChEBI ChEMBL ChemSpider ECHA InfoCard 100.000.688 EC Number 82076 KEGG RTECS number UNII UN number 2831 InChI=1S/C2H3Cl3/c1-2(3,4)5/h1H3
Y Key: UOCLXMDMGBRAIB-UHFFFAOYSA-N
Y InChI=1/C2H3Cl3/c1-2(3,4)5/h1H3
Key: UOCLXMDMGBRAIB-UHFFFAOYAP
Properties C2 H3 Cl3 or CH3 CCl3 Molar mass 133.40 g/mol Appearance Colourless liquid Odor mild, chloroform-like[ 1] Density 1.32 g/cm3 Melting point −33 °C (−27 °F; 240 K) Boiling point 74 °C (165 °F; 347 K) 0.4% (20 °C)[ 1] [ 2] Vapor pressure 100 mmHg (20°C)[ 1] 1.437[ 3] Hazards Occupational safety and health Main hazards
Ozone layer impact. Irritant to the upper respiratory tract. Causes severe irritation and swelling to eyes. GHS labellingWarning H332, H420 P261, P271, P304+P312, P304+P340, P312, P502 NFPA 704 Explosive limits 7.5–12.5%[ 1] Lethal dose or concentration (LD, LC):9600 mg/kg (oral, rat)[ 4] 3911 ppm (mouse, 2 hr)[ 4] NIOSH TWA 350 ppm (1900 mg/m3 )[ 1] C 350 ppm (1900 mg/m3 ) [15-minute][ 1] 700 ppm[ 1] Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
1,1,1-Trichloroethane , also known asmethyl chloroform andchlorothene , is achloroalkane with the chemical formula CH3 CCl3 . It is an isomer of1,1,2-trichloroethane . A colourless and sweet-smelling liquid, it was once produced industrially in large quantities for use as asolvent .[ 5] Montreal Protocol as an ozone-depleting substance, and as such, use has declined since 1996. Trichloroethane should not be confused with the similar-soundingtrichloroethene which is also commonly used as a solvent.
1,1,1-Trichloroethane was first reported byHenri Victor Regnault in 1840. Industrially, it is usually produced in a two-step process fromvinyl chloride . In the first step, vinyl chloride reacts withhydrogen chloride at 20–50 °C to produce1,1-dichloroethane :
H2 C=CHCl + HCl → CH3 CHCl2 This reaction iscatalyzed by a variety ofLewis acids , mainlyaluminium chloride ,iron(III) chloride , orzinc chloride . The 1,1-dichloroethane is then converted to 1,1,1-trichloroethane by reaction withchlorine underultraviolet irradiation:
CH3 CHCl2 + Cl2 → CH3 CCl3 + HCl This reaction proceeds at 80–90% yield, and the hydrogen chloride byproduct can be recycled to the first step in the process. The major side-product is the related compound1,1,2-trichloroethane , from which the 1,1,1-trichloroethane can be separated bydistillation .
A somewhat smaller amount of 1,1,1-trichloroethane is produced from the reaction of1,1-dichloroethene andhydrogen chloride in the presence of aniron(III) chloride catalyst:
CH2 =CCl2 + HCl → CH3 CCl3 1,1,1-Trichloroethane is sold with stabilizers because it is unstable with respect to dehydrochlorination and attacks some metals. Stabilizers comprise up to 8% of the formulation, including acid scavengers (epoxides, amines) andcomplexants .
1,1,1-Trichloroethane is an excellent solvent for manyorganic compounds and also one of the least toxic of thechlorinated hydrocarbons . It is generally considered non-polar , but owing to the goodpolarizability of the chlorine atoms, it is a superior solvent for organic compounds that do not dissolve well in hydrocarbons such ashexane . Prior to the Montreal Protocol, it was widely used for cleaning metal parts andcircuit boards , as aphotoresist solvent in theelectronics industry, as anaerosol propellant, as acutting fluid additive, and as a solvent for inks, paints,adhesives , and other coatings. 1,1,1-trichloroethane was used todry-clean leather andsuede and it was one of the components ofDow Chemical 's "Dowclene" dry cleaning fluid among with tetrachloroethylene, first marketed in the late 1930s. Use of 1,1,1-trichloroethane in dry-cleaning remained until the 1980s, meanwhile tetrachloroethylene is still widely used. 1,1,1-Trichloroethane is also used as aninsecticidal fumigant .[ 6]
It was also the standard cleaner forphotographic film (movie/slide/negatives, etc.). Other commonly available solvents damage emulsion and base (acetone will dissolve triacetate base on most films), and thus are not suitable for this application. The standard replacement,Forane 141 is much less effective, and tends to leave a residue. 1,1,1-Trichloroethane was used as a thinner incorrection fluid products such asliquid paper . Many of its applications previously usedcarbon tetrachloride (which was banned in US consumer products in 1970). In turn, 1,1,1-trichloroethane itself is now being replaced by other solvents in the laboratory.[ 7] trichloroethylene in metal degreasing.[ 6]
Methyl chloroform was also used as a veterinaryanthelmintic .
Anaesthetic research [ edit ] 1,1,1-Trichloroethane was one of the volatile organochlorides that have been tried as alternatives tochloroform in anaesthesia.[ 8] [ 9] [ 10]
In 1880, 1,1,1-trichloroethane was suggested as an anaesthetic. It was first referred to as "methyl-chloroform" in the same year. At the time, the narcotic effects ofchloral hydrate were owed to a hypothetical metabolic pathway to chloroform in "alkaline blood". Trichloroethane was studied for its structural similarity to chloral and potential anaesthetic effects. However, trichloroethane did not exhibit any conversion to chloroform in laboratory experiments. The1,1,2-Trichloroethane (vinyl trichloride) isomer, which lacked atrichloromethyl group , exhibited anaesthetic effects even stronger than the 1,1,1 isomer.[ 11]
Although not astoxic as many similar compounds, inhaled or ingested 1,1,1-trichloroethane does act as acentral nervous system depressant and can cause effects similar to those ofethanol intoxication , includingdizziness , confusion, and, in sufficiently high concentrations,unconsciousness and death.[ 12] intentional inhalation of trichloroethane have been reported.[ 13] [ 14] [ 15] [ 16]
Prolonged skin contact with the liquid can result in theremoval of fats from the skin , resulting in skin irritation.
TheInternational Agency for Research on Cancer places 1,1,1-trichloroethane inGroup 2A as a probablecarcinogen .[ 17]
Atmospheric concentration [ edit ] 1,1,1-Trichloroethane (Methyl chloroform, CH3 CCl3 ) measured by the Advanced Global Atmospheric Gases Experiment (AGAGE ) in the lower atmosphere (troposphere ) at stations around the world. Abundances are given as pollution free monthly mean mole fractions inparts-per-trillion . 1,1,1-Trichloroethane timeseries at various latitudes. 1,1,1-Trichloroethane is a fairly potentgreenhouse gas with a 100-yearglobal warming potential of 169 relative tocarbon dioxide .[ 18] carbon tetrachloride — which it replaced as a solvent — due to its relatively shortatmospheric lifetime of about 5 years.[ 19]
The Montreal Protocol targeted 1,1,1-trichloroethane as a compound responsible forozone depletion and banned its use beginning in 1996. Since then, its manufacture and use have been phased out throughout most of the world, and its atmospheric concentration has declined substantially.[ 19]
^a b c d e f g NIOSH Pocket Guide to Chemical Hazards."#0404" .National Institute for Occupational Safety and Health (NIOSH). ^ "International Programme On Chemical Safety, Environmental Health Criteria 136" . World Health Organization, Geneva. 1990. Retrieved25 December 2017 .^ Timmermans, Jean , Physico-chemical constants of pure organic compounds (1950),p. 242 ^a b "Methyl chloroform" .Immediately Dangerous to Life or Health Concentrations .National Institute for Occupational Safety and Health .^ Manfred Rossberg, Wilhelm Lendle, Gerhard Pfleiderer, Adolf Tögel, Eberhard-Ludwig Dreher, Ernst Langer, Heinz Rassaerts, Peter Kleinschmidt, Heinz Strack, Richard Cook, Uwe Beck, Karl-August Lipper, Theodore R. Torkelson, Eckhard Löser, Klaus K. Beutel, Trevor Mann "Chlorinated Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim.doi :10.1002/14356007.a06_233.pub2 . ^a b Morrison, R. D., Murphy, B. L. (2013). Chlorinated Solvents: A Forensic Evaluation. UK Royal Society of Chemistry. ^ Use of Ozone Depleting Substances in Laboratories. TemaNord 516/2003 Archived 2008-02-27 at theWayback Machine ^ The American Practitioner 1881-01: Volume 23,page 28 ^ Methyl-Chloroform (1887) in Saint Louis Medical and Surgical Journal,page 121 ^ An introduction to modern therapeutics (1892), Brunton, T. Lauder,page 122 ^ On Two New Anaesthetics (1880), The American Journal of Pharmacy 1881-03: Vol 53,pages 119–120 ^ Toxicological Profile for 1,1,1-Trichloroethane Archived 2008-05-09 at theWayback Machine , Agency for Toxic Substances and Disease Registry (ATSDR). 2006^ King, Gregory S.; Smialek, John E.; Troutman, William G. (15 March 1985)."Sudden Death in Adolescents Resulting From the Inhalation of Typewriter Correction Fluid" JAMA: The Journal of the American Medical Association .253 (11):1604– 1606.doi :10.1001/jama.253.11.1604 .PMID 3974043 .Archived from the original on 23 February 2013. Retrieved5 January 2010 .We describe four cases of sudden death in adolescents associated with recreational sniffing of typewriter correction fluid occurring during the period 1979 through mid-1984. ^ D'costa, DF; Gunasekera, NP (August 1990)."Fatal cerebral oedema following trichloroethane abuse" .Journal of the Royal Society of Medicine .83 (8):533– 534.doi :10.1177/014107689008300823 .PMC 1292788 PMID 2231588 . ^ Winekab, Charles L.; Wahba, Wagdy W.; Huston, Robert; Rozin, Leon (6 June 1997)."Fatal inhalation of 1,1,1-trichloroethane" .Forensic Science International .87 (2):161– 165.doi :10.1016/S0379-0738(97)00040-6 .PMID 9237378 .A 13-year-old male was found dead in the woods subsequent to 1,1,1-trichloroethane (TCE) inhalation. ^ Wodka, Richard M.; Jeong, Erwin W. S. (1 January 1989)."Cardiac Effects of Inhaled Typewriter Correction Fluid" Annals of Internal Medicine .110 (1):91– 92.doi :10.7326/0003-4819-110-1-91_2 .PMID 2908837 .Archived from the original on 14 April 2013. Retrieved5 January 2010 . ^ IARC.1,1,1-Trichloroethane and Four Other Industrial Chemicals ISBN 978-92-832-0197-7 ^ Hodnebrog Ø, Aamaas B, Fuglestvedt JS, Marston G, Myhre G, Nielsen CJ, Sandstad M, Shine KP, Wallington TJ (September 2020)."Updated Global Warming Potentials and Radiative Efficiencies of Halocarbons and Other Weak Atmospheric Absorbers" .Reviews of Geophysics .58 (3) e2019RG000691.Bibcode :2020RvGeo..5800691H .doi :10.1029/2019RG000691 .PMC 7518032 PMID 33015672 . ^a b "Chapter 8, Table 8.A.1".AR5 Climate Change 2013: The Physical Science Basis Doherty, R.E. (2000). "A History of the Production and Use of Carbon Tetrachloride, Tetrachloroethylene, Trichloroethylene and 1,1,1-Trichloroethane in the United States: Part 2 - Trichloroethylene and 1,1,1-Trichloroethane".Environmental Forensics .1 (2):83– 93.Bibcode :2000EnvFo...1...83D .doi :10.1006/enfo.2000.0011 .S2CID 97370778 .
Alcohols Barbiturates Benzodiazepines Carbamates Flavonoids Imidazoles Kava constituentsMonoureides Neuroactive steroids Nonbenzodiazepines Phenols Piperidinediones Pyrazolopyridines Quinazolinones Volatiles /gases Others/unsorted 3-Hydroxybutanal α-EMTBL AA-29504 Alogabat Avermectins (e.g.,ivermectin )Bromide compounds (e.g.,lithium bromide ,potassium bromide ,sodium bromide )Carbamazepine Chloralose Chlormezanone Clomethiazole Darigabat DEABL Deuterated etifoxine Dihydroergolines (e.g.,dihydroergocryptine ,dihydroergosine ,dihydroergotamine ,ergoloid (dihydroergotoxine) )DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g.,flufenamic acid ,mefenamic acid ,niflumic acid ,tolfenamic acid )Fluoxetine Flupirtine Hopantenic acid KRM-II-81 Lanthanum Lavender oil Lignans (e.g.,4-O-methylhonokiol ,honokiol ,magnolol ,obovatol )Loreclezole Menthyl isovalerate (validolum) Monastrol Nicotinic acid Nicotinamide Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g.,sulfonmethane (sulfonal) ,tetronal ,trional )Terpenoids (e.g.,borneol )Topiramate Valerian constituents (e.g.,isovaleric acid ,isovaleramide ,valerenic acid ,valerenol )
Receptor (ligands )
GlyR Tooltip Glycine receptor Positive modulators: Alcohols (e.g.,brometone ,chlorobutanol (chloretone) ,ethanol (alcohol) ,tert -butanol (2M2P)tribromoethanol ,trichloroethanol ,trifluoroethanol )Alkylbenzene sulfonate Anandamide Barbiturates (e.g.,pentobarbital ,sodium thiopental )Chlormethiazole D12-116 Dihydropyridines (e.g.,nicardipine )Etomidate Ginseng constituents (e.g.,ginsenosides (e.g.,ginsenoside-Rf ))Glutamic acid (glutamate) Ivermectin Ketamine Neuroactive steroids (e.g.,alfaxolone ,pregnenolone (eltanolone) ,pregnenolone acetate ,minaxolone ,ORG-20599 )Nitrous oxide Penicillin G Propofol Tamoxifen Tetrahydrocannabinol Triclofos Tropeines (e.g.,atropine ,bemesetron ,cocaine ,LY-278584 ,tropisetron ,zatosetron )Volatiles /gases (e.g.,chloral hydrate ,chloroform ,desflurane ,diethyl ether (ether) ,enflurane ,halothane ,isoflurane ,methoxyflurane ,sevoflurane ,toluene ,trichloroethane (methyl chloroform) ,trichloroethylene )Xenon Zinc Antagonists: 2-Aminostrychnine 2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine Diaboline Endocannabinoids (e.g.,2-AG ,anandamide (AEA) )Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline N-Methylstrychnine N,N-Dimethylmuscimol Nipecotic acid Pitrazepin Pseudostrychnine Quinolines (e.g.,4-hydroxyquinoline ,4-hydroxyquinoline-3-carboxylic acid ,5,7-CIQA ,7-CIQ ,7-TFQ ,7-TFQA )RU-5135 Sinomenine Strychnine THAZ Thiocolchicoside Tutin Negative modulators: Amiloride Benzodiazepines (e.g.,bromazepam ,clonazepam ,diazepam ,flunitrazepam ,flurazepam )Corymine Cyanotriphenylborate Daidzein Dihydropyridines (e.g.,nicardipine ,nifedipine ,nitrendipine )Furosemide Genistein Ginkgo constituents (e.g.,bilobalide ,ginkgolides (e.g.,ginkgolide A ,ginkgolide B ,ginkgolide C ,ginkgolide J ,ginkgolide M ))Imipramine NBQX Neuroactive steroids (e.g.,3α-androsterone sulfate ,3β-androsterone sulfate ,deoxycorticosterone ,DHEA sulfate ,pregnenolone sulfate ,progesterone )Opioids (e.g.,codeine ,dextromethorphan ,dextrorphan ,levomethadone ,levorphanol ,morphine ,oripavine ,pethidine ,thebaine )Picrotoxin (i.e.,picrotin andpicrotoxinin )PMBA Riluzole Tropeines (e.g.,bemesetron ,LY-278584 ,tropisetron ,zatosetron )Verapamil Zinc NMDAR Tooltip N-Methyl-D-aspartate receptor
Transporter (blockers )
GlyT1 Tooltip Glycine transporter 1 GlyT2 Tooltip Glycine transporter 2
AMPAR Tooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor KAR Tooltip Kainate receptor NMDAR Tooltip N-Methyl-D-aspartate receptor
5-HT1
5-HT1A
Agonists: 4-F-5-MeO-pyr-T 5-MeO-pip-T 5-MeO-pyr-T 8-OH-DPAT Adatanserin Amphetamine Antidepressants (e.g.,etoperidone ,hydroxynefazodone ,nefazodone ,trazodone ,triazoledione ,vilazodone ,vortioxetine )Atypical antipsychotics (e.g.,aripiprazole ,asenapine ,brexpiprazole ,cariprazine ,clozapine ,lurasidone ,quetiapine ,ziprasidone )Azapirones (e.g.,buspirone ,eptapirone ,gepirone ,perospirone ,tandospirone )Bay R 1531 Befiradol BMY-14802 Cannabidiol Dimemebfe Dopamine Ebalzotan Eltoprazine Enciprazine Ergolines (e.g.,bromocriptine ,cabergoline ,dihydroergotamine ,ergotamine ,lisuride ,LSD ,methylergometrine (methylergonovine) ,methysergide ,pergolide )F-11461 F-12826 F-13714 F-14679 F-15063 F-15599 Flesinoxan Flibanserin Flumexadol Hypidone Lesopitron LY-293284 LY-301317 mCPP MKC-242 Naluzotan NBUMP Osemozotan Oxaflozane Pardoprunox Piclozotan Rauwolscine Repinotan Roxindole RU-24969 S-14506 S-14671 S-15535 Sarizotan Serotonin (5-HT) SSR-181507 Sunepitron Tryptamines (e.g.,5-CT ,5-MeO-DMT ,5-MT ,bufotenin ,DMT ,indorenate ,N-Me-5-HT ,psilocin ,psilocybin )TGBA01AD TMU4142 U-92016-A Urapidil Vilazodone Xaliproden Yohimbine Antagonists: Atypical antipsychotics (e.g.,iloperidone ,risperidone ,sertindole )AV965 Beta blockers (e.g.,alprenolol ,carteolol ,cyanopindolol ,iodocyanopindolol ,isamoltane ,oxprenolol ,penbutolol ,pindobind ,pindolol ,propranolol ,tertatolol )BMY-7378 CSP-2503 Dotarizine Ergolines (e.g.,metergoline )FCE-24379 Flopropione GR-46611 Isamoltane Lecozotan Mefway Metitepine (methiothepin) MIN-117 (WF-516) MPPF NAN-190 Robalzotan S-15535 SB-649915 SDZ 216-525 Spiperone Spiramide Spiroxatrine UH-301 WAY-100135 WAY-100635 Xylamidine
5-HT1B
Agonists: Anpirtoline AZ10419369 Benzofurans (e.g.,5-MAPB ,6-MAPB ,BK-5-MAPB ,BK-6-MAPB )Benzothiophenes (e.g.,5-MAPBT ,6-MAPBT ,BK-5-MAPBT )CGS-12066A CP-93129 CP-94253 CP-122288 CP-135807 Eltoprazine Ergolines (e.g.,bromocriptine ,dihydroergotamine ,ergotamine ,methylergometrine (methylergonovine) ,methysergide ,pergolide )mCPP Methylenedioxyphenethylamines (e.g.,MDMA ,methylone )PZKKN-94 RU-24969 Serotonin (5-HT) Triptans (e.g.,avitriptan ,donitriptan ,eletriptan ,sumatriptan ,zolmitriptan )TFMPP Tryptamines (e.g.,5-BT ,5-CT ,5-MT ,DMT )Vortioxetine
5-HT1D
Agonists: CP-122288 CP-135807 CP-286601 Ergolines (e.g.,bromocriptine ,cabergoline ,dihydroergotamine ,ergotamine ,LSD ,methysergide )GR-46611 L-694247 L-772405 mCPP PNU-109291 PNU-142633 Serotonin (5-HT) TGBA01AD Triptans (e.g.,almotriptan ,avitriptan ,donitriptan ,eletriptan ,frovatriptan ,naratriptan ,rizatriptan ,sumatriptan ,zolmitriptan )Tryptamines (e.g.,5-BT ,5-CT ,5-Et-DMT ,5-MT ,5-(nonyloxy)tryptamine ,DMT )
5-HT1E
5-HT1F
5-HT2
5-HT2A
Agonists: 25H/NB series (e.g.,25I-NBF ,25I-NBMD ,25I-NBOH ,25I-NBOMe ,25B-NBOMe ,25C-NBOMe ,25TFM-NBOMe ,2CBCB-NBOMe ,25CN-NBOH ,2CBFly-NBOMe )2Cs (e.g.,2C-B ,2C-E ,2C-I ,2C-T-2 ,2C-T-7 ,2C-T-21 )2C-B-FLY 2CB-Ind 5-Methoxytryptamines (5-MeO-DET ,5-MeO-DiPT ,5-MeO-DMT ,5-MeO-DPT ,5-MT )α-Alkyltryptamines (e.g.,5-Cl-αMT ,5-Fl-αMT ,5-MeO-αET ,5-MeO-αMT ,α-Me-5-HT ,αET ,αMT )AL-34662 AL-37350A Bromo-DragonFLY Dimemebfe DMBMPP DOx (e.g.,DOB ,DOC ,DOI ,DOM )Efavirenz Ergolines (e.g.,1P-LSD ,ALD-52 ,bromocriptine ,cabergoline ,ergine (LSA) ,ergometrine (ergonovine) ,ergotamine ,lisuride ,LA-SS-Az ,LSB ,LSD ,LSD-Pip ,LSH ,LSP ,methylergometrine (methylergonovine) ,pergolide )Flumexadol IHCH-7113 Jimscaline Lorcaserin MDxx (e.g.,MDA (tenamfetamine) ,MDMA (midomafetamine) ,MDOH ,MMDA )O-4310 Oxaflozane PHA-57378 PNU-22394 PNU-181731 RH-34 SCHEMBL5334361 Phenethylamines (e.g.,lophophine ,mescaline )Piperazines (e.g.,BZP ,quipazine ,TFMPP )Serotonin (5-HT) TCB-2 TFMFly Tryptamines (e.g.,5-BT ,5-CT ,bufotenin ,DET ,DiPT ,DMT ,DPT ,psilocin ,psilocybin ,tryptamine )Antagonists: 5-I-R91150 5-MeO-NBpBrT AC-90179 Adatanserin Altanserin Antihistamines (e.g.,cyproheptadine ,hydroxyzine ,ketotifen ,perlapine )AMDA Atypical antipsychotics (e.g.,amperozide ,aripiprazole ,asenapine ,blonanserin ,brexpiprazole ,carpipramine ,clocapramine ,clorotepine ,clozapine ,fluperlapine ,gevotroline ,iloperidone ,lurasidone ,melperone ,mosapramine ,ocaperidone ,olanzapine ,paliperidone ,quetiapine ,risperidone ,sertindole ,zicronapine ,ziprasidone ,zotepine )Chlorprothixene Cinanserin CSP-2503 Deramciclane Dotarizine Eplivanserin Ergolines (e.g.,amesergide ,LY-53857 ,LY-215840 ,mesulergine ,metergoline ,methysergide ,sergolexole )Fananserin Flibanserin Glemanserin Irindalone Ketanserin KML-010 Landipirdine LY-393558 mCPP Medifoxamine Metitepine (methiothepin) MIN-117 (WF-516) Naftidrofuryl Nantenine Nelotanserin Opiranserin (VVZ-149) Pelanserin Phenoxybenzamine Pimavanserin Pirenperone Pizotifen Pruvanserin Rauwolscine Ritanserin Roluperidone S-14671 Sarpogrelate Serotonin antagonists and reuptake inhibitors (e.g.,etoperidone ,hydroxynefazodone ,lubazodone ,mepiprazole ,nefazodone ,triazoledione ,trazodone )SR-46349B TGBA01AD Teniloxazine Temanogrel Tetracyclic antidepressants (e.g.,amoxapine ,aptazapine ,esmirtazapine ,maprotiline ,mianserin ,mirtazapine )Tricyclic antidepressants (e.g.,amitriptyline )Typical antipsychotics (e.g.,chlorpromazine ,fluphenazine ,haloperidol ,loxapine ,perphenazine ,pimozide ,pipamperone ,prochlorperazine ,setoperone ,spiperone ,spiramide ,thioridazine ,thiothixene ,trifluoperazine )Volinanserin Xylamidine Yohimbine
5-HT2B
Agonists: 4-Methylaminorex Aminorex Amphetamines (e.g.,chlorphentermine ,cloforex ,dexfenfluramine ,fenfluramine ,levofenfluramine ,norfenfluramine )BW-723C86 DOx (e.g.,DOB ,DOC ,DOI ,DOM )Ergolines (e.g.,cabergoline ,dihydroergocryptine ,dihydroergotamine ,ergotamine ,methylergometrine (methylergonovine) ,methysergide ,pergolide )Lorcaserin MDxx (e.g.,MDA (tenamfetamine) ,MDMA (midomafetamine) ,MDOH ,MMDA )Piperazines (e.g.,TFMPP )PNU-22394 Ro60-0175 Serotonin (5-HT) Tryptamines (e.g.,5-BT ,5-CT ,5-MT ,α-Me-5-HT ,bufotenin ,DET ,DiPT ,DMT ,DPT ,psilocin ,psilocybin ,tryptamine )Antagonists: Agomelatine Atypical antipsychotics (e.g.,amisulpride ,aripiprazole ,asenapine ,brexpiprazole ,cariprazine ,clozapine ,N-desalkylquetiapine (norquetiapine) ,N-desmethylclozapine (norclozapine) ,olanzapine ,pipamperone ,quetiapine ,risperidone ,ziprasidone )Cyproheptadine EGIS-7625 Ergolines (e.g.,amesergide ,bromocriptine ,lisuride ,LY-53857 ,LY-272015 ,mesulergine )Ketanserin LY-393558 mCPP Metadoxine Metitepine (methiothepin) Pirenperone Pizotifen Propranolol PRX-08066 Rauwolscine Ritanserin RS-127445 Sarpogrelate SB-200646 SB-204741 SB-206553 SB-215505 SB-221284 SB-228357 SDZ SER-082 Tegaserod Tetracyclic antidepressants (e.g.,amoxapine ,mianserin ,mirtazapine )Trazodone Typical antipsychotics (e.g.,chlorpromazine )TIK-301 Yohimbine
5-HT2C
Agonists: 2Cs (e.g.,2C-B ,2C-E ,2C-I ,2C-T-2 ,2C-T-7 ,2C-T-21 )5-Methoxytryptamines (5-MeO-DET ,5-MeO-DiPT ,5-MeO-DMT ,5-MeO-DPT ,5-MT )α-Alkyltryptamines (e.g.,5-Cl-αMT ,5-Fl-αMT ,5-MeO-αET ,5-MeO-αMT ,α-Me-5-HT ,αET ,αMT )A-372159 AL-38022A Alstonine CP-809101 Dimemebfe DOx (e.g.,DOB ,DOC ,DOI ,DOM )Ergolines (e.g.,ALD-52 ,cabergoline ,dihydroergotamine ,ergine (LSA) ,ergotamine ,lisuride ,LA-SS-Az ,LSB ,LSD ,LSD-Pip ,LSH ,LSP ,pergolide )Flumexadol Lorcaserin MDxx (e.g.,MDA (tenamfetamine) ,MDMA (midomafetamine) ,MDOH ,MMDA )MK-212 ORG-12962 ORG-37684 Oxaflozane PHA-57378 Phenethylamines (e.g.,lophophine ,mescaline )Piperazines (e.g.,aripiprazole ,BZP ,mCPP ,quipazine ,TFMPP )PNU-22394 PNU-181731 Ro60-0175 Ro60-0213 Serotonin (5-HT) Tryptamines (e.g.,5-BT ,5-CT ,bufotenin ,DET ,DiPT ,DMT ,DPT ,psilocin ,psilocybin ,tryptamine )Vabicaserin WAY-629 WAY-161503 YM-348 Antagonists: Adatanserin Agomelatine Atypical antipsychotics (e.g.,asenapine ,clorotepine ,clozapine ,fluperlapine ,iloperidone ,melperone ,olanzapine ,paliperidone ,quetiapine ,risperidone ,sertindole ,ziprasidone ,zotepine )Captodiame CEPC Cinanserin Cyproheptadine Deramciclane Desmetramadol Dotarizine Eltoprazine Ergolines (e.g.,amesergide ,bromocriptine ,LY-53857 ,LY-215840 ,mesulergine ,metergoline ,methysergide ,sergolexole )Etoperidone Fluoxetine FR-260010 Irindalone Ketanserin Ketotifen Latrepirdine (dimebolin) Medifoxamine Metitepine (methiothepin) Nefazodone Pirenperone Pizotifen Propranolol Ritanserin RS-102221 S-14671 SB-200646 SB-206553 SB-221284 SB-228357 SB-242084 SB-243213 SDZ SER-082 Tedatioxetine Tetracyclic antidepressants (e.g.,amoxapine ,aptazapine ,esmirtazapine ,maprotiline ,mianserin ,mirtazapine )TIK-301 Tramadol Trazodone Tricyclic antidepressants (e.g.,amitriptyline ,nortriptyline )Typical antipsychotics (e.g.,chlorpromazine ,loxapine ,pimozide ,pipamperone ,thioridazine )Xylamidine
5-HT3 –7
5-HT3
Agonists: Alcohols (e.g.,butanol ,ethanol (alcohol) ,trichloroethanol )m-CPBG Phenylbiguanide Piperazines (e.g.,BZP ,mCPP ,quipazine )RS-56812 Serotonin (5-HT) SR-57227 SR-57227A Tryptamines (e.g.,2-Me-5-HT ,5-CT ,bufotenidine (5-HTQ) )Volatiles/gases (e.g.,halothane ,isoflurane ,toluene ,trichloroethane )YM-31636 Antagonists: Alosetron Anpirtoline Arazasetron AS-8112 Atypical antipsychotics (e.g.,clozapine ,olanzapine ,quetiapine )Azasetron Batanopride Bemesetron (MDL-72222) Cilansetron CSP-2503 Dazopride Dolasetron Galanolactone Granisetron Lerisetron Memantine Ondansetron Palonosetron Ramosetron Renzapride Ricasetron Tedatioxetine Tetracyclic antidepressants (e.g.,amoxapine ,mianserin ,mirtazapine )Thujone Tropanserin Tropisetron Typical antipsychotics (e.g.,loxapine )Volatiles/gases (e.g.,nitrous oxide ,sevoflurane ,xenon )Vortioxetine Zacopride Zatosetron
5-HT4
5-HT5A
5-HT6
Agonists: Ergolines (e.g.,dihydroergocryptine ,dihydroergotamine ,ergotamine ,lisuride ,LSD ,mesulergine ,metergoline ,methysergide )Hypidone Serotonin (5-HT) Tryptamines (e.g.,2-Me-5-HT ,5-BT ,5-CT ,5-MT ,Bufotenin ,E-6801 ,E-6837 ,EMD-386088 ,EMDT ,LY-586713 ,N-Me-5-HT ,ST-1936 ,tryptamine )WAY-181187 WAY-208466 Antagonists: ABT-354 Atypical antipsychotics (e.g.,aripiprazole ,asenapine ,clorotepine ,clozapine ,fluperlapine ,iloperidone ,olanzapine ,tiospirone )AVN-101 AVN-211 AVN-322 AVN-397 BGC20-760 BVT-5182 BVT-74316 Cerlapirdine EGIS-12233 GW-742457 Idalopirdine Ketanserin Landipirdine Latrepirdine (dimebolin) Masupirdine Metitepine (methiothepin) MS-245 PRX-07034 PZKKN-94 Ritanserin Ro 04-6790 Ro 63-0563 SB-258585 SB-271046 SB-357134 SB-399885 SB-742457 Tetracyclic antidepressants (e.g.,amoxapine ,mianserin )Tricyclic antidepressants (e.g.,amitriptyline ,clomipramine ,doxepin ,nortriptyline )Typical antipsychotics (e.g.,chlorpromazine ,loxapine )
5-HT7
Antagonists: Atypical antipsychotics (e.g.,amisulpride ,aripiprazole ,asenapine ,brexpiprazole ,clorotepine ,clozapine ,fluperlapine ,olanzapine ,risperidone ,sertindole ,tiospirone ,ziprasidone ,zotepine )Butaclamol DR-4485 EGIS-12233 Ergolines (e.g.,2-Br-LSD (BOL-148) ,amesergide ,bromocriptine ,cabergoline ,dihydroergotamine ,ergotamine ,LY-53857 ,LY-215840 ,mesulergine ,metergoline ,methysergide ,sergolexole )JNJ-18038683 Ketanserin LY-215840 Metitepine (methiothepin) Ritanserin SB-258719 SB-258741 SB-269970 SB-656104 SB-656104A SB-691673 SLV-313 SLV-314 Spiperone SSR-181507 Tetracyclic antidepressants (e.g.,amoxapine ,maprotiline ,mianserin ,mirtazapine )Tricyclic antidepressants (e.g.,amitriptyline ,clomipramine ,imipramine )Typical antipsychotics (e.g.,acetophenazine ,chlorpromazine ,chlorprothixene ,fluphenazine ,loxapine ,pimozide )Vortioxetine
