Template:Distinguish2
3,4-MethylenedioxyamphetamineINN : Tenamfetamine Routes of administration Oral, sublingual, insufflation, intravenous ATC code Legal status
Metabolism Hepatic (CYP extensively involved)Excretion Renal
1-(2H -1,3-Benzodioxol-5-yl)propan-2-amine
CAS Number PubChem CID DrugBank ChemSpider UNII ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.230.706 Formula C 10 H 13 N O 2 Molar mass 179.22 g/mol g·mol−1 3D model (JSmol )
InChI=1S/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3
Y Key:NGBBVGZWCFBOGO-UHFFFAOYSA-N
Y
N Y (what is this?) (verify)
3,4-Methylenedioxyamphetamine (MDA ), is an empathogen-entactogen , psychostimulant , and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug . In terms of pharmacology , MDA acts most importantly as a serotonin-norepinephrine-dopamine releasing agent (SNDRA). Due to its euphoriant and hallucinogenic effects, the drug is a controlled substance and its possession and sale are illegal in most countries.
MDA is rarely sought after as a recreational drug compared to other drugs in the amphetamine family, however it remains an important and widely used drug due to it being a primary metabolite,[1] the product of hepatic N-dealkylation,[2] of MDMA (ecstasy), In addition, it's not uncommon to find MDA as an adulterant of illicitly bought MDMA.[3] [4]
Uses
Medical MDA currently has no accepted medical use.
Recreational Although illegal, MDA is bought, sold, and used as a recreational 'love drug', due to its enhancement of mood and empathy .[5] A recreational dose of MDA is commonly between 100 and 160 mg.[6]
Adverse effects MDA produces serotonergic neurotoxic effects,[7] [8] thought to be activated by initial metabolism of MDA.[2] In addition, MDA activates a response of the neuroglia , though this subsides after use.[7]
Overdose
Symptoms of acute toxicity may include agitation , sweating , increased blood pressure and heart rate , dramatic increase in body temperature , convulsions , and death . Death is usually caused by cardiac effects and subsequent hemorrhaging in the brain (stroke ).[9]
Interactions This section needs expansion. You can help by
adding to it . (April 2017)
Pharmacology
Pharmacodynamics MDA is a substrate of the serotonin , norepinephrine , dopamine , and vesicular monoamine transporters , as well as a TAAR1 agonist ,[10] [11] and for these reasons acts as a reuptake inhibitor and releasing agent of serotonin , norepinephrine , and dopamine (that is, it is an SNDRA Tooltip serotonin-norepinephrine-dopamine releasing agent ).[12] It is also an agonist of the serotonin 5-HT2A ,[13] 5-HT2B ,[14] and 5-HT2C receptors [15] and shows affinity for the α2A - , α2B - , and α2C -adrenergic receptors and serotonin 5-HT1A and 5-HT7 receptors .[16]
The (S )-optical isomer of MDA is more potent than the (R )-optical isomer as a psychostimulant, possessing greater affinity for the three monoamine transporters .
In terms of the subjective and behavioral effects of MDA, it is thought that serotonin release is required for its empathogen-entactogen effects, release of dopamine and norepinephrine is responsible for its psychostimulant effects, dopamine release is necessary for its euphoriant (rewarding and addictive ) effects, and direct agonism of the serotonin 5-HT2A receptor is causative of its psychedelic effects.[medical citation needed ]
Comparison with MDMA
The effect on serotonin may explain the similar entactogenic effects of MDMA and MDA. However, (S )-MDA has higher potency as an agonist of the 5-HT2A receptor than (R )-MDMA; thus MDA tends to cause more psychedelic-like effects, such as visual hallucinations . MDMA can also produce psychedelic-like visual effects, though these are generally less pronounced than those of MDA or require higher doses to become apparent. Relative to MDMA, MDA is also a more potent releasing agent of norepinephrine and dopamine and hence is more stimulating in comparison. In addition, MDA is notably several-fold more neurotoxic to serotonergic neurons in comparison to MDMA.
Pharmacokinetics The duration of the drug has been reported as about 6 to 8 hours.[6]
Chemistry MDA is a substituted methylenedioxyated phenethylamine and amphetamine derivative . In relation to other phenethylamines and amphetamines, it is the 3,4-methylenedioxy, α-methyl derivative of β-phenylethylamine , the 3,4-methylenedioxy derivative of amphetamine , and the N -demethyl derivative of MDMA.
Synonyms In addition to 3,4-methylenedioxyamphetamine , MDA is also known by other chemical synonyms such as the following:
α-Methyl-3,4-methylenedioxy-β-phenylethylamine
1-(3,4-Methylenedioxyphenyl)-2-propanamine
1-(1,3-Benzodioxol-5-yl)-2-propanamine
Synthesis MDA is typically synthesized from essential oils such as safrole or piperonal . Common approaches from these precursors include:
Detection in body fluids MDA may be quantitated in blood, plasma or urine to monitor for use, confirm a diagnosis of poisoning or assist in the forensic investigation of a traffic or other criminal violation or a sudden death. Some drug abuse screening programs rely on hair, saliva, or sweat as specimens. Most commercial amphetamine immunoassay screening tests cross-react significantly with MDA and major metabolites of MDMA, but chromatographic techniques can easily distinguish and separately measure each of these substances. The concentrations of MDA in the blood or urine of a person who has taken only MDMA are, in general, less than 10% those of the parent drug.[26] [27] [28]
Derivatives MDA constitutes part of the core structure of the β-adrenergic receptor agonist protokylol .
History MDA was first synthesized by C. Mannich and W. Jacobsohn in 1910.[20] It was first ingested in July 1930 by Gordon Alles who later licensed the drug to Smith, Kline & French .[29] MDA was first used in animal tests in 1939, and human trials began in 1941 in the exploration of possible therapies for Parkinson's disease . From 1949 to 1957, more than 500 human subjects were given MDA in an investigation of its potential use as an antidepressant and/or anorectic by Smith, Kline & French . The United States Army also experimented with the drug, code named EA-1298, while working to develop a truth drug or incapacitating agent. Harold Blauer [30] died in January 1953 after being intravenously injected, without his knowledge nor consent, with 450 mg of the drug as part of Project MKUltra . MDA was patented as a cough suppressant by H. D. Brown in 1958, as an ataractic by Smith, Kline & French in 1960, and as an anorectic under the trade name "Amphedoxamine" in 1961. MDA began to appear on the recreational drug scene around 1963 to 1964. It was then inexpensive and readily available as a research chemical from several scientific supply houses. Several researchers, including Claudio Naranjo and Richard Yensen, have explored MDA in the field of psychotherapy .[31] [32]
Society and culture
Name When MDA was under development as a potential pharmaceutical drug, it was given the INN tenamfetamine .
Legal status
Australia MDA is schedule 9 prohibited substance under the Poisons Standards .[33] A schedule 9 substance is listed as a "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities."[33]
United States MDA is a Schedule I controlled substance in the US.
Research In 2010, the ability of MDA to invoke mystical experiences and alter vision in healthy volunteers was studied.[6]
References
^ Crean, R. D.; Davis, S. A.; Von Huben, S. N.; Lay, C. C.; Katner, S. N.; Taffe, M. A. (13 October 2006). "Effects of (±)3,4-methylenedioxymethamphetamine, (±)3,4-methylenedioxyamphetamine and methamphetamine on temperature and activity in rhesus macaques" . Neuroscience . 142 (2): 515–525. doi :10.1016/j.neuroscience.2006.06.033 . PMC 1853374 . PMID 16876329 .
^ a b de la Torre, R; Farre, M; Roset, Pn; Pizzaro, N; Abanades, S; Segura, M; Segura, M; Camí, J (2004). "Human pharmacology of MDMA: pharmacokinetics, metabolism, and disposition" . Therapeutic Drug Monitoring . 26 : 137–144. doi :10.1097/00007691-200404000-00009 .
^ EcstasyData.org. "EcstasyData.org: Test Result Statistics: Substances by Year" . www.ecstasydata.org . Retrieved 27 June 2017 .
^ "Trans European Drug Information" . idpc.net . Retrieved 27 June 2017 .
^ Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE (1993). "Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine". Journal of Medicinal Chemistry . 36 (23): 3700–3706. doi :10.1021/jm00075a027 . PMID 8246240 .
^ a b c Baggott, MJ; Siegrist, JD; Galloway, GP; Robertson, LC; Coyle, JR; Mendelson, JE. "Investigating the Mechanisms of Hallucinogen-Induced Visions Using 3,4-Methylenedioxeamphetamine (MDA): A Randomized Controlled Trial in Humans" . PLOS ONE . 5 : e14074. doi :10.1371/journal.pone.0014074 . PMC 2996283 . PMID 21152030 . ((cite journal ))
: CS1 maint: unflagged free DOI (link )
^ a b Herndon, Joseph M.; Cholanians, Aram B.; Lau, Serrine S.; Monks, Terrence J. (March 2014). "Glial Cell Response to 3,4-(±)-Methylenedioxymethamphetamine and Its Metabolites" . Toxicological Sciences . 138 (1): 130–138. doi :10.1093/toxsci/kft275 . ISSN 1096-6080 . PMC 3930364 . PMID 24299738 .
^ Kalant, Harold (2 October 2001). "The pharmacology and toxicology of "ecstasy" (MDMA) and related drugs" . CMAJ: Canadian Medical Association Journal . 165 (7): 917–928. ISSN 0820-3946 . PMC 81503 . PMID 11599334 .
^ Diaz, Jaime. How Drugs Influence Behavior. Englewood Cliffs: Prentice Hall, 1996.
^ Lewin AH, Miller GM, Gilmour B (December 2011). "Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class" . Bioorg. Med. Chem . 19 (23): 7044–8. doi :10.1016/j.bmc.2011.10.007 . PMC 3236098 . PMID 22037049 .
^ Wallach, J.V. (2009). "Endogenous hallucinogens as ligands of the trace amine receptors: A possible role in sensory perception". Medical Hypotheses . 72 (1): 91–94. doi :10.1016/j.mehy.2008.07.052 . ISSN 0306-9877 . PMID 18805646 .
^ Rothman RB, Baumann MH (2006). "Therapeutic potential of monoamine transporter substrates" . Curr Top Med Chem . 6 (17): 1845–59. doi :10.2174/156802606778249766 . PMID 17017961 .
^ Giuseppe Di Giovanni; Vincenzo Di Matteo; Ennio Esposito (2008). Serotonin-dopamine Interaction: Experimental Evidence and Therapeutic Relevance . Elsevier. pp. 294–. ISBN 978-0-444-53235-0 .
^ Rothman, Richard B; Baumann, Michael H (2009). "Serotonergic drugs and valvular heart disease" . Expert Opinion on Drug Safety . 8 (3): 317–329. doi :10.1517/14740330902931524 . ISSN 1474-0338 . PMC 2695569 . PMID 19505264 .
^ Nash JF, Roth BL, Brodkin JD, Nichols DE, Gudelsky GA (1994). "Effect of the R(-) and S(+) isomers of MDA and MDMA on phosphatidyl inositol turnover in cultured cells expressing 5-HT2A or 5-HT2C receptors". Neurosci. Lett . 177 (1–2): 111–5. doi :10.1016/0304-3940(94)90057-4 . PMID 7824160 .
^ Manzoni, Olivier Jacques; Ray, Thomas S. (2010). "Psychedelics and the Human Receptorome" . PLoS ONE . 5 (2): e9019. doi :10.1371/journal.pone.0009019 . ISSN 1932-6203 . PMC 2814854 . PMID 20126400 . ((cite journal ))
: CS1 maint: unflagged free DOI (link )
^ Muszynski, I.E. (1961). "Production of some amphetamine derivatives". Acta poloniae pharmaceutica . 18 : 471–478. PMID 14477621 .
^ a b c Shulgin, Alexander; Manning, Tania; Daley, Paul (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds (1st ed.). Berkeley, CA: Transform Press. p. 165. ISBN 9780963009630 .
^ Noggle, FT Jr; DeRuiter, J.; Long, MJ. (1986). "Spectrophotometric and liquid chromatographic identification of 3,4-methylenedioxyphenylisopropylamine and its N-methyl and N-ethyl homologs". Journal Association of Official Analytical Chemists . 69 (4): 681–686. PMID 2875058 .
^ a b Mannich, C.; Jacobsohn, W.; Mannich, Hr. C. (1910). "Über Oxyphenyl-alkylamine und Dioxyphenyl-alkylamine". Berichte der deutschen chemischen Gesellschaft . 41 (1): 189–197. doi :10.1002/cber.19100430126 .
^ Ho, Beng-Thong; McIsaac, William M.; An, Rong; Tansey, L. Wayne; Walker, Kenneth E.; Englert Jr., Leo F.; Noel, Michael B. (1970). "Analogs of a-methylphenethylamine". Journal of Medicinal Chemistry . 13 (1): 26–30. doi :10.1021/jm00295a007 . PMID 5412110 .
^ Butterick, John R.; Unrau, A. M. (1974). "Reduction of β-nitrostyrene with sodium bis-(2-methoxyethoxy)-aluminium dihydride. A convenient route to substituted phenylisopropylamines". Journal of the Chemical Society, Chemical Communications . 8 (8): 307–308. doi :10.1039/C39740000307 .
^ Toshitaka, Ohshita; Hiroaka, Ando (1992). "Synthesis of Phenethylamine Derivatives as Hallucinogen" (PDF) . Japanese Journal of Toxicology and Environmental Health . 38 (6): 571–580. Retrieved 20 June 2014 .
^ Shulgin, Alexander; Shulgin, Ann (1991). PiHKAL: A Chemical Love Story . Lafayette, CA: Transform Press. ISBN 9780963009609 .
^ Elks, J.; Hey, D. H. (1943). "7. β-3 : 4-Methylenedioxyphenylisopropylamine". J. Chem. Soc . 0 (0): 15–16. doi :10.1039/JR9430000015 . ISSN 0368-1769 .
^ Kolbrich EA, Goodwin RS, Gorelick DA, Hayes RJ, Stein EA, Huestis MA. Plasma pharmacokinetics of 3,4-methylenedioxymethamphetamine after controlled oral administration to young adults. Ther. Drug Monit. 30: 320–332, 2008.
^ Barnes AJ, De Martinis BS, Gorelick DA, Goodwin RS, Kolbrich EA, Huestis MA (2009). "Disposition of MDMA and metabolites in human sweat following controlled MDMA administration" (PDF) . Clinical Chemistry . 55 (3): 454–62. doi :10.1373/clinchem.2008.117093 . PMC 2669283 . PMID 19168553 .
^ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man , 9th edition, Biomedical Publications, Seal Beach, California, 2011, pp. 1078–1080.
^ "The First MDA trip and the measurement of 'mystical experience' after MDA, LSD, and Psilocybin" . Psychedelic research. 18 July 2008. Archived from the original on 13 July 2012.
^ The History Channel documented details of his death here https://www.youtube.com/watch?v=ySw-0uY4CUA See minute 2:38 onward.
^ Naranjo, C.; Shulgin, A. T.; Sargent, T. (1967). "Evaluation of 3, 4-methylenedioxeamphetamine (MDA) as an adjunct to psychotherapy" . Pharmacology . 17 (4): 359–364. doi :10.1159/000137100 .
^ Yensen, R.; Di Leo, F. B.; Rhead, J. C.; Richards, W. A.; Soskin, R. A.; Turek, B.; Kurland, A. A. (1976). "MDA-assisted psychotherapy with neurotic outpatients: a pilot study". The Journal of Nervous and Mental Disease . 163 (4): 233–245. doi :10.1097/00005053-197610000-00002 . PMID 972325 .
^ a b Poisons Standard (October 2015) https://www.comlaw.gov.au/Details/F2015L01534/Html/Text#_Toc420496379
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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-215,840 , 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)
Bupropion
Cilansetron
CSP-2503
Dazopride
Dolasetron
Galanolactone
Granisetron
Hydroxybupropion
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-12,233
GW-742457
Idalopirdine
Ketanserin
Landipirdine
Latrepirdine (dimebolin)
Masupirdine
Metitepine (methiothepin)
MS-245
PRX-07034
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-12,233
Ergolines (e.g., 2-Br-LSD (BOL-148) , amesergide , bromocriptine , cabergoline , dihydroergotamine , ergotamine , LY-53857, LY-215,840 , mesulergine , metergoline , methysergide , sergolexole )
JNJ-18038683
Ketanserin
LY-215,840
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
TAAR1
TAAR2
Agonists‡
Neutral antagonists
TAAR5
Agonists‡ Neutral antagonists Inverse agonists‡
‡ References for synthetic TAAR1 agonists can be found at TAAR1 or in the associated compound articles. For TAAR2 and TAAR5 agonists and inverse agonists, see TAAR for references.
See also: Receptor/signaling modulators