Chemical compound
Psilocin (also known as 4-HO-DMT , 4-hydroxy DMT , psilocine , psilocyn , or psilotsin ) is a substituted tryptamine alkaloid and a serotonergic psychedelic substance . It is present in most psychedelic mushrooms [3] together with its phosphorylated counterpart psilocybin . Psilocin is a Schedule I drug under the Convention on Psychotropic Substances .[4] Acting on the 5-HT2A receptors, psilocin modulates the production and reuptake of serotonin .[5] The mind-altering effects of psilocin are highly variable and subjective and resemble those of LSD and DMT .
YouTube Encyclopedic
1 / 5
Views: 1 634
16 829
278 042
1 208
982
Psychedelics and their therapeutic potential for mental illness
Magic mushrooms: A magical cure for depression?
Here's Why You Want To Know About Mushrooms and Depression
Psilocin bound to Serotonin Receptors Part 1
4-AcO DMT to Psilocin Mechanism
Chemistry
Psilocin and its phosphorylated cousin, psilocybin , were first isolated and named in 1958 by Swiss chemist Albert Hofmann . Hofmann obtained the chemicals from laboratory-grown specimens of the entheogenic mushroom Psilocybe mexicana . Hofmann also succeeded in finding synthetic routes to these chemicals.[6]
Psilocin can be obtained by dephosphorylation of natural psilocybin under strongly acidic or under alkaline conditions (hydrolysis ). A synthetic route uses the Speeter–Anthony tryptamine synthesis procedure. First, 4-hydroxyindole is Friedel-Crafts -acylated with oxalyl chloride in position 3. The compound is further reacted with dimethylamine , yielding the indole-3-yl-glyoxamide. Finally, this 4-hydroxyindole-3-N,N-dimethylglyoxamide is reduced by lithium aluminum hydride yielding psilocin.[7]
Psilocin is relatively unstable in solution due to its phenolic hydroxy (-OH) group. In the presence of oxygen , it readily forms bluish and dark black degradation products.[8] Similar products are also formed in the presence of oxygen and Fe3+ ions .
Structural analogs
Sulfur analogs are known with a benzothienyl replacement[9] as well as 4-SH -DMT.[10] 1-Methylpsilocin is a functionally 5-HT2C receptor preferring agonist.[11] 4-Fluoro-N ,N -dimethyltryptamine is known.[11] O-Acetylpsilocin (4-AcO-DMT) is the ester of acetic acid with psilocin. Additionally, replacement of a methyl group at the dimethylated nitrogen with an isopropyl or ethyl group yields 4-HO-MIPT (4-hydroxy-N -methyl-N -isopropyltryptamine) and 4-HO-MET (4-hydroxy-N -methyl-N -ethyltryptamine), respectively. 4-Acetoxy-MET (4-Acetoxy-N-methyl-N-ethyltryptamine), also known as 4-AcO-MET, is the acetate ester of 4-HO-MET, and a homologue of 4-AcO-DMT.
Pharmacology
Psilocin is the pharmacologically active agent in the body after ingestion of psilocybin or some species of psychedelic mushrooms.
Psilocybin is rapidly dephosphorylated in the body to psilocin which acts as a 5-HT2A , 5-HT2C and 5-HT1A agonist or partial agonist . Psilocin exhibits functional selectivity in that it activates phospholipase A2 instead of activating phospholipase C as the endogenous ligand serotonin does. Psilocin is structurally similar to serotonin (5-HT),[12] differing only by the hydroxyl group being on the 4-position rather than the 5 and the dimethyl groups on the nitrogen . Its effects are thought to come from its agonist activity at 5-HT2A serotonin receptors in the prefrontal cortex .
Psilocin has no significant effect on dopamine receptors (unlike LSD ) and only affects the noradrenergic system at very high dosages.[13]
Psilocin's half-life ranges from 1 to 3 hours.[2]
Behavioral and non-behavioral effects
Dried psilocybin mushrooms . (Notice the characteristic blue bruising by the stems of the mushrooms.)
Its physiological effects are similar to a sympathetic arousal state. Specific effects observed after ingestion can include but are not limited to tachycardia , dilated pupils, restlessness or arousal, euphoria , open and closed eye visuals (common at medium to high doses), synesthesia (e.g. hearing colours and seeing sounds), increased body temperature , headache , sweating and chills, and nausea . Psilocin acts as a 5-HT2A, 5-HT2C, and 5-HT1A receptor agonist or partial agonist. Such receptors are claimed to significantly regulate visuals, decision making, mood, decreased blood pressure, and heart rate.[12]
There has been no direct lethality associated with psilocin.[12] [14] There has been no reported withdrawal syndrome when chronic use of this drug is ceased.[12] [15] There is cross tolerance among psilocin, mescaline , LSD ,[12] [16] and other 5-HT2A , 5-HT2C , and 5-HT1A agonists due to down-regulation of these receptors.
Legal status
The United Nations Convention on Psychotropic Substances (adopted in 1971) requires its members to prohibit psilocybin, and parties to the treaty are required to restrict the use of the drug to medical and scientific research under strictly controlled conditions.
Australia
Psilocin is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[17] A Schedule 9 substance is a substance 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.[17]
Russia
Psilocin and psilocybin are banned in Russia, due to their status as narcotic drugs, with a criminal penalty for possession of more than 50 mg.[18]
See also
References
^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27 .
^ a b Tylš F, Páleníček T, Horáček J (March 2014). "Psilocybin--summary of knowledge and new perspectives". European Neuropsychopharmacology . 24 (3): 342–356. doi :10.1016/j.euroneuro.2013.12.006 . PMID 24444771 . S2CID 10758314 .
^ Gotvaldová K, Borovička J, Hájková K, Cihlářová P, Rockefeller A, Kuchař M (November 2022). "Extensive Collection of Psychotropic Mushrooms with Determination of Their Tryptamine Alkaloids" . International Journal of Molecular Sciences . 23 (22): 14068. doi :10.3390/ijms232214068 . PMC 9693126 . PMID 36430546 .
^ "List of psychotropic substances under international control" (PDF) (23rd ed.). Vienna Austria: International Narcotics Control Board . August 2003. Archived from the original (PDF) on 4 February 2012. Retrieved 2012-10-11 .
^ Madsen MK, Fisher PM, Burmester D, Dyssegaard A, Stenbæk DS, Kristiansen S, et al. (June 2019). "Psychedelic effects of psilocybin correlate with serotonin 2A receptor occupancy and plasma psilocin levels" . Neuropsychopharmacology . 44 (7): 1328–1334. doi :10.1038/s41386-019-0324-9 . PMC 6785028 . PMID 30685771 .
^ Hofmann A, Heim R, Brack A, Kobel H, Frey A, Ott H, Petrzilka T, Troxler F (1959). "Psilocybin und Psilocin, zwei psychotrope Wirkstoffe aus mexikanischen Rauschpilzen" [Psilocybin and psilocin, two psychotropic substances in Mexican magic mushrooms]. Helvetica Chimica Acta (in German). 42 (5): 1557–72. doi :10.1002/hlca.19590420518 .
^ Kargbo RB, Sherwood A, Walker A, Cozzi NV, Dagger RE, Sable J, et al. (July 2020). "Direct Phosphorylation of Psilocin Enables Optimized cGMP Kilogram-Scale Manufacture of Psilocybin" . ACS Omega . 5 (27): 16959–16966. doi :10.1021/acsomega.0c02387 . PMC 7364850 . PMID 32685866 . S2CID 220599227 .
^ Lenz C, Wick J, Braga D, García-Altares M, Lackner G, Hertweck C, et al. (January 2020). "Injury-Triggered Blueing Reactions of Psilocybe "Magic" Mushrooms" . Angewandte Chemie . 59 (4): 1450–1454. doi :10.1002/anie.201910175 . PMC 7004109 . PMID 31725937 .
^ Chapman NB, Scrowston RM, Sutton TM (1972). "Synthesis of the sulphur analogue of psilocin and some related compounds" . Journal of the Chemical Society, Perkin Transactions 1 : 3011–15. doi :10.1039/P19720003011 .
^ CH 421960 , Hofmann A, Troxler F, issued 1967 ; CA 68:95680n
^ a b Sard H, Kumaran G, Morency C, Roth BL , Toth BA, He P, Shuster L (October 2005). "SAR of psilocybin analogs: discovery of a selective 5-HT 2C agonist". Bioorganic & Medicinal Chemistry Letters . 15 (20): 4555–4559. doi :10.1016/j.bmcl.2005.06.104 . PMID 16061378 .
^ a b c d e Diaz J (1996). How Drugs Influence Behavior: A Neurobehavioral Approach . Englewood Cliffs: Prentice Hall. ISBN 978-0-02-328764-0 .
^ Jerome L (March–April 2007). "Psilocybin Investigator's Brochure" (PDF) . Retrieved 2012-10-11 .
^ Garcia-Romeu A, Kersgaard B, Addy PH (August 2016). "Clinical applications of hallucinogens: A review" . Experimental and Clinical Psychopharmacology . 24 (4): 229–68. doi :10.1037/pha0000084 . PMC 5001686 . PMID 27454674 .
^ Assessing Drug Risks: A Scientific Framework . European Monitoring Centre for Drugs and Drug Addiction. Luxembourg: EMCDDA. 2016.
^ Nichols DE (April 2016). "Psychedelics" . Pharmacological Reviews . 68 (2): 264–355. doi :10.1124/pr.115.011478 . PMC 4813425 . PMID 26841800 .
^ a b "Poisons Standard" . Therapeutics Goods Administration, Department of Health . Australian Government. October 2015.
^ "On approval of significant, large and particularly large amounts of narcotic drugs and psychotropic substances, as well as significant, large and particularly large sizes for plants containing narcotic drugs or psychotropic substances, or parts thereof, containing narcotic drugs or psychotropic substances for the purposes of articles 228, 228.1, 229 and 229.1 of the Criminal Code of the Russian Federation (as amended) (translated)" . Resolution of the Government of the Russian Federation . Criminal Code of the Russian Federation. 1 October 2012. 1002. Retrieved 1 April 2018 .
External links
Psychedelics (5-HT2A agonists)
Benzofurans Lyserg‐ amides Phenethyl‐ amines
2C-x 25x -NBx
25x -NB 25x -NB3OMe
25B-NB3OMe
25C-NB3OMe
25D-NB3OMe
25E-NB3OMe
25H-NB3OMe
25I-NB3OMe
25N-NB3OMe
25P-NB3OMe
25T2-NB3OMe
25T4-NB3OMe
25T7-NB3OMe
25TFM-NB3OMe
25x -NB4OMe
25B-NB4OMe
25C-NB4OMe
25D-NB4OMe
25E-NB4OMe
25H-NB4OMe
25I-NB4OMe
25N-NB4OMe
25P-NB4OMe
25T2-NB4OMe
25T4-NB4OMe
25T7-NB4OMe
25TFM-NB4OMe
25x -NBF 25x -NBMD
25B-NBMD
25C-NBMD
25D-NBMD
25E-NBMD
25F-NBMD
25H-NBMD
25I-NBMD
25P-NBMD
25T2-NBMD
25T7-NBMD
25TFM-NBMD
25x -NBOH 25x -NBOMe Atypical structures
25x -NMx
25B-NMe7BF
25B-NMe7BT
25B-NMe7Bim
25B-NMe7Box
25B-NMe7DHBF
25B-NMe7Ind
25B-NMe7Indz
25B-NMePyr
25I-NMe7DHBF
25I-NMeFur
25I-NMeTHF
25I-NMeTh
N-(2C)-fentanyl
N-(2C-B) fentanyl
N-(2C-C) fentanyl
N-(2C-D) fentanyl
N-(2C-E) fentanyl
N-(2C-G) fentanyl
N-(2C-H) fentanyl
N-(2C-I) fentanyl
N-(2C-IP) fentanyl
N-(2C-N) fentanyl
N-(2C-P) fentanyl
N-(2C-T) fentanyl
N-(2C-T-2) fentanyl
N-(2C-T-4) fentanyl
N-(2C-T-7) fentanyl
N-(2C-TFM) fentanyl
3C-x 4C-x DOx HOT-x MDxx Mescaline (subst.) TMAs
TMA
TMA-2
TMA-3
TMA-4
TMA-5
TMA-6
Others
Piperazines Tryptamines
alpha -alkyltryptaminesx -DALT x -DET x -DiPT x -DMT
4,5-DHP-DMT
2,N,N-TMT
4-AcO-DMT
4-HO-5-MeO-DMT
4,N,N-TMT
4-Propionyloxy-DMT
5,6-diBr-DMT
5-AcO-DMT
5-Bromo-DMT
5-MeO-2,<i>N</i>,<i>N</i>-TMT
5-MeO-4,<i>N</i>,<i>N</i>-TMT
5-MeO-α,N,N-TMT
5-MeO-DMT
5-N ,N -TMT
7,N,N-TMT
α,N,N-TMT
(Bufotenin) 5-HO-DMT
DMT
Norbaeocystin
(Psilocin) 4-HO-DMT
(Psilocybin) 4-PO-DMT
x -DPT Ibogaine-related x -MET x -MiPT Others
Others
Dissociatives (NMDAR antagonists )
Deliriants (mAChR antagonists ) Others
1-Methylpsilocin
2,alpha-DMT
2-Me-DET
2-Methyl-5-HT
2,N,N-TMT
4,5-DHP-DMT
4,5-MDO-DMT
4,5-MDO-DiPT
4-AcO-DALT
4-AcO-DET
4-AcO-DMT
4-AcO-DiPT
4-AcO-EPT
4-AcO-NMT
4-AcO-MALT
4-AcO-MET
4-AcO-DPT
4-AcO-MiPT
4-F-5-MeO-DMT
4-HO-5-MeO-DMT
4-HO-DALT
4-HO-DBT
4-HO-DET
4-HO-DiPT
4-HO-DPT
4-HO-DSBT
4-HO-EPT
4-HO-MALT
4-HO-MET
4-HO-McPT
4-HO-McPeT
4-HO-MiPT
4-HO-MPMI
4-HO-MPT
4-HO-MsBT
4-HO-NMT
4-HO-PiPT
4-HO-pyr-T
4-HO-αMT
4-Me-αET
4-Me-αMT
4-MeO-DiPT
4-MeO-DMT
4-MeO-MiPT
4-PrO-DMT
5,6-MeO-MiPT
5,6-MDO-DiPT
5,6-MDO-DMT
5,6-MDO-MiPT
5,7-Dihydroxytryptamine
5-BT
5-Bromo-DMT
5-CT
5-Chloro-αMT
5-Chloro-DMT
5-Ethoxy-αMT
5-Ethoxy-DMT
5-Ethyl-DMT
5-Fluoro-AET
5-Fluoro-αMT
5-Fluoro-DET
5-Fluoro-DMT
5-Fluoro-EPT
5-Fluoro-MET
5-HO-αMT
5-HO-DiPT
5-HTP
5-iPrO-AMT
5-MeS-DMT
5-Methoxytryptamine
5-MeO-7,N,N-TMT
5-Methyl-αET
5-MeO-2-TMT
5-MeO-αET
5-MeO-αMT
5-MeO-DALT
5-MeO-DBT
5-MeO-DET
5-MeO-DiPT
5-MeO-DMT
5-MeO-DPT
5-MeO-EiPT
5-MeO-EPT
5-MeO-MALT
5-MeO-MET
5-MeO-MiPT
5-MeO-MPMI
5-MeO-NMT
5-MeO-pyr-T
5-MeO-NBpBrT
5-Methyl-DMT
5-(Nonyloxy)tryptamine
6-Fluoro-αMT
6-Fluoro-DMT
6-Hydroxymelatonin
6-MeO-THH
7-Chloro-AMT
7-Methyl-α-ethyltryptamine
7-Methyl-DMT
Acetryptine
Aeruginascin
αET
Alpha,N-DMT
α,N,N-Trimethyltryptamine
Alpha,N,O-TMS
AL-37350A
αMT
Baeocystin
BNC-210
Bufotenidine
Bufotenin (5-HO-DMT)
BW-723C86
Convolutindole A
CP-132,484
DALT
DBT
Desformylflustrabromine
DET
DiPT
DPT
E-6801
E-6837
Ethocybin
EiPT
EMDT
EPT
FGIN-127
FGIN-143
Harmaline
HIOC
Ibogaine
Idalopirdine
Indorenate
Iprocin
Lespedamine
Luzindole
MET
Methylbutyltryptamine
MiPT
MPT
Miprocin
Melatonin
MPMI
MS-245
NAS
N-Ethyltryptamine
N-Feruloylserotonin
NMT
DMT
Norbaeocystin
Normelatonin
N-t-Butyltryptamine
O-4310
Oxypertine
Plakohypaphorine
PiPT
Psilocin (4-HO-DMT)
Psilocybin (4-PO-DMT)
Pyr-T
Rizatriptan
RU-28306
Serotonin
ST-1936
Sumatriptan
Tryptamine
Tryptophan
Yohimbine
Yuremamine
Zolmitriptan
5-HT1
5-HT1A
Agonists: 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-11,461
F-12826
F-13714
F-14679
F-15063
F-15,599
Flesinoxan
Flibanserin
Flumexadol
Hypidone
Lesopitron
LY-293284
LY-301317
mCPP
MKC-242
Naluzotan
NBUMP
Osemozotan
Oxaflozane
Pardoprunox
Piclozotan
Rauwolscine
Repinotan
Roxindole
RU-24,969
S-14,506
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
U-92,016-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-7,378
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-649,915
SDZ 216-525
Spiperone
Spiramide
Spiroxatrine
UH-301
WAY-100135
WAY-100635
Xylamidine
5-HT1B
Agonists: Anpirtoline
CGS-12066A
CP-93129
CP-94253
CP-122,288
CP-135807
Eltoprazine
Ergolines (e.g., bromocriptine , dihydroergotamine , ergotamine , methylergometrine (methylergonovine) , methysergide , pergolide )
mCPP
RU-24,969
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-122,288
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-215,840 , 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-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
This page was last edited on 29 February 2024, at 13:02