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Corynanthine

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From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

Corynanthine
Clinical data


Other names	Rauhimbine
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name (16β,17α)-17-hydroxy-yohimban-16-carboxylic acid methyl ester
CAS Number	483-10-3
PubChemCID	92766
IUPHAR/BPS	5345
ChemSpider	83744
UNII	F5Z7C9RK8U
CompTox Dashboard(EPA)	DTXSID401317915
ECHA InfoCard	100.006.901
Chemical and physical data
Formula	C₂₁H₂₆N₂O₃
Molar mass	354.450 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(OC)[C@H]5[C@H]4C[C@H]3c2[nH]c1ccccc1c2CCN3C[C@@H]4CC[C@@H]5O

Corynanthine, also known asrauhimbine, is analkaloid found in theRauvolfia andCorynanthe (includingPausinystalia) genera of plants.^[1]^[2] It is one of the twodiastereoisomers ofyohimbine, the other beingrauwolscine.^[3]^[4] It is also related toajmalicine.

Corynanthine acts as anα₁-adrenergic andα₂-adrenergic receptor antagonist with approximately 10-foldselectivity for the former site over the latter.^[3]^[4] This is in contrast to yohimbine and rauwolscine which have around 30-fold higher affinity for the α₂-adrenergic receptor over the α₁-adrenergic receptor.^[3]^[4] As a result, corynanthine is not astimulant (or anaphrodisiac for that matter), but adepressant, and likely plays a role in theantihypertensive properties ofRauvolfia extracts. Like yohimbine and rauwolscine, corynanthine has also been shown to possess some activity atserotonin receptors.^[5]

References

[edit]

^PHILLIPS DD, CHADHA MS (September 1955). "The alkaloids of Rauwolfia serpentina Benth".Journal of the American Pharmaceutical Association.44 (9):553–67.doi:10.1002/jps.3030440912.PMID 13251932.
^"Alkaloids from Rauvolfia canescens; Pharmaceutical Biology - 39(3):Pages 239-240 - Informa Healthcare".Pharmaceutical Biology.doi:10.1076/phbi.39.3.239.5923.S2CID 85168336.
^^a ^b ^cShepperson NB, Duval N, Massingham R, Langer SZ (November 1981)."Pre- and postsynaptic alpha adrenoceptor selectivity studies with yohimbine and its two diastereoisomers rauwolscine and corynanthine in the anesthetized dog".The Journal of Pharmacology and Experimental Therapeutics.219 (2):540–6.PMID 6270312.
^^a ^b ^cDoxey JC, Lane AC, Roach AG, Virdee NK (February 1984). "Comparison of the alpha-adrenoceptor antagonist profiles of idazoxan (RX 781094), yohimbine, rauwolscine and corynanthine".Naunyn-Schmiedeberg's Archives of Pharmacology.325 (2):136–44.doi:10.1007/bf00506193.PMID 6144048.S2CID 24276613.
^Feuerstein TJ, Hertting G, Jackisch R (May 1985). "Endogenous noradrenaline as modulator of hippocampal serotonin (5-HT)-release. Dual effects of yohimbine, rauwolscine and corynanthine as alpha-adrenoceptor antagonists and 5-HT-receptor agonists".Naunyn-Schmiedeberg's Archives of Pharmacology.329 (3):216–21.doi:10.1007/bf00501871.PMID 2991775.S2CID 19770424.

Sympatholytic (and closely related)antihypertensives (C02)

Sympatholytics
(antagonizeα-adrenergic
vasoconstriction)

Central

α₂-Adrenergic receptor agonists	Clonidine Guanabenz Guanfacine Guanoxabenz Methyldopa^# Tiamenidine^‡
Adrenergic release inhibitors	Bethanidine Bretylium Debrisoquine Guanadrel Guanazodine Guancydine Guanethidine Guanoclor Guanoxan
Imidazoline receptor agonists	Moxonidine Rilmenidine Tolonidine
Ganglion-blocking/nicotinic antagonists	Hexamethonium^‡ Mecamylamine Pentolinium Trimethaphan

Peripheral

Indirect

Monoamine oxidase inhibitors	Pargyline^‡
VMAT inhibitors	Bietaserpine Deserpidine Methoserpidine Reserpine Syrosingopine
Tyrosine hydroxylase inhibitors	Metirosine

Direct

α₁-Adrenergic receptor blockers	Doxazosin Ketanserin Indoramin Prazosin Trimazosin Urapidil
Non-selective α-adrenergic receptor blockers	Phentolamine

Otherantagonists

Serotonin receptor antagonists	Ketanserin Lidanserin
Endothelin receptor antagonists (for PHTooltip Pulmonary hypertension)	dual (Aprocitentan,Bosentan,Macitentan (+tadalafil),Riociguat) selective (Ambrisentan (+tadalafil),Sitaxentan,Sotatercept)

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Adrenergic receptor modulators

α₁

Agonists

Antagonists

α₂

Agonists

Antagonists

Agonists

Antagonists

See also:Receptor/signaling modulators
Dopaminergics
Serotonergics
Monoamine reuptake inhibitors
Monoamine releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins

Serotonin receptor modulators

5-HT₁

5-HT_1A

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-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 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
Unknown/unsorted:Acetryptine Carvedilol Ergolines (e.g.,ergometrine (ergonovine))

5-HT_1B

Agonists:Anpirtoline CGS-12066A CP-93129 CP-94253 CP-122288 CP-135807 Eltoprazine Ergolines (e.g.,bromocriptine,dihydroergotamine,ergotamine,methylergometrine (methylergonovine),methysergide,pergolide) mCPP 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
Antagonists:AR-A000002 Beta blockers (e.g.,alprenolol,carteolol,isamoltane,oxprenolol,penbutolol,propranolol,tertatolol) Elzasonan Ergolines (e.g.,metergoline) GR-127935 Isamoltane LY-393558 Metitepine (methiothepin) SB-216641 SB-224289 SB-236057 Yohimbine
Unknown/unsorted:Ergolines (e.g.,cabergoline,ergometrine (ergonovine),lisuride)

5-HT_1D

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)
Antagonists:Alniditan BRL-15572 Elzasonan Ergolines (e.g.,metergoline) GR-127935 Ketanserin LY-310762 LY-367642 LY-393558 LY-456219 LY-456220 Metitepine (methiothepin) Mianserin Ritanserin Yohimbine Ziprasidone
Unknown/unsorted:Acetryptine Ergolines (e.g.,lisuride,lysergol,pergolide)

5-HT_1E

Agonists:BRL-54443 Ergolines (e.g.,methysergide) Serotonin (5-HT) Triptans (e.g.,eletriptan) Tryptamines (e.g.,tryptamine)
Antagonists:Metitepine (methiothepin)
Unknown/unsorted:Ergolines (e.g.,ergometrine (ergonovine),lysergol,methylergometrine (methylergonovine)

5-HT_1F

Agonists:BRL-54443 CP-122288 Ergolines (e.g.,bromocriptine,lysergol,methylergometrine (methylergonovine)methysergide) Lasmiditan LY-334370 LY-344864 Serotonin (5-HT) Triptans (e.g.,eletriptan,naratriptan,sumatriptan) Tryptamines (e.g.,5-MT)
Antagonists:Metitepine (methiothepin) Mianserin

5-HT₂

5-HT_2A

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
Unknown/unsorted:Ergolines (e.g.,dihydroergotamine,nicergoline)

5-HT_2B

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
Unknown/unsorted:Ergolines (e.g.,ergometrine (ergonovine))

5-HT_2C

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
Unknown/unsorted:Efavirenz Ergolines (e.g.,ergometrine (ergonovine),methylergometrine (methylergonovine))

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
Unknown/unsorted:LY-53857 Piperazines (e.g.,naphthylpiperazine)

5-HT₄

Agonists:5-MT BIMU8 Capeserod Cinitapride Cisapride CJ-033466 Dazopride Metoclopramide Minesapride Mosapride Prucalopride PRX-03140 Renzapride RS-67333 RS-67506 Serotonin (5-HT) Tegaserod Usmarapride Velusetrag Zacopride
Antagonists:GR-113808 GR-125487 L-Lysine Piboserod RS-39604 RS-67532 SB-203186 SB-204070

5-HT_5A

Agonists:Ergolines (e.g.,2-Br-LSD (BOL-148),ergotamine,LSD) Serotonin (5-HT) Tryptamines (e.g.,5-CT) UCSF648 Valerenic acid
Antagonists:Asenapine Latrepirdine (dimebolin) Metitepine (methiothepin) Ritanserin SB-699551 Unknown/unsorted:Ergolines (e.g.,metergoline,methysergide) Piperazines (e.g.,naphthylpiperazine)

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 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)
Unknown/unsorted:Ergolines (e.g.,2-Br-LSD (BOL-148),bromocriptine,lergotrile,pergolide) Piperazines (e.g.,naphthylpiperazine)

5-HT₇

Agonists:8-OH-DPAT AS-19 Bifeprunox E-55888 Ergolines (e.g.,LSD) LP-12 LP-44 LP-211 RU-24969 Sarizotan Serotonin (5-HT) Triptans (e.g.,frovatriptan) Tryptamines (e.g.,5-CT,5-MT,bufotenin,N-Me-5-HT)
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
Unknown/unsorted:Ergolines (e.g.,lisuride,pergolide) Piperazines (e.g.,naphthylpiperazine)

See also:Receptor/signaling modulators
Adrenergics
Dopaminergics
Melatonergics
Monoamine reuptake inhibitors andreleasing agents
Monoamine metabolism modulators
Monoamine neurotoxins

v t e Tryptamines
Tryptamines	1-Methyl-T 2-HO-NMT 2-Methyl-DET 2,N,N-TMT (2-Me-DMT) 3-IAAR 4-Fluoro-DMT 4-Fluoro-T 5-Bromo-DMT 5-Bromo-T 5-Chloro-DMT 5-Chloro-T 5-CT 5-Ethyl-DMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-T 5-Me-MiPT 5-MeS-DMT 5-Methyl-DMT 5-Methyl-T 6-Fluoro-DET 6-Fluoro-DMT 6-Fluoro-T 6-MeO-DMT 6-MeO-T 6-Methyl-T 6,7-DHT 7-Chloro-T 7-MeO-T 7-Methyl-DMT 7-Methyl-T Acetryptine (5-AT) ALiPT Benzotript (4-CB-Trp) BGE Bretisilocin (5-fluoro-MET; GM-2505) Convolutindole A (2,4,6-TBr,1,7-DiMeO-DMT) DALT DBT Desformylflustrabromine DET DiPT DMT DPT E-6801 E-6837 EiPT EPT FGIN-127 FGIN-143 Idalopirdine Lespedamine (1-MeO-DMT) MBT MET MiPT MPT MSBT N-DEAOP-NET N-DEAOP-NMT NBoc-DMT NET/NETP NiPT NMT NSBT NTBT PiPT ST-1936 (2-Me-5-Cl-DMT) Tryptamine (T; indolylethylamine) Tryptophan (Trp) Yuremamine Z2876442907
4-Hydroxytryptamines andesters/ethers	1-Methylpsilocin (CMY-16) 4-AcO-DALT 4-AcO-DET (ethacetin, ethylacybin) 4-AcO-DiPT (ipracetin) 4-AcO-DMT (psilacetin;O-acetylpsilocin) 4-AcO-DPT (depracetin) 4-AcO-EPT 4-AcO-MALT 4-AcO-MET (metacetin) 4-AcO-MiPT (mipracetin) 4-AcO-NMT 4-AcO-TMT 4-HO-5-MeO-T 4-HO-DALT (dalocin) 4-HO-DBT 4-HO-DET (ethocin; CZ-74) 4-HO-DPT (deprocin) 4-HO-DSBT 4-HO-EiBT (eibucin) 4-HO-EPT 4-HO-MALT 4-HO-MET (metocin) 4-HO-McPT 4-HO-McPeT 4-HO-MiPT (miprocin) 4-HO-MPT (meprocin) 4-HO-MsBT 4-HO-NALT 4-HO-NiPT 4-HO-PiPT (piprocin) 4-HO-TMT 4-HT (dinorpsilocin) 4-MeO-DiPT 4-MeO-DMT 4-MeO-MiPT 4-MeO-T 4-PrO-DMT 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT Aeruginascin (4-PO-TMT) Baeocystin (4-PO-NMT) EB-002 (EB-373) Ethocybin (4-PO-DET; CEY-19) Iprocin (4-HO-DiPT) MSP-1014 Norbaeocystin (4-PO-T) Norpsilocin (4-HO-NMT) O-4310 (1-iPrO-6-F-psilocin) Psilocin (4-HO-DMT; CX-59) Psilocybin (4-PO-DMT; CY-39) Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) RE-104 (FT-104; 4-GO-DiPT) RE-109 (4-GO-DMT)
5-Hydroxy- and 5-methoxytryptamines	2-Methyl-5-HT 4-HO-5-MeO-T 4-F-5-MeO-DMT 4,5-DHP-DMT 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Ethoxy-DMT 5-HO-DiPT 5-HO-NiPT 5-HTP (oxitriptan) 5-MeO-2-TMT 5-MeO-34MPEMT 5-MeO-7,N,N-TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (N,N,O-TMS;O-methylbufotenine) 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-NET 5-MeO-NiPT 5-MeO-NMT (O,N-DMS) 5-MeO-PiPT 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine;O-methylserotonin) 5-MeO-T-NBOMe 5-MT-NB3OMe 5-NOT 5,6-DHT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-MeO-MiPT 5,7-DHT Arachidonoyl serotonin BAB Benanserin (BAS; SQ-4788) BGC20-761 Bufotenidine (5-HTQ;N,N,N-TMS) Bufotenin (5-HO-DMT;N,N-DMS; mappine) Bufoviridine (5-SO-DMT) CP-132,484 Cqd 280 Cqd 285 Cqdd 280 EMDT (2-Et-5-MeO-DMT) HIOC Indorenate (TR-3369) Isamide (N-CA-5-MT) L-741604 MS-245 N-DEAOP-5-MeO-NET N-DEAOP-5-MeO-NMT N-Feruloylserotonin (moschamine) Norbufotenin (5-HO-NMT; NMS) O-Acetylbufotenine (5-AcO-DMT) O-Pivalylbufotenine (5-(t-BuCO)-DMT) Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) Serotonin (5-HT)
N-Acetyltryptamines	2-Iodomelatonin 2-Phenylmelatonin 5-Methoxyluzindole 6-Chloromelatonin 6-Fluoromelatonin 6-Hydroxymelatonin 6-Methoxymelatonin 6,7-Dichloro-2-methylmelatonin α-Methylmelatonin Luzindole Melatonin (N-Ac-O-Me-serotonin;N-Ac-5-MeO-T) Normelatonin (N-acetylserotonin; NAS) N-Acetyltryptamine N-Butanoylmelatonin N-Propionylmelatonin Piromelatine TIK-301 (LY-156735)
α-Alkyltryptamines	1-Methyl-AMT 2,α-DMT (2-Me-AMT) 4-HO-αMT (MP-14) 4-Methyl-αET 4-Methyl-αMT (MP-809) 5-Chloro-αET (PAL-526) 5-Chloro-αMT (PAL-542) 5-Fluoro-αET (PAL-545) 5-Fluoro-αMT (PAL-212; PAL-544) 5-Methyl-αET 6-Fluoro-αMT 7-Chloro-αMT 7-Me-αET α-Methyltryptophan (αMTP) α,N-DMT (N-Me-αMT; SKF-7024, Ro 3-1715) α,N,N-TMT (α-Me-DMT; Alpha-N) αET (etryptamine; Monase) αMT (Indopan; IT-290; 3-API; 3-IT) IPAP (α,N-DPT) Soclenicant (BNC-210; Ile–Trp) 5-Hydroxy- and 5-alkoxy-α-alkyltryptamines:1-Pr-5-MeO-AMT 5-Allyloxy-AMT 5-Ethoxy-αMT 5-iPrO-αMT 5-MeO-αET 5-MeO-αMT (α,O-DMS; Alpha-O) α-Methyl-5-HTP α-Methylmelatonin α-Methylserotonin (5-HO-αMT; α-Me-5-HT) α,N,O-TMS (5-MeO-α,N-DMT) α,N,N,O-TeMS (5-MeO-α,N,N-TMT) AL-37350A (4,5-DHP-αMT) BW-723C86 β-Keto-α-alkyltryptamines:BK-5Br-NM-AMT BK-5Cl-NM-AMT BK-5F-NM-AMT BK-NM-AMT
Triptans	Almotriptan Donitriptan Eletriptan Frovatriptan L-694247 Rizatriptan Sumatriptan Zolmitriptan
Cyclized tryptamines	Barettin Bufothionine Ciclindole Cyclic 3-OHM Ergolines andlysergamides (e.g.,LSD) Flucindole Frovatriptan Harmala alkaloids andβ-carbolines (e.g.,6-MeO-THH,9-Me-BC,β-carboline (norharman),harmaline,harmalol,harmane,harmine,pinoline,tetrahydroharmine,tryptoline) Iboga alkaloids (e.g.,ibogaine,ibogamine,noribogaine,tabernanthine) Ibogalogs (e.g.,ibogainalog,ibogaminalog (DM-506),noribogainalog,tabernanthalog) Imidazolylindoles (e.g.,AGH-107,AGH-192,AH-494) LY-266,097 Metralindole O-Methylnordehydrobufotenine Partial ergolines and lysergamides (e.g.,NDTDI,RU-27849,RU-28251,RU-28306,LY-178210,Bay R 1531 (LY-197206),LY-293284,10,11-seco-LSD,10,11-secoergoline (α,N-Pip-T),CT-5252) Pertines (e.g.,alpertine,milipertine,oxypertine,solypertine) PHA-57378 Piperidinylethylindoles (e.g.,Pip-T,indolylethylfentanyl) PNU-22394 Pyrrolidinylethylindoles (e.g.,Pyr-T,4-HO-pyr-T,5-MeO-pyr-T,4-F-5-MeO-pyr-T) Pyrrolidinylmethylindoles (e.g.,MPMI,4-HO-MPMI (lucigenol),5F-MPMI,5-MeO-MPMI,CP-135807,eletriptan) Tetrahydropyridinylindoles (e.g.,RS134-49,RU-28253) Yohimbans (e.g.,yohimbine,rauwolscine,spegatrine,corynanthine,ajmalicine,reserpine,deserpidine,rescinnamine)
Isotryptamines	5-MeO-isoDMT 6-MeO-isoDMT isoAMT (1-API; 1-IT; α-Me-isoT) isoDMT Isotryptamine (isoT) Ro60-0175 VER-3323 Zalsupindole (DLX-001, AAZ-A-154) Cyclized isotryptamines:JRT PNU-181731
Related compounds	2-Azapsilocin 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAA 5-HIAL 5-HITCA 5-MIAL 7-Aza-5-MeO-DiPT Amedalin Benzindopyrine Benzofurans (e.g.,3-APB,5-MeO-DiBF,BPAP,3-F-BPAP,dimemebfe,mebfap) Benzothiophenes (e.g.,3-APBT) CP-94253 CT-4436 Daledalin Gramine Histamine I-32 IAL IN-399 Indazoles (e.g.,AL-34662,AL-38022A,VU6067416,YM-348) Indenes (e.g.,C-DMT) Indolizines (e.g.,TACT908 (2ZEDMA),1ZP2MA,1Z2MAP1O) Indolylaminopropanes (e.g.,1-API,2-API,4-API,5-API (5-IT; PAL-571),6-API (6-IT),7-API) Iprindole Latrepirdine Masupirdine Medmain Molindone Non-tryptaminetriptans (e.g.,avitriptan,LY-334370,naratriptan) Phenethylamines (e.g.,phenethylamine,amphetamine) Piperidinylindoles (e.g.,BRL-54443,LY-334370,naratriptan,sertindole,SN-22) Pirlindole Pyridinylindoles (e.g.,tepirindole) Pyrrolylethylamines (e.g.,2-pyrrolylethylamine (NEA),3-pyrrolylethylamine (3-NEA),3-pyrrolylpropylamine) Quinolinylethylamines (e.g.,mefloquine) (R)-69 (3IQ) Ro60-0213 Selisistat Tetrahydropyridinylindoles (e.g.,EMD-386088,LY-367265,RU-24,969) Tetrindole Tiflucarbine Tipindole Zilpaterol (RU-42173)
See also:Phenethylamines Ergolines and lysergamides Psychedelics

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