Monoamine releaser and entactogen
Pharmaceutical compound
BK-NM-AMT , orβk-NM-αMT , also known asβ-keto-N -methyl-αMT orα,N -dimethyl-β-ketotryptamine , as well as3-indoylmethcathinone , is aserotonin–dopamine releasing agent (SDRA) and putativeentactogen of thetryptamine ,α-alkyltryptamine , andβ-ketotryptamine families.[ 1] [ 2] [ 3] [ 4]
BK-NM-AMT acts as aserotonin–dopamine releasing agent (SDRA).[ 2] [ 5] EC50 Tooltip half-maximal effective concentration values of BK-NM-AMT formonoamine release are 41.3 nM forserotonin and 92.8 nM fordopamine in rat brainsynaptosomes , whereas it only induced 55% release ofnorepinephrine at a concentration of 10 μM.[ 2] α-ethyltryptamine (αET),5-chloro-αMT and5-fluoro-αET , it is one of the few SDRAs known.[ 6] [ 2]
BK-NM-AMT, also known as β-keto-N -methyl-α-methyltryptamine, is theN -methyl and β-keto derivative ofα-methyltryptamine (αMT).[ 2] [ 4] cathinone -like tryptamine and can be thought of as the tryptamine orindole analogue of thephenethylamine methcathinone (β-keto-N -methylamphetamine).[ 2] [ 4]
Analogues of BK-NM-AMT includeα-methyltryptamine (AMT) andα,N -dimethyltryptamine (α,N -DMT; NM-AMT), among others.
Several 5-halogenated derivatives of BK-NM-AMT have also been described.[ 5] BK-5F-NM-AMT ,[ 10] [ 11] BK-5Cl-NM-AMT ,[ 12] [ 13] BK-5Br-NM-AMT .[ 14] [ 15] [ 5] agonists ofserotonin receptors including the5-HT1 ,5-HT2 , and5-HT3 receptors .[ 5] monoamine oxidase inhibitors (MAOIs).[ 5]
BK-NM-AMT and its 5-halogenated analogues werepatented byMatthew Baggott andTactogen in late 2024.[ 3] [ 4] [ 5]
^ Yadav, Barkha J (16 July 2019).Understanding Structure–Activity Relationship of Synthetic Cathinones (Bath Salts) Utilizing Methylphenidate VCU Scholars Compass (Thesis). p. 40.doi :10.25772/MJQW-8C64 . Retrieved24 November 2024 . ^a b c d e f g Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, Rothman RB (March 2019)."The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes" .Psychopharmacology (Berl) .236 (3):915– 924.doi :10.1007/s00213-018-5063-9 .PMC 6475490 PMID 30341459 . ^a b c US 20240335414 , Matthew J. Baggott & Sean Dalziel, "Specialized combinations for mental disorders or mental enhancement", published 10 October 2024, assigned toTactogen Inc. ^a b c d "1-(1H-indol-3-yl)-2-(methylamino)propan-1-one" .PubChem . U.S. National Library of Medicine. Retrieved13 November 2024 .^a b c d e f g h i WO 2022061242 , Matthew Baggott , "Advantageous tryptamine compositions for mental disorders or enhancement", published 2023 March 24, assigned toTactogen ^a b c d Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB (October 2014)."Alpha-ethyltryptamines as dual dopamine-serotonin releasers" .Bioorg Med Chem Lett .24 (19):4754– 4758.doi :10.1016/j.bmcl.2014.07.062 .PMC 4211607 PMID 25193229 . ^ Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014)."Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes" .Psychopharmacology .231 (21):4135– 4144.doi :10.1007/s00213-014-3557-7 .PMC 4194234 PMID 24800892 . ^ Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain".European Journal of Pharmacology .559 (2– 3):132– 137.doi :10.1016/j.ejphar.2006.11.075 .PMID 17223101 . ^a b Banks ML, Bauer CT, Blough BE, Rothman RB, Partilla JS, Baumann MH, Negus SS (June 2014)."Abuse-related effects of dual dopamine/serotonin releasers with varying potency to release norepinephrine in male rats and rhesus monkeys" .Experimental and Clinical Psychopharmacology .22 (3):274– 284.doi :10.1037/a0036595 .PMC 4067459 PMID 24796848 . ^ "1-(5-fluoro-1H-indol-3-yl)-2-(methylamino)propan-1-one" .PubChem . Retrieved11 November 2024 .^ "β-Oxo-5-fluoro-α-methyl-NMT" .Isomer Design . 10 November 2024. Retrieved11 November 2024 .^ "1-(5-chloro-1H-indol-3-yl)-2-(methylamino)propan-1-one" .PubChem . Retrieved11 November 2024 .^ "β-Oxo-5-chloro-α-methyl-NMT" .Isomer Design . 10 November 2024. Retrieved11 November 2024 .^ "1-(5-bromo-1H-indol-3-yl)-2-(methylamino)propan-1-one" .PubChem . Retrieved11 November 2024 .^ "β-Oxo-5-bromo-α-methyl-NMT" .Isomer Design . 10 November 2024. Retrieved11 November 2024 .
DRAs Tooltip Dopamine releasing agents
NRAs Tooltip Norepinephrine releasing agents
SRAs Tooltip Serotonin releasing agents
Others
Tryptamines 1-Methyl-DMT (1,N ,N -TMT, 1-TMT) 1-Methyl-T 2-HO-NMT 2-Methyl-DET 2-Methyl-DiPT 2-Methyl-iPALT (ASR-3002) 2,N ,N -TMT (2-methyl-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-HO-DET 6-HO-DMT 6-HO-T (6-HT) 6-MeO-DMT 6-MeO-T 6-Methyl-T 6,7-DHT 7-Chloro-T 7-HO-T (7-HT) 7-MeO-DMT 7-MeO-T 7-Methyl-DMT 7-Methyl-T Acetryptine (5-AT) Almotriptan Benzotript (4-CB-Trp) BGE Bretisilocin (5-fluoro-MET; GM-2505) Convolutindole A (2,4,6-TBr,1,7-DiMeO-DMT) DALT DAT DBT Desformylflustrabromine DET (T-9) DHT DiPT DMT DPT E-6801 E-6837 EB-003 EiPT EPT FGIN-127 FGIN-143 Idalopirdine iPALT (ALiPT; ASR-3003) Lespedamine (1-MeO-DMT) L-694247 MBT MET MiPT MPT MsBT N -Benzyltryptamine (T-NB, NB-T)N -DEAOP-NETN -DEAOP-NMTNAT NBoc-DMT NET/NETP NHT NiPT NMT NsBT NtBT PALT (ASR-3004) PiPT Rizatriptan ST-1936 (2-Me-5-Cl-DMT) Sumatriptan TCS-1205 Tryptamine (T; indolylethylamine) Tryptophan (Trp) WAY-181187 Yuremamine Z2876442907 Zolmitriptan 4-Hydroxytryptamines esters /ethers 5-Hydroxy- and5-methoxytryptamines 2-Methyl-5-HT 2-Methyl-5-MeO-DALT 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-DET 5-HO-DiPT 5-HO-NiPT 5-HO-DPT 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 ASR-3001 (5-MeO-iPALT) 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 Donitriptan EMDT (2-Et-5-MeO-DMT) HIOC Indorenate (TR-3369) Isamide (N -CA-5-MT) L-741604 MS-245 N -DEAOP-5-MeO-NETN -DEAOP-5-MeO-NMTN -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 -Acetyltryptaminesα-Alkyltryptamines 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 Cyclized tryptamines 5-MeO-IsoqT Barettin Cyclic 3-OHM Ergolines andlysergamides (e.g.,LSD )Harmala alkaloidsβ-carbolines (e.g.,5-methoxyharmalan ,6-MeO-THH ,6-methoxyharmalan ,9-Me-BC ,β-carboline (norharman) ,fenharmane ,harmaline ,harmalol ,harmane ,harmine ,LY-266,097 ,pinoline ,tetrahydroharmine ,tryptoline )Iboga alkaloidsibogaine ,ibogamine ,noribogaine ,tabernanthine )Ibogalogs (e.g.,catharanthalog ,fluorogainalog ,ibogainalog ,ibogaminalog (DM-506) ,LS-22925 ,noribogainalog ,noribogaminalog ,PHA-57378 ,PNU-22394 ,tabernanthalog )Imidazolylindoles (e.g.,AGH-107 ,AGH-192 ,AH-494 )Metralindole Morpholinylethylindoles (e.g.,mor-T ,5-MeO-mor-T )Partial ergolines and lysergamides (e.g.,NDTDI ,RU-27849 ,RU-28251 ,RU-28306 ,FHATHBIN ,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 )Piperidinylethylindoles (e.g.,pip-T ,5-MeO-pip-T ,indolylethylfentanyl )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-122288 ,CP-135807 ,eletriptan )Tetrahydrocarbazolamines (e.g.,ciclindole ,flucindole ,frovatriptan ,LY-344864 ,ramatroban )Tetrahydropyridinylindoles (e.g.,RS134-49 ,RU-28253 ,NEtPhOH-THPI )Tetrahydropyrroloquinolines (e.g.,bufothionine ,O -methylnordehydrobufotenineYohimbans (e.g.,yohimbine ,rauwolscine ,spegatrine ,corynanthine ,ajmalicine ,reserpine ,deserpidine ,rescinnamine )Isotryptamines 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 α-Carboline γ-Carbolines (pyridoindoles) (e.g.,γ-carboline ,alosetron ,gevotroline ,latrepirdine ,lurosetron ,mebhydrolin ,tiflucarbine )Amedalin Benzindopyrine Benzofurans (e.g.,3-APB ,5-MeO-DiBF ,BPAP ,3-F-BPAP ,dimemebfe ,mebfap ,oxa-noribogaine )Benzothiophenes (e.g.,3-APBT )Carmoxirole CT-4436 Daledalin Gramine Histamine Homotryptamines (e.g.,HT ,DMHT )I-32 IAL IN-399 Indazolethylamines (e.g.,AL-34662 ,AL-38022A ,O -methyl-AL-34662VU6067416 ,YM-348 )Indenylethylamines (e.g.,C-DMT )Indolizinylethylamines (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 Masupirdine Medmain Molindone Non-tryptaminetriptans (e.g.,avitriptan ,LY-334370 ,naratriptan ) Ondansetron Oxazinopyridoindoles (e.g.,IHCH-8134 )Phenethylamines (e.g.,phenethylamine ,amphetamine )Piperidinylbenzimidazolines (e.g.,benperidol ,timiperone )Piperazinylbenzisothiazoles (e.g.,lurasidone ,perospirone ,tiospirone ,ziprasidone )Piperidinylbenzisoxazoles (e.g.,iloperidone ,milsaperidone ,ocaperidone ,paliperidone ,risperidone )Piperidinylindoles (e.g.,BRL-54443 ,LY-334370 ,naratriptan ,sertindole ,SN-22 )Pirlindole Pyridinylbenzimidazoles (e.g.,droperidol )Pyridinylindoles (e.g.,tepirindole )Pyridopyrroloquinoxalines (e.g.,IHCH-7113 ,IHCH-7079 ,IHCH-7086 ,lumateperone ,deulumateperone ,ITI-1549 )Pyrrolylethylamines (e.g.,2-pyrrolylethylamine (NEA) ,3-pyrrolylethylamine (3-NEA) ,3-pyrrolylpropylamine )Pyrrolopyridinylethylamines (e.g.,WAY-208466 )Quinolinylethylamines (e.g.,mefloquine )Ro60-0213 Selisistat Tetrahydropyridinylindoles (e.g.,EMD-386088 ,LY-367265 ,RU-24,969 )Tetrahydropyridinylpyrrolopyridines (e.g.,(R )-69 (3IQ) ,(R )-70 ,CP-94253 )Tetrindole Tipindole Zilpaterol (RU-42173)
