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Pharmaceutical compound
BK-5Cl-NM-AMT Other names βk-5Cl-NM-αMT; β-Keto-5-chloro-N -methyl-αMT; β-Keto-5-chloro-N -methyl-AMT; α,N -Dimethyl-5-chloro-β-ketotryptamine; β-Oxo-5-chloro-α-methyl-NMT Drug class Monoamine releasing agent 
1-(5-chloro-1H -indol-3-yl)-2-(methylamino)propan-1-one
 CAS Number PubChem  CID Formula C 12 H 13 Cl N 2 O Molar mass −1 3D model (JSmol ) 
CC(C(=O)C1=CNC2=C1C=C(C=C2)Cl)NC
 
InChI=1S/C12H13ClN2O/c1-7(14-2)12(16)10-6-15-11-4-3-8(13)5-9(10)11/h3-7,14-15H,1-2H3
Key:JNYZOLQTXCZJRL-UHFFFAOYSA-N
 
BK-5Cl-NM-AMT , or βk-5Cl-NM-αMT , also known as β-keto-5-chloro-N -methyl-αMT  or α,N -dimethyl-5-chloro-β-ketotryptamine , is a monoamine releasing agent  of the tryptamine , α-alkyltryptamine , and β-ketotryptamine  families.[ 1] 
It is known to induce the release of serotonin  and dopamine , with respective EC50  Tooltip half-maximal effective concentration  values of 200  nM and 865  nM in rat brain synaptosomes , whereas norepinephrine  release was not reported.[ 1] agonist  of serotonin receptors  including the 5-HT1  , 5-HT2  , and 5-HT3  receptors .[ 1] α-methyltryptamine  (αMT), it is inactive as a monoamine oxidase inhibitor  (MAOI).[ 1] 
BK-5Cl-NM-AMT was first described in the literature by 2023.[ 1] patented  by Matthew Baggott  and Tactogen  as a potential novel entactogen .[ 1] chloro  derivative  of BK-NM-AMT .[ 1] [ 2] [ 3] [ 4] analogues  of the drug include BK-5F-NM-AMT  and BK-5Br-NM-AMT .[ 1] 
^ a b c d e f g h   WO 2022061242 , Baggott MJ , "Advantageous tryptamine compositions for mental disorders or enhancement", published 2023 March 24,  assigned to Tactogen   ^ Yadav BJ (16 July 2019). Understanding Structure–Activity Relationship of Synthetic Cathinones (Bath Salts) Utilizing Methylphenidate Theses and Dissertations  (Doctor of Philosophy thesis). Virginia Commonwealth University. p. 40. doi :10.25772/MJQW-8C64 . Retrieved 24 November  2024  – via VCU Scholars Compass. ^ Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, et al. (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 . ^ US 20240335414 , Baggott MJ  , Dalziel S, "Specialized combinations for mental disorders or mental enhancement", published 10 October 2024,  assigned to Tactogen Inc.     
DRAs Tooltip Dopamine releasing agents 
NRAs Tooltip Norepinephrine releasing agents 
SRAs Tooltip Serotonin releasing agents 
Others 
Tryptamines 4-Hydroxytryptamines esters /ethers 5-Hydroxy-  and5-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-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 
Barettin Cyclic 3-OHM Ergolines  and lysergamides  (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 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 , 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 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-tryptamine triptans  (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)