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4-Methyl-α-ethyltryptamine

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Chemical compound

Pharmaceutical compound

4-Methyl-α-ethyltryptamine
Clinical data

Other names	4-Methyl-AET; 4-Methyl-αET; 4-Me-AET; 4-Me-αET
ATC code	None
Legal status
Legal status	Illegal in Singapore
Identifiers
IUPAC name 1-(4-methyl-1H-indol-3-yl)butan-2-amine
CAS Number	28289-30-7^Y
PubChemCID	57466062
ChemSpider	26234938^Y
UNII	SBF4N6JJ4L
CompTox Dashboard(EPA)	DTXSID20726715
Chemical and physical data
Formula	C₁₃H₁₈N₂
Molar mass	202.301 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Cc2c1c(CC(N)CC)c[nH]c1ccc2
InChI InChI=1S/C13H18N2/c1-3-11(14)7-10-8-15-12-6-4-5-9(2)13(10)12/h4-6,8,11,15H,3,7,14H2,1-2H3^Y Key:XKHCIOVNXOVPIK-UHFFFAOYSA-N^Y
(verify)

4-Methyl-α-ethyltryptamine (4-Me-αET) is adrug of thetryptamine andα-alkyltryptamine families.^[1] It is adesigner drug and has been sold online as a "research chemical".^[2]

Chemistry

Analogues

Analogues of 4-methyl-AET includeα-ethyltryptamine (AET),4-methyl-AMT,4-methyl-DMT,5-fluoro-AET,7-methyl-AET,7-chloro-AMT, andRS134-49 (4-methyl-THPI), among others.^[3]

Society and culture

Legal status

Singapore

4-Me-AET is illegal inSingapore.^[4]

See also

Substituted α-alkyltryptamine

References

^Cerletti A, Taeschler M, Weidmann H (1968). "Pharmacologic studies on the structure-activity relationship of hydroxyindole alkylamines".Pharmacology, Behavior, and Clinical Aspects, Proceedings of a Symposium held at the College of Physicians and Surgeons, Columbia University, New York. Advances in Pharmacology. Vol. 6. pp. 233–46.doi:10.1016/s1054-3589(08)60322-1.ISBN 978-0-12-032906-9.PMID 5658327.
^Chapman SJ (1 Mar 2018)."PeakAL: Protons I Have Known and Loved, Too — Another Fifty Shades of Grey-Market Spectra".Blotter (5).doi:10.16889/isomerdesign-5. Retrieved3 April 2018.
^Shulgin, Alexander;Shulgin, Ann (September 1997).TiHKAL: The Continuation.Berkeley, California:Transform Press.ISBN 0-9630096-9-9.OCLC 38503252.
^"Misuse of Drugs Act - Singapore Statutes Online".sso.agc.gov.sg.

v t e Tryptamines
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 4-Methyl-DMT 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-DMT 6-Methyl-T 6,7-DHT 7-Chloro-T 7-HO-DMT 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 McPT MET MiPT MPT MsBT N-Benzyltryptamine (T-NB, NB-T) N-DEAOP-NET N-DEAOP-NMT NAT NBoc-DMT (NB-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 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-EiPT (ethipracetin) 4-AcO-EPT 4-AcO-MALT 4-AcO-McPT 4-AcO-MET (metacetin) 4-AcO-MiPT (mipracetin) 4-AcO-MPT 4-AcO-NMT 4-AcO-TMT 4-HO-5-MeO-T 4-HO-DALT (daltocin) 4-HO-DBT 4-HO-DET (ethocin; CZ-74) 4-HO-DiBT 4-HO-DiPT (iprocin) 4-HO-DPT (deprocin) 4-HO-DsBT 4-HO-EiBT (eibucin) 4-HO-EiPT 4-HO-EPT (eprocin) 4-HO-MALT (maltocin) 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-NBnT 4-HO-NcHT 4-HO-NET 4-HO-NiPT 4-HO-NBT (4-HO-NnBT) 4-HO-NPT 4-HO-NtBT 4-HO-PiPT (piprocin) 4-HO-TMT 4-HT (dinorpsilocin) 4-MeO-DET 4-MeO-DiPT 4-MeO-DMT 4-MeO-MiPT 4-MeO-T 4-PrO-DiPT 4-PrO-DMT 4-PrO-MET 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) Luvesilocin (4-GO-DiPT; RE-104; FT-104) 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-109 (4-GO-DMT)
5-Hydroxy- and 5-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-DPT 5-HO-MET 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-MsBT 5-MeO-NET 5-MeO-NiPT 5-MeO-NMT (O,N-DMS) 5-MeO-NsBT 5-MeO-PiPT 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine;O-methylserotonin) 5-MeO-T-NBOMe 5-MeO-T-NB3OMe 5-MTP (cytoguardin) 5-NOT 5-PhO-T (OVT2) 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) IS-159 Isamide (N-CA-5-MT) L-741604 MS-245 N-DEAOP-5-MeO-NET N-DEAOP-5-MeO-NMT N-Feruloylserotonin (moschamine) NB-5-MeO-DALT NB-5-MeO-MiPT 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-αET 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) N-Hydroxy-AMT 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
α-Ketotryptamines	AB-CHMIATA ADB-FUBIATA (ADB-FUBIACA) ADB-IACA AFUBIATA CH-FUBIATA (CH-FUBIACA) CH-HEXIATA CH-IACA CH-PIATA CH-PIATAN-(4-carboxybutyl) CH-PIATAN-(4-hydroxypentyl) CHM-FUBIATA
Cyclized tryptamines	5-MeO-IsoqT Barettin BML-190 (indomethacin morpholinylamide) Cyclic 3-OHM Ergolines andlysergamides (e.g.,LSD) Harmala alkaloids andβ-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 alkaloids (e.g.,ibogaine,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,L-760790) Pyrrolidinylmethylindoles (e.g.,MPMI,4-HO-MPMI (lucigenol),5F-MPMI,5-MeO-MPMI,CP-122288,CP-135807,eletriptan,MSP-2020) Tetrahydrocarbazolamines (e.g.,ciclindole,flucindole,frovatriptan,LY-344864,ramatroban) Tetrahydropyridinylindoles (e.g.,RS134-49,RU-28253,NEtPhOH-THPI) Tetrahydropyrroloquinolines (e.g.,bufothionine,O-methylnordehydrobufotenine,dehydrobufotenine) 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 α-Carboline γ-Carbolines (pyridoindoles) (e.g.,γ-carboline,alosetron,gevotroline,latrepirdine,lurosetron,mebhydrolin,tiflucarbine) Amedalin Benzindopyrine Benzofurans (e.g.,3-APB (1-oxa-AMT),5-MeO-DiBF (1-oxa-5-MeO-DiPT),BPAP,3-F-BPAP,dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT),mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT),MiPBF (1-oxa-MiPT),oxa-noribogaine) Benzothiophenes (e.g.,S-DMT (1-thia-DMT),3-APBT (1-thia-AMT)) 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-34662,VU6067416,YM-348) Indenylethylamines (e.g.,C-DMT (1-carba-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-93129,CP-94253) Tetrindole Tipindole Zilpaterol (RU-42173)
See also:Phenethylamines Ergolines and lysergamides Psychedelics Simple tryptamines and common derivatives

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