7-Methyl-α-ethyltryptamine

7-Methyl-α-ethyltryptamine
Identifiers
	IUPAC name 1-(7-methyl-1H-indol-3-yl)butan-2-amine;
CAS Number	13712-80-6freebase; 13518-76-8 hydrochloride salt;
PubChemCID	57469234;
ChemSpider	26286844;
UNII	7H5EU45L83;
CompTox Dashboard(EPA)	DTXSID60726754;
Chemical and physical data
Formula	C13H18N2
Molar mass	202.301g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(N)CC1=CNC2=C(C)C=CC=C21;
	InChI InChI=1S/C13H18N2/c1-3-11(14)7-10-8-15-13-9(2)5-4-6-12(10)13/h4-6,8,11,15H,3,7,14H2,1-2H3; Key:NBLFITFQOPGXLS-UHFFFAOYSA-N;

7-Methyl-α-ethyltryptamine(7-Me-αET) is atryptaminederivative related toα-ethyltryptamine(αET). It was discovered by a team atUpjohnin the early 1960s.^[1]It has similar pharmacological effects to αET, but is both 3-4 times more potent as aserotonin releasing agent,and 10 times more potent as amonoamine oxidase inhibitor,^[2]^[3]making it potentially hazardous as this pharmacological profile is shared with drugs such asPMAand4-MTA,which are known to be dangerous in humans when used at high doses.

References

^U.S. patent 3,296,072
^Hester JB, Greig ME, Anthony WC, Heinzelman RV, Szmuszkovicz J (May 1964). "Enzyme Inhibitory Activity of 3-(2-Aminobutyl)indole Derivatives".Journal of Medicinal Chemistry.7(3): 274–9.doi:10.1021/jm00333a006.PMID 14204959.
^Burningham RA, Arimura GK, Yunis AA (July 1966). "Effect of Monase and related compounds on uptake of 5-hydroxytryptamine by platelets".Proceedings of the Society for Experimental Biology and Medicine.122(3): 711–4.doi:10.3181/00379727-122-31233.PMID 5918937.S2CID 24949288.

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[1] U.S. patent 3,296,072

[2] Hester JB, Greig ME, Anthony WC, Heinzelman RV, Szmuszkovicz J (May 1964). "Enzyme Inhibitory Activity of 3-(2-Aminobutyl)indole Derivatives".Journal of Medicinal Chemistry.7(3): 274–9.doi:10.1021/jm00333a006.PMID 14204959.

[pmid5918937-3] Burningham RA, Arimura GK, Yunis AA (July 1966). "Effect of Monase and related compounds on uptake of 5-hydroxytryptamine by platelets".Proceedings of the Society for Experimental Biology and Medicine.122(3): 711–4.doi:10.3181/00379727-122-31233.PMID 5918937.S2CID 24949288.

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v t e Tryptamines
Tryptamines	1-Methylpsilocin 2-HO-NMT 2-Me-DET 2-Methyl-5-HT 2,N,N-TMT 4,5-DHP-DMT 4-AcO-DALT 4-AcO-DET 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-MPT 4-HO-MsBT 4-HO-NALT 4-HO-NMT 4-HO-PiPT 4-HO-pyr-T 4-MeO-DiPT 4-MeO-DMT 4-MeO-MiPT 4-PrO-DMT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Bromo-DMT 5-CT 5-Chloro-DMT 5-Ethoxy-DMT 5-Ethyl-DMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-MET 5-HO-DiPT 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 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-NMT 5-MeO-pyr-T 5-MeO-NBpBrT 5-MeO-T-NBOMe 5-MeS-DMT 5-Methoxytryptamine (5-MT; mexamine) 5-Methyl-DMT 5-Methyltryptamine 5-MT-NB3OMe 5-(Nonyloxy)tryptamine 5,6-MeO-MiPT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-DHT 5,7-DHT 6-Fluoro-DMT 7-Methyl-DMT Acetryptine (5-AT) Aeruginascin (4-PO-TMT) AGH-107 AGH-192 AH-494 ALiPT Baeocystin (4-PO-NMT) Benzotript (4-chlorobenzoyl-L-tryptophan) Bufotenidine (5-HTQ) Bufotenin (5-HO-DMT) Convolutindole A CP-132,484 DALT DBT Desformylflustrabromine DET DiPT DMT DPT E-6801 E-6837 EiPT EMDT EPT Ethocybin (4-PO-DET) FGIN-127 FGIN-143 FT-104 HIOC Idalopirdine Indolylethylfentanyl Indorenate Iprocin (4-HO-DiPT) Lespedamine MET Methylbutyltryptamine Miprocin (4-HO-MiPT) MiPT MPT Milipertine MS-245 MSBT N-Feruloylserotonin (moschamine) NET NMT Norbaeocystin (4-PO-T) NTBT O-4310 Oxypertine PiPT Psilacetin (O-acetylpsilocin; 4-AcO-DMT) Psilocin (4-HO-DMT) Psilocybin (4-PO-DMT) Pyr-T RS134-49 Serotonin (5-HT) Solypertine ST-1936 Tryptamine Tryptophan Yuremamine Z2876442907
N-Acetyltryptamines	2-Iodomelatonin 2-Phenylmelatonin 5-Methoxyluzindole 6-Chloromelatonin 6-Fluoromelatonin 6-Hydroxymelatonin 6-Methoxymelatonin 6,7-Dichloro-2-methylmelatonin Luzindole Melatonin Normelatonin (N-acetylserotonin; NAS) N-Acetyltryptamine N-Butanoylmelatonin N-Propionylmelatonin Piromelatine TIK-301
α-Alkyltryptamines	2,α-DMT 4-HO-αMT 4-HO-MPMI (lucigenol) 4-Me-αET 4-Me-αMT 5-Chloro-αMT 5-Ethoxy-αMT 5-Fluoro-αET 5-Fluoro-αMT 5-iPrO-αMT 5-MeO-αET 5-MeO-αMT 5-MeO-MPMI 5-Methyl-αET 6-Fluoro-αMT 7-Chloro-αMT 7-Methyl-αET α-Methylserotonin (5-HO-αMT) α-Methyltryptophan (αMTP) α,N-DMT (N-methyl-αMT) α,N,N-TMT α,N,O-TMS αET (etryptamine) αMT AL-37350A (4,5-DHP-αMT) BNC-210 BW-723C86 CP-135807 IPAP (α,N-DPT) MPMI
Triptans	Almotriptan Donitriptan Eletriptan Frovatriptan L-694247 Rizatriptan Sumatriptan Zolmitriptan
Cyclized tryptamines	Bay R 1531 Ciclindole Cyclic 3-OHM Ergolinesandlysergamides(e.g.,LSD) Flucindole Harmalaalkaloidsandβ-carbolines(e.g.,6-MeO-THH,9-Me-BC,β-carboline (norharman),harmaline,harmalol,harmane,harmine,pinoline,tetrahydroharmine,tryptoline) Ibogaalkaloidsand related (e.g.,DM-506 (ibogaminalog),ibogaine,ibogamine,noribogaine,tabernanthalog,tabernanthine) Metralindole NDTDI PHA-57378 PNU-22394 PNU-181731 RU-28306 Yohimbans(e.g.,yohimbine,rauwolscine,spegatrine,corynanthine,ajmalicine,reserpine,deserpidine,rescinnamine)
Related compounds	2-Azapsilocin 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAL 5-MIAL 7-Aza-5-MeO-DiPT AAZ-A-154 AL-34662 AL-38022A BRL-54443 CP-94253 EMD-386088 I-32 IAL Latrepirdine LY-367265 Pirlindole (R)-69 (3IQ) Ro60-0175 Ro60-0213 RU-24,969 Sertindole SN-22 Substituted benzofurans(e.g.,3-APB,5-MeO-DiBF,BPAP,dimemebfe,mebfap) Tepirindole Tetrindole Triptans(e.g.,avitriptan,LY-334370,naratriptan) VER-3323 VU6067416 YM-348

See also

References