Α-Ethyltryptamine

Template:Short description Template:Lowercase title Template:Cs1 config Template:Main other {{#invoke:Infobox|infobox}}Template:Template other{{#invoke:TemplatePar |check |template=Template:Infobox_drug |all= |opt= pronounce= pronounce_ref= pronounce_comment= ATC_prefix= ATC_suffix= ATC_supplemental= ATCvet= biosimilars= CAS_number_Ref= CAS_number= CAS_supplemental= ChEBI= ChEBI_Ref= ChEMBL_Ref= ChEMBL= ChemSpiderID= ChemSpiderID_Ref= chirality= class= container_only= DailyMedID= data_page= DrugBank_Ref= DrugBank= Drugs.com= duration_of_action= INN= INN_EMA= IUPAC_name= IUPHAR_ligand= KEGG_Ref= KEGG= MedlinePlus= NIAID_ChemDB= PDB_ligand= PubChemSubstance= PubChem= StdInChIKey_Ref= StdInChIKey= StdInChI_Ref= StdInChI_comment= StdInChI= UNII_Ref= UNII= DTXSID= Verifiedfields= Watchedfields= addiction_liability= alt2= altL= altR= alt= bioavailability= boiling_high= boiling_notes= boiling_point= captionLR= caption= caption2= charge= chemical_formula= chemical_formula_ref= chemical_formula_comment= class1= class2= class3= class4= class5= class6= component1= component2= component3= component4= component5= component6= density= density_notes= dependency_liability= drug_name= elimination_half-life= engvar= excretion= image2= imageL= imageR= image= image_class= image_class2= image_classL= image_classR= Jmol= legal_AU= legal_BR= legal_CA= legal_DE= legal_EU= legal_NZ= legal_UK= legal_UN= legal_US= legal_AU_comment= legal_BR_comment= legal_CA_comment= legal_DE_comment= legal_UK_comment= legal_NZ_comment= legal_US_comment= legal_UN_comment= legal_EU_comment= legal_status= licence_CA= licence_EU= licence_US= license_CA= license_EU= license_US= mab_type= melting_high= melting_notes= melting_point= metabolism= metabolites= molecular_weight= molecular_weight_round= molecular_weight_unit= molecular_weight_ref= molecular_weight_comment= onset= pregnancy_AU= pregnancy_AU_comment= pregnancy_category= protein_bound= routes_of_administration= SMILES= smiles= solubility= sol_units= source= specific_rotation= synonyms= target= tradename= type= vaccine_type= verifiedrevid= width2= widthL= widthR= width= AAN= BAN= JAN= USAN= source_tissues= target_tissues= receptors= agonists= antagonists= precursor= biosynthesis= gt_target_gene= gt_vector= gt_nucleic_acid_type= gt_editing_method= gt_delivery_method= sec_combustion= Ac=Ag=Al=Am=Ar=As=At=Au=B=Ba=Be=Bh=Bi=Bk=Br=C=Ca=Cd=Ce=Cf=Cl=Cm=Cn=Co=Cr=Cs=Cu= D=Db=Ds=Dy=Er=Es=Eu=F=Fe=Fl=Fm=Fr=Ga=Gd=Ge=H=He=Hf=Hg=Ho=Hs=I=In=Ir=K=Kr=La=Li=Lr=Lu=Lv= Mc=Md=Mg=Mn=Mo=Mt=N=Na=Nb=Nd=Ne=Nh=Ni=No=Np=O=Og=Os=P=Pa=Pb=Pd=Pm=Po=Pr=Pt=Pu=Ra=Rb=Re=Rf=Rg=Rh=Rn=Ru=S=Sb=Sc=Se=Sg=Si=Sm=Sn=Sr=Ta=Tb=Tc=Te=Th=Ti=Tl=Tm=Ts=U=V=W=Xe=Y=Yb=Zn=Zr= index_label= index2_label= index_comment= index2_comment= CAS_number2= CAS_supplemental2= ATC_prefix2= ATC_suffix2= ATC_supplemental2= PubChem2= PubChemSubstance2= IUPHAR_ligand2= DrugBank2= ChemSpiderID2= UNII2= KEGG2= ChEBI2= ChEMBL2= PDB_ligand2= NIAID_ChemDB2= SMILES2= smiles2= StdInChI2= StdInChIKey2= CAS_number2_Ref= ChEBI2_Ref= ChEMBL2_Ref= ChemSpiderID2_Ref= DrugBank2_Ref= KEGG2_Ref= StdInChI2_Ref= StdInChIKey2_Ref= UNII2_Ref= DTXSID2= QID= QID2=PLLR= pregnancy_US= pregnancy_US_comment= |cat=Pages using infobox drug with unknown parameters |format=0|errNS=0

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}}{{Infobox drug/maintenance categoriesTemplate:Yesno | drug_name = α-Ethyltryptamine | INN = Etryptamine | _drugtype =

| _has_physiological_data= | _has_gene_therapy=

| vaccine_type= | mab_type= | _number_of_combo_chemicals={{#invoke:ParameterCount |main |component1 |component2 |component3 |component4|component5|component6 }} | _vaccine_data= | _mab_data= | _mab_vaccine_data= | _mab_other_data=12162CCC(N)CC1=CNC2=CC=CC=C121S/C12H16N2/c1-2-10(13)7-9-8-14-12-6-4-3-5-11(9)12/h3-6,8,10,14H,2,7,13H2,1H3ZXUMUPVQYAFTLF-UHFFFAOYSA-NTemplate:StdinchiciteTemplate:Stdinchicite222223 | _combo_data= | _physiological_data= | _clinical_data= Oral<ref name="GlennonDukat2023" />Monase<ref name="GlennonDukat2023" />Entactogen; Stimulant; Monoamine releasing agent; Serotonin receptor agonist; Monoamine oxidase inhibitor<ref name="GlennonDukat2023" />None | _legal_data=<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>F2Schedule IIIAnlage IClass AP ISchedule I

| _other_data=1-(1H-indol-3-yl)butan-2-amine

| _image_0_or_2 = AET.svgAlpha-Ethyltryptamine-3d-sticks.png | _image_LR =

| _datapage = Α-Ethyltryptamine (data page) | _vaccine_target={{#ifeq: | vaccine | | _type_not_vaccine }} | _legal_all=F2Schedule IIIClass ASchedule IP I | _ATC_prefix_supplemental=None | _has_EMA_link = | CAS_number=2235-90-7 | PubChem=8367 | ChemSpiderID=8064 | ChEBI=134838 | ChEMBL=1619758 | DrugBank=DB01546 | KEGG=D04092 | _hasInChI_or_Key={{#if:1S/C12H16N2/c1-2-10(13)7-9-8-14-12-6-4-3-5-11(9)12/h3-6,8,10,14H,2,7,13H2,1H3ZXUMUPVQYAFTLF-UHFFFAOYSA-N |yes}} | UNII=GR181O3R32 | _hasJmol02 = |_hasMultipleCASnumbers = |_hasMultiplePubChemCIDs = |_hasMultipleChEBIs =

| _countSecondIDs={{#invoke:ParameterCount |main |CAS_number2 |ATC_prefix2 |PubChem2 |PubChemStructure2 |IUPHAR_ligand2 |DrugBank2 |ChemSpiderID2 |UNII2 |KEGG2 |ChEBI2 |ChEMBL2 |PDB_ligand2 |NIAID_ChemDB2 |SMILES2 |smiles2 |StdInChI2 |StdInChIKey2 |DTXCID2}} | _countIndexlabels={{#invoke:ParameterCount |main |index_label |index2_label}} | _trackListSortletter= |QID = |QID2 = |Verifiedfields= |Watchedfields= |verifiedrevid=447115140}} α-Ethyltryptamine (αET, AET), also known as etryptamine, is an entactogen and stimulant drug of the tryptamine family.<ref name="GlennonDukat2023">Template:Cite journal</ref><ref name="Oeri2021">Template:Cite journal</ref><ref name="TiHKAL">Template:Cite book</ref> It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s before being withdrawn due to toxicity.<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="US3296072">Template:Cite patent</ref>

Side effects of αET include facial flushing, headache, gastrointestinal distress, insomnia, irritability, appetite loss, and sedation, among others.<ref name="Barceloux2012" /> A rare side effect of αET is agranulocytosis.<ref name="GlennonDukat2023" /><ref name="TiHKAL" /><ref name="Butin1962">Template:Cite journal</ref> αET acts as a releasing agent of serotonin, norepinephrine, and dopamine, as a weak serotonin receptor agonist, and as a weak monoamine oxidase inhibitor.<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="BloughLandavazo2014" /> It may also produce serotonergic neurotoxicity.<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="HuangJohnsonNichols1991" /> αET is a substituted tryptamine and is closely related to α-methyltryptamine (αMT) and other α-alkylated tryptamines.<ref name="GlennonDukat2023" /><ref name="Oeri2021" />

αET was first described in 1947.<ref name="GlennonDukat2023" /><ref name="SnyderKatz1947" /> It was used as an antidepressant for about a year around 1961.<ref name="GlennonDukat2023" /> The drug started being used recreationally in the 1980s and several deaths have been reported.<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="VarìPichiniGiorgetti2019" /><ref name="Barceloux2012" /> αET is a controlled substance in various countries, including the United States and United Kingdom.<ref name="GlennonDukat2023" /><ref name="VarìPichiniGiorgetti2019" /> There has been renewed interest in αET, for instance as an alternative to MDMA, with the development of psychedelics and entactogens as medicines in the 2020s.<ref name="GlennonDukat2023" /><ref name="Oeri2021" />

Medical uses

αET was previously used medically as an antidepressant and "psychic energizer" to treat people with depression.<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="Barceloux2012" /><ref name="TiHKAL" /> It was used for this indication under the brand name Monase.<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="Barceloux2012" /><ref name="TiHKAL" />

Available forms

αET was available pharmaceutically as the acetate salt under the brand name Monase in the form of 15Template:Nbspmg oral tablets.<ref name="RockyMountainDruggist1961">Template:Cite book</ref><ref name="GlennonDukat2023" />

Effects

αET is reported to have entactogen and weak psychostimulant effects.<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="TiHKAL" /> Euphoria, increased energy, openness, and empathy have been specifically reported.<ref name="Oeri2021" /><ref name="GlennonDukat2023" /><ref name="TiHKAL" /> Unlike αMT and other tryptamines, αET is not reported to have psychedelic or hallucinogenic effects.<ref name="Oeri2021" /><ref name="TiHKAL" /> The drug is described as less stimulating and intense than MDMA ("ecstasy") but as otherwise having entactogenic effects resembling those of MDMA.<ref name="Oeri2021" /><ref name="GlennonDukat2023" /> The dose of αET used recreationally has been reported to be 100 to 160Template:Nbspmg, its onset of action has been reported to be 0.5 to 1.5Template:Nbsphours, and its duration of action at the preceding doses is described as 6 to 8Template:Nbsphours.<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="Barceloux2012" /><ref name="TiHKAL" /> Rapid tolerance to repeated administration of αET has been described.<ref name="TiHKAL" />

Side effects

Side effects of αET at antidepressant doses have included facial flushing, headache, gastrointestinal distress, insomnia, irritability, and sedation.<ref name="Barceloux2012" /> Additional side effects of αET at recreational doses have included appetite loss and feelings of intoxication.<ref name="Barceloux2012" /> Feelings of lethargy and sedation can occur once the drug wears off.<ref name="Barceloux2012" />

As with many other serotonin releasing agents, toxicity, such as serotonin syndrome, can occur when excessive doses are taken or when combined with certain drugs such as monoamine oxidase inhibitors (MAOIs).<ref name="Gillman2005">Template:Cite journal</ref> Several deaths have been associated with recreational use of αET.<ref name="GlennonDukat2023" /><ref name="VarìPichiniGiorgetti2019">Template:Cite journal</ref><ref name="Barceloux2012" />

Rarely, agranulocytosis has occurred with prolonged administration of αET at antidepressant doses and has been said to have resulted in several cases and/or deaths.<ref name="GlennonDukat2023" /><ref name="Barceloux2012" /><ref name="Butin1962" />

Overdose

αET has been administered in clinical studies at doses of up to 300Template:Nbspmg per day.<ref name="GlennonDukat2023" /><ref name="Barceloux2012" /><ref name="TurnerMerlis1961">Template:Cite journal</ref> An approximate but unconfirmed 700Template:Nbspmg dose resulted in fatal hyperthermia and agitated delirium in one case.<ref name="GlennonDukat2023" /><ref name="Barceloux2012" /> LD₅₀ doses of αET for various species have been studied and described.<ref name="GlennonDukat2023" /> Treatment of αET intoxication or overdose is supportive.<ref name="Barceloux2012" /> Severe and potentially life-threatening hyperthermia may occur.<ref name="Barceloux2012" /> Serotonergic toxicity associated with serotonergic agents like αET can be managed with benzodiazepines and with the serotonin receptor antagonist cyproheptadine.<ref name="SchifanoNapoletanoChiappini2019">Template:Cite journal</ref>

Pharmacology

Pharmacodynamics

Similarly to αMT, αET is a releasing agent of serotonin, norepinephrine and dopamine, with serotonin being the primary neurotransmitter affected.<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="BloughLandavazo2014">Template:Cite journal</ref> It is about 10-fold more potent in inducing serotonin release than in inducing dopamine release and about 28-fold more potent in inducing serotonin release than in inducing norepinephrine release.<ref name="GlennonDukat2023" /><ref name="BloughLandavazo2014" /> The (+)-enantiomer of αET, (+)-αET, is a serotonin–dopamine releasing agent (SDRA) and is one of the few such agents known.<ref name="BloughLandavazo2014" /> It is about 1.7-fold more potent in inducing serotonin release than in inducing dopamine release, about 17-fold more potent in inducing serotonin release than in inducing norepinephrine release, and is about 10-fold more potent in inducing dopamine release than in inducing norepinephrine release.<ref name="BloughLandavazo2014" />

In addition to acting as a monoamine releasing agent, αET acts as a serotonin receptor agonist.<ref name="GlennonDukat2023" /> It is known to act as a weak partial agonist of the serotonin 5-HT_2A receptor (Template:Abbrlink > 10,000Template:NbspnM; E_max = 21%).<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="BloughLandavazo2014" /> (–)-αET is inactive as a 5-HT_2A receptor agonist at concentrations of up to 10Template:NbspμM, whereas (+)-αET is a 5-HT_2A receptor agonist with an EC₅₀ value of 1,250Template:NbspnM and an E_max value of 61%.<ref name="BloughLandavazo2014" /> αET has also been found to have weak affinity for the 5-HT₁, 5-HT_1E, 5-HT_1F, and 5-HT_2B receptors.<ref name="GlennonDukat2023" />

Activities of αET, its enantiomers, and related compounds

Compound	Monoamine release (Template:Abbrlink, nM)			5-HT2A receptor agonism
	Serotonin	Dopamine	Norepinephrine	Template:Abbrlink (nM)	Emax (%)
Tryptamine	32.6 ± 2.6	164 ± 16	716 ± 46	7.36 ± 0.56	104 ± 4
Serotonin	44.4 ± 5.3	>10,000	>10,000	Template:Abbr	Template:Abbr
N,N-DMT	114 ± 15	>10,000	4,166 ± 317	38.3 ± 0.81	83 ± 0.4
αMT	21.7 ± 1.0	78.6 ± 4.0	112 ± 6	23.1 ± 2.4	103 ± 3
αET	23.2 ± 1.7	232 ± 17	640 ± 76a	>10,000	21 ± 11
Template:NbspTemplate:Nbsp(–)-αET	54.9 ± 7.8	654 ± 50	3,670 ± 1,190a	>10,000	–
Template:NbspTemplate:Nbsp(+)-αET	34.7 ± 4.9	57.6 ± 3.1	592 ± 97a	1,250 ± 310	61 ± 8
MDMA	56.6 ± 2.1	376 ± 16	77.4 ± 3.4	Template:Abbr	Template:Abbr
Notes: The smaller the value, the more strongly the compound produces the effect. Footnotes: a = αET, (–)-αET, and (+)-αET were norepinephrine partial releasers with Emax values of 78%, 75%, and 71%, respectively. Refs: <ref name="GlennonDukat2023" /><ref name="BloughLandavazo2014" /><ref name="BloughLandavazoDecker2014">Template:Cite journal</ref><ref name="RothmanBaumann2003">Template:Cite journal</ref>

αET is a weak monoamine oxidase inhibitor (MAOI).<ref name="GlennonDukat2023" /><ref name="AskFagervallRoss1983">Template:Cite journal</ref> It is specifically a selective and reversible inhibitor of monoamine oxidase A (MAO-A).<ref name="GlennonDukat2023" /><ref name="AskFagervallRoss1983" /> An Template:Abbrlink value of 260Template:NbspμM in vitro and 80 to 100% inhibition of MAO-A at a dose of 10Template:Nbspmg/kg in rats in vivo have been reported.<ref name="GlennonDukat2023" /><ref name="Rényi1986">Template:Cite journal</ref> αET is described as slightly more potent as an MAOI than dextroamphetamine.<ref name="GlennonDukat2023" /> Both enantiomers of αET have similar activity as MAOIs, whereas αET's major metabolite 6-hydroxy-αET is inactive.<ref name="GlennonDukat2023" /> The relatively weak MAOI actions of αET have been considered unlikely to be involved in its stimulant, antidepressant, and other psychoactive effects by certain sources.<ref name="GlennonDukat2023" /><ref name="TiHKAL" />

The stimulant effects of αET have been said to lie primarily in (–)-αET, whereas hallucinogenic effects have been said to be present in (+)-αET.<ref name="GlennonDukat2023" /><ref name="Barceloux2012" /> However, these claims appear to be based on animal drug discrimination studies and are not necessarily in accordance with functional studies.<ref name="GlennonDukat2023" /><ref name="BloughLandavazo2014" /> Generalization to Template:Abbrlink may have been anomalous and due to the serotonin-releasing actions of αET rather than due to serotonin 5-HT_2A receptor activation and associated psychedelic effects.<ref name="GlennonDukat2023" /> Accordingly, αET does not produce the head-twitch response in rodents, unlike known psychedelics.<ref name="GlennonDukat2023" /> In addition, clear hallucinogenic effects of αET have never been documented in humans even at high doses, although the individual enantiomers of αET have never been studied in humans.<ref name="GlennonDukat2023" />

αET has been found to produce serotonergic neurotoxicity similar to that of MDMA and para-chloroamphetamine (PCA) in rats.<ref name="Oeri2021" /><ref name="GlennonDukat2023" /><ref name="HuangJohnsonNichols1991">Template:Cite journal</ref> This has included long-lasting reductions in serotonin levels, 5-hydroxyindoleacetic acid (5-HIAA) levels, and serotonin uptake sites in the frontal cortex and hippocampus.<ref name="Oeri2021" /><ref name="HuangJohnsonNichols1991" /> The dosage of αET employed was 8Template:Nbspdoses of 30Template:Nbspmg/kg by subcutaneous injection with doses spaced by 12-hour intervals.<ref name="Oeri2021" /><ref name="HuangJohnsonNichols1991" /> There are prominent species differences in the neurotoxicity of monoamine releasing agents.<ref name="CapelaCarmoRemião2009">Template:Cite journal</ref><ref name="MoratallaKhairnarSimola2017">Template:Cite journal</ref> Primates appear to be more susceptible to the damage caused by serotonergic neurotoxins like MDMA than rodents.<ref name="CapelaCarmoRemião2009" />

Pharmacokinetics

The absorption of αET appears to be rapid.<ref name="Barceloux2012" /> It has a relatively large volume of distribution.<ref name="Barceloux2012" /> The drug undergoes hydroxylation to form the major metabolite 6-hydroxy-αET (3-(2-aminobutyl)-6-hydroxyindole).<ref name="GlennonDukat2023" /><ref name="Barceloux2012" /> This metabolite is inactive.<ref name="Barceloux2012" /> αET is eliminated primarily in urine and a majority of a dose is excreted in urine within 12 to 24Template:Nbsphours.<ref name="Barceloux2012" /> Its elimination half-life is approximately 8Template:Nbsphours.<ref name="Barceloux2012" />

Chemistry

αET, also known as 3-(2-aminobutyl)indole, is a substituted tryptamine and α-alkyltryptamine derivative.<ref name="GlennonDukat2023" /><ref name="Oeri2021" /> Analogues of αET include α-methyltryptamine (αMT) and other substituted α-alkylated tryptamines like 5-MeO-αET, 5-chloro-αMT (PAL-542), and 5-fluoro-αET (PAL-545).<ref name="BloughLandavazo2014" />

History

αET was first described in the scientific literature in 1947.<ref name="GlennonDukat2023" /><ref name="SnyderKatz1947">Template:Cite journal</ref> The enantiomers of αET were first individually described in 1970.<ref name="GlennonDukat2023" />

Originally believed to exert its effects predominantly via monoamine oxidase inhibition, αET was developed during the 1960s as an antidepressant by Upjohn chemical company in the United States under the generic name etryptamine and the brand name Monase, but was withdrawn from potential commercial use due to incidence of idiosyncratic agranulocytosis in several patients.<ref name="GlennonDukat2023" /><ref name="TiHKAL" /><ref name="Butin1962" /> It was on the market for about a year, around 1961, and was given to more than 5,000Template:Nbsppatients, before being withdrawn.<ref name="GlennonDukat2023" /> αET was usually used as an antidepressant at doses of 30 to 40Template:Nbspmg/day (but up to 75Template:Nbspmg/day), which are lower than the doses that have been used recreationally.<ref name="GlennonDukat2023" /><ref name="Oeri2021" />

αET gained limited recreational popularity as a designer drug with MDMA-like effects in the 1980s.<ref name="GlennonDukat2023" /> Subsequently, in the United States it was added to the Schedule I list of illegal substances in 1993 or 1994.<ref name="GlennonDukat2023" /><ref name="TiHKAL" />

Society and culture

Names

Etryptamine is the formal generic name of the drug and its Template:Abbrlink and Template:Abbrlink.<ref name="Elks2014">Template:Cite book</ref> In the case of the acetate salt, its generic name is etryptamine acetate and this is its Template:Abbrlink.<ref name="Elks2014" /> Etryptamine was used pharmaceutically as etryptamine acetate.<ref name="Elks2014" /><ref name="GlennonDukat2023" /><ref name="RockyMountainDruggist1961" /> Etryptamine is much more well known as alpha-ethyltryptamine or α-ethyltryptamine (abbreviated as αET, α-ET, or AET).<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="TiHKAL" /> Other synonyms of αET and/or its acetate salt include 3-(2-aminobutyl)indole, 3-indolylbutylamine, PAL-125, U-17312E, Ro 3-1932, NSC-63963, and NSC-88061, as well as its former brand name Monase.<ref name="Elks2014" /><ref name="CAS-αET">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="CAS-αET-acetate">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="BloughLandavazo2014" />

Recreational use

αET has been used as a recreational drug since the 1980s.<ref name="GlennonDukat2023" /><ref name="Oeri2021" /><ref name="VarìPichiniGiorgetti2019" /><ref name="Barceloux2012">Template:Cite book</ref> Purported street names include Trip, ET, Love Pearls, and Love Pills.<ref name="GlennonDukat2023" /><ref name="Barceloux2012" />

Legal status

αET is a Schedule I controlled substance in the United States and a Class A controlled substance in the United Kingdom.<ref name="GlennonDukat2023" /><ref name="VarìPichiniGiorgetti2019" />

Research

Besides depression, αET has been studied in people with schizophrenia and other conditions.<ref name="GlennonDukat2023" />

External links

• #11. α-ET - TiHKAL - Erowid
• #11 α-ET - TiHKAL - isomer design
• AET - Erowid

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