para-Ethoxyamphetamine

{{Short description|Chemical compound}}

{{DISPLAYTITLE:para-Ethoxyamphetamine}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 462273090

| IUPAC_name = 1-(4-ethoxyphenyl)propan-2-amine

| image = 4-EtOamph.png

| image_class = skin-invert-image

| width = 180

| drug_name = para-Ethoxyamphetamine

| tradename =

| legal_CA = Schedule I

| legal_US = Schedule I (isomer of PMMA)

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 129476-58-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = C1417507NO

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 161985

| PubChem = 125379

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 111573

| synonyms = 4-Ethoxyamphetamine; 4-ETA; 4-EtO-A

| C=11 | H=17 | N=1 | O=1

| SMILES = O(c1ccc(cc1)CC(N)C)CC

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C11H17NO/c1-3-13-11-6-4-10(5-7-11)8-9(2)12/h4-7,9H,3,8,12H2,1-2H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = CCAMEVFYMFXHEN-UHFFFAOYSA-N

}}

para-Ethoxyamphetamine, also known as 4-ethoxyamphetamine (4-ETA), is a psychoactive drug and research chemical of the phenethylamine and amphetamine chemical classes which is closely related to the infamous para-methoxyamphetamine (PMA). para-Ethoxyamphetamine has similar effects to PMA in animal studies, although with slightly weaker stimulant effects.{{cite journal |vauthors=Martin-Iverson MT, Yamada N, By AW, Lodge BA |title="Designer" amphetamines: effects on behavior and monoamines with or without reserpine and/or alpha-methyl-para-tyrosine pretreatment |journal=Journal of Psychiatry & Neuroscience |volume=16 |issue=5 |pages=253–61 |date=December 1991 |pmid=1686728 |pmc=1188362 }}{{cite journal |vauthors=Corrigall WA, Robertson JM, Coen KM, Lodge BA |title=The reinforcing and discriminative stimulus properties of para-ethoxy- and para-methoxyamphetamine |journal=Pharmacology Biochemistry and Behavior |volume=41 |issue=1 |pages=165–9 |date=January 1992 |pmid=1539067 |doi= 10.1016/0091-3057(92)90077-S|citeseerx=10.1.1.670.6929 |s2cid=30080516 }}{{cite journal |vauthors=Hegadoren KM, Greenshaw AJ, Baker GB, Martin-Iverson MT, Lodge B, Soin S |title=4-Ethoxyamphetamine: effects on intracranial self-stimulation and in vitro uptake and release of 3H-dopamine and 3H-serotonin in the brains of rats |journal=Journal of Psychiatry & Neuroscience |volume=19 |issue=1 |pages=57–62 |date=January 1994 |pmid=8148367 |pmc=1188563 }} Like PMA, it has prominent MAOI activity,{{cite journal |vauthors=Martin-Iverson MT, Lodge BA |title=Effects of chronic treatment of rats with "designer" amphetamines on brain regional monoamines |journal=Canadian Journal of Physiology and Pharmacology |volume=69 |issue=12 |pages=1825–32 |date=December 1991 |pmid=1802356 |doi= 10.1139/y91-270}} and is likely to have similar dangers associated with its use.