:6-APT

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 451350040

| IUPAC_name = 1-(5,6,7,8-Tetrahydronaphthalen-2-yl)propan-2-amine

| image = Tetralinylaminopropane.svg

| tradename =

| pregnancy_category =

| legal_status = Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries)

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number = 3160-20-1

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

| UNII = F26UB8P44X

| ATC_prefix = none

| ATC_suffix =

| ChEMBL = 331488

| PubChem = 14964398

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

| ChemSpiderID = 23204045

| C=13 | H=19 | N=1

| smiles = CC(CC1=CC2=C(CCCC2)C=C1)N

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

| StdInChI = 1S/C13H19N/c1-10(14)8-11-6-7-12-4-2-3-5-13(12)9-11/h6-7,9-10H,2-5,8,14H2,1H3

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

| StdInChIKey = UTVKUFYOPJCDPE-UHFFFAOYSA-N

}}

6-(2-Aminopropyl)tetralin (6-APT), also sometimes called tetralinylaminopropane (TAP), is a drug of the amphetamine class which acts as a selective serotonin releasing agent (SSRA).{{cite journal | vauthors = Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE | title = Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine | journal = Journal of Medicinal Chemistry | volume = 36 | issue = 23 | pages = 3700–3706 | date = November 1993 | pmid = 8246240 | doi = 10.1021/jm00075a027 }} It has IC₅₀ values of 121 nM, 6,436 nM, and 3,371 nM for inhibiting the reuptake of serotonin, dopamine, and norepinephrine, respectively. Though it possesses an appreciable in vitro profile, in animal drug discrimination studies it was not found to substitute for MMAI or amphetamine and to only partially substitute for MBDB. This parallels Alexander Shulgin's finding that EDMA (the 1,4-benzodioxine analogue of 6-APT) is limitedly active,{{cite book | vauthors = Shulgin A, Shulgin A | date = 13 May 2016 | chapter = EDMA · 3,4-Ethylenedioxy-N-methylamphetamine | title = Pihkal: A Chemical Love Story | publisher = Transform Press | isbn = 978-0-9630096-0-9 | chapter-url = http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=110}} and appears to indicate that the pharmacokinetics of both EDMA and 6-APT may not be favorable.