5-APDI

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 415662463

| IUPAC_name = (±)-1-(2,3-dihydro-1H-inden-5-yl)propan-2-amine

| image = Indanylaminopropane.svg

| image_class = skin-invert-image

| chirality = Racemic mixture

| drug_name = Indanylaminopropane

| tradename =

| pregnancy_category =

| legal_UK = Class B

| legal_CA = Schedule III

| legal_DE = NpSG

| legal_status =

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 13396-94-6

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

| UNII = 4PH68L63R9

| ATC_prefix = none

| ATC_suffix =

| PubChem = 192600

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

| ChemSpiderID = 167142

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

| ChEMBL = 6842

| C=12 | H= 17 | N= 1

| smiles = c1cc(cc2c1CCC2)CC(N)C

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

| StdInChI = 1S/C12H17N/c1-9(13)7-10-5-6-11-3-2-4-12(11)8-10/h5-6,8-9H,2-4,7,13H2,1H3

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

| StdInChIKey = QYVNZHBQYJRLEX-UHFFFAOYSA-N

| synonyms = 5-APDI; 1-(5-Indanyl)-2-aminopropane; Indanylaminopropane; IAP; Indanametamine; 2-Aminopropylindane; 2-API; Indanylamphetamine

}}

5-(2-Aminopropyl)-2,3-dihydro-1H-indene (5-APDI), also known as indanylaminopropane (IAP), 2-aminopropylindane (2-API), indanametamine, and, incorrectly, as indanylamphetamine,{{cite journal | vauthors = Casale JF, McKibben TD, Bozenko JS, Hays PA | title = Characterization of the "Indanylamphetamines" | journal = Microgram Journal | volume = 3 | issue = 1–2 | pages = 3–10 | year = 2005 | url = http://www.usdoj.gov/dea/programs/forensicsci/microgram/journal_v3/mj05_v3_pg1.html | access-date = 2009-08-06 | archive-url = https://web.archive.org/web/20090317054109/http://www.usdoj.gov/dea/programs/forensicsci/microgram/journal_v3/mj05_v3_pg1.html | archive-date = 2009-03-17 | url-status = dead }} is an entactogen and psychedelic drug of the amphetamine family.{{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 = 3700–6 |date=November 1993 | pmid = 8246240 | doi = 10.1021/jm00075a027}}{{cite journal | vauthors = Parker MA, Marona-Lewicka D, Kurrasch D, Shulgin AT, Nichols DE | title = Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA) | journal = Journal of Medicinal Chemistry | volume = 41 | issue = 6 | pages = 1001–5 |date=March 1998 | pmid = 9526575 | doi = 10.1021/jm9705925| citeseerx = 10.1.1.688.9559 }} It has been sold by online vendors through the Internet and has been encountered as a designer drug since 2003, but its popularity and availability has diminished in recent years.

5-APDI appears to act as a potent and weakly selective serotonin releasing agent (SSRA) with IC₅₀ values of 82 nM, 1,848 nM, and 849 nM for inhibiting the reuptake of serotonin, dopamine, and norepinephrine, respectively. It fully substitutes for MBDB but not amphetamine in trained animals, though it does produce disruption for the latter at high doses.

5-APDI has been classified as a class B drug under the Misuse of Drugs Act 1971 since 10 June 2014.