2-Aminotetralin

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 477212588

| IUPAC_name = 1,2,3,4-tetrahydronaphthalen-2-amine

| image = 2-Aminotetralin Structure.svg

| width =

| tradename =

| pregnancy_category =

| legal_status = Uncontrolled

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

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

| CAS_number = 2954-50-9

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

| UNII = LGX8T83G7X

| ATC_prefix = none

| ATC_suffix =

| PubChem = 34677

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

| ChemSpiderID = 31912

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

| ChEMBL = 30294

| C=10 | H=13 | N=1

| smiles = C1CC2=CC=CC=C2CC1N

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

| StdInChI = 1S/C10H13N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4,10H,5-7,11H2

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

| StdInChIKey = LCGFVWKNXLRFIF-UHFFFAOYSA-N

}}

2-Aminotetralin (2-AT), also known as 1,2,3,4-tetrahydronaphthalen-2-amine (THN), is a stimulant drug with a chemical structure consisting of a tetralin core with an amine as substituent.{{cite journal | vauthors = Oberlender R, Nichols DE | s2cid = 19069907 | title = Structural variation and (+)-amphetamine-like discriminative stimulus properties | journal = Pharmacology, Biochemistry, and Behavior | volume = 38 | issue = 3 | pages = 581–586 | date = March 1991 | pmid = 2068194 | doi = 10.1016/0091-3057(91)90017-V | url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=77437efa02b4a0f688e4038b153ddfafde6da614 | quote = In previous studies, 2-AT either did not stimulate spontaneous motor activity in mice (1,8), or it had 10% of the activity of amphetamine (24). Yet, in the present study, it mimicked (+)-amphetamine as a DS in rats, in agreement with the results of Glennon et al. (7). However, 2-AT was one-half as potent as (+)-amphetamine in that study but only one-eighth as potent as (+)-amphetamine in the present experiment. | url-access = subscription }}{{cite journal | vauthors = Marley E, Stephenson JD | title = Actions of dexamphetamine and amphetamine-like amines in chickens with brain transections | journal = British Journal of Pharmacology | volume = 42 | issue = 4 | pages = 522–542 | date = August 1971 | pmid = 5116035 | pmc = 1665761 | doi = 10.1111/j.1476-5381.1971.tb07138.x }}

2-AT is a rigid analogue of phenylisobutylamine and fully substitutes for d-amphetamine in rat drug discrimination tests, although at one-half to one-eighth the potency.{{cite journal | vauthors = Glennon RA, Young R, Hauck AE, McKenney JD | title = Structure-activity studies on amphetamine analogs using drug discrimination methodology | journal = Pharmacol Biochem Behav | volume = 21 | issue = 6 | pages = 895–901 | date = December 1984 | pmid = 6522418 | doi = 10.1016/s0091-3057(84)80071-4 | url = }} It showed greater potency than a variety of other amphetamine homologues, including 2-amino-1,2-dihydronapthalene (2-ADN), 2-aminoindane (2-AI), 1-naphthylaminopropane (1-NAP), 2-naphthylaminopropane (2-NAP), 1-phenylpiperazine (1-PP), {{Abbrlink|6-AB|6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene}}, and {{Abbrlink|7-AB|7-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene}}.{{cite journal |vauthors=Hathaway BA, Nichols DE, Nichols MB, Yim GK | title = A new, potent, conformationally restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene | journal = Journal of Medicinal Chemistry | volume = 25 | issue = 5 | pages = 535–538 |date=May 1982 | pmid = 6123601 | doi = 10.1021/jm00347a011}}

2-AT has been shown to inhibit the reuptake of serotonin and norepinephrine, and might induce their release as well.{{cite journal | vauthors = Bruinvels J | title = Evidence for inhibition of the reuptake of 5-hydroxytryptamine and noradrenaline by tetrahydronaphthylamine in rat brain | journal = British Journal of Pharmacology | volume = 42 | issue = 2 | pages = 281–286 | date = June 1971 | pmid = 5091160 | pmc = 1667157 | doi = 10.1111/j.1476-5381.1971.tb07109.x }}{{cite journal | vauthors = Bruinvels J, Kemper GC | title = Role of noradrenaline and 5-hydroxytryptamine in tetrahydronaphthylamine-induced temperature changes in the rat | journal = British Journal of Pharmacology | volume = 43 | issue = 1 | pages = 1–9 | date = September 1971 | pmid = 4257629 | pmc = 1665934 | doi = 10.1111/j.1476-5381.1971.tb07151.x }} It is also likely to act on dopamine on account of its full substitution of d-amphetamine in rodent studies.