:2-Methoxyamphetamine

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 477213867

| IUPAC_name = 1-(2-methoxyphenyl)propan-2-amine

| image = 2-Methoxyamphetamine.png

| image_class = skin-invert-image

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

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

| CAS_number = 15402-84-3

| ATC_prefix = none

| ATC_suffix =

| PubChem = 159755

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

| ChemSpiderID = 140465

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

| ChEMBL = 16451

| C=10 | H=15 | N=1 | O=1

| smiles = O(c1ccccc1CC(N)C)C

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

| StdInChI = 1S/C10H15NO/c1-8(11)7-9-5-3-4-6-10(9)12-2/h3-6,8H,7,11H2,1-2H3

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

| StdInChIKey = VBAHFEPKESUPDE-UHFFFAOYSA-N

}}

2-Methoxyamphetamine (2-MA), also known as ortho-methoxyamphetamine (OMA), is a drug of the amphetamine class. It is substantially weaker in inhibiting the reuptake of and inducing the release of the monoamine neurotransmitters compared to related agents such as amphetamine, MMA, and PMA,{{cite journal | vauthors = Tseng LF, Menon MK, Loh HH | title = Comparative actions of monomethoxyamphetamines on the release and uptake of biogenic amines in brain tissue | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 197 | issue = 2 | pages = 263–271 | date = May 1976 | pmid = 1271280 | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=1271280 | author-link3 = Horace Loh }} and may instead act as a β-adrenergic receptor agonist similarly to its N-methylated analogue methoxyphenamine.{{cite book | vauthors = Shulgin A, Shulgin A | title = Pihkal: A Chemical Love Story | publisher = Transform Press | year = 1991 | isbn = 0-9630096-0-5 | url = http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=97}}