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{{Short description|Drug belonging to the tryptamine class}}
{{Drugbox
{{Drugbox
| verifiedrevid = 424655246
| verifiedrevid = 458137296
| IUPAC_name = 1-methyl-2-(4-methyl-1''H''-indol-3-yl)-ethylamine
| IUPAC_name = 1-methyl-2-(4-methyl-1''H''-indol-3-yl)-ethylamine
| image = 4-Methyl-AMT.png
| image = 4-Methyl-AMT.png
| image2 = 4-Me-AMT.png


<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
| pregnancy_category =
| pregnancy_category =
| legal_status = Uncontrolled <small>(but may be covered under the [[Federal Analogue Act]] in the [[United States]] and under similar bills in other countries)</small>
| legal_status = Uncontrolled <small>(but may be covered under the [[Federal Analogue Act]] in the [[United States]] and under similar bills in other countries)</small>
| routes_of_administration = Oral
| routes_of_administration = Oral


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability =
| bioavailability =
| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 3569-29-7
| CAS_number = 3569-29-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = QY99ES7YWD
| ATC_prefix = none
| ATC_prefix = none
| PubChem = 28806639
| PubChem = 28806639
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 25392939
| ChemSpiderID = 25392939
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| InChI = 1/C12H16N2/c1-8-4-3-5-11-12(8)10(7-14-11)6-9(2)13/h3-5,7,9,14H,6,13H2,1-2H3
| InChIKey = KEOYEGHPRBDSKD-UHFFFAOYAH
| StdInChI = 1S/C12H16N2/c1-8-4-3-5-11-12(8)10(7-14-11)6-9(2)13/h3-5,7,9,14H,6,13H2,1-2H3
| StdInChI = 1S/C12H16N2/c1-8-4-3-5-11-12(8)10(7-14-11)6-9(2)13/h3-5,7,9,14H,6,13H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KEOYEGHPRBDSKD-UHFFFAOYSA-N
| StdInChIKey = KEOYEGHPRBDSKD-UHFFFAOYSA-N


<!--Chemical data-->
<!--Chemical data-->
| C=12 | H=16 | N=2
| C=12 | H=16 | N=2
⚫
| smiles = CC(N)Cc2c1c([nH]c2)cccc1C
| molecular_weight = 188.26 g/mol
⚫
| smiles = CC(N)Cc2c1c(nc2)cccc1C
}}
}}


'''4-Methyl-αMT''' ('''MP-809'''), also known as '''4,α-dimethyltryptamine''' ('''4,α-DMT'''), is a [[drug]] belonging to the [[tryptamine]] class that was investigated as an [[antidepressant]] in the early 1960s but was never marketed.<ref name="urlTHE EFFECT OF MP-809 IN DEPRESSIVE STATES: A MULTI-BLIND STUDY -- AZIMA et al. 119 (6): 573 -- Am J Psychiatry">{{cite web | url = http://ajp.psychiatryonline.org/cgi/content/abstract/119/6/573 | title = THE EFFECT OF MP-809 IN DEPRESSIVE STATES: A MULTI-BLIND STUDY -- AZIMA et al. 119 (6): 573 -- Am J Psychiatry | format = | work = | accessdate = }}</ref><ref>{{cite journal | author = Brodey, James F.; Steiner, Wm. G.; Himwich, Harold E. | title = An electrographic study of psilocin and 4-methyl-α'-methyl-tryptamine (MP-809 Sandoz) | journal = Journal of Pharmacology and Experimental Therapeutics | year = 1963 | volume = 140 | pages = 8–18 | pmid = 14015664}}</ref> It was briefly mentioned in ''[[TiHKAL]]'' by [[Alexander Shulgin]] as a [[psychedelic drug|psychedelic]], with oral doses of 20&nbsp;mg producing "feelings of unreality" in human subjects, as well as [[peripheral]] [[side effect]]s such as [[Flushing (physiology)|flushing]], [[muscle tension|muscle tightness]], and [[mydriasis]].<ref name="urlErowid Online Books : TIHKAL - #48 a-MT">{{cite web | url = http://www.erowid.org/library/books_online/tihkal/tihkal48.shtml | title = Erowid Online Books : "TIHKAL" - #48 a-MT | work = | accessdate = }}</ref>
'''4-Methyl-α-methyltryptamine''' ('''4-Me-αMT'''), also known as '''4,α-dimethyltryptamine''' ('''4,α-DMT'''), and '''MP-809''', is a [[drug]] belonging to the [[tryptamine]] class that was investigated as an [[antidepressant]] in the early 1960s but was never marketed.<ref name="pmid13965759">{{cite journal | vauthors = Azima H, Arthurs D, Silver A, Azima FJ | title = The effect of MP-809 in depressive states: a multi-blind study | journal = The American Journal of Psychiatry | volume = 119 | issue = 6| pages = 573–4 | date = December 1962 | pmid = 13965759 | doi = 10.1176/ajp.119.6.573 }}</ref><ref>{{cite journal | vauthors = Brodey JF, Steiner WG, Himwich HE | title = An electrographic study of psilocin and 4-methyl-alpha-methyl tryptamine (MP-809) | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 140 | pages = 8–18 | date = April 1963 | pmid = 14015664 }}</ref>


== See also ==
== See also ==
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* [[alpha-Ethyltryptamine|α-Ethyltryptamine]] (αET)
* [[alpha-Ethyltryptamine|α-Ethyltryptamine]] (αET)
* [[alpha-Methyltryptamine|α-Methyltryptamine]] (αMT)
* [[alpha-Methyltryptamine|α-Methyltryptamine]] (αMT)
* [[RS134-49]]


== References ==
== References ==
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{{Antidepressants}}
{{Antidepressants}}
{{Hallucinogens}}
{{Hallucinogens}}
{{Serotonin receptor modulators}}
{{Serotonergics}}
{{Monoamine releasing agents}}
{{Tryptamines}}
{{Tryptamines}}


[[Category:Psychedelic tryptamines]]
[[Category:Psychedelic tryptamines]]
[[Category:Serotonin receptor agonists]]
[[Category:Serotonin-norepinephrine-dopamine releasing agents]]
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