View source for Chemistry:6-(2-Aminopropyl)indole

{{Short description|Chemical compound}}
{{Infobox drug
| IUPAC_name         = 1-(1''H''-Indol-6-yl)propan-2-amine
| image              = 6-API.svg

<!--Clinical data-->| tradename          = 
| pregnancy_category = 
| legal_DE           = Uncontrolled
| legal_DE_comment   = <ref name="New Psychoactive Substances Act" />
| legal_status       = Uncontrolled <small>(but covered under the Federal Analogue Act in the {{wipe|United States}} and {{wipe|Australia}} and likely under similar bills in other countries{{clarification needed|date=November 2021}}){{citation needed|date=November 2021}}</small>
| routes_of_administration = Oral

<!--Pharmacokinetic data-->| bioavailability    = 
| metabolism         = 
| elimination_half-life = 
| excretion          = <!--Identifiers-->
| CAS_number         = 22196-72-1
| UNII_Ref           = {{fdacite|correct|FDA}}
| UNII               = M7C77J017A
| ATC_prefix         = 
| ATC_suffix         = 
| PubChem            = 30999
| ChemSpiderID       = 28759
| C                  = 11
| H                  = 14
| N                  = 2
| smiles             = C1=C2C(=CC=C1CC(C)N([H])[H])C=C[N]2[H]
| StdInChI_Ref       = {{stdinchicite|correct|chemspider}}
| StdInChI           = 1S/C11H14N2/c1-8(12)6-9-2-3-10-4-5-13-11(10)7-9/h2-5,7-8,13H,6,12H2,1H3
| StdInChIKey_Ref    = {{stdinchicite|correct|chemspider}}
| StdInChIKey        = QCFIFKAOUKPFPU-UHFFFAOYSA-N
}}

'''6-(2-Aminopropyl)indole''' ('''6-API''', '''6-IT''') is an [[Chemistry:Indole|indole]] derivative which was first identified being sold on the [[Chemistry:Designer drug|designer drug]] market by a laboratory in the Czechia in July 2016.<ref>[http://www.emcdda.europa.eu/system/files/publications/4724/TDAN17001ENN_PDFWEB.pdf Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA]</ref>

Alexander Shulgin says in his book [[Chemistry:TiHKAL|TiHKAL]] "From the normal 3-position to the 2, the 4, the 5, the 6 or the 7-positions. All five alpha-methyltryptamine isomers are known, but only one is known to be active in man as a [[Biology:Central nervous system|CNS]] active material. This is the 5-isomer, 5-(2-aminopropyl)indole or [[Biology:5-IT|5-IT]]"[http://www.erowid.org/library/books_online/tihkal/tihkal48.shtml].

Studies in dogs have also shown the drug to increase [[Biology:Hemoglobin|hemoglobin]] levels in the bloodstream.<ref>{{cite journal | vauthors = Maxwell GM | title = The effects of an indole derivative 692'-amino-propyl indole) on the general and coronary haemodynamics of the intact dog | journal = Experientia | volume = 20 | issue = 9 | pages = 526–7 | date = September 1964 | pmid = 5856353 | doi = 10.1007/BF02154095 | s2cid = 7574163 }}</ref>

== Legality ==
* 6-API is a positional isomer of αMT, and as such may be covered by the analogue act in the USA (depending on the nature of its psychoactive effect).
* 6-API / 6-IT is illegal in the UK, as it was banned as a [[Medicine:Temporary class drug|temporary class drug]] in June 2013, along with 9 other related compounds.<ref name='ACMD report'>{{cite web | url = https://www.gov.uk/government/publications/temporary-class-drug-order-report-on-benzofury-and-nbome-compounds | title = Temporary class drug order report on 5-6APB and NBOMe compounds | access-date = 2013-07-11 | date = 4 Jun 2013 | publisher = UK Home Office}}</ref> On March 5, 2014, the UK Home Office announced that 6-API would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs.<ref>{{cite web | url = http://www.legislation.gov.uk/ukdsi/2014/9780111110904 | title = The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014 | access-date = 2014-03-11 | author = UK Home Office | date = 2014-03-05 | publisher = UK Government}}</ref>
* 6-API is covered by the Australian analogue act as an analogue of MDA "by the replacement of up to 2 carbocyclic or heterocyclic ring structures with different carbocyclic or heterocyclic ring structures"<ref name='aus analogue act'>{{cite web | url = http://www.comlaw.gov.au/ComLaw/Legislation/ActCompilation1.nsf/0/1B4A2DD73EF9A4BBCA2576040024B600/$file/CriminalCode1995_WD02.pdf | title = Criminal Code Act 1995 | access-date = 2012-02-08 | date = 2009-08-05 | publisher = Australian Government | quote = PAGE 503}}</ref>
*6-API is uncontrolled in Germany, as indole rings are not included as rings under the 2-phenethylamine derived section of the NPsG.<ref name="New Psychoactive Substances Act">{{cite web|title=New Psychoactive Substances Act (Neue-psychoaktive-Stoffe-Gesetz) (NpSG) Non-official translation|url=https://www.bundesgesundheitsministerium.de/fileadmin/Dateien/3_Downloads/Gesetze_und_Verordnungen/GuV/N/NpSG_englisch.pdf|access-date=9 November 2021}}</ref>

== References ==
{{Reflist}}

{{Entactogens|state=expanded}}
{{Stimulants}}
{{Adrenergics}}
{{Dopaminergics}}
{{Serotonergics}}
{{Phenethylamines}}

{{DEFAULTSORT:Aminopropyl)indole, 6-(2-}}
[[Category:Indoles]]
[[Category:Stimulants]]
[[Category:Entactogens and empathogens]]
[[Category:Substituted amphetamines]]

{{Sourceattribution|6-(2-Aminopropyl)indole}}