{{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | verifiedrevid = 415659854 | drug_name = | image = IDNNA.svg | image_class = skin-invert-image | width = 200px | caption =
<!-- Clinical data --> | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = Oral<ref name="PiHKAL" /> | class = | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = Unknown<ref name="PiHKAL" /> | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 85563-10-6 | CAS_supplemental = | PubChem = 135056 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 119009 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = M6Q9NK9RFD | KEGG = | ChEBI = | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 11043 | NIAID_ChemDB = | PDB_ligand = | synonyms = 4-Iodo-2,5-dimethoxy-''N'',''N''-dimethylamphetamine; 2,5-Dimethoxy-4-iodo-''N,N''-dimethylamphetamine; ''N'',''N''-Dimethyl-DOI
<!-- Chemical data --> | IUPAC_name = 1-(4-iodo-2,5-dimethoxyphenyl)-''N'',''N''-dimethylpropan-2-amine | C=13 | H=20 | N=1 | O=2 | I=1 | SMILES = Ic1cc(OC)c(cc1OC)CC(N(C)C)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C13H20INO2/c1-9(15(2)3)6-10-7-13(17-5)11(14)8-12(10)16-4/h7-9H,6H2,1-5H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = XBCUSBRGRALQID-UHFFFAOYSA-N }}
'''IDNNA''', also known as '''4-iodo-2,5-dimethoxy-''N'',''N''-dimethylamphetamine''' or as '''''N'',''N''-dimethyl-DOI''', is a chemical compound of the phenethylamine, amphetamine, and DOx families.<ref name="PiHKAL" /><ref name="Shulgin2003">{{cite book | vauthors = Shulgin AT | year = 2003 | veditors = Laing RR | chapter = Basic Pharmacology and Effects | title = Hallucinogens: A Forensic Drug Handbook | publisher = Elsevier Science | pages = 67–137 | isbn = 978-0-12-433951-4 | url = https://books.google.com/books?id=l1DrqgobbcwC | archive-date = 13 July 2025 | archive-url = https://web.archive.org/web/20250713013624/https://bibliography.maps.org/resources/download/12634 | series = Forensic Drug Handbook Series | chapter-url = https://bibliography.maps.org/resources/download/12634 | quote = The N,N-dimethyl homologue of DOI was called IDNNA (2,5-dimethoxy-N,N-dimethyl-4-iodoamphetamine) and, although not active at levels where DOI would be, it led to an extensive series of some 15 mono- and di-N-alkylated amines related to DOI. They were prepared for studies of 131I labelled compounds for rat pharmacology (and eventual 122I PET scanning agents for human studies) but none of them had been clinically explored. }}</ref><ref name="TrachselLehmannEnzensperger2013">{{cite book | vauthors = Trachsel D, Lehmann D, Enzensperger C | year = 2013 | title = Phenethylamine: von der Struktur zur Funktion | language = de | publisher = Nachtschatten-Verlag | edition = 1 | isbn = 978-3-03788-700-4 | url = https://books.google.com/books?id=-Us1kgEACAAJ | access-date = 23 February 2026 | archive-date = 13 November 2025 | archive-url = https://web.archive.org/web/20251113135159/https://books.google.com/books?id=-Us1kgEACAAJ | trans-title = Phenethylamines: From Structure to Function | location = Solothurn | series = Nachtschatten-Science | oclc = 858805226 | url-status = bot: unknown }}</ref> It is the ''N'',''N''-dimethyl derivative of the psychedelic drug DOI.<ref name="PiHKAL" /><ref name="Shulgin2003" /><ref name="TrachselLehmannEnzensperger2013" />
==Use and effects== In his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved''), Alexander Shulgin lists IDNNA's dose as greater than 2.6{{nbsp}}mg orally and its duration as unknown.<ref name="PiHKAL">{{CitePiHKAL}} [http://www.erowid.org/library/books_online/pihkal/pihkal090.shtml IDNNA Entry]</ref><ref name="Shulgin2003" /><ref name="TrachselLehmannEnzensperger2013" /> IDNNA produced no effects at tested doses.<ref name="PiHKAL" /> Higher doses were not assessed.<ref name="PiHKAL" />
==Chemistry== ===Synthesis=== The chemical synthesis of IDNNA has been described.<ref name="PiHKAL" />
===Analogues=== Analogues of IDNNA include DOI, ''N''-methyl-DOI, methyl-DOB (''N''-methyl-DOB), Beatrice (''N''-methyl-DOM), ''N''-methyl-DOET, ''N''-methyl-2C-I, and ''N''-methyl-2C-B, among others.<ref name="PiHKAL" /><ref name="Shulgin2003" /><ref name="TrachselLehmannEnzensperger2013" />
==History== IDNNA was first described in the scientific literature by Alexander Shulgin and colleagues in 1982.<ref name="SargentShulginMathis1982">{{cite journal | vauthors = Sargent T, Shulgin AT, Mathis CA | date = 1982 | title = New iodinated amphetamines by rapid synthesis for use as brain blood flow indicators | journal = Journal of Labelled Compounds and Radiopharmaceuticals | volume = 19 | issue = 11–12 | pages = 1307–1308 | doi = 10.1002/jlcr.2580191102 | url = https://bibliography.maps.org/resources/download/8831 | archive-date = 2025-07-12 | archive-url = https://web.archive.org/web/20250712232752/https://bibliography.maps.org/resources/download/8831 }}</ref> Subsequently, it was described in greater detail by Shulgin in his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'') in 1991.<ref name="PiHKAL" />
==Society and culture== ===Legal status=== ====Canada==== IDNNA is a controlled substance in Canada under phenethylamine blanket-ban language.<ref name="CDSA">{{cite web | title = Controlled Drugs and Substances Act | website = Department of Justice Canada | url = https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date = 19 January 2026 }}</ref>
====United Kingdom==== This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.<ref>{{cite web | title = UK Misuse of Drugs act 2001 Amendment summary | publisher = Isomer Design | url = http://isomerdesign.com/Cdsa/scheduleUK.php?schedule=1&ion=30&structure=C | access-date = 12 March 2014 | archive-date = 22 October 2017 | archive-url = https://web.archive.org/web/20171022085110/http://isomerdesign.com/Cdsa/scheduleUK.php?schedule=1&ion=30&structure=C | url-status = dead }}</ref>
== See also == * DOx (psychedelics)
== References == {{Reflist}}
== External links == * [https://isomerdesign.com/pihkal/explore/90 IDNNA - Isomer Design] * [https://www.erowid.org/library/books_online/pihkal/pihkal090.shtml IDNNA - PiHKAL - Erowid] * [https://isomerdesign.com/pihkal/read/pk/90 IDNNA - PiHKAL - Isomer Design]
{{Phenethylamines}}
Category:Dimethylamino compounds Category:DOx (psychedelics) Category:Iodobenzene derivatives Category:Phenol ethers Category:PiHKAL