5-IAI

{{Short description|Chemical compound}}

{{Redirect|NRG-5|the compact food biscuit used for disaster relief|BP-5 Compact Food}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 477224727

| IUPAC_name = 5-iodo-2,3-dihydro-1H-inden-2-amine

| image = 5-iodo-2-aminoindane.svg

| width =

| tradename =

| pregnancy_category = ?

| legal_BR = F2

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}

| legal_UK = PSA

| legal_DE = NpSG

| legal_status = Uncontrolled

| routes_of_administration = Oral, Insufflated, Rectal

| bioavailability =

| protein_bound =

| metabolism =

| metabolites =

| elimination_half-life =

| excretion =

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

| CAS_number = 132367-76-1

| ATC_prefix = none

| ATC_suffix =

| PubChem = 131506

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

| ChemSpiderID = 116224

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

| UNII = 7X16E45Y1X

| synonyms = 5-IAI; NRG-5

| C=9 | H=10 | I=1 | N=1

| SMILES = c2c1CC(N)Cc1ccc2I

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

| StdInChI = 1S/C9H10IN/c10-8-2-1-6-4-9(11)5-7(6)3-8/h1-3,9H,4-5,11H2

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

| StdInChIKey = BIHPYCDDPGNWQO-UHFFFAOYSA-N

}}

5-Iodo-2-aminoindane (5-IAI) is an entactogen drug of the 2-aminoindane group. Human anecdotal reports suggest that it is entactogenic but produces little euphoria or stimulation.

The drug acts as a releasing agent of serotonin, norepinephrine, and dopamine.{{cite journal | vauthors = Johnson MP, Conarty PF, Nichols DE | title = [3H]monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues | journal = European Journal of Pharmacology | volume = 200 | issue = 1 | pages = 9–16 |date=July 1991 | pmid = 1685125 | doi = 10.1016/0014-2999(91)90659-E}} It produces much less serotonergic neurotoxicity than MDMA in animals.

5-IAI was developed in the 1990s by a team led by David E. Nichols at Purdue University.{{cite journal | vauthors = Nichols DE, Johnson MP, Oberlender R | title = 5-Iodo-2-aminoindan, a nonneurotoxic analogue of p-iodoamphetamine | journal = Pharmacology Biochemistry and Behavior | volume = 38 | issue = 1 | pages = 135–9 |date=January 1991 | pmid = 1826785 | doi = 10.1016/0091-3057(91)90601-W| s2cid = 20485505 }} It has been encountered as a recreational designer drug but never gained widespread popularity.

Effects

The human dosage of 5-IAI has been described as 100 to 200{{nbsp}}mg and its duration of action as 2 to 4{{nbsp}}hours. Human anecdotal reports suggest that 5-IAI is entactogenic and that it increases sociability and trust. On the other hand, it is reported that 5-IAI produces very little euphoria and is far less stimulating than MDMA and other amphetamines. Relatedly, 2-aminoindanes like 5-IAI never gained widespread popularity as recreational drugs, probably due to their relative lack of euphoria.

Pharmacology

Similarly to MDMA, 5-IAI acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA).{{cite journal | vauthors = Oeri HE | title = Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy | journal = J Psychopharmacol | volume = 35 | issue = 5 | pages = 512–536 | date = May 2021 | pmid = 32909493 | pmc = 8155739 | doi = 10.1177/0269881120920420 | url = }} Its {{Abbrlink|EC50|half-maximal effective concentration}} values for induction of monoamine release have not been reported. In any case, its relative potency for monoamine release is serotonin > dopamine > norepinephrine. In addition, 5-IAI's affinity (Ki) values for the monoamine transporters are 879{{nbsp}}nM for the serotonin transporter (SERT), 311{{nbsp}}nM for the norepinephrine transporter (NET), and 992{{nbsp}}nM for the dopamine transporter (DAT), whereas its values in terms of functional inhibition have been reported to be 241{{nbsp}}nM or 2,500{{nbsp}}nM at the SERT, 612{{nbsp}}nM or 760{{nbsp}}nM at the NET, and 992{{nbsp}}nM or 2,300{{nbsp}}nM at the DAT in two different respective studies.

In addition to its interactions with the monoamine transporters, 5-IAI shows high affinity for the serotonin 5-HT1A, 5-HT2A, 5-HT2B, and 5-HT2C receptors, as well as affinity for the α2A-, α2B-, and α2C-adrenergic receptors. The high affinity for the serotonin receptors is in contrast to MDAI.

5-IAI and MDAI fully substitute for MDMA in drug discrimination tests in rodents. This suggests that they produce MDMA-like subjective and entactogenic effects in rodents.

Unlike related 2-aminoindane derivatives like MDAI and MMAI, 5-IAI causes some serotonergic neurotoxicity in rats (15% or less reduction of serotonergic markers), but is less neurotoxic than its corresponding amphetamine homologue para-iodoamphetamine (pIA) and the doses employed have been described as "extremely high". In any case, regular high-dose 5-IAI has been found to produce cognitive and memory deficits in rodents.

Legal status

= Finland =

Scheduled in the "government decree on psychoactive substances banned from the consumer market".https://finlex.fi/fi/lainsaadanto/2014/1130

= Sweden =

Sweden's public health agency suggested classifying 5-IAI as a hazardous substance, on September 25, 2019.{{cite web | url=https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2019/september/tretton-amnen-foreslas-klassas-som-narkotika-eller-halsofarlig-vara/ | title=Tretton ämnen föreslås klassas som narkotika eller hälsofarlig vara | publisher=Folkhälsomyndigheten | language=sv | date=25 September 2019 | access-date=11 November 2019 | archive-date=31 October 2019 | archive-url=https://web.archive.org/web/20191031144424/https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2019/september/tretton-amnen-foreslas-klassas-som-narkotika-eller-halsofarlig-vara/ | url-status=dead }}

References

{{Reflist}}

{{Entactogens}}

{{Monoamine releasing agents}}

{{Serotonin receptor modulators}}

{{Adrenergic receptor modulators}}

{{Monoamine neurotoxins}}

{{DEFAULTSORT:Iodo-2-aminoindane, 5-}}

Category:2-Aminoindanes

Category:Entactogens

Category:Monoaminergic neurotoxins

Category:Serotonin-norepinephrine-dopamine releasing agents