5-IAI

5-IAI
Clinical data
Other names5-Iodo-2-aminoindane; 5-Iodo-2-aminoindan; 5-IAI; NRG-5
Routes of
administration		Oral, insufflation, rectal
Drug classSerotonin–norepinephrine–dopamine releasing agent; Entactogen
ATC code
  • None
Legal status
Legal status
Identifiers
  • 5-iodo-2,3-dihydro-1H-inden-2-amine
CAS Number
  • 132367-76-1 ☒N
PubChem CID
  • 131506
ChemSpider
  • 116224 checkY
UNII
  • 7X16E45Y1X
CompTox Dashboard (EPA)
  • DTXSID60927643
Chemical and physical data
FormulaC9H10IN
Molar mass259.090 g·mol−1
3D model (JSmol)
  • Interactive image
  • c2c1CC(N)Cc1ccc2I
  • InChI=1S/C9H10IN/c10-8-2-1-6-4-9(11)5-7(6)3-8/h1-3,9H,4-5,11H2 checkY
  • Key:BIHPYCDDPGNWQO-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

5-Iodo-2-aminoindane (5-IAI) is an entactogen drug of the 2-aminoindane family.[2][3] Human anecdotal reports suggest that it is entactogenic but produces little euphoria or stimulation.[3][2]

The drug acts as a releasing agent of serotonin, norepinephrine, and dopamine.[3][2][4] It produces much less serotonergic neurotoxicity than MDMA in animals.[3][2]

5-IAI was developed in the 1990s by a team led by David E. Nichols at Purdue University.[2][5] It was encountered as a novel recreational designer drug in 2010, but never gained widespread popularity.[3][2]

Use and effects

The human dosage of 5-IAI has been described as 100 to 200 mg and its duration of action as 2 to 4 hours.[3] Human anecdotal reports suggest that 5-IAI is entactogenic and that it increases sociability and trust.[3] On the other hand, it is reported that 5-IAI produces very little euphoria and is far less stimulating than MDMA and other amphetamines.[3] Relatedly, 2-aminoindanes like 5-IAI never gained widespread popularity as recreational drugs, probably due to their relative lack of euphoria.[3]

Interactions

Pharmacology

Pharmacodynamics

Similarly to MDMA, 5-IAI acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA).[3] Its EC50Tooltip half-maximal effective concentration values for induction of monoamine release have not been reported.[3] In any case, its relative potency for monoamine release is serotonin > dopamine > norepinephrine.[3] In addition, 5-IAI's affinity (Ki) values for the monoamine transporters are 879 nM for the serotonin transporter (SERT), 311 nM for the norepinephrine transporter (NET), and 992 nM for the dopamine transporter (DAT), whereas its values in terms of functional inhibition have been reported to be 241 nM or 2,500 nM at the SERT, 612 nM or 760 nM at the NET, and 992 nM or 2,300 nM at the DAT in two different respective studies.[3]

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.[3] The high affinity for the serotonin receptors is in contrast to MDAI.[3]

5-IAI and MDAI fully substitute for MDMA in drug discrimination tests in rodents.[3][5] This suggests that they produce MDMA-like subjective and entactogenic effects in rodents.[3]

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".[3][4] In any case, regular high-dose 5-IAI has been found to produce cognitive and memory deficits in rodents.[3]

History

5-IAI was first described in the scientific literature by David E. Nichols and colleagues at Purdue University in 1991.[2][5] It was encountered as a novel designer drug online in 2010 and in the United Kingdom in 2011.[2]

Society and culture

Finland

Scheduled in the "government decree on psychoactive substances banned from the consumer market".[6]

Sweden

Sweden's public health agency suggested classifying 5-IAI as a hazardous substance, on September 25, 2019.[7]

See also

References

  1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ^ a b c d e f g h Coppola M, Mondola R (March 2013). "5-Iodo-2-aminoindan (5-IAI): chemistry, pharmacology, and toxicology of a research chemical producing MDMA-like effects". Toxicol Lett. 218 (1): 24–29. doi:10.1016/j.toxlet.2013.01.008. PMID 23347877.
  3. ^ a b c d e f g h i j k l m n o p q r s Oeri HE (May 2021). "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". J Psychopharmacol. 35 (5): 512–536. doi:10.1177/0269881120920420. PMC 8155739. PMID 32909493.
  4. ^ a b Johnson MP, Conarty PF, Nichols DE (July 1991). "[3H]monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues". European Journal of Pharmacology. 200 (1): 9–16. doi:10.1016/0014-2999(91)90659-E. PMID 1685125.
  5. ^ a b c Nichols DE, Johnson MP, Oberlender R (January 1991). "5-Iodo-2-aminoindan, a nonneurotoxic analogue of p-iodoamphetamine". Pharmacology Biochemistry and Behavior. 38 (1): 135–9. doi:10.1016/0091-3057(91)90601-W. PMID 1826785. S2CID 20485505.
  6. ^ "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista | 1130/2014 | Lainsäädäntö | Finlex".
  7. ^ "Tretton ämnen föreslås klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 25 September 2019. Archived from the original on 31 October 2019. Retrieved 11 November 2019.
  • 5-IAI - Isomer Design
Retrieved from "https://en.wikipedia.org/w/index.php?title=5-IAI&oldid=1322444109"