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

Quick Facts Clinical data, Other names ...
5-IAI
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Clinical data
Other names5-IAI; NRG-5
Pregnancy
category
  •  ?
Routes of
administration
Oral, Insufflated, Rectal
ATC code
  • none
Legal status
Legal status
Identifiers
  • 5-iodo-2,3-dihydro-1H-inden-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC9H10IN
Molar mass259.090 g·mol−1
3D model (JSmol)
  • 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)
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The drug acts as a releasing agent of serotonin, norepinephrine, and dopamine.[2][3] It produces much less serotonergic neurotoxicity than MDMA in animals.[2]

5-IAI was developed in the 1990s by a team led by David E. Nichols at Purdue University.[4] It has been encountered as a recreational designer drug but never gained widespread popularity.[2]

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.[2] Human anecdotal reports suggest that 5-IAI is entactogenic and that it increases sociability and trust.[2] On the other hand, it is reported that 5-IAI produces very little euphoria and is far less stimulating than MDMA and other amphetamines.[2] Relatedly, 2-aminoindanes like 5-IAI never gained widespread popularity as recreational drugs, probably due to their relative lack of euphoria.[2]

Pharmacology

Similarly to MDMA, 5-IAI acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA).[2] Its EC50Tooltip half-maximal effective concentration values for induction of monoamine release have not been reported.[2] In any case, its relative potency for monoamine release is serotonin > dopamine > norepinephrine.[2] 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.[2]

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.[2] The high affinity for the serotonin receptors is in contrast to MDAI.[2]

5-IAI and MDAI fully substitute for MDMA in drug discrimination tests in rodents.[2][4] This suggests that they produce MDMA-like subjective and entactogenic effects in rodents.[2]

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".[2][3] In any case, regular high-dose 5-IAI has been found to produce cognitive and memory deficits in rodents.[2]

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

References

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