5-IAI

Clinical data
Other names	5-Iodo-2-aminoindane; 5-Iodo-2-aminoindan; 5-IAI; NRG-5
Routes of administration	Oral,insufflation,rectal
Drug class	Serotonin–norepinephrine–dopamine releasing agent;Entactogen
ATC code	None
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)[1] DE: NpSG (Industrial and scientific use only) UK: UnderPsychoactive Substances Act In general: uncontrolled
Identifiers
IUPAC name 5-iodo-2,3-dihydro-1H-inden-2-amine
CAS Number	132367-76-1 N
PubChemCID	131506
ChemSpider	116224 Y
UNII	7X16E45Y1X
CompTox Dashboard(EPA)	DTXSID60927643
Chemical and physical data
Formula	C9H10IN
Molar mass	259.090 g·mol−1
3D model (JSmol)	Interactive image
SMILES c2c1CC(N)Cc1ccc2I
InChI InChI=1S/C9H10IN/c10-8-2-1-6-4-9(11)5-7(6)3-8/h1-3,9H,4-5,11H2 Y Key:BIHPYCDDPGNWQO-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

5-Iodo-2-aminoindane (5-IAI) is anentactogendrug of the2-aminoindane family.^[2][3] Humananecdotal reports suggest that it is entactogenic but produces littleeuphoria orstimulation.^[3][2]

The drug acts as areleasing agent ofserotonin,norepinephrine, anddopamine.^[3][2][4] It produces much lessserotonergic neurotoxicity thanMDMA in animals.^[3][2]

5-IAI was developed in the 1990s by a team led byDavid E. Nichols atPurdue University.^[2][5] It was encountered as a novelrecreationaldesigner drug in 2010, but never gained widespread popularity.^[3][2]

The human dosage of 5-IAI has been described as 100 to 200 mg and itsduration of action as 2 to 4 hours.^[3] Humananecdotal reports suggest that 5-IAI isentactogenic and that it increasessociability andtrust.^[3] On the other hand, it is reported that 5-IAI produces very littleeuphoria and is far lessstimulating than MDMA and otheramphetamines.^[3] Relatedly,2-aminoindanes like 5-IAI never gained widespread popularity asrecreational drugs, probably due to their relative lack of euphoria.^[3]

Similarly toMDMA, 5-IAI acts as aserotonin–norepinephrine–dopamine releasing agent (SNDRA).^[3] ItsEC₅₀Tooltip half-maximal effective concentration values for induction of monoamine release have not been reported.^[3] In any case, its relativepotency for monoamine release is serotonin > dopamine > norepinephrine.^[3] In addition, 5-IAI'saffinity (K_i) values for themonoamine transporters are 879 nM for theserotonin transporter (SERT), 311 nM for thenorepinephrine transporter (NET), and 992 nM for thedopamine transporter (DAT), whereas its values in terms offunctional 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 theserotonin5-HT_1A,5-HT_2A,5-HT_2B, and5-HT_2C receptors, as well as affinity for theα_2A-,α_2B-, andα_2C-adrenergic receptors.^[3] The high affinity for theserotonin receptors is in contrast toMDAI.^[3]

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

Unlike related2-aminoindane derivatives like MDAI andMMAI, 5-IAI causes someserotonergic neurotoxicity in rats (15% or less reduction of serotonergic markers), but is less neurotoxic than its correspondingamphetamine homologuepara-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 producecognitive andmemory deficits in rodents.^[3]

5-IAI was first described in thescientific literature byDavid E. Nichols and colleagues atPurdue University in 1991.^[2][5] It was encountered as a noveldesigner drug online in 2010 and in theUnited Kingdom in 2011.^[2]

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

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

• Substituted 2-aminoindane
• Cyclized phenethylamine

• 5-IAI - Isomer Design

• Drugs not assigned an ATC code
• 2-Aminoindanes
• David E. Nichols
• Entactogens
• Monoaminergic neurotoxins
• Serotonin-norepinephrine-dopamine releasing agents

• CS1 Brazilian Portuguese-language sources (pt-br)
• CS1 Swedish-language sources (sv)
• Articles with short description
• Short description matches Wikidata
• Short description is different from Wikidata
• Drugs with non-standard legal status
• Articles with changed CASNo identifier
• Articles without EBI source
• Chemical pages without DrugBank identifier
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• Drugboxes which contain changes to verified fields