2-Aminoindane

2-Aminoindane (2-AI) is an aminoindane and research chemical that has been sold as a designer drug.^[2]

2-Aminoindane

Clinical data
Other names	2-Indanylamine; 2-Indanamine, SU-8629.[1]
Routes of administration	Oral
ATC code	none
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act In general: uncontrolled
Identifiers
IUPAC name 2,3-Dihydro-1H-inden-2-amine
CAS Number	2975-41-9 N
PubChem CID	76310
ChemSpider	68787 Y
UNII	1P810SQ3EY
CompTox Dashboard (EPA)	DTXSID40183902
ECHA InfoCard	100.019.111
Chemical and physical data
Formula	C9H11N
Molar mass	133.194 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1C(CC2=CC=CC=C21)N
InChI InChI=1S/C9H11N/c10-9-5-7-3-1-2-4-8(7)6-9/h1-4,9H,5-6,10H2 Y Key:LMHHFZAXSANGGM-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Pharmacology

Pharmacodynamics

2-AI is a monoamine releasing agent acting as a selective substrate for NET and DAT.^[3][4] It partially substitutes for amphetamine in rodent drug discrimination tests.^[5][6]

Activities of 2-aminoindanes and amphetamine relatives

Compound	Monoamine release (EC50Tooltip half-maximal effective concentration, nM)			Ref
	Serotonin	Norepinephrine	Dopamine
2-AI	>10,000	86	439	[7]
MDAI	114	117	1,334	[7]
MMAI	31	3,101	>10,000	[7]
MEAI	134	861	2,646	[7]
d-Amphetamine	698–1,765	6.6–7.2	5.8–24.8	[8][9][10][11][12]
MDA	160–162	47–108	106–190	[13][10][14]
MDMA	50–85	54–110	51–278	[8][15][16][13][14]
3-MA	ND	58.0	103	[10]
Notes: The smaller the value, the more strongly the compound produces the effect. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs: [7]

Chemistry

Analogues

2-AI is a rigid analogue of amphetamine and has similar effects in rodents.^[5][6] Other related homologues and rigid analogues of amphetamine include 2-aminotetralin (2-AT), 2-amino-1,2-dihydronapthalene (2-ADN), 1-naphthylaminopropane (1-NAP), 2-naphthylaminopropane (2-NAP), 1-phenylpiperazine (1-PP), 6-ABTooltip 6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene, and 7-ABTooltip 7-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene.^[6][5][17]

Derivatives

There are a number of notable derivatives of 2-aminoindane that exist, including:

• 5-IAI
• Aprindine
• BFAI
• BFMAI
• DHAI
• DOM-AI^[18][19]
• ETAI
• Indanorex
• Indantadol
• MDAI
• MEAI (5-MeO-AI)
• MDMAI
• MMAI
• NM-2-AI
• PNU-99,194
• TAI

A number of notable derivatives of 1-aminoindan, a positional isomer of 2-aminoindan, also exist, such as rasagiline and ladostigil, among others.

Jimscaline, 2CB-Ind, and AMMI are derivatives of 1-aminomethylindane, an indane- and amine-containing compound related to 1-aminoindan.

Society and culture

Legal status

China

As of October 2015 2-AI is a controlled substance in China.^[20]

Finland

Scheduled in the "Government decree on psychoactive substances banned from the consumer market".^[21]

Sweden

Sweden's public health agency suggested classifying 2-AI as a hazardous substance, on June 24, 2019.^[22]

United States

2-Aminoindane is not scheduled at the federal level in the United States,^[23] but may be considered an analog of amphetamine, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act.

Research

Synthetic aminoindanes were originally developed in the context of anti-Parkinsonian drugs as a metabolite of rasagiline and as a tool to be used in psychotherapy. Deaths related to their toxic effects have been observed both in the laboratory in animal studies and in clinical encounters.^[24]

See also

• Cyclized phenethylamine
• 1-Aminoindane
• 1-Aminomethylindane
• 2-Aminotetralin