5-APDI

5-(2-Aminopropyl)-2,3-dihydro-1H-indene (5-APDI), also known as indanylaminopropane (IAP), 2-aminopropylindane (2-API), indanametamine, and, incorrectly, as indanylamphetamine,^[1] is an entactogen and psychedelic drug of the amphetamine family.^[2][3] It has been sold by online vendors through the Internet and has been encountered as a designer drug since 2003,^[1] but its popularity and availability has diminished in recent years.

Indanylaminopropane

Clinical data
Other names	5-APDI; 1-(5-Indanyl)-2-aminopropane; Indanylaminopropane; IAP; Indanametamine; 2-Aminopropylindane; 2-API; Indanylamphetamine
Routes of administration	Oral
ATC code	none
Legal status
Legal status	CA: Schedule III DE: NpSG (Industrial and scientific use only) UK: Class B
Identifiers
IUPAC name (±)-1-(2,3-dihydro-1H-inden-5-yl)propan-2-amine
CAS Number	13396-94-6 N
PubChem CID	192600
ChemSpider	167142 Y
UNII	4PH68L63R9
ChEMBL	ChEMBL6842 Y
CompTox Dashboard (EPA)	DTXSID00896945
Chemical and physical data
Formula	C12H17N
Molar mass	175.275 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES c1cc(cc2c1CCC2)CC(N)C
InChI InChI=1S/C12H17N/c1-9(13)7-10-5-6-11-3-2-4-12(11)8-10/h5-6,8-9H,2-4,7,13H2,1H3 Y Key:QYVNZHBQYJRLEX-UHFFFAOYSA-N Y
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5-APDI appears to act as a potent and weakly selective serotonin releasing agent (SSRA) with IC₅₀ values of 82 nM, 1,848 nM, and 849 nM for inhibiting the reuptake of serotonin, dopamine, and norepinephrine, respectively.^[2][3] It fully substitutes for MBDB but not amphetamine in trained animals, though it does produce disruption for the latter at high doses.^[2]

5-APDI has been classified as a class B drug under the Misuse of Drugs Act 1971 since 10 June 2014.

See also

• DiFMDA
• 5-MAPDI
• 6-APT