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
(verify)

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.

The fusion of 5-APDI with 3,3-Diphenylpropylamine was reported in a 1968 patent.^[4] The dose (of the HCl salt) was judged to be 55mg per tablet (corr. to 50mg of the Fb). The compound had valuable pharmacodynamic properties whilst it's toxicity was low. It produces a vasodilatation and thus improves peripheral blood circulation and a pronounced coronary dilatation. The compound further exhibits a blood pressure lowering effect and is therefore indicated for use in the treatment of hypertonia and circulatory illnesses, especially Angina pectoris and other stenocardiac disorders and in the treatment of organic or functional coronary insufficiencies and peripheral blood circulation disorders.

See also

• Substituted methylenedioxyphenethylamine § Related compounds
• DiFMDA
• 5-MAPDI
• 6-APT
• 2C-G-3