5-APDI

5-APDI
Clinical data
Other names5-APDI; 1-(5-Indanyl)-2-aminopropane; Indanylaminopropane; IAP; Indanametamine; 2-Aminopropylindane; 2-API; Indanylamphetamine
Routes of
administration		Oral
Drug classStimulant; Psychedelic; Serotonin releasing agent
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Duration of action5–8 hours
Identifiers
  • (±)-1-(2,3-dihydro-1H-inden-5-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H17N
Molar mass175.275 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • CC(CC1=CC2=C(CCC2)C=C1)N
  • 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 checkY
  • Key:QYVNZHBQYJRLEX-UHFFFAOYSA-N checkY
  (verify)

5-(2-Aminopropyl)-2,3-dihydro-1H-indene (5-APDI), also known as indanylaminopropane (IAP), 2-aminopropylindane (2-API), indanametamine, and, incorrectly, as indanylamphetamine, is a stimulant drug of the phenethylamine and amphetamine families related to 3,4-methylenedioxyamphetamine (MDA). It is the analogue of MDA in which the oxygen atoms within the methylenedioxy ring have been replaced with carbon atoms. The drug has been sold by online vendors through the Internet and has been encountered as a designer drug starting in 2003.

Use and effects

According to Alexander Shulgin in his book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds, 5-APDI is active at a dose of 40 to 80 mg orally. Its duration and effects were not described. Per Daniel Trachsel in his book Phenethylamine: von der Struktur zur Funktion (Phenethylamines: From Structure to Function), based on anecdotal reports, its dose is 30 to 60 mg orally and its duration is 5 to 8 hours. The effects of 5-APDI are said to be somewhat controversial. It is said to bear only a very slight resemblance to MDMA in terms of its effects and hence does not seem to be an entactogen. The drug is described as a rather distinct substance, reportedly inducing euphoria, amphetamine-like stimulant effects, and, rarely, even psychedelic effects.

Pharmacology

Pharmacodynamics

5-APDI appears to act as a potent and weakly selective serotonin releasing agent (SSRA) with IC50Tooltip half-maximal inhibitory concentration values of 82 nM, 1,848 nM, and 849 nM for inhibiting the reuptake of serotonin, dopamine, and norepinephrine, respectively.

It fully substitutes for the entactogen MBDB but not the stimulant amphetamine in drug discrimination tests in animals, though it does produce disruption for the latter at high doses.

Chemistry

Synthesis

The chemical synthesis of 5-APDI has been described.

Analogues

Derivatives of 5-APDI like the N-methyl, N-ethyl, and α-ethyl analogues could conceivably exist and be active but have not been scientifically investigated. However, the N-methyl derivative 5-MAPDI subsequently emerged as a novel designer drug in the mid-2010s. Some other related compounds include 3,4-methylenedioxyamphetamine (MDA), 5-APDB, 6-APDB, IBF5MAP (5-MAPP), 6-APT (tetralinylaminopropane; TAP), G-3, and 2C-G-3.

The fusion of 5-APDI with 3,3-diphenylpropylamine was reported in a 1968 patent. 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 its 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.

History

5-APDI was first described in the scientific literature by David E. Nichols and colleagues in 1993. The properties of 5-APDI in humans were described by Alexander Shulgin in his book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds in 2011, citing personal communication with an individual named Igor. Then, in 2013, its properties and effects were further described by Daniel Trachsel in his book Phenethylamine: von der Struktur zur Funktion (Phenethylamines: From Structure to Function).

Society and culture

United Kingdom

5-APDI has been classified as a class B drug in the United Kingdom under the Misuse of Drugs Act 1971 since 10 June 2014.[citation needed]

See also

References

  1. 1 2 3 4 5 6 7 Shulgin A, Manning T, Daley PF (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
  2. 1 2 3 4 5 6 7 8 9 10 11 12 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
  3. 1 2 3 4 5 Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE (November 1993). "Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine". Journal of Medicinal Chemistry. 36 (23): 3700–3706. doi:10.1021/jm00075a027. PMID 8246240.
  4. 1 2 Parker MA, Marona-Lewicka D, Kurrasch D, Shulgin AT, Nichols DE (March 1998). "Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA)". Journal of Medicinal Chemistry. 41 (6): 1001–1005. doi:10.1021/jm9705925. PMID 9526575.
  5. 1 2 Casale JF, McKibben TD, Bozenko JS, Hays PA (2005). "Characterization of the "Indanylamphetamines"". Microgram Journal. 3 (1–2): 3–10. Archived from the original on 2009-03-17. Retrieved 2009-08-06.
  6. 1 2 3 Nichols DE (1994). "Medicinal Chemistry and Structure–Activity Relationships". In Cho AK, Segal DS (eds.). Amphetamine and Its Analogs: Psychopharmacology, Toxicology, and Abuse. Academic Press. pp. 3–41. ISBN 978-0-12-173375-9.
  7. 1 2 Cozzi NV (1994). Pharmacological studies of some psychoactive phenylalkylamines: Entactogens, hallucinogens, and anorectics (Ph.D. thesis). University of Wisconsin, Madison. Retrieved 15 April 2025.
  8. ↑ "European Monitoring Center for Drugs and Drug Addiction – Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA" (PDF). www.emcdda.europa.eu.
  9. ↑ Frank Troxler & Albert Hofman, GB1133457 (1968 to Sandoz KK). https://patents.google.com/patent/GB1133457/