5-APDI

Last updated
Indanylaminopropane
Indanylaminopropane.svg
Clinical data
Other names5-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
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
Formula C12H17N
Molar mass 175.275 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
  • c1cc(cc2c1CCC2)CC(N)C
  • 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 Yes check.svgY
  • Key:QYVNZHBQYJRLEX-UHFFFAOYSA-N Yes check.svgY
   (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, [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.

Contents

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.

Although this agent is obviously possible, it's just another analog of the better known agents Prenylamine & Droprenilamine.

See also

References

  1. 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.
  2. 1 2 3 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): 3700–6. doi:10.1021/jm00075a027. PMID   8246240.
  3. 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): 1001–5. CiteSeerX   10.1.1.688.9559 . doi:10.1021/jm9705925. PMID   9526575.
  4. ↑ Frank Troxler & Albert Hofman, GB1133457 (1968 to Sandoz KK).
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