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4-(2-Aminopropyl)indole

From Wikipedia, the free encyclopedia
(Redirected from4-API)
Not to be confused withα-Methylisotryptamine.
Pharmaceutical compound
4-(2-Aminopropyl)indole
Clinical data
Other names4-API; 4-IT; α-Methylisotryptamine; α-Me-isotryptamine; α-Me-isoT
Drug classSerotonin receptor modulator;Serotonin5-HT2 receptormodulator;Monoamine oxidase inhibitor
ATC code
  • None
Identifiers
  • 1-(1H-indol-4-yl)propan-2-amine
CAS Number
PubChemCID
ChemSpider
Chemical and physical data
FormulaC11H14N2
Molar mass174.247 g·mol−1
3D model (JSmol)
  • CC(CC1=C2C=CNC2=CC=C1)N
  • InChI=1S/C11H14N2/c1-8(12)7-9-3-2-4-11-10(9)5-6-13-11/h2-6,8,13H,7,12H2,1H3
  • Key:FSNFARLFBCWJMF-UHFFFAOYSA-N

4-(2-Aminopropyl)indole (4-API), also known in the past asα-methylisotryptamine (α-Me-isoT), is aserotonin receptor modulator of thephenethylamine andamphetamine families.[1][2][3][4] It is one of seven possiblepositional isomers of(2-aminopropyl)indole (API), with other examples includingα-methyltryptamine (AMT; 3-API) andα-methylisotryptamine (isoAMT; 1-API).[2][3][4] The drug is a sort of hybridstructure between phenethylamines andtryptamines.[1][2][3][4]

It showsaffinity for theserotonin5-HT2 receptor (Ki = 5,000 nM), with its affinity being only 2-fold lower than that of AMT (Ki = 2,500 nM) in the same study.[3] The drug reverses the facilitation ofpentylenetetrazol-inducedseizures evoked by themonoamine depleting agentreserpine in rodents, albeit with much lowerpotency than AMT (10-fold) and certain other API positional isomers.[2] It showed activity as amonoamine oxidase inhibitor (MAOI)in vitro, with slightly higher potency than AMT.[2]

Thesynthesis andidentification of 4-API have been described.[3][4]

4-API was first described in the literature in apatent as a potentialantiasthmatic agent byAlbert Hofmann and Franz Troxler atSandoz in 1963.[1][5] Subsequently, it was studied by Aurelio Cerletti and colleagues in 1968[2] and byRichard Glennon and colleagues in 1988.[3] The drug was referred to as "α-methyl-isotryptamine" or "α-Me-isoT" by Glennon and colleagues, but this term subsequently came to be used to refer to 1-API instead.[3] Certain APIs, such as AMT and5-(2-aminopropyl)indole (5-API), have been encountered as noveldesigner drugs, but 4-API does not appear to have been encountered as of 2014.[4]

Chemical structures of selected APIs and related compounds

See also

[edit]

References

[edit]
  1. ^abcTrachsel, 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. p. 470.ISBN 978-3-03788-700-4.OCLC 858805226. Archived fromthe original on 21 August 2025.Compound 50 has an indole structure in which the alkylamine side chain is located at the 4-position, not at the 3-position as in tryptamine derivatives. On the one hand, the compound was mentioned in a 1963 patent by Hofmann and Troxler of the Sandoz company for possible use as an asthma treatment [48], and on the other hand, it was included in a SAR study on hydroxyindolealkylamines [49]. [...] [48] A. Hofmann, F. Troxler. 4(or 5 or 6)-(2Aminoalkyl)indoles. FR1344579, 1963. [49] A. Cerletti, M. Taeschler, H. Weidmann. Adv. Pharmacol. 1968, 6, 233.
  2. ^abcdefCerletti A, Taeschler M, Weidmann H (1968). "Pharmacologic studies on the structure-activity relationship of hydroxyindole alkylamines".Adv Pharmacol (1962).6 (Pt B):233–246.doi:10.1016/s1054-3589(08)60322-1.PMID 5658327.
  3. ^abcdefgLyon RA, Titeler M, Seggel MR, Glennon RA (January 1988). "Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens".Eur J Pharmacol.145 (3):291–297.doi:10.1016/0014-2999(88)90432-3.PMID 3350047.
  4. ^abcdeScott KR, Power JD, McDermott SD, O'Brien JE, Talbot BN, Barry MG, Kavanagh PV (2014). "Identification of (2-aminopropyl)indole positional isomers in forensic samples".Drug Test Anal.6 (7–8):598–606.doi:10.1002/dta.1508.PMID 23836607.
  5. ^"Nouveaux dérivés de l'indole et leur préparation" [New indole derivatives and their preparation].Google Patents. 21 November 1962. Retrieved10 February 2026.

External links

[edit]
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Non-specific
AAADTooltip Aromatic L-amino acid decarboxylase
MAOTooltip Monoamine oxidase
Phenethylamines
(dopamine,epinephrine,
norepinephrine)
PAHTooltip Phenylalanine hydroxylase
THTooltip Tyrosine hydroxylase
DBHTooltip Dopamine beta-hydroxylase
PNMTTooltip Phenylethanolamine N-methyltransferase
COMTTooltip Catechol-O-methyl transferase
Tryptamines
(serotonin,melatonin)
TPHTooltip Tryptophan hydroxylase
AANATTooltip Serotonin N-acetyl transferase
ASMTTooltip Acetylserotonin O-methyltransferase
Histamine
HDCTooltip Histidine decarboxylase
HNMTTooltip Histamine N-methyltransferase
DAOTooltip Diamine oxidase
Phenethylamines
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Cyclized
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(phenidates)
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Phenyloxazolamines
(aminorexes)
Isoquinolines and
tetrahydroisoquinolines
2-Aminoindanes
2-Aminotetralins
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