Buy 5-(2-Aminopropyl) (indanylaminopropane) Cas 13396-94-6

Buy 5-(2-Aminopropyl) (indanylaminopropane) Cas 13396-94-6

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. Buy 5-(2-Aminopropyl) (indanylaminopropane) Cas 13396-94-6

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.

5-(2-Aminopropyl)-2,3-dihydro-1H-indene, also known as 5-(2-aminopropyl)indene, is a chemical compound categorized under the class of indenes. It possesses significant interest in pharmacology due to its potential effects on neurotransmitter systems. The compound is primarily recognized for its role as a serotonin releasing agent and its implications in neuropharmacology.

Source

This compound can be synthesized from indanone through reductive amination processes, often involving 2-aminopropane as a reactant. The hydrochloride salt form, 5-(2-Aminopropyl)-2,3-dihydro-1H-indene hydrochloride, is commonly studied for its biochemical properties and applications in research.

Classification

5-(2-Aminopropyl)-2,3-dihydro-1H-indene is classified as a psychoactive substance and a monoamine releasing agent. Its structural classification falls under the category of indenes, which are bicyclic compounds containing a fused benzene and cyclopentene ring.

Synthesis Analysis

Methods

The synthesis of 5-(2-Aminopropyl)-2,3-dihydro-1H-indene typically involves the following steps:

Starting Material: Indanone serves as the primary starting material.
Reductive Amination: Indanone reacts with 2-aminopropane in the presence of a reducing agent such as sodium cyanoborohydride. This process forms the indane structure with an attached aminopropyl group.
Hydrochloride Formation: The resultant free base is then treated with hydrochloric acid to obtain the hydrochloride salt form.

Technical Details

Industrial production may utilize batch or continuous flow reactors to ensure consistency and quality. Purification techniques such as recrystallization and chromatography are employed to achieve high purity levels necessary for research applications.

Molecular Structure Analysis

Structure

The molecular formula of 5-(2-Aminopropyl)-2,3-dihydro-1H-indene hydrochloride is $C_{12} H_{18} ClN$ . Its structure comprises:

A bicyclic indene core.
An aminopropyl side chain attached at the 5-position.

Data

Spectroscopic techniques confirm the identity and purity of the compound:

Melting Point: 214-215 °C.
Nuclear Magnetic Resonance (NMR): Provides detailed structural information.
Gas Chromatography-Flame Ionization Detection (GC-FID): Indicates high purity levels, with initial analyses showing mean values around 99% .

Chemical Reactions Analysis

Types of Reactions

5-(2-Aminopropyl)-2,3-dihydro-1H-indene undergoes several notable chemical reactions:

Oxidation: Can be oxidized to form ketones or carboxylic acids.
Reduction: Reduction reactions can modify either the indane ring or the aminopropyl side chain.
Substitution: Electrophilic substitution can introduce various functional groups onto the aromatic ring.

Common Reagents and Conditions

Oxidizing Agents: Potassium permanganate or chromium trioxide.
Reducing Agents: Sodium borohydride or lithium aluminum hydride.
Catalysts: Palladium on carbon for hydrogenation reactions .

Mechanism of Action

Process

5-(2-Aminopropyl)-2,3-dihydro-1H-indene acts primarily as a serotonin releasing agent. It inhibits the reuptake of key neurotransmitters—serotonin, dopamine, and norepinephrine—resulting in increased concentrations within the synaptic cleft.

Data

The compound exhibits specific inhibitory concentrations (IC50 values) for neurotransmitter uptake:

Serotonin: 82 nM
Dopamine: 1,848 nM
Norepinephrine: 849 nM .

This mechanism suggests significant implications for mood regulation and potential therapeutic uses in disorders related to neurotransmitter imbalances.

Physical and Chemical Properties Analysis

Physical Properties

Key physical properties include:

Melting Point: 214-215 °C
Solubility: Soluble in common organic solvents; specific solubility data may vary based on conditions.

Chemical Properties

Chemical properties include:

Reactivity towards oxidation and reduction processes.
Ability to participate in electrophilic aromatic substitution reactions.

Analytical methods such as thermogravimetric analysis and Karl Fischer analysis indicate low moisture content and non-volatile residue levels below 0.2% .

Applications

5-(2-Aminopropyl)-2,3-dihydro-1H-indene has various scientific uses:

Pharmacological Research: Studied for its effects on neurotransmitter systems and potential therapeutic applications in mood disorders.
Psychoactive Substance Research: Investigated within contexts of legal highs and their implications on public health.
Drug Development: Explored as a lead compound for developing new medications targeting monoamine oxidase inhibition and related pathways .

Properties

CAS Number

13396-94-6

Product Name

5-(2-Aminopropyl)-2,3-dihydro-1H-indene

IUPAC Name

1-(2,3-dihydro-1H-inden-5-yl)propan-2-amine

Molecular Formula

C12H17N

Molecular Weight

175.27 g/mol

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

InChI Key

QYVNZHBQYJRLEX-UHFFFAOYSA-N

SMILES

CC(CC1=CC2=C(CCC2)C=C1)N

Synonyms

5-(2-aminopropyl)-2,3-dihydro-1H-indene
5-NProp-DI HCl

Canonical SMILES

CC(CC1=CC2=C(CCC2)C=C1)N

5-(2-Aminopropyl)-2,3-dihydro-1H-indene

Catalog No.

S578401

CAS No.

13396-94-6

M.F

C12H17N

M. Wt

175.27 g/mol

Availability

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* This item is exclusively intended for research purposes and is not designed for human therapeutic applications or veterinary use.

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General Information

Forensic labs using generic amphetamine standards misidentify indane-based designer drugs due to altered fragmentation. 5-APDI offers a distinct cyclopentane ring replacing the methylenedioxy group, shifting EI fragmentation and retention times for unambiguous differentiation from MDA/5-APB. • Reference standard: Enables accurate GC-MS/LC-MS calibration with validated purity. • SERT probe: 22-fold selectivity (IC50=82 nM vs DAT 1848 nM) supports monoamine transporter mapping. • Stable indane scaffold: Resists hepatic metabolism for reproducible in vitro assays. High purity, in stock for global shipping.

CAS Number

13396-94-6

Product Name

5-(2-Aminopropyl)-2,3-dihydro-1H-indene

IUPAC Name

1-(2,3-dihydro-1H-inden-5-yl)propan-2-amine

Molecular Formula

C12H17N

Molecular Weight

175.27 g/mol

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

InChI Key

QYVNZHBQYJRLEX-UHFFFAOYSA-N

SMILES

CC(CC1=CC2=C(CCC2)C=C1)N

Synonyms

5-(2-aminopropyl)-2,3-dihydro-1H-indene, 5-NProp-DI HCl

Canonical SMILES

CC(CC1=CC2=C(CCC2)C=C1)N

Purity

≥98%

Package Size

1 mg, 5 mg, 10 mg

5-APDI Reference Standard

5-(2-Aminopropyl)-2,3-dihydro-1H-indene (CAS 13396-94-6), commonly referred to as 5-APDI or IAP, is an indane-based amphetamine derivative primarily utilized as a certified reference material in forensic toxicology and a pharmacological probe in monoamine transporter assays. By replacing the methylenedioxy ring of MDA with a sterically similar but electronically distinct cyclopentane ring, 5-APDI serves as a critical baseline for evaluating structure-activity relationships (SAR) in serotonin, dopamine, and norepinephrine reuptake inhibition [1]. Procurement of high-purity 5-APDI is essential for laboratories requiring reliable standards to calibrate GC-MS/LC-MS instrumentation and to conduct reproducible in vitro synaptosomal uptake studies [2].

Research Fit

Aminoindane research scaffold with non-oxygenated indane core

Monoamine transporter pharmacology probe for SERT, DAT, and NET studies

Behavioral discrimination research context; reported entactogen-like cue profile

References

5-APDI vs. MDA Analogs: Non-Interchangeability

Substituting 5-APDI with its oxygenated analog MDA, or its positional isomer 6-APDI, fundamentally compromises both analytical resolution and pharmacological assay integrity [1]. In forensic and toxicological screening, the absence of the methylenedioxy oxygen atoms in 5-APDI alters its electron ionization (EI) mass fragmentation pattern and chromatographic retention time, meaning generic amphetamine standards cannot accurately quantify 5-APDI in complex matrices [2]. Furthermore, in in vitro transport assays, 5-APDI exhibits a highly specific monoamine transporter binding profile—acting as a potent serotonin reuptake inhibitor while displaying significantly lower affinity for dopamine transporters—a ratio that is not replicated by standard amphetamine or non-indane entactogens[1].

Substitution Risk

Ring expansion shifts transporter engagement

Indane-to-tetralin ring expansion may alter monoamine transporter engagement profile; 5-APDI and 6-APT may not be directly interchangeable in SAR studies.

Non-oxygenated core differs from methylenedioxy analogs

The indane isostere may confer SERT/DAT/NET selectivity distinct from MDA and MDAI; class-based substitution may require transporter-by-transporter verification.

Class membership alone may not predict behavioral profile

Discriminative stimulus properties may differ materially among aminoindane analogs; in vivo behavioral profile should be confirmed for the specific compound selected.

References

5-APDI Quantitative Evidence

High-Selectivity SERT Inhibition

5-APDI demonstrates a highly skewed affinity for the serotonin transporter (SERT) over the dopamine transporter (DAT), making it a valuable selective probe. Quantitative synaptosomal assays reveal that 5-APDI inhibits serotonin reuptake with an IC50 of 82 nM, while its inhibition of dopamine reuptake requires a much higher concentration (IC50 = 1,848 nM) [1]. This ~22-fold selectivity for SERT over DAT sharply contrasts with standard amphetamine, which is heavily dopaminergic, and allows researchers to isolate serotonin-mediated pathways in mixed monoamine models .

Evidence Dimension	Transporter Inhibition IC50 (SERT vs DAT)
Target Compound Data	SERT IC50 = 82 nM; DAT IC50 = 1,848 nM
Comparator Or Baseline	Standard Amphetamine (DAT-selective)
Quantified Difference	~22-fold selectivity for SERT over DAT
Conditions	In vitro crude synaptosomal uptake assay

Procurement of 5-APDI is critical for neurochemical assays requiring a structurally rigid, non-oxygenated amphetamine analog with pronounced serotonergic selectivity.

SERT IC50

Head-to-head

5-APDI 82 nM vs 6-APT 121 nM

Supports SERT engagement comparison

Reported within-assay indane vs tetralin data; 1.5-fold difference

Pharmacological Differentiation from Stimulants

In established drug discrimination models used to classify psychoactive properties, 5-APDI fully substitutes for the entactogen MBDB but fails to substitute for classical amphetamine at standard doses [1]. This behavioral and pharmacological divergence is driven by its specific indane core, which dictates its primary role as a weakly selective serotonin releasing agent (SSRA) rather than a direct dopaminergic stimulant[1].

Evidence Dimension	Substitution in trained animal models
Target Compound Data	Full substitution for MBDB
Comparator Or Baseline	Amphetamine (No substitution)
Quantified Difference	Complete behavioral generalization to MBDB, zero to amphetamine
Conditions	In vivo drug discrimination paradigm

This distinct pharmacological profile makes 5-APDI an indispensable reference standard for laboratories mapping the structure-activity relationships of novel psychoactive substances (NPS).

DAT / NET Activity

Head-to-head

DAT: 1848 vs 6436 nM | NET: 849 vs 3371 nM

Supports broader transporter profiling context

Reported ring-expansion effect; 3.5× DAT, 4.0× NET difference

Metabolic Stability via Indane Substitution

The replacement of the methylenedioxy bridge found in MDA with a fully carbon-based cyclopentane ring in 5-APDI eliminates the vulnerability to cytochrome P450-mediated demethylenation [1]. This structural modification provides a chemically robust scaffold that resists the primary metabolic degradation pathways typical of methylenedioxy-phenethylamines, ensuring greater stability during prolonged in vitro incubations[2].

Evidence Dimension	Susceptibility to demethylenation
Target Compound Data	0% demethylenation (lacks methylenedioxy group)
Comparator Or Baseline	MDA / MDMA (Highly susceptible to CYP450 demethylenation)
Quantified Difference	Complete elimination of the demethylenation metabolic pathway
Conditions	In vitro hepatic microsome stability assays / structural analysis

For long-term analytical studies and in vitro metabolic profiling, 5-APDI offers a more stable, non-oxygenated baseline comparator than traditional designer drugs.

SERT vs MDAI

Context-dependent

5-APDI IC50 ~6.2× lower than MDAI

Cross-platform potency context; data to verify

Different assay systems limit direct comparison; head-to-head confirmation needed

Discriminative Cue

Head-to-head

Full MBDB substitution; no amphetamine substitution

Supports entactogen-like cue profiling

Reported binary discrimination outcome; two-lever paradigm

5-HT Neurotoxicity

Class-level

Aminoindanes lack MDA-like 5-HT depletion

Class-level neurotoxicity context; data to verify

Direct 5-APDI neurotoxicity data not available; class inference only

5-APDI Application Scenarios

GC-MS/LC-MS Calibration for NPS Screening

Due to its unique indane structure and specific mass fragmentation pattern, 5-APDI is utilized as a certified reference material for calibrating analytical instruments in forensic laboratories. It enables the precise differentiation of indane-based designer drugs from their methylenedioxy (MDA) or benzofuran (5-APB) counterparts in complex biological matrices [1].

In Vitro Monoamine Reuptake Inhibition Studies

Leveraging its ~22-fold selectivity for SERT (IC50 = 82 nM) over DAT (IC50 = 1,848 nM), 5-APDI is procured for synaptosomal assays to map the binding pockets of monoamine transporters. It serves as a rigid, non-oxygenated probe to evaluate how steric bulk affects serotonin versus dopamine reuptake [2].

SAR Development

The metabolic stability of the indane ring compared to the easily metabolized methylenedioxy group makes 5-APDI a valuable lead scaffold in medicinal chemistry. Researchers use this compound to design new therapeutic agents that require serotonergic activity without the rapid hepatic degradation associated with traditional entactogens [2].

Application Fit Matrix

Ring-size SAR transporter studies

Indane scaffold transporter profile

SERT/DAT/NET selectivity verification

Behavioral discrimination research

Entactogen-like discriminative cue

MBDB-type vs amphetamine-type cue confirmation

Neurotoxicity model comparison

Aminoindane scaffold neurotoxicity context

Serotonergic marker endpoint review

Transporter selectivity panel screening

Intermediate SERT-catecholamine profile

Selectivity ratio verification across platforms

5-APDI CAS # 13396-94-6 or 5-(2-Aminopropyl)-2,3-dihydro-1H-indene also known as indanylaminopropane (IAP), IAP (psychedelic), 2-API(2-aminopropylindane), indanametamine, and, incorrectly, as indanylamphetamine, is an entactogen and psychedelic drug of the amphetamine family.

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. Buy 5-(2-Aminopropyl) (indanylaminopropane) Cas 13396-94-6

1-(2,3-dihydro-1H-inden-5-yl)propan-2-amine(13396-94-6)

CAS Registry Number:: 13396-94-6
Synonyms:: 2-Aminopropylindane;IAP;UNII-4PH68L63R9;2-API;5-Indanethylamine, alpha-methyl-;Indanametamine;5-(2-Aminopropyl)-2,3-dihydro-1H-indene;5-Nprop-di hcl;Indanylaminopropane;
Molecular Formula:: C₁₂H₁₇N
Molecular Weight:: 175.274
EINECS:

CAS No.:13396-94-6

Name: 1-(2,3-dihydro-1H-inden-5-yl)propan-2-amine

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