Buy Indalpine (Upstène) Online
Buy Indalpine (Upstène) Online
Buy Indalpine (Upstène) Online
Indalpine, sold under the brand name Upstène, is a selective serotonin reuptake inhibitor (SSRI) that was briefly marketed as an antidepressant for treatment of depression.[1][2][3][4] It was marketed in France and a few other European countries.[4]
Indalpine is a selective serotonin reuptake inhibitor (SSRI) and antihistamine.[2]
Indalpine was invented by 1977 and was introduced for medical use in France in 1983.[2][3] Two years later, in 1985, it was withdrawn from the market due to toxicity.[2][4] Indalpine has sometimes been said to be the first SSRI.[2][3] However, it was preceded by the SSRI zimelidine (Zelmid), which was invented in 1969 and was introduced to the market in 1981 (then similarly withdrawn due to toxicity in 1983).[2][5][4]
Pharmacology
Pharmacodynamics
Indalpine is a selective serotonin reuptake inhibitor (SSRI) and antihistamine.[2]
Chemistry
Indalpine is an indole and is structurally similar to tryptamines but is not a tryptamine itself.
Synthesis
Metalation of indole (1) using methyl magnesium iodide forms the organo-magnesium derivative (2) which reacts with 1-benzyloxycarbonyl-4-piperidyl-acetyl chloride (3) to give (4). Acid-catalyzed removal of the benzyloxycarbonyl (Cbz) protecting group gives the ketone (5). Reduction with lithium aluminium hydride yields indalpine.
Buy Indalpine (Upstène) Online
Buy Indalpine (Upstène) Online
Buy Indalpine (Upstène) Online
Buy Indalpine (Upstène) Online
Buy Indalpine (Upstène) Online
Buy Indalpine (Upstène) Online
Buy Indalpine (Upstène) Online
Buy Indalpine (Upstène) Online
Buy Indalpine (Upstène) Online
Indalpine hydrochloride

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Researchers needing a specific SSRI profile for reproducible neuropharmacology outcomes rely on Indalpine hydrochloride. Its distinct binding signature eliminates the variability of generic SSRIs.
- High-affinity SERT inhibitor – ideal reference standard for competitive binding assays.
- Moderate SERT/NET selectivity – enables unbalanced serotonin-norepinephrine reuptake studies.
- Antihistamine activity – used with ‘clean’ SSRIs to dissect histaminergic contributions.
- Withdrawn drug, exclusive for in-vitro/in-vivo non-clinical research; ensures historical comparability.
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Indalpine hydrochloride is a piperidinyl-indole compound and an early-generation selective serotonin reuptake inhibitor (SSRI). [1] Its primary mechanism of action is the high-affinity binding to the serotonin transporter (SERT), which blocks the reuptake of serotonin from the synaptic cleft. [2] This activity made it a subject of significant research in neuropharmacology. As a hydrochloride salt, the compound is prepared for enhanced solubility and stability, facilitating its use in a laboratory setting for the preparation of aqueous stock solutions and buffers. While historically used as an antidepressant, it was withdrawn from the market due to toxicity, and its modern procurement is exclusively for in-vitro and in-vivo non-clinical research applications where its specific pharmacological profile is required. [3]
Research Fit
References
- [1] Mereu, G., et al. Focus on Human Monoamine Transporter Selectivity. New Human DAT and NET Models, Experimental Validation, and SERT Affinity Exploration. ACS Chem. Neurosci. 2020, 11, 21, 3436–3449.
- [2] Ablain, W., et al. The [3H]indalpine binding sites have been characterized in slide-mounted cat brain sections. J. Neurochem. 1986, 46, S1, 13.
- [3] Indalpine. Wikipedia. Accessed May 7, 2026.
While compounds like fluoxetine and escitalopram are also classified as SSRIs, they are not functionally interchangeable with indalpine in a research context. Each SSRI possesses a unique binding affinity and selectivity profile across the three primary monoamine transporters (SERT, NET, DAT), meaning substitution can introduce significant experimental variability. [1] Furthermore, off-target activities, such as indalpine’s known antihistamine properties, can confound results in assays where histamine signaling is a relevant variable. [2] For reproducible and historically comparable results, particularly in neuropharmacology studies where secondary activities can produce distinct physiological or behavioral phenotypes, specifying the exact SSRI used is critical. Procuring indalpine is therefore a deliberate choice for researchers needing its specific, documented pharmacological signature rather than a generic serotonin reuptake inhibition effect.
Substitution Risk
hSERT Binding Affinity
In a comparative analysis of binding affinities at cloned human monoamine transporters, indalpine demonstrated potent inhibition of the serotonin transporter (hSERT) with a Ki of 79.4 nM. [1] This affinity is distinct from other common SSRIs evaluated in the same study context, such as fluoxetine (Ki = 239.9 nM) and escitalopram (Ki = 354.8 nM), positioning indalpine as a higher-affinity ligand at hSERT in this specific dataset. [1]
| Evidence Dimension | Binding Affinity (Ki) at hSERT |
| Target Compound Data | 79.4 nM |
| Comparator Or Baseline | Fluoxetine: 239.9 nM | Escitalopram: 354.8 nM |
| Quantified Difference | 3.0x higher affinity than Fluoxetine; 4.5x higher affinity than Escitalopram |
| Conditions | In-vitro radioligand binding assay with cloned human monoamine transporters. |
For researchers requiring a high-potency reference compound for SERT binding assays or studying dose-dependent serotonergic effects, this specific affinity profile justifies its selection over lower-affinity alternatives.
18.5× higher vs fluoxetine (54)
Transporter Selectivity Profile
Indalpine exhibits a distinct selectivity profile for the serotonin transporter (SERT) over the norepinephrine (NET) and dopamine (DAT) transporters. Based on comparative binding data, indalpine is approximately 6.5-fold selective for SERT over NET and 7.6-fold selective for SERT over DAT. [1] This profile is notably different from fluoxetine, which shows higher selectivity over both NET (~13.2-fold) and DAT (~15.8-fold), and escitalopram, which has lower selectivity over NET (~4.7-fold) but higher selectivity over DAT (~17.8-fold). [1]
| Evidence Dimension | Selectivity Ratio (Ki at NET or DAT / Ki at SERT) |
| Target Compound Data | SERT vs NET: ~6.5x | SERT vs DAT: ~7.6x |
| Comparator Or Baseline | Fluoxetine: ~13.2x (NET), ~15.8x (DAT) | Escitalopram: ~4.7x (NET), ~17.8x (DAT) |
| Quantified Difference | Indalpine has a moderate and balanced selectivity profile, contrasting with the higher selectivity of fluoxetine or the varied profile of escitalopram. |
| Conditions | Calculated from Ki values from in-vitro binding assays with cloned human monoamine transporters. |
This specific selectivity ‘fingerprint’ is critical for studies where moderate off-target inhibition of NET and DAT is either tolerable or experimentally desirable, distinguishing it from more highly selective or differently selective SSRIs.
3–5× higher affinity vs fluoxetine (8–10 nM)
Antihistamine Activity
Unlike highly selective SSRIs such as escitalopram, which has negligible affinity for histamine receptors, indalpine is documented to possess antihistamine properties. [REFS-1, REFS-2] This secondary pharmacology is a key differentiator for experimental design. Centrally-acting H1-histamine receptor antagonists are known to produce distinct physiological effects, including sedation and weight gain. [3] The presence of this activity in indalpine makes it unsuitable for studies requiring pure serotonergic manipulation but valuable for research exploring dual-activity compounds or for understanding the historical context of early SSRI side-effect profiles.
| Evidence Dimension | Off-Target Receptor Activity |
| Target Compound Data | Possesses antihistamine activity |
| Comparator Or Baseline | Escitalopram: No or very low affinity for histamine (H1-3) receptors. |
| Quantified Difference | Qualitatively distinct secondary pharmacology profile compared to highly selective SSRIs. |
| Conditions | Pharmacological characterization from historical and review literature. |
For researchers investigating the interplay between serotonergic and histaminergic systems, or those needing to control for antihistamine effects, procuring indalpine provides a specific tool that cannot be replicated by ‘cleaner’ SSRIs.
Mianserin: no effect up to 10 mg/kg
Hydrochloride Salt Form
Indalpine is supplied as a hydrochloride (HCl) salt, a common strategy in pharmaceutical chemistry to improve the physicochemical properties of basic compounds. Compared to the corresponding free base, the HCl salt form typically confers significantly greater aqueous solubility and improved chemical stability in solid form and in solution. [1] This facilitates reliable and reproducible preparation of stock solutions for in-vitro assays and dosing solutions for in-vivo studies, reducing experimental variability that can arise from poor solubility or degradation of the active compound.
Indalpine
Researchers needing a highly selective and potent SERT inhibitor for mechanistic studies face limited supply due to Indalpine’s market withdrawal. Indalpine (LM 5008) offers a validated benchmark with quantifiable differentiation.
- Ki=2 nM for SERT binding; 1,800-fold selectivity over DAT, ideal as a reference in novel SERT ligand screening.
- ED50=0.33 mg/kg (IV) for dorsal raphe 5-HT neuron firing inhibition, enabling acute pharmacodynamic studies.
- Rapid clinical onset (day 3 vs. placebo) and 10.4-hour half-life support translational PK/PD modeling.
Sourced from qualified suppliers with full analytical traceability (HPLC, NMR). Standard B2B shipping; inquire for bulk or custom preparations.
| Evidence Dimension | Physicochemical Form |
| Target Compound Data | Hydrochloride salt |
| Comparator Or Baseline | Free base form |
| Quantified Difference | Qualitatively improved aqueous solubility and handling characteristics. |
| Conditions | General principles of medicinal and process chemistry. |
This ensures consistent, reliable preparation of experimental solutions, a critical and practical procurement consideration for ensuring data quality and reproducibility in any laboratory workflow.
Fluoxetine: slow-wave pattern; Citalopram: arousal
Multiple agranulocytosis cases (pharmacovigilance)
Not shared by fluoxetine, citalopram, paroxetine
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