Milnacipran Hydrochloride

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Cat Number

API101152947

CAS Number

101152-94-7

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Product Detail Description Scientific Support Customer Q&A

CAS Number

101152-94-7

EINECS

620-477-4

Storage

Store at room temperature

Synonyms

Milnacipran HCl; Dalcipran; Toledomin; DTXSID4046785; RNZ43O5WW5

Molecular Formula

C15H23ClN2O

Molecular Weight

282.81

Smiles

CCN(CC)C(=O)[C@@]1(C[C@@H]1CN)C2=CC=CC=C2.Cl

Appearance

White to off-white crystalline powder

Melting Point

228-228.5°C

Boiling Point

393°C at 760 mmHg

Relative Density

1.077

General Description

Milnacipran hydrochloride is a selective serotonin and norepinephrine reuptake inhibitor (SNRI) with a unique cyclopropane ring, structurally distinct from other SNRIs like venlafaxine or duloxetine. Its structure is (1R,2S)-2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide hydrochloride.

Mechanism of Action

Milnacipran potently inhibits the reuptake of both serotonin (5-HT) and norepinephrine (NE) at the presynaptic membrane by binding to their respective transporters (SERT and NET), with a slightly greater potency for norepinephrine. The drug has no significant affinity for monoamine oxidase (MAO), histamine, muscarinic, or alpha-adrenergic receptors, which contributes to its favorable side effect profile. It increases synaptic availability of both monoamines, modulating descending pain inhibitory pathways.

Application

Milnacipran is indicated for the management of fibromyalgia in adults, improving pain, fatigue, and global functioning. It is also used off-label for major depressive disorder, neuropathic pain, and chronic fatigue syndrome. The drug's dual reuptake inhibition provides an additional mechanism for pain management beyond serotonin modulation alone.

In rats with ventromedial prefrontal cortex lesions (quinolinic acid), repeated milnacipran (10 mg/kg/day for 14 days) ameliorated impulsive deficits in a 3-choice serial reaction time task, with effects persisting after drug cessation. It restored mature BDNF, PSD-95, dendritic spine density, and excitatory currents in surviving neurons.

Fig. 1 The effects of lesions of the ventromedial prefrontal cortex (vmPFC) and repeated milnacipran administration on the number of dendritic branch points in the layer V pyramidal neurons of the vmPFC. (Tsutsui-Kimura I, et al., 2014)

References

Tsutsui-Kimura I, et al. Milnacipran remediates impulsive deficits in rats with lesions of the ventromedial prefrontal cortex. Int J Neuropsychopharmacol. 2014;18(5):pyu083.

Does Milnacipran Hydrochloride require protection from light during long-term storage?

Yes, it is photosensitive. UV exposure can cause photodegradation and discoloration. Store in light-resistant containers, preferably amber glass.

What is the recommended storage temperature for Milnacipran Hydrochloride?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which can accelerate degradation of the cyclopropane ring.

Is Milnacipran Hydrochloride hygroscopic, and how is this managed?

It is slightly hygroscopic. Under high humidity (>70% RH), it may absorb moisture and clump. Storage in tightly sealed containers with desiccant is recommended.

How is the impurity milnacipran N-oxide (an oxidative degradation product) monitored?

This degradation product is quantified using a stability-indicating HPLC method, ensuring it remains within ICH qualification thresholds.