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What are the chemical properties of adrenochrome?
Executive Summary
Adrenochrome is a red‑violet, redox‑active oxidation product of adrenaline with empirical formula C9H9NO3 and a molar mass near 179.17 g·mol⁻¹; it exists in multiple tautomeric and redox states and is chemically unstable, readily polymerizing to melanin‑like pigments under nonacidic conditions [1] [2]. Sources converge on a reactive quinone identity, note a variety of reported physical parameters (melting point ~115–125 °C, variable density and solubility figures), and agree the stabilized monosemicarbazone derivative carbazochrome has documented hemostatic use, while adrenochrome itself has no approved therapeutic application [3] [2] [4]. This report extracts the core claims, compares conflicting numeric values, highlights biological redox behavior and hazards, and identifies where older reviews and modern databases diverge in reported physical constants [1] [4] [3].
1. What people claimed — distilled into the scientific assertions that matter
Analyses collectively assert several core factual claims about adrenochrome: it is the oxidation product of epinephrine/adrenaline; it is a quinone‑type, redox‑active compound with violet coloration; its chemical formula is C9H9NO3 and molar mass ~179.17 g·mol⁻¹; it is unstable and prone to further oxidation or polymerization; and carbazochrome (the monosemicarbazone derivative) is a stabilized form used as a hemostatic agent [2] [1] [3]. Additional claims concern physical constants (melting point, density, solubility), redox cycling with biological reductases, and potential cellular effects; these are presented across reviews, databases and older organic chemistry work and form the basis for the subsequent technical comparisons [4] [5] [1].
2. Physical data — where sources agree and where numbers diverge dramatically
Multiple sources cite melting/decay around 115–125 °C, and consistent pigment/color descriptions (deep violet to red‑violet), yet reported density and solubility figures vary between entries: some analyses list densities of ~1.28–1.4 g·cm⁻³, others report implausible high values (3.785 g·cm³) that conflict with typical small organic molecules [3] [4] [6]. Predicted logP and polar surface area estimates indicate low lipophilicity and moderate polarity, supporting water solubility figures that range from quite low to moderately soluble depending on pH and tautomeric state [4]. These discrepancies reflect differing measurement methods, sample purity, and whether the data refer to adrenochrome, its hydrate, or stabilized salts and derivatives [7] [3].
3. Chemical reactivity and redox behavior — the heart of adrenochrome’s identity
Authoritative chemical reviews and mechanistic studies characterize adrenochrome as a reactive quinone formed by two‑electron oxidation of catecholamines; it undergoes further oxidation, tautomerization, and polymerization to melanin‑like pigments, and participates in redox cycling with biological reductases and metal ions [1] [5]. Spectroscopic signatures (UV‑Vis absorption bands near ~500 nm) and redox potentials (~+0.5 V vs. SHE in reviews) reflect its oxidizing quinone nature, and reactivity with nucleophiles and metal ions is documented; stability is pH‑dependent, with greater stability in mildly acidic media and rapid decomposition under alkaline conditions [1] [7].
4. Biological implications, toxicity signals, and therapeutic context
Biochemical and toxicological notes show adrenochrome can be generated in vivo by oxidation of adrenaline and is implicated in in vitro cellular effects — it can produce reactive oxygen species via redox cycling, be reduced enzymatically by NADPH‑dependent systems, and has been discussed in older hypotheses on neurotoxicity and cardiovascular effects, though clinical utility of adrenochrome itself is unsupported [5] [8]. The clinically used related compound, carbazochrome (adrenochrome monosemicarbazone), is the only derivative with recognized hemostatic use; adrenochrome itself is described as unstable and potentially harmful if ingested, inhaled or contacted, according to hazard summaries [3] [8].
5. Where data conflict and why you see divergent numbers in reputable sources
Conflicting numeric values (density 3.785 g·cm³ vs. ~1.28–1.4 g·cm³; boiling points reported variably, melting point listed from 115 °C to 125 °C or decomposing ranges) arise from different experimental conditions, impurity or polymer content, salt forms, and whether values apply to adrenochrome, its hydrated state, or its semicarbazone derivative [3] [7] [6]. Older crystallographic and organic chemistry literature focuses on structural tautomers and derivatives, whereas modern metabolome and database entries include predicted properties (logP, pKa) from computational models; cross‑checking sample identity, measurement method and whether the entry is predicted or measured resolves many discrepancies [1] [4].
6. Bottom line and reading strategy — what to trust and what to verify next
The consolidated evidence establishes adrenochrome as a reactive, redox‑active quinone derived from adrenaline with formula C9H9NO3 and molar mass ≈179.17 g·mol⁻¹, unstable under neutral-to-basic conditions and documented to polymerize and engage in biological redox cycles; carbazochrome remains the stabilized derivative with medical use, while adrenochrome itself lacks approved therapeutic applications [1] [2] [3]. For precise physical constants, use primary experimental reports or validated database entries that specify sample form and measurement conditions; prioritize recent database records for predicted physicochemical parameters and classic reviews for mechanistic redox chemistry [4] [1].