Spermine dihydrate - ≥97% , CAS No.403982-64-9

CAS: 403982-64-9 Cat. No.: S134151 Formula: C₁₀H₂₆N₄·2H₂O Molecular Weight: 238.37 Beilstein Registry Number: 7526933 EC Number: 687-801-4

GRADE & PURITY ≥97%

Synonyms

Gerontine | Musculamine | N,N′-Bis(3-aminopropyl)-1,4-diaminobutane | Neuridine

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Specifications

Synonyms

Gerontine | Musculamine | N,N′-Bis(3-aminopropyl)-1,4-diaminobutane | Neuridine

Specifications & Purity

≥97%

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥97%

Names and Identifiers

Canonical Smiles

C(CCNCCCN)CNCCCN.O.O

IUPAC Name

N,N'-bis(3-aminopropyl)butane-1,4-diamine;dihydrate

InChIKey

MTNRSMVAYLLBAV-UHFFFAOYSA-N

INCHI

1S/C10H26N4.2H2O/c11-5-3-9-13-7-1-2-8-14-10-4-6-12;;/h13-14H,1-12H2;2*1H2

Isomeric SMILES

C(CCNCCCN)CNCCCN.O.O

WGK Germany

3

Molecular Weight

238.37

Beilstein

7526933

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Class Organonitrogen compounds
      • Subclass Amines
        • Level5 Secondary amines
          • Level6 Dialkylamines

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Class: Organonitrogen compounds
• Subclass: Amines
• Intermediate Tree Nodes: Secondary amines
• Direct Parent: Dialkylamines
• Alternative Parents: Organic oxides Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Secondary aliphatic amine - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Primary amine - Primary aliphatic amine - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: Air and moisture sensitive
• Molecular Weight: 238.370 g/mol
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 238.237 Da
• Monoisotopic Mass: 238.237 Da
• Topological Polar Surface Area: 78.100 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 86.100
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 3

XLogP3

Application Protocols

No manufacturer-validated protocols are provided for this SKU. The following are literature-style, non-spec guidance for common laboratory uses of spermine.

A. Stock solution preparation (general)

• Dissolve spermine dihydrate in CO2-free water to 100–1000 mM depending on use. Adjust pH to 7.0–7.4 with HCl to ensure full dissolution. Filter-sterilize (0.22 µm) if required. Store aliquots at 2–8°C under inert gas.

B. DNA condensation/polyplex formation (screening conditions; literature)

• Mix DNA (e.g., plasmid in 10 mM HEPES, pH 7.4) with spermine solution at N/P ratios from 1 to 10. Incubate 10–30 min at room temperature before analysis (gel shift, DLS) or deposition on substrates.

C. Surface amination via NHS ester coupling

• Activate carboxyl-functional surfaces or polymers with EDC/NHS in MES buffer (pH 5.5–6.0). Rinse, then expose to 1–50 mM spermine in buffer (pH 7.0–8.0) for 15–120 min. Quench with ethanolamine; rinse thoroughly.

D. Michael addition to acrylates (solution)

• Combine acrylate (1.0 eq diacrylate) with spermine (0.5–1.0 eq) in ethanol at 25–50°C. Monitor by NMR/FTIR. Cure or precipitate product as needed.

These procedures are illustrative only; optimize for your system and consult primary literature.

Biological Roles

Literature background (non-spec; for context only)

• Endogenous metabolite: spermine is a ubiquitous cellular polyamine derived from ornithine via putrescine and spermidine pathways. It is abundant in the cytosol and nucleus across bacteria, plants, and animals.
• Molecular interactions: multivalent binding to nucleic acids (DNA/RNA), ribosomes, and acidic phospholipids; modulates macromolecular packing, translation efficiency, and ion channel behavior in vitro.
• Charge state: at physiological pH, spermine carries multiple positive charges (typically +3 to +4), enabling electrostatic screening and condensation of polyanions.
• Enzymatic context: biosynthesis involves spermidine synthase and spermine synthase; catabolism via acetylation (SSAT) and oxidation (PAO/SMOX) producing aldehydes and H2O2.
• Laboratory relevance: used to stabilize nucleic acid structures, assemble polyelectrolyte complexes, and probe polyamine–protein interactions.

Note

• This information is provided solely to inform research design. No medical, diagnostic, or therapeutic claims are made for this product.

Buffer Applications

Applicability

• Spermine dihydrate is not a classical buffering agent with a narrow, well-defined pKa near the target pH. However, its multiple amines provide broad buffering capacity across mildly acidic to neutral ranges and strong polycationic behavior useful for certain formulations.

Literature guidance (non-spec)

• pH range: broad acid–base capacity roughly between pH ~6–10 due to multiple protonation steps; not recommended as a primary pH buffer where precise pH control is required.
• Uses: as a polycation additive to stabilize nucleic acids, promote condensation/precipitation (e.g., with sulfate/acetate counterions), and in assembling layer-by-layer films with polyanions (alginate, DNA, PSS).
• Practical hints: prepare solutions in CO2-free water to avoid carbamate formation and pH drift; adjust pH with HCl to desired value. Filter-sterilize (0.22 µm) for biopolymer work.

If a tightly controlled pH buffer is required, choose conventional systems (e.g., HEPES pH 7.0–8.0, Tris pH 7.5–8.5, acetate pH 3.6–5.6) and add spermine as a functional additive if needed.

Green Alternatives

Context

• Spermine dihydrate is a high-functionality, nitrogen-rich building block. Green considerations center on solvent choice, energy input, and end-of-life of polymers or complexes formed with it.

Alternatives and trade-offs (literature)

• Biogenic polyamines: putrescine and spermidine (microbially derived) can substitute in some templating or complexation roles with lower nitrogen content (reduced eutrophication potential on release), but may deliver weaker binding/templating performance than spermine.
• Polymer substitutes: chitosan (bio-based polycation) can replace spermine in polyelectrolyte films; however, it has broader MW distribution and lower process precision.
• Solvent changes: use water or bio-based alcohols (ethanol, 2-propanol) instead of DMF/DMSO when feasible; run at ambient temperature and atmospheric pressure to reduce energy use.

Comparison snapshot (general)

• Spermine vs spermidine: spermine offers stronger multivalent binding (4 N vs 3 N) at the cost of higher nitrogen loading and potentially higher ecotoxicity if released.
• Spermine vs PEI (polyethylenimine): spermine is a defined small molecule (easier characterization) and can be less persistent; PEI can deliver higher charge density but is less biodegradable and often harsher to cells and aquatic life.

Best practices

• Optimize dose to minimize excess amine in effluents.
• Select greener solvents and aqueous processing.
• Implement capture/reuse of amine-containing waste streams (acid scrubbers, ion exchange).

Pharmaceutical Uses

Scope

• No therapeutic claims. The following reflects formulation/manufacturing roles reported in the literature and general industry practices; item-specific pharmacopeial status is not established.

Potential formulation roles (literature; non-spec)

• Excipient/functionality: cationic crosslinker for polyanionic excipients (e.g., alginate, hyaluronate) to modulate gelation and mechanical properties in experimental dosage forms.
• Ion-pairing agent: can form ion pairs with acidic drugs, potentially modifying solubility or membrane interactions in research systems.
• Polymer cure/chain extender: reacts with epoxy- or acrylate-terminated prepolymers to produce amine-cured networks for device or coating research.

Considerations

• Regulatory: spermine is not a standard compendial excipient; any use in regulated products would require full toxicology and quality justification.
• Impurities: residual low-MW amines and metals can influence stability and color; request CoA details if considering pre-formulation studies.
• Safety: polyamines are irritants; ensure worker protection and appropriate residual limits in manufacturing environments.

For clinical development or GMP manufacturing, consult appropriate pharmacopeias and regulatory guidance; this catalog item is for research use only.

Physical Properties

Item-specific specifications

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula and weight: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general properties (non-spec; for guidance only)

• Physical state: polyamine dihydrates are typically low-melting solids or viscous, hygroscopic materials; spermine free base is a viscous liquid/oil, while hydrates can be crystalline due to hydrogen bonding.
• Solubility: highly miscible with water; soluble in lower alcohols (methanol, ethanol), partially soluble in polar aprotic solvents (DMF, DMSO); essentially insoluble in hydrocarbons and other nonpolar solvents.
• Basicity (approximate pKa, literature): stepwise pKa values for spermine are typically in the ranges ~10–11 (terminal), ~9–10, and ~8–9 for internal nitrogens; at neutral pH it exists predominantly as a multi-protonated polycation.
• LogP/logD: free base has low logP; protonated forms are highly hydrophilic (logD << 0 at neutral pH).
• Hygroscopicity: appreciable; readily absorbs CO2 and moisture; hydrates can gain/lose water depending on humidity.
• Refractive index/density/MP/BP: Not broadly standardized for the dihydrate; consult primary references or the CoA for item-specific data if critical.

Note: Use the item’s CoA to source definitive numerical specifications for QC-sensitive work (e.g., water content, assay, residual solvents, and UV cutoffs).

Quality & Grades

Item-specific grade/purity

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and implications (general guidance)

• Without a stated grade (e.g., BioUltra, ACS, HPLC), end-users should verify suitability for their application via the CoA: assay method (titrimetric vs. NMR), residual water (Karl Fischer), inorganic residues (sulfated ash/ICP), and bioburden/endotoxin if used in sensitive biochemical workflows.
• For nucleic acid–related work, low UV-absorbing impurities and low metal content are desirable; request UV trace (200–300 nm) and metals screening if critical to your protocol.
• Stabilizers: none are typically used for neat polyamines; however, hydrates inherently modulate water content. If your process requires strictly anhydrous conditions, consider converting to a salt and re-free-basing or performing in situ drying (e.g., azeotrope with toluene) while monitoring composition.
• Batch-to-batch control: monitor amine value (meq/g), water content, and color (APHA) as practical QC surrogates.

Documentation

• Refer to the CoA for this lot of S134151 for definitive specifications, analytical methods, and release criteria.

Reaction & Applications

General research applications (literature; non-spec)

• Polyelectrolyte complexation: condenses DNA/RNA due to multivalent cationic character; used in nucleic acid precipitation, protection, and assembly of polyplexes for materials research.
• Inorganic templating: acts as a structure-directing agent for mesoporous silica/zeolites and metal–organic frameworks.
• Surface functionalization: provides multi-dentate amine termini for modifying silica, carbon materials, and polymers via amide coupling, silane anchoring (through linker chemistry), or epoxy ring opening.
• Polymer chemistry: reacts with diepoxides, diacrylates, and diisocyanates to yield poly(amine)s, poly(urea)s, and crosslinked networks; useful as a curing agent and chain extender.
• CO2 capture studies: forms carbamates/bicarbonates in aqueous solutions; investigated in absorbent blends.

Named/representative transformations (literature)

• Schiff base formation with aldehydes/ketones; subsequent reduction to secondary/tertiary amines (Reductive amination).
• Michael addition to activated alkenes (acrylates, maleimides) at ambient to moderate temperatures.
• Amide coupling with activated esters/acid chlorides (EDC/NHS, DCC, or acyl halides) to introduce multi-cationic handles on biomolecules and surfaces.

Practical tips

• Control pH: maintain mildly acidic conditions (pH 5–7) to ensure solubility while retaining nucleophilicity of at least one amine for selective reactions.
• Stoichiometry: leverage differential basicity to achieve partial functionalization; protect selectively if required (e.g., Boc protection of terminal amines).
• Workup: protonate with dilute acid for aqueous extraction; free-base with NaOH/K2CO3 and extract into alcohols when needed.

Reaction Conditions

General conditions (literature; guidance only)

• Reductive amination: mix carbonyl compound with spermine in methanol or ethanol, pH adjusted to mildly acidic (acetic acid), then reduce with NaBH3CN or NaBH(OAc)3 at 0–25°C; reaction times 1–16 h depending on substrate.
• Amide coupling: in DMF, DCM, or aqueous buffer using NHS esters/EDC or acid chlorides at 0–25°C; control stoichiometry to avoid over-acylation; typical times 0.5–4 h.
• Michael addition: to acrylates/maleimides in alcohols or neat; 20–60°C; catalytic base may be unnecessary due to inherent basicity; 1–8 h.
• Epoxy curing: with diglycidyl ethers (e.g., DGEBA) at 25–80°C; exothermic; formulate with diluents to control viscosity and gel time.
• Metal coordination/templating: aqueous solutions (0.1–1 M) at pH 6–9; ambient to 80°C for sol–gel or hydrothermal steps.

Selectivity/leverage

• Protonation state controls reactivity: perform reactions under conditions that keep non-participating amines protonated to limit overreaction.
• Protecting groups: Boc protection (tert-Boc anhydride, Et3N, dioxane/water, 0–25°C) is widely used; deprotect with TFA at 0–25°C.

Yields

• Highly substrate-dependent; small-molecule couplings often 60–95% (literature). Always confirm with pilot experiments.

Note: Drying the dihydrate prior to strictly anhydrous reactions may be necessary; confirm by Karl Fischer.

Safety & Handling

Item-specific hazard information

• Signal word: Not specified for this item; refer to SDS.
• H-statements / GHS classification / pictograms: Not specified for this item; refer to SDS.

General safety considerations for polyamines (literature; non-spec)

• Hazards: aliphatic amines are skin/eye irritants; high-pH aqueous solutions can be corrosive. Polyamines may cause respiratory irritation as aerosols/vapors when heated or nebulized. Avoid contact and inhalation.
• Peroxide formation: Not a peroxide-forming solvent; low propensity for autoxidation but can yellow on air exposure due to slow oxidative processes.
• Incompatibilities: strong oxidizers; acid chlorides/anhydrides, isocyanates (exothermic reactions); carbonyls (can form imines/Schiff bases); CO2 (forms carbamates); halogenated solvents under strong base.
• PPE: lab coat, nitrile gloves (consider double-gloving for extended contact), splash goggles; use in a fume hood, especially when heating or handling concentrated solutions.
• First aid (overview; defer to SDS): rinse skin/eyes with water for ≥15 min on exposure; remove contaminated clothing. If inhaled, move to fresh air; if ingested, rinse mouth—seek medical attention in all cases.
• Spill response: absorb with inert material; neutralize cautiously if needed; avoid discharge to drains. For aqueous solutions, dilution and neutralization followed by appropriate waste disposal.

Always consult the Aladdin SDS for authoritative hazard and emergency information.

Solvent Selection

Applicability

• This product is a solid/liquid polyamine hydrate rather than a solvent. The section below provides selection advice for dissolving or processing spermine dihydrate.

Solubility and polarity (literature)

• Highly polar, polycationic under neutral/acidic conditions; excellent solubility in water.
• Miscible/soluble: water, methanol, ethanol; good solubility in formamide, DMSO, DMF.
• Poorly soluble: acetone (variable), acetonitrile (limited), ethers, chlorinated and hydrocarbon solvents in the free-base form.

Selection guidance

• For biochemical work: use water or buffered aqueous media (e.g., HEPES, Tris). Maintain pH below or near the lowest pKa to keep the polyamine protonated and fully soluble.
• For organic synthesis: use polar aprotic solvents (DMF, DMSO, NMP) or alcohols when coupling or performing Michael additions. If required in less polar media, convert to a salt or use phase-transfer strategies.
• Dry media: because this is a dihydrate and hygroscopic, strictly anhydrous applications may require vacuum drying under inert gas, with verification by KF.

Quick comparison (general)

• Water: best biopolymer complexation and process safety; easiest handling.
• Alcohols: facilitate esterifications/transesterifications with appropriate controls; moderate volatility helpful for workup.
• DMF/DMSO: superior solvation of salts and polymers; consider downstream removal and toxicity profiles.

Storage & Reconstitution

Item-specific conditions (from Product Data)

• Storage: Store at 2–8°C, argon charged.
• Shipped: Wet ice.

General handling guidance

• Hygroscopic/CO2-sensitive: minimize headspace; keep tightly closed under inert gas to prevent carbamate formation and pH drift.
• Container: use air-tight, chemically compatible bottles (e.g., HDPE with PTFE-lined cap or glass) purged with argon.
• Reconstitution: dissolve in high-purity water or suitable polar solvent. For biopolymer work, adjust to desired pH with HCl and filter-sterilize (0.22 µm). For anhydrous reactions, consider drying the dihydrate under high vacuum at ambient to mild temperature, monitoring by Karl Fischer.
• Freeze–thaw: if preparing aqueous aliquots, avoid repeated freeze–thaw; store working solutions at 2–8°C for short term. For longer term, freeze aliquots at ≤−20°C; thaw on ice and use promptly.
• Stability/shelf-life: Not specified for this item; refer to CoA/Spec Sheet. Inspect periodically for discoloration or precipitation.

Disposal

• Treat waste as amine-containing; neutralize and dispose according to institutional and local regulations.

Structure & Identity

Item-specific (from Product Data)

• SKU: S134151
• Product name: Spermine dihydrate
• CAS: 403982-64-9
• CID: 20849112
• InChIKey (as provided): 228128
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed identity (for context; non-spec)

• Core scaffold: spermine is a linear aliphatic tetraamine with spacer lengths 3–4–3 carbons between nitrogens; the dihydrate contains two equivalents of H2O associated with the free base.
• Representative SMILES (spermine, anhydrous; literature): NCCCNCCCCNCCCN (dihydrate would be this plus .O.O)
• Functional groups: four amines (two primary terminal –NH2; two internal secondary –NH–); no stereocenters; fully flexible aliphatic chain.
• Typical molecular formulae (literature): spermine free base C10H26N4; spermine dihydrate C10H26N4·2H2O = C10H30N4O2.
• Approximate formula mass (literature): spermine 202.34 g/mol; dihydrate ~238.35 g/mol.

2D structure description (general)

• A linear chain of ten methylene carbons: H2N–(CH2)3–NH–(CH2)4–NH–(CH2)3–NH2. Terminal primary amines cap both ends; two secondary amines interrupt the chain. The dihydrate comprises two water molecules hydrogen-bonded to the polyamine, enhancing crystallinity and handling.

Synthetic Utility

Functional group landscape

• Four amine nitrogens (two primary, two secondary) enable multi-point reactivity: acylation, alkylation, urea/thiourea formation, imine formation, and conjugation to activated esters.

Applications (literature)

• Linker/spacer: introduces a 3–4–3 carbon spacer with terminal amines for bioconjugation or surface attachment; internal secondary amines can be left unmodified or derivatized.
• Crosslinker: reacts with di/tri-functional electrophiles (epoxides, acrylates, isocyanates) to build hydrogels, coatings, and poly(amine) networks.
• Macrocyclization/chelation: serves as a multidentate ligand precursor; condensation with dialdehydes yields Schiff-base macrocycles that can be reduced to stable polyamines.
• Site-selective chemistry: differential pKa and sterics allow partial protection/functionalization (e.g., Boc-protect terminals to target internal nitrogens, or vice versa using orthogonal protecting groups such as Cbz, Fmoc, Alloc).

Practical notes

• Handling as dihydrate improves weighability versus the oily free base; verify actual amine equivalents after drying (amine value titration or NMR) when stoichiometry is critical.
• For clean mono- vs di-acylation, control equivalents, temperature, and base; consider in situ salt formation to modulate nucleophilicity.
• Workup leverages acid/base extraction: protonate to drive into aqueous phase; basify to free-base for organic extraction when desired.

Target Specificity

Not applicable to this product type.

• This item is a small-molecule polyamine, not an antibody, enzyme, or affinity reagent. No antigen/epitope, clone, isotype, or species reactivity data are relevant.