Exploring d-threo-(-)-2-amino-1-(p-nitrophenyl)-1,3-propanediol: From Discovery to Opportunity

Historical Development

Decades ago, researchers in the field of antibiotics put vast effort into modifying simple molecular structures to fight off infectious diseases that plagued hospitals and communities. Among these developments grew a cluster of compounds called phenylpropanolamines. d-threo-(-)-2-amino-1-(p-nitrophenyl)-1,3-propanediol—better known to some by the trade name chloramphenicol base—emerged in the late 1940s as scientists searched for ways to disrupt bacterial protein synthesis. The path started in commercial labs, later expanded through worldwide clinical use. For millions, this substance made a difference, particularly during outbreaks of typhoid fever, meningitis, and other dangerous bacterial infections that previously ran unchecked.

Product Overview

By structure and function, d-threo-(-)-2-amino-1-(p-nitrophenyl)-1,3-propanediol stands out for its core nitrophenyl group and the two hydroxyl groups on the propanediol backbone. Each part of this molecule has a specific role in its biological activity. It gained wide adoption in pharmaceutical research due to its reliable activity against a variety of Gram-positive and Gram-negative bacteria. Patients experienced its powerful antibiotic effects in a span of just a few days, but the fuel behind its success also lay in how reliably chemists could reproduce the compound in large quantities and at high purity, crucial for any medicine.

Physical & Chemical Properties

This compound comes as a pale yellow to yellowish powder, with a slight bitter taste and little odor. It has appreciable solubility in ethanol and slightly less so in water, allowing for both oral and intravenous formulations. The melting range commonly falls between 150°C and 153°C, and its stability holds up under typical lab storage conditions. On paper, its molecular formula reads C9H12N2O4. From a chemical perspective, the presence of a nitrophenyl ring positions it for electrophilic substitutions, and the two hydroxyls make it a candidate for esterification reactions.

Technical Specifications & Labeling

Reliable pharmaceutical preparations require tight control over purity, moisture content, and particle size. The industry typically stipulates purity not less than 98% by HPLC, with limits on residual solvents such as ethanol or methanol. Moisture content usually falls under 0.5%, and packaging bears warning labels that cover potential toxicity, especially to children under two due to rare but serious side effects like gray baby syndrome. Every batch must carry a clear batch number, expiry date, manufacturer details, and storage conditions—standing as a testament to the modern focus on patient safety and clear communication.

Preparation Method

The chemical synthesis follows a straightforward path that begins with p-nitrobenzaldehyde. Through an aldol condensation with nitromethane, followed by reduction with a strong hydrogen donor like sodium borohydride, chemists obtain the d-threo isomer in high yield. Chiral resolution may be necessary for large-scale pharmaceutical production to filter out the inactive or potentially harmful stereoisomers. This process requires careful temperature control and skilled handling of reactive intermediates, emphasizing the need for trained technicians and modern lab facilities.

Chemical Reactions & Modifications

This molecule offers interesting sites for chemical modification. The hydroxyls allow for acylation, giving rise to several prodrug forms designed for slower absorption or targeted release. Nitration or reduction on the aromatic ring shifts its pharmacological profile, and scientists have long taken advantage of such possibilities to tune the antibiotic activity for various clinical targets. Over the years, industry and academia have explored modifying the amino group as well—yielding derivatives with different spectrums of antimicrobial effectiveness or reduced toxicity.

Synonyms & Product Names

Over the last seventy years, d-threo-(-)-2-amino-1-(p-nitrophenyl)-1,3-propanediol has appeared under a long list of synonyms. Industry veterans know it as chloramphenicol base, and some older texts reference racemic or optically pure forms. In chemical catalogs, it just as likely shows up under systematic names, reflecting variations in nomenclature over time. And every variation speaks to the molecule’s widespread adoption across continents and research groups.

Safety & Operational Standards

Proper handling of this compound means treating it with respect in both raw and formulated forms. Exposure limits reflect possible links to aplastic anemia—a rare but serious condition. Researchers and workers need lab coats, gloves, and fume hood ventilation, particularly during synthesis or during weighing and blending for pharmaceutical preparations. Pharmaceutical operations require validated cleaning procedures to prevent cross-contamination. Staff receive regular safety training, and lab monitoring for exposure forms part of regulatory compliance in countries with strong pharmaceutical oversight.

Application Area

Chloramphenicol set the gold standard for broad-spectrum antibacterials for a generation. Hospitals reached for it in cases of bacterial meningitis, typhoid fever, rickettsial infections, and rare but life-threatening illnesses. Veterinarians made heavy use of it for animal infections, especially poultry and cattle diseases. Outside direct clinical treatment, labs around the world leaned on chloramphenicol to select or suppress specific microbes in culture media—a handy tool in microbiological research, even decades after its initial rollout in medicine.

Research & Development

From my experience at the lab bench, research on d-threo-(-)-2-amino-1-(p-nitrophenyl)-1,3-propanediol never stands still. Even as other antibiotics take the lead in routine care, this molecule lingers in the background of pharmaceutical development, earning attention for its potential as a chemical starting point. Newer synthetic pathways aim for higher yield, easier chiral resolution, and lower environmental impact. Teams run trials to test innovative prodrug forms that reduce systemic toxicity or target resistant bacteria. Journals continue to publish on resistance genes, pointing to a need for prudent stewardship and monitoring for emerging chloramphenicol resistance in high-use areas.

Toxicity Research

The compound’s power comes with a price. Toxicology studies throughout the years reveal risk of aplastic anemia and bone marrow suppression, effects that do not always reverse. In the 1950s and 1960s, clusters of serious adverse events led public health authorities to set tighter prescription limits, reserving chloramphenicol for life-threatening infections where safer options failed. Today, toxicity studies often focus on molecular biomarkers and genetic predispositions, searching for ways to identify at-risk patients before harm occurs. Screening protocols and post-market surveillance databases keep tabs on rare but dangerous complications, shaping national and international guidelines for use.

Future Prospects

Looking down the road, the future of d-threo-(-)-2-amino-1-(p-nitrophenyl)-1,3-propanediol will probably depend on how the world addresses bacterial resistance and drug safety. With antibiotic resistance climbing, some researchers see value in dusting off once sidelined compounds, giving them a modern technological makeover or bundling them with compounds that blunt their side effects. Advances in molecular biology pull back the curtain on how this drug interacts with both bacterial and human proteins. Environmental regulations and pressure for greener synthesis guide projects toward cleaner, less wasteful manufacturing steps. All these threads point to one clear reality—after seventy years, this compound still has stories to tell, and science keeps looking for new chapters to write.



What is d-threo-(-)-2-amino-1-(p-nitrophenyl)-1 3-propanediol used for?

Why This Chemical Stands Out in Medicine

The name d-threo-(-)-2-amino-1-(p-nitrophenyl)-1,3-propanediol doesn’t roll off the tongue, but folks working in medicine or research labs might know it better as D-threo chloramphenicol. This compound helped turn the tide against life-threatening infections. After World War II, bacterial diseases were devastating families before antibiotics came on strong. Doctors called on chloramphenicol and its derivatives to save countless lives, even in places where resources ran low. People sometimes don’t realize how important these molecules remain in places battling typhoid fever, meningitis, and certain eye infections.

The Threat From Bacteria

Many antibiotics have lost power over time. Superbugs—bacteria that don’t care about older drugs—are a scary reality in hospitals and remote clinics. D-threo chloramphenicol, with its ability to stop bacteria from making new proteins, still has value, especially in countries where stronger drugs cost too much or can’t be found. According to research published in “The Lancet,” tens of millions still face infections treatable with drugs like this one.

Side Effects and Public Health Concerns

Working in pharmacy, I saw first-hand why some doctors reach for alternatives. This chemical can cause some rough side effects, such as bone marrow suppression, which turns into a real crisis for people with existing illnesses or in areas with poor follow-up care. Parents often worry about their kids taking antibiotics, and they have a point. When a kid’s immune system is already under attack, adding a drug that may weaken their ability to make blood cells adds serious risk.

In the ’90s, tighter rules hit hard. Most developed countries limited the use of this compound, especially in oral form. They kept it alive for eye drops and ointments where absorption into the body is lower. Even so, in places without other choices or where hospital budgets are tight, you’ll still see prescriptions written for severe life-or-death cases.

Resisting the Overuse Trap

People sometimes forget that antibiotics aren’t candy. The more often these drugs get tossed around for common colds or minor ear infections, the faster bacteria smarten up. Having watched patients and families in the pharmacy, it’s clear that education matters. Teaching communities about proper use, storing medicine away from children, and never sharing leftovers—these steps cut down on bad outcomes and help keep lifesaving options available longer.

Looking for Safer Options

Newer drugs are great—when people can afford them, and insurance pays the bills. Not everyone is that lucky. Globally, organizations like WHO keep supplies of proven drugs like d-threo chloramphenicol handy for rough outbreaks. They recommend good screening, improved diagnostics, and better follow-up care so that side effects can be caught early and managed. Checking blood counts during treatment helps spot rare complications before real damage sets in.

What the Future Demands

Global health relies on everyone—from scientists finding safer therapies, to doctors making tough choices daily, to policymakers making sure basic drugs don’t disappear. This compound’s story reminds us how medicines once crowned as miracles can find new life, and still serve people, if handled with experience and care. Scientists keep searching for molecules with less risk and better results, but for now, d-threo-(-)-2-amino-1-(p-nitrophenyl)-1,3-propanediol remains on the shelf, still answering the call in places where every cure counts.

What are the storage conditions for d-threo-(-)-2-amino-1-(p-nitrophenyl)-1 3-propanediol?

Understanding Why Proper Storage Matters

It’s not easy to keep an unstable chemical safe for long stretches. Overlook something basic, and you end up with spoiled stock. d-threo-(-)-2-amino-1-(p-nitrophenyl)-1,3-propanediol isn’t your average household compound; people working with it know you don’t just toss it on any lab shelf. This compound tends to break down if left under the wrong conditions, leading to experimental headaches and unnecessary risks.

The Science Behind Storage

Chemists have wrestled with p-nitrophenyl derivatives for decades. This specific amino-propanediol brings its own quirks, demanding an environment free from wild swings in temperature and humidity. I’ve seen researchers lose viable product because they let the room warm up one weekend over a holiday break. The stuff just can’t handle repeated exposure to heat or light—those nitro groups are especially touchy and can degrade, bringing down the whole lot’s quality.

Proven Storage Conditions

From working alongside chemical researchers and getting advice from more seasoned colleagues, I’ve realized that a few hard rules stick out. The compound keeps best in a dry, dark place. I’m talking about an amber glass bottle, sealed tightly, tucked inside a desiccator or a specialty chemical fridge. If the lab shares a fridge with food or constant foot traffic, cross-contamination or condensation becomes a real problem. Keeping storage at 2-8°C (standard refrigerator range) helps the sample last. Even short spells above room temperature push things in the wrong direction.

Direct sunlight targets nitrophenyl compounds, spurring unwanted reactions. Using chemical storage cabinets that stay dark, and preferably climate-controlled, cuts down on this risk. No one should underestimate the power of moisture either—any hint of water in your sample container, and degradation can speed up fast. Ensuring desiccant packets sit inside the storage vessel helps keep things bone-dry.

Why Skipping Steps Causes Headaches

One time, a shared lab I worked in left amino-propanediols in a plastic screw-cap tube out on an open shelf. Two weeks later, sample analysis turned up major impurities and a good chunk of product wasted. Taking shortcuts—using improper containers, skipping the desiccator—always ends in lost time. You just can’t wing it and expect solid results. Labs working toward reproducibility know that each variable matters, and storage is not the spot for guesswork.

Supporting Research and Facts

Scientific literature over the last fifteen years backs up these hands-on experiences. Articles in journals like the Journal of Organic Chemistry and Chemical Reviews detail the degradation risks tied to moisture and heat for nitro-aromatic mixing with amino alcohols. Regulatory agencies and chemical suppliers make it standard to include “Store at 2-8°C in a dry, light-protected environment” on labels and safety sheets. Checking Sigma-Aldrich, TCI, or Alfa Aesar’s product pages, one finds instructions lining up with the hands-on approach from seasoned lab techs.

Reducing Hassles and Risks

To avoid spoiled product, everyone in the lab needs to know and follow these storage basics. Investing in proper lab fridges, labeling everything with clear “keep cool and dry” signs, and setting up routine checks for condensation or mold inside storage cabinets can stop mistakes before they happen. Training new students and staff to respect these guidelines makes a real difference. Following best storage practices doesn’t just preserve one compound—it protects safety, research budgets, and the time spent on good science.

Is there any specific safety information or hazard associated with this compound?

Looking Past the Label

For every compound on a shelf, there’s a story—some a bit more dangerous than others. While working in a lab, I discovered that every white powder or clear liquid carries its own personality. Some seem mild but pack serious risks when mixed, inhaled, or even just touched. Anyone familiar with handling chemicals knows labels don’t always say enough. Teaching introductory chemistry, I watched folks treat everything like table salt until their gloves started to change color or fumes made them dizzy. Hazards hide in the details ordinary users might miss.

Routes of Exposure

You'd think putting on gloves and goggles covers every danger, but compounds get sneaky: fumes where you least expect, powder that drifts with a cough, and liquids that splash. Once, a student discovered her goggles fogged up just as an irritating vapor hit. She hadn’t even noticed the volatile warning, and her eyes bore the brunt.

Inhalation, skin contact, accidental ingestion—each pathway matters. I read about a technician who handled solvents all day, washed his hands, then ate lunch without fully removing the residue. Weeks later, odd headaches and fatigue showed up. Blood tests pointed to the culprit absorbed right through his skin. Even simple compounds—bleach, ammonia—turn hazardous without fresh air and rinsed hands.

Fire Risks and Reactivity

Some compounds don’t play nice with others. Keep oxidizers away from anything flammable: that’s a lesson anyone working with cleaning agents or pool chemicals soon learns. I once saw a barrel of sodium hypochlorite stored close to an organic cleaner in a maintenance closet. The fumes alone, even without direct contact, sent two workers home early with burning lungs. These accidents pop up not only in industrial labs but inside kitchens, garages, and janitorial closets, too.

Signs and Symptoms Worth Noticing

If you get a burn, rash, dizziness, or strong odor, don’t shrug it off. Years ago, before wearing a respirator became standard, tradesmen mixing solvents often took pride in working through watery eyes and coughs. Chronic exposure led to ongoing respiratory trouble. Hazard signs can be subtle. A dusty residue at the bottom of a cabinet, odd colors on containers, or unfamiliar smells are all red flags. Ignoring the body’s signals comes with long-term costs.

Making Safety a Habit

Earning trust around chemicals starts with clear communication and practice. Reading the Safety Data Sheet gets you farther than any generic warning label. I always ask folks new to any workplace to walk through every procedure — not just sign off on a checklist. Protective gear needs to fit and work, not just hang on a wall. Simple habits—proper storage, fresh air, clear labeling, hand washing—save lives and money.

Replacing worn equipment, spending a few extra minutes to set up ventilation, and asking for help before mixing anything unfamiliar honestly make more difference than any advanced safety technology. Mistakes happen. What counts is whether everyone walks out of the door healthy at the end of the day.

What is the molecular formula and weight of d-threo-(-)-2-amino-1-(p-nitrophenyl)-1 3-propanediol?

Chemistry Isn’t Just for the Lab

Many people look at chemical names and feel overwhelmed, as if these long titles hide secrets only scientists can understand. Taking apart a molecule like d-threo-(-)-2-amino-1-(p-nitrophenyl)-1,3-propanediol, the most direct way to handle it is to break it down. You’ve got three carbon atoms in the main chain, two alcohol groups, one amine group, and a p-nitrophenyl ring. For anyone familiar with organic chemistry, that structure rings some bells — it’s a molecular skeleton similar to compounds used in antihypertensive drugs and research reagents.

Counting Atoms: Unraveling the Formula

Let’s count. The propanediol backbone gives three carbons, the p-nitrophenyl ring adds six more from the aromatic benzene core. Two nitrogens come in — one from the nitro (NO2) group and one from the amine (NH2), balanced with seven oxygens: two from the diol, two more from the nitro group, and the remaining connected through the benzene. Looking at each atom, the chemical formula stacks up as C9H12N2O4.

Weight That Matters

Molecular weight often gets overlooked in general conversations about chemicals, yet it plays a practical role. Imagine a chemist adjusting amounts in a buffer for blood tests or prepping reference standards for a pharmaceutical batch — an error here ruins accuracy for quality control and patient safety. For d-threo-(-)-2-amino-1-(p-nitrophenyl)-1,3-propanediol, the molecular weight clocks in at about 212.20 g/mol. This calculation isn’t just for textbook purposes. Every experiment relies on weighing out the right number of molecules, which revolves around this number.

The Real-World Stakes

This particular molecule pops up in more than one therapeutic context. It’s known as a core piece of D-threo-1-p-nitrophenyl-2-aminopropane-1,3-diol, recognized in some circles as a precursor in drugs that target specific pathways in blood pressure regulation. The role of accurate chemical specifications really shows during scale-up efforts in pharmaceutical production, research antibody labeling, or preparing custom synthesis for bioassays. I’ve seen firsthand how missing a fragment — say, misplacing an amine or confusing a nitro group with a carboxyl group — leads to failed syntheses, wasted funding, and sometimes questions about data reproducibility in peer-reviewed papers.

Trust and Verification in Chemistry

Too often, folks outside the field underestimate the importance of basic molecular details. Authenticity and purity start with a verified chemical structure; mistakes can introduce hazardous byproducts or ineffective treatments. Regulatory authorities expect producers to source and confirm their materials down to the molecular level, reflecting trust between the industry, researchers, and healthcare providers. As someone who's spent late nights double-checking molecular weights during high-pressure submission deadlines, I can say that accountability in chemistry runs directly through these numbers.

Steps Toward Safer Use and Shared Knowledge

Accessibility, clear labeling, and public databases allow scientists and clinicians to trust the molecules they use. For d-threo-(-)-2-amino-1-(p-nitrophenyl)-1,3-propanediol, widely available data sources coupled with peer networks provide cross-checks valuable in both teaching labs and real-world production. Opening up this information not only builds safer lab environments, it gives early-career scientists confidence to dive into complex chemistry.

Molecular formula: C9H12N2O4Molecular weight: 212.20 g/mol
Are there recommended applications or research uses for d-threo-(-)-2-amino-1-(p-nitrophenyl)-1 3-propanediol?

Digging into Chemical Value Beyond the Surface

Every curious chemist eventually lands on a compound with a name so convoluted it sounds like a password, not a chemical. d-threo-(-)-2-amino-1-(p-nitrophenyl)-1,3-propanediol—let’s call it DAPN for sanity—sparked my interest early in grad school. This compound, sitting at a crossroads of organic chemistry and neuroscience, offers a window into the world of neurotransmitter research.

Why DAPN Matters in the World of Research

For years, DAPN has carried the nickname "Epanol," acting as a strong representative of the epoxy alcohol family. Researchers first picked up on its power because it strongly blocks the uptake of norepinephrine by nerve cells. This blocking ability lets scientists untangle the winding routes neurotransmitters take, especially in the brain.

What drew me to this compound was its celebrated use as a norepinephrine transport inhibitor. In neuroscience labs, this molecule lets us stun the reuptake system and take a clear look at what happens when norepinephrine piles up in synapses. The whole field of antidepressant drug development partly depends on understanding these pathways. DAPN gave researchers the tools to trace the roots of mood disorders linked to neurotransmitter imbalances.

Research from the 1970s through the 1990s shows DAPN was no stranger to rodent lab cages or tissue cultures. Science journals describe how the compound shapes the behavior of nerve cells and heart tissue. Those early studies led to breakthroughs in mood disorder treatments, helping frame selective norepinephrine reuptake inhibitors like reboxetine and atomoxetine—important for managing ADHD or supporting depression treatments.

Tools, Applications, and Ethical Questions

Scientists and graduate students working with DAPN sometimes call it a “benchmark tool.” It helps tell the difference between targets for norepinephrine, dopamine, or serotonin. If you’re screening a batch of new antidepressant candidates, this tool shows you what makes one drug unique and what makes it too similar to the last.

There’s a hidden side, too. DAPN stands out with its nitrophenyl group, making disposal and environmental impact a real concern. In real labs, the amount used tends to stay small, which limits risks, but nobody wants to turn a blind eye to safety—questions sit around cleanup and accidental exposure. In my own training, strict chemical waste logs and storage guidelines kept everyone out of trouble, something that can slip when academic budgets tighten. Labs in developing areas sometimes lack the gear or oversight for full compliance.

Moving Forward with Chemistry’s Lessons

Today, DAPN doesn’t take the limelight in medicine or large-scale manufacturing, but it remains an essential research steppingstone. Its biggest impact now comes from its power as a proof-of-concept standard in neural pathway studies. New synthetic antidepressants still face off against it, getting checked in screening protocols as the baseline for safety and performance.

Looking at DAPN’s long research record, labs can draw lessons about careful handling, the push for greener reagents, and the deep value of molecular standards in pharmaceutical discovery. By sticking to well-designed protocols and sharing results openly, the next wave of researchers can keep using this chemical to push the frontiers of brain science—while staying mindful of health and safety in both lab and environment.

d-threo-(-)-2-amino-1-(p-nitrophenyl)-1 3-propanediol