Azacyclonol stepped into the pharmaceutical landscape during the 1950s at a time when psychiatric treatment faced real limitations. Chemists at Wander AG, later part of Sandoz, synthesized this compound to look for new ways to tackle mental illnesses, especially those that brought confusion or agitation. Researchers recognized Azacyclonol as a powerful tranquilizer, but not in the muscle relaxant sense. It found a place as an antipsychotic adjunct, helping reduce the motor restlessness caused by drugs like LSD and some early antipsychotics. Its development reflects the urgency of postwar optimism in medicinal chemistry—a period marked by trial, error, and sometimes unexpected promise.
At its core, Azacyclonol, also known by the name frenquel, offers a straightforward chemical profile. Used mostly as a pharmacological research tool now, it was once commercialized in tablet and injectable forms by manufacturers catering to psychiatric clinics. It doesn’t act as a sedative in the classical sense; instead, it can blunt excessive stimulation from certain psychoactive drugs. Over the decades, as safer and more targeted drugs entered the scene, Azacyclonol became more of a reference compound for neurochemical studies. In current times, most suppliers only offer the product for research use.
Azacyclonol’s structure centers around a piperidine ring—a six-membered cycle with one nitrogen atom. Its IUPAC designation, 1-(4-Pyridinyl)-2-azacyclohexanol, points directly to that skeletal framework. White to off-white crystalline powder, Azacyclonol remains stable at ambient temperatures and has a melting point around 140–142°C. Solubility leans toward organic solvents such as ethanol and chloroform, which fits with most secondary amines. It offers a molecular formula of C13H16N2O, and a molecular weight just above 216 g/mol. Standard analytical techniques such as NMR, IR, and mass spectrometry confirm its purity and structure, giving genuine clarity in laboratory settings.
Pharmaceutical and research suppliers typically specify Azacyclonol’s purity at 98% or higher, with HPLC traces confirming the absence of most major organic contaminants. Typical packaging includes amber glass vials for research powders, tightly sealed to block moisture and UV exposure. Commercial labels accurately reflect the IUPAC name, batch number, intended use (research or former medicinal), hazard codes, and storage guidance. SDS sheets advise on accidental exposure, reactivity, and environmental precautions. Regulatory standards require traceability, and proper labeling stands as part of meeting modern compliance frameworks for chemical acquisition.
Classic preparation of Azacyclonol starts with a Mannich-type reaction using pyridine as one starting material. Cyclohexanone and formaldehyde usually form the aminomethyl intermediate, which gets cyclized and then hydrogenated in the presence of suitable catalysts to produce the piperidine skeleton. Synthetic protocols emphasize careful temperature control, as over-reduction or unwanted side reactions lead to impure byproducts. Final purification relies on recrystallization or chromatographic separation. Literature on the subject details minor tweaks that yield better recoveries, but the essence of its synthesis remains rooted in solid – and somewhat classic – organic chemistry toolkits.
Azacyclonol’s structure permits selective substitutions along the piperidine ring or on the pyridyl moiety. The tertiary amine nitrogen allows for N-alkylation or acylation, producing pharmacological analogs or tagged derivatives for analytical work. Electrophilic substitutions and oxidations on the aromatic ring help generate metabolites, often needed for toxicological studies. Scientists have explored demethylation and other modifications to better understand how tiny changes affect neuropharmacological action. In comparison with other central nervous system agents, Azacyclonol offers a reasonably robust platform for synthetic manipulations, which extends its stay in research labs even after its clinical heyday ended.
Azacyclonol has traveled under several banners. Frenquel and Ataractan served as branded pharmaceuticals, particularly in European markets through the middle of the twentieth century. Chemists might run across synonyms like α-piperidyl-4-pyridinyl carbinol or its registry number, CAS 115-46-8. In research texts, names often shift to more systematic descriptors, reducing ambiguity for scientific communication. The diversity of names across languages and decades sometimes clouds literature searches, but most modern chemical indexes now harmonize synonyms to CAS identifiers, smoothing the way for accurate sourcing.
Handling Azacyclonol in a lab or formulation facility demands routine attention to safety. As a tertiary amine with central nervous system activity, this compound needs careful respect for its pharmacological potency. Laboratories provide gloves, goggles, and adequate ventilation to limit inhalation or skin contact, since accidental exposure could provoke neurological symptoms. Disposal of waste follows standard protocols for amines and nitrogen-heterocycle drugs, preventing environmental contamination. Storage in cool, dry conditions slows degradation and enhances shelf life. Labels and safety data outlines instructions in the event of spills or accidental ingestion. These guidelines built over years of use mean that both novice and seasoned chemists can reliably manage Azacyclonol without unexpected hazards.
Azacyclonol’s primary legacy rests in neuropharmacology—especially early efforts to counteract hallucinations and agitation from LSD or schizophrenia-linked drugs. The rise of newer antipsychotics and anxiolytics eventually squeezed Azacyclonol out of mainstream therapeutic use, but its pharmacological fingerprint continued to attract basic research. It aids neurotransmitter receptor studies and sometimes serves as a reference compound for behavioral models in laboratory animals. Toxicologists leverage its known effects for calibration, while analytical chemists develop methods to probe its breakdown and excretion from the body. In industrial chemistry, such central nervous system agents form templates for screening more selective, less toxic molecules, so Azacyclonol retains downstream influence in discovery pipelines.
Academic and industrial chemists still see Azacyclonol as a relevant research target due to its well-characterized action on serotonin and histamine receptors. Studies on animal models shed light on old-school tranquilizers’ modes of action, making Azacyclonol a case study in how medicinal chemistry has evolved. Modern research efforts span computational modeling of brain-receptor interactions, metabolic pathway elucidation, and efforts to revive structurally related molecules with updated pharmacokinetic profiles. Efforts to minimize central nervous system side effects in next-gen drugs draw on what Azacyclonol’s data sets reveal, especially in the field of neuroprotection and agitation control.
Toxicological studies on Azacyclonol suggest its low acute toxicity at moderate doses, though extended exposure or massive ingestion can provoke central nervous system depression, confusion, and even cardiovascular instability. Early clinical trials catalogued mild anticholinergic symptoms—dry mouth, blurred vision, drowsiness—and some risk of paradoxical agitation in sensitive individuals. Laboratory animals display dose-dependent central effects, underlining the importance of respecting its pharmacology. Chronic studies hint at a relatively wide therapeutic index compared with first-generation antipsychotics, still, newer drugs have displaced Azacyclonol by offering improved safety profiles. Ongoing research into its metabolites, tissue distribution, and enzyme interactions helps round out understanding of hazards, supporting risk assessments both for lab handling and retrospective clinical studies.
Despite retirement from regular clinical use, Azacyclonol still casts a long shadow in drug development. The renewed attention on neuropsychiatric disorders and a global push for novel mental health therapies keep older compounds like this one under review. New synthetic methods allow production of more tailored derivatives, aiming for greater selectivity or fewer side effects. As personalized medicine grows—matching patients to treatment according to genetic and metabolic markers—legacy compounds enrich compound libraries and inform decisions that shape the next generation of neuroactive therapies. Azacyclonol’s careful documentation and robustness in research settings mean it likely stays on the chemical shelf as a comparative, a teaching tool, and perhaps—as understanding deepens—a springboard for even more advanced discovery.
Azacyclonol doesn’t show up on new drug lists or glossy pharmacy ads. Most doctors coming up in the last decade probably haven’t scribbled its name on a prescription pad. Despite flying under the radar these days, Azacyclonol has a fascinating past, tied closely to psychiatry in the mid-1900s. In the 1950s, researchers thought differently about mental health, and approached treatment by trying out compounds that could change how the mind works on a deep, chemical level.
Doctors and scientists once believed Azacyclonol could blunt the intensity of hallucinogens like LSD. People taking hallucinogens sometimes spun out, unable to distinguish reality from imagination. With mental hospitals crowded and therapies still crude, doctors wanted something to gently bring patients back to earth. Trials showed Azacyclonol could reduce hallucinations for some patients, although the change wasn’t always dramatic. Over time, its importance faded as drugs like antipsychotics, with clearer benefits and known safety profiles, replaced it.
To understand medicine’s evolution, look at what knocked older drugs off shelves. Azacyclonol had a reputation as a “tranquilizer” or “ataractic”—words almost never heard today. Medicine kept searching for treatments with clearer benefits, more measurable effects, and fewer side effects. Stronger antipsychotics, introduced in the ’60s and ’70s, shaped how psychiatry handled schizophrenia, mania, and psychosis. These newer drugs, like chlorpromazine and haloperidol, changed the landscape forever. Azacyclonol just didn’t have the same muscle or clinical results behind it.
Every person in healthcare, whether nurse, pharmacist, or physician, knows yesterday’s solutions might show up again in some form. Consider how medicines once dismissed can circle back into research. We’ve all seen stories of old drugs finding new life—sometimes as treatments for different illnesses. But Azacyclonol hasn’t experienced any such renaissance yet. Research into neuropsychiatric disorders has mostly left it behind. There’s a lesson here about how scientific consensus forms and reshapes itself, based on patient outcomes and solid evidence.
Patients with psychotic and hallucinatory disorders still need meaningful, safe interventions. Instead of focusing on single old drugs, modern researchers prioritize deeper understanding of brain chemistry, genetics, and even targeted therapies using technology. The field also places more emphasis on quality of life, not just symptom control. Critically, regulatory standards grew more robust, and doctors now rely on treatments with significant research backing, reducing the risk that patients face unknown harms.
Trust in medicine builds when practitioners emphasize safety, honest risk communication, and scientific rigor. Medical communities learned a lot from older drugs that got replaced over time. Emerging treatments must demonstrate real-world improvement for people living with serious conditions. Clear evidence, patient stories, and community feedback carry more weight than simple laboratory findings. Instead of quick fixes, care teams collaborate on thoughtful, holistic treatment plans for those who need it most.
Azacyclonol hasn’t grabbed headlines in the ways that blockbuster drugs or even standard antidepressants have, but it still plays a role in specific treatments. In the mid-20th century, doctors turned to it for schizophrenia and related conditions. Its story faded fast as clozapine and risperidone arrived with stronger evidence. Azacyclonol didn’t exactly vanish—researchers kept an eye on safety.
People taking azacyclonol often describe feeling sleepy or groggy. Drowsiness tops the list of everyday complaints. Some users also find their mouths dry, almost like chewing cotton balls. Dry mouth seems minor at first, but over time it raises risks for cavities and trouble swallowing. Doctors used to ask patients to keep some water handy, since thirst could get distracting. These stories cross international lines—the same feedback turned up in clinical trials as well as family conversations in living rooms.
Dizziness comes up in patient reports, sometimes alongside a sense of confusion. Balance takes a hit for some folks, raising the risk of falls, especially among older adults. I remember reading early case reports where nurses kept a closer watch on patients just making their way to the bathroom. Keeping spaces clear of clutter became more important—a simple rug could suddenly be a hazard.
Some people saw their blood pressure dip lower than expected after starting azacyclonol. Low blood pressure might sound technical, but in practice it means standing up could make black spots dance in your vision or bring on a sudden headache. Sharing these signs with a doctor made a difference, since dose adjustments could mean safer treatment. Rapid heartbeats cropped up, too—doctors called this tachycardia. Any shift in heart rhythm needs attention, especially if someone already takes other medications that affect the heart.
A few patients described feeling more withdrawn or struggling to concentrate. Words did not always come as easily. For someone managing psychosis or anxiety, a medicine that scrambles thoughts even more can be tough to tolerate. Friends and family noticed the fog: missed appointments, forgotten conversations, confusion over simple tasks. This strain led researchers to search for better drug options over the years.
Though uncommon, some folks developed allergic responses—rashes, itching, or swelling after a dose. These cases surfaced in early research and real-world clinics. Rapid swelling or trouble breathing calls for immediate care, no matter the drug involved. It’s rare, but the risk deserves respect.
Care teams choose medicines after weighing risks and benefits. Today, doctors rarely reach for azacyclonol. Safer, easier-to-tolerate drugs often work better. But history tells us that people sometimes still encounter the medicine, especially in locations with limited access or for conditions outside the normal run. Good practice means talking openly with doctors about all new symptoms, keeping up with routine check-ups, and leaning on pharmacists for advice.
Medical journals like the British Journal of Psychiatry and Journal of Clinical Psychopharmacology have documented these side effects for decades. In my own work, I’ve seen how practical support—addressing dry mouth, fall prevention, blood pressure monitoring—matters as much as tracking drug levels. Plenty of stories from clinics underline that even older treatments need respect and vigilance.
Azacyclonol doesn’t come up in most everyday conversations about medicine. In fact, outside a handful of pharmacology circles, the name barely registers. Dig a bit and you’ll see why. Decades ago, chemists explored this compound as a potential treatment for psychic and behavioral symptoms—especially those linked to schizophrenia. The story, though, hits a twist. Researchers didn’t find the clinical results they wanted. The world of medicine kept moving, leaving azacyclonol on the sidelines.
Walk into a pharmacy, ask about azacyclonol, and you’ll probably get blank stares. It doesn’t show up on prescription lists, drugstore shelves, or hospital inventories in the United States, the UK, or pretty much anywhere in Europe. Health regulators haven’t signed off on this compound, and clinical guidelines don’t reference it anymore. Modern doctors rarely, if ever, bring it up during patient consults.
Back in the 1950s and 1960s, psychiatry was still figuring things out. Azacyclonol caught some attention because it seemed to blunt certain side effects of early antipsychotics. Yet, better alternatives showed up quickly. Doctors and families started trusting drugs like chlorpromazine, haloperidol, and later the atypical antipsychotics. These offered bigger benefits, more predictable effects, and left fewer patients grappling with hard-to-manage reactions.
By now, most pharmacy reference books describe azacyclonol as a discontinued or abandoned compound. The US Food and Drug Administration doesn’t include it in the Orange Book, which lists approved drugs. Searching the British National Formulary or similar references in Canada, Australia, or Japan gives the same result—not available, not approved, not in use. Pharmacists don’t see it in ordering systems. Medical insurance plans ignore it, so people couldn’t get it covered if they tried.
Medications earn their spot on the prescription list after passing tough safety and effectiveness tests. Regulators want proof that any new medicine helps patients more than it puts them at risk. Azacyclonol didn’t meet those standards. With no solid studies backing long-term benefits, and with no manufacturer stepping up to submit fresh data, the drug faded away. This process actually protects people. When a compound loses scientific support or falls short in real-world care, treatment guidelines move on quickly.
Doctors and pharmacists have a responsibility to keep up with what works and what doesn’t. The growth in evidence-based medicine over the past two decades means abandoned drugs stay on the sidelines unless new information changes minds. If someone wants to access a drug like azacyclonol for off-label or experimental use, they’ll hit real barriers. Import rules, regulatory red tape, and insurance denials lock out options that haven’t passed safety checks.
Communities facing neurological or psychiatric illness know the weight of failed treatments. Each time a drug fades away, hope sometimes takes a hit. The silver lining lies in the search for safer and more effective therapies. For psychiatrists, losing access to something old usually coincides with something better making its way to the clinic. Today’s patients meet new standards. Medications like aripiprazole and olanzapine stand on firmer ground, with ongoing research and monitoring for rare but serious side effects.
Looking back at azacyclonol, its disappearance shows how science moves forward through both small setbacks and breakthroughs. Staying curious about why some drugs don’t survive can help patients and families ask good questions, push for better options, and build trust with healthcare providers. Stories like this one remind us that medicine isn’t just about what’s possible—it’s about what truly helps.
Azacyclonol once walked a peculiar path in the world of pharmaceuticals. Initially developed as an antipsychotic, today it finds more attention as a subject of research or as a component in some other medicines. It may show up in circles discussing old-school approaches to schizophrenia or in labs focused on drug development. Most folks never hear about it at the pharmacy, but those who do deserve real talk about safety and practical use.
This drug typically comes in tablet form. Doctors—those with proper experience managing psychiatric medicines—determine dose. Most cases will see a recommendation for oral administration, which means swallowing the tablet with water. Some users combine it with food to ease possible stomach discomfort. Consistency proves key, so regular times each day help maintain steady levels in the body.
No magic one-size-fits-all amount exists for azacyclonol. People differ. Conditions differ. Doctors look at weight, age, other meds, and the problem being treated. Skipping doses or doubling up after missing one raises risks of side effects or complications. A simple routine, paired with a daily reminder or pill organizer, helps people avoid mix-ups.
Like many psychiatric medications, azacyclonol can bring side effects. Drowsiness, dry mouth, dizziness, upset stomach—these can appear, especially at the start. Some people complain of blurred vision or feeling lightheaded. Anyone noticing severe symptoms, like confusion or heart problems, needs immediate medical attention.
Taking azacyclonol alongside alcohol, sedatives, or certain antihistamines can compound drowsiness or lead to other problems. Even over-the-counter painkillers or cold remedies can stir up trouble. Always speaking up about all medicines in use—herbal, prescription, or recreational—gives the care team a chance to spot dangerous combinations early.
Doctors and pharmacists know a lot, but no one can guess how another person feels day to day. Speaking openly about experiences with side effects, concerns about skipped doses, or other meds goes a long way. Periodic check-ins often allow dose adjustments, monitoring for progress, and a check that no new symptoms have snuck in.
People sometimes stay quiet about struggles, fearing judgment or thinking symptoms are “just in their head.” That thinking leads to missed opportunities for safer care. Telling care teams about difficulty with side effects, cost issues, or misunderstandings about instructions makes all the difference. Some even keep a journal, making it easier to recall details during appointments.
Keep azacyclonol tablets in a dry, cool place, out of reach of children or pets. Humidity in bathrooms or kitchens can affect medicines, so a bedroom drawer or cabinet away from the stove may work better. Pay attention to expiration dates, tossing old or unused pills at the pharmacy, not down the drain or in the trash.
Many medicines from earlier decades have faded from mainstream use for reasons that shine light on better practices today. For azacyclonol, that means careful dosing, respect for interactions, and open lines of communication. People who stick to a practical plan, stay honest with care teams, and pay attention to their bodies tend to avoid most common pitfalls.
Azacyclonol rarely pops up in conversations about commonly prescribed drugs these days. First developed in the mid-20th century, it once carried a certain hope as an antipsychotic, aiming to address hallucinations brought on by LSD. For most clinicians today, though, it’s mostly a historical curiosity. Still, old drugs sometimes land back in the spotlight, often because folks go digging for alternatives or because a rare prescription turns up in someone’s medical record. Questions about side effects and safety just come with the territory, especially for those balancing complicated medication lists.
Aging populations, growing rates of chronic conditions, and the rise of polypharmacy have turned drug interactions into frontline issues in healthcare. Standard guides like Drugs.com or the FDA’s medication safety overviews stress that even drugs considered obsolete can cause trouble if they mix with the wrong substances. Just because Azacyclonol left the mainstream doesn’t mean it plays nicely with modern medicines.
Azacyclonol has an antiserotonergic action—pretty much its main claim to fame. The theory behind its use was to dull the intense serotonin-mediated effects of psychedelics. Unlike the new generation of antipsychotics, Azacyclonol doesn’t come with a stack of robust clinical trials. Instead, most data were collected decades ago. From personal experience combing through the literature, it’s some digging to find anything recent or applicable to current practice. That’s already a red flag for potential safety gaps.
Unlike headline-making drugs with hundreds of studies, Azacyclonol doesn’t show up with a neatly organized list of established drug interactions. Absence of evidence never means safety. Drugs affecting the serotonin system often stack poorly with other central nervous system (CNS) agents. We already know older drugs used for sedation or psychosis—such as chlorpromazine or barbiturates—can blend in unpredictable, risky ways. Drugs altering liver enzymes, like carbamazepine or some antibiotics, might tinker with the body’s ability to process Azacyclonol. Even though no blockbuster interaction is widely published, guessing that this drug sits safely on the sidelines just because data are thin isn’t wise.
Pharmacists and doctors rely on thorough medication reviews and up-to-date records to catch gaps and flag risk. One lesson from decades of medication mishaps: patients don’t benefit from guesswork. Whenever a drug like Azacyclonol appears, a deeper review starts with the basics—checking not just for headline-grabbing interactions but also for smaller, cumulative risks. Patients juggling mood stabilizers, sleep medications, or certain heart drugs should approach any new or old prescription with caution.
Dependable sources such as Lexicomp or the American Society of Health-System Pharmacists still recommend screening for even rare medication combinations. They emphasize the role of patient history, lab monitoring, and honest discussion about drug histories—especially for folks using mail-order pharmacies or supplements. It’s tough to spot a hidden risk unless everyone is on the same page.
Azacyclonol shows how history shapes today’s medication safety landscape. The real challenge isn’t just knowing which interactions have been reported, but realizing that lack of data creates its own danger zone. No one benefits from blind spots. Open conversations among patients, prescribers, and pharmacists remain vital. As new medications keep pushing boundaries, the responsibility to close old gaps grows. Old drugs still deserve modern scrutiny—anything less invites risks no one ever wanted in the first place.
| Names | |
| Preferred IUPAC name | 1-piperazin-2-yl-1-phenylpropan-1-ol |
| Other names |
Frenquel Frenquelina Azacyclanol Acyclanol |
| Pronunciation | /ˌeɪ.zə.saɪˈkloʊ.nɒl/ |
| Identifiers | |
| CAS Number | 115-46-8 |
| Beilstein Reference | 1209248 |
| ChEBI | CHEBI:2956 |
| ChEMBL | CHEMBL1416 |
| ChemSpider | 1203 |
| DrugBank | DB00825 |
| ECHA InfoCard | The ECHA InfoCard of product 'Azacyclonol' is: 100.042.285 |
| EC Number | 3.4.3.7 |
| Gmelin Reference | 84844 |
| KEGG | C06587 |
| MeSH | D000365 |
| PubChem CID | 2156 |
| RTECS number | BU2525000 |
| UNII | W6S3C0978K |
| UN number | UN2811 |
| Properties | |
| Chemical formula | C13H17NO |
| Molar mass | 263.351 g/mol |
| Appearance | White crystalline powder |
| Odor | Odorless |
| Density | 1.142 g/cm³ |
| Solubility in water | Slightly soluble |
| log P | 1.95 |
| Vapor pressure | 6.2E-8 mmHg |
| Acidity (pKa) | 15.13 |
| Basicity (pKb) | 6.75 |
| Magnetic susceptibility (χ) | -71.0·10^-6 cm³/mol |
| Refractive index (nD) | 1.604 |
| Viscosity | Viscous oil |
| Dipole moment | 2.17 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 230 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | -56.7 kJ/mol |
| Pharmacology | |
| ATC code | N06AX09 |
| Hazards | |
| Main hazards | May cause irritation to the skin, eyes, and respiratory tract. |
| GHS labelling | GHS labelling: "Warning; H302; H315; H319; P261; P264; P270; P301+P312; P305+P351+P338; P337+P313 |
| Pictograms | 🛑⚠️❌ |
| Signal word | Warning |
| Hazard statements | No hazard statements. |
| Precautionary statements | P261, P264, P271, P272, P280, P302+P352, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362+P364, P501 |
| NFPA 704 (fire diamond) | Health: 2, Flammability: 1, Instability: 0, Special: - |
| Flash point | Flash point: 151.7°C |
| Autoignition temperature | 608°C |
| Lethal dose or concentration | LD50 (rat, oral): 430 mg/kg |
| LD50 (median dose) | LD50 2200 mg/kg (rat, oral) |
| NIOSH | PB8225000 |
| PEL (Permissible) | PEL: Not established |
| REL (Recommended) | 0.1–0.2 mg/kg |
| IDLH (Immediate danger) | Unknown |
| Related compounds | |
| Related compounds |
Diphenylmethylpiperazine Cinnarizine Meclizine |
